UNITED STATES SENTENCING COMMISSION ║ OFFICE OF THE GENERAL COUNSEL

This document provides brief summaries of select Supreme Court cases that involve the guidelines 

and other aspects of federal sentencing. The list of cases and the summaries themselves are not 

intended to be comprehensive. Instead, this document summarizes only a few of the relevant 

cases, focusing on selected sentencing topics that may be of current interest. The Commission’s 

legal staff publishes this document to assist in understanding and applying the sentencing 

guidelines. The information in this document does not necessarily represent the official position of 

the Commission, and it should not be considered definitive or comprehensive.

SELECTED

SUPREME COURT CASES 

ON SENTENCING ISSUES

November 2019

PREPARED BY THE OFFICE OF THE GENERAL COUNSEL
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page i

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

SELECTED SUPREME COURT CASES ON SENTENCING ISSUES

Table of Contents

United States v. Haymond, 139 S. Ct. 2369 (2019)..................................................................1

United States v. Davis, 139 S. Ct. 2319 (2019). ........................................................................2

Stokeling v. United States, 139 S. Ct. 544 (2019).....................................................................3

Rosales-Mireles v. United States, 138 S. Ct. 1897 (2018). .......................................................4

Koons v. United States, 138 S. Ct. 1783 (2018). .......................................................................5

Hughes v. United States, 138 S. Ct. 1765 (2018)......................................................................6

Sessions v. Dimaya, 138 S. Ct. 1204 (2018). ............................................................................7

Honeycutt v. United States, 137 S. Ct. 1626 (2017). ................................................................8

Dean v. United States, 137 S. Ct. 1170 (2017). ........................................................................8

Beckles v. United States, 137 S. Ct. 886 (2017). ......................................................................9

Mathis v. United States, 136 S. Ct. 2243 (2016)........................................................................9

Torres v. Lynch, 136 S. Ct. 1619 (2016)...................................................................................10

Molina-Martinez v. United States, 136 S. Ct. 1338 (2016). ....................................................11

Welch v. United States, 136 S. Ct. 1257 (2016)......................................................................12

Johnson v. United States, 135 S. Ct. 2551 (2015). .................................................................13

Paroline v. United States, 572 U.S. 434 (2014). ......................................................................14

Abramski v. United States, 573 U.S. 169 (2014).....................................................................15

United States v. Castleman, 572 U.S. 157 (2014)...................................................................15

Burrage v. United States, 571 U.S. 204 (2014)........................................................................15

Descamps v. United States, 570 U.S. 254 (2013). ..................................................................16

Alleyne v. United States, 570 U.S. 99 (2013). .........................................................................17

Peugh v. United States, 569 U.S. 530 (2013). .........................................................................18

Dorsey v. United States, 567 U.S. 260 (2012). ........................................................................19

Setser v. United States, 566 U.S. 231 (2012). ..........................................................................20

Southern Union Co. v. United States, 567 U.S. 343 (2012).....................................................21

DePierre v. United States, 564 U.S. 70 (2011).........................................................................22

Freeman v. United States, 564 U.S. 522 (2011)......................................................................22

McNeill v. United States, 563 U.S. 816 (2011). .......................................................................23

Pepper v. United States, 562 U.S. 476 (2011).........................................................................24
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page ii

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Sykes v. United States, 564 U.S. 1 (2011) (overruled by Johnson v. United States, 135 S. Ct. 

2551 (2015)).............................................................................................................................25

Tapia v. United States, 564 U.S. 319 (2011)............................................................................26

Abbott v. United States, 562 U.S. 8 (2010). ............................................................................26

Dillon v. United States, 560 U.S. 817 (2010)............................................................................27

Johnson v. United States, 559 U.S. 133 (2010).......................................................................28

United States v. O’Brien, 560 U.S. 218 (2010).........................................................................29

Chambers v. United States, 555 U.S. 122 (2009). ..................................................................31

Spears v. United States, 555 U.S. 261 (2009)..........................................................................32

Begay v. United States, 553 U.S. 137 (2008). .........................................................................33

Greenlaw v. United States, 554 U.S. 237 (2008). ...................................................................34

Irizarry v. United States, 553 U.S. 708 (2008)..........................................................................36

United States v. Rodriquez, 553 U.S. 377 (2008). ...................................................................38

Cunningham v. California, 549 U.S. 270 (2007). ...................................................................40

Gall v. United States, 552 U.S. 38 (2007). ...............................................................................40

James v. United States, 550 U.S. 192 (2007)..........................................................................42

Kimbrough v. United States, 552 U.S. 85 (2007). ...................................................................42

Logan v. United States, 552 U.S. 23 (2007). ...........................................................................44

Rita v. United States, 551 U.S. 338 (2007)...............................................................................45

Watson v. United States, 552 U.S. 74 (2007)...........................................................................46

Washington v. Recuenco, 548 U.S. 212 (2006)......................................................................48

Shepard v. United States, 544 U.S. 13 (2005).........................................................................48

United States v. Booker, 543 U.S. 220 (2005). ........................................................................49

Blakely v. Washington, 542 U.S. 296 (2004)...........................................................................51

Leocal v. Ashcroft, 543 U.S. 1 (2004)......................................................................................52

Schriro v. Summerlin, 542 U.S. 348 (2004)..............................................................................52

Harris v. United States, 536 U.S. 545 (2002) (overruled by Alleyne v. United States, 570 U.S. 

99 (2013)).................................................................................................................................53

Ring v. Arizona, 536 U.S. 584 (2002).......................................................................................54

United States v. Cotton, 535 U.S. 625 (2002)..........................................................................55

Buford v. United States, 532 U.S. 59 (2001). ...........................................................................55

Apprendi v. New Jersey, 530 U.S. 466 (2000). ......................................................................56

Castillo v. United States, 530 U.S. 120 (2000).........................................................................57

United States v. Johnson, 529 U.S. 53 (2000).........................................................................58

United States v. Johnson, 529 U.S. 694 (2000).......................................................................58
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page iii

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Jones v. United States, 526 U.S. 227 (1999). ..........................................................................59

Mitchell v. United States, 526 U.S. 314 (1999)........................................................................59

Almendarez-Torres v. United States, 523 U.S. 224 (1998). ....................................................60

Edwards v. United States, 523 U.S. 511 (1998).......................................................................60

Muscarello v. United States, 524 U.S. 125 (1998). .................................................................60

United States v. Gonzales, 520 U.S. 1 (1997). ........................................................................61

United States v. LaBonte, 520 U.S. 751 (1997). ......................................................................61

United States v. Watts, 519 U.S. 148 (1997)............................................................................62

Koon v. United States, 518 U.S. 81 (1996). .............................................................................62

Melendez v. United States, 518 U.S. 120 (1996). ...................................................................63

Neal v. United States, 516 U.S. 284 (1996). ............................................................................63

United States v. Armstrong, 517 U.S. 456 (1996)....................................................................64

Bailey v. United States, 516 U.S. 137 (1995)...........................................................................64

Witte v. United States, 515 U.S. 389 (1995).............................................................................65

Custis v. United States, 511 U.S. 485 (1994). ..........................................................................65

Nichols v. United States, 511 U.S. 738 (1994).........................................................................65

United States v. Granderson, 511 U.S. 39 (1994)...................................................................66

Deal v. United States, 508 U.S. 129 (1993). ............................................................................66

Smith v. United States, 508 U.S. 223 (1993)............................................................................67

Stinson v. United States, 508 U.S. 36 (1993). ..........................................................................67

United States v. Dunnigan, 507 U.S. 87 (1993).......................................................................68

United States v. R.L.C., 503 U.S. 291 (1992)............................................................................68

United States v. Wilson, 503 U.S. 329 (1992). .........................................................................68

Wade v. United States, 504 U.S. 181 (1992). ..........................................................................69

Williams v. United States, 503 U.S. 193 (1992). ......................................................................69

Braxton v. United States, 500 U.S. 344 (1991). .......................................................................69

Burns v. United States, 501 U.S. 129 (1991). ...........................................................................70

Chapman v. United States, 500 U.S. 453 (1991)....................................................................70

Mistretta v. United States, 488 U.S. 361 (1989).......................................................................70

Subject Matter Index..............................................................................................................71
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 1

UNITED STATES SENTENCING COMMISSION ║ OFFICE OF THE GENERAL COUNSEL

SELECTED SUPREME COURT CASES ON SENTENCING ISSUES

United States v. Haymond, 139 S. Ct. 2369 (2019).

The Supreme Court struck down 18 U.S.C. § 3583(k), a provision of the federal supervised release statute requiring a 5-year mandatory minimum sentence for offenders who 

commit certain enumerated offenses while on supervised release. A plurality of the Court 

held that section 3583(k) violates the Fifth and Sixth Amendments.

Haymond was convicted of possessing child pornography and sentenced to 

38 months in prison, followed by ten years of supervised release. While on supervised release, Haymond was found with images that appeared to be child pornography. At his revocation hearing, the district court found, by a preponderance of the evidence, that he knowingly downloaded and possessed 13 images of child pornography. The statute for Haymond’s 

original offense of conviction generally authorizes a new prison term of zero to two years for 

a supervised release violation. However, section 3583(k) mandates an additional prison 

term of five years to life for certain enumerated offenses, including Haymond’s offense. The 

district court, pursuant to section 3583(k), imposed a 5-year sentence but stated that section 3583(k) was “repugnant” without the traditional protections of a jury verdict reached 

under the reasonable doubt standard. The Tenth Circuit vacated and remanded Haymond’s 

sentence, holding that section 3583(k) violated the Fifth and Sixth Amendments by requiring a new and higher sentencing range based on facts found by a judge by a preponderance.

The Supreme Court agreed with the Tenth Circuit, holding that section 3583(k) impermissibly increased “the legally prescribed range of allowable sentences” in violation of 

the Fifth and Sixth Amendments. See Apprendi v. New Jersey, 530 U. S. 466 (2000) (holding 

that “other than the fact of the prior conviction, any fact that increases the penalty for a 

crime beyond the prescribed statutory maximum must be submitted to a jury, and proved 

beyond a reasonable doubt.”); Alleyne v. United States, 570 U. S. 99 (2013) (applying Apprendi to facts increasing the mandatory minimum). The Court rejected the government’s 

argument that the Sixth Amendment jury protections do not extend beyond the issuance of 

a sentence to “postjudgment sentence-administration proceedings.” The Court instead held 

that such protections extend until a “final sentence” is imposed, which includes any supervised release sentence. The Court distinguished section 3583(k) from traditional parole and 

probation, which only allow a defendant to be sentenced to serve the remaining term authorized by his original conviction, as well as prison disciplinary procedures, which involve 

adjusting the terms of confinement rather than adding a significant new sentence of imprisonment. 

The Court also dismissed the government’s argument that the jury’s verdict authorized a term of supervised release, which was always subject to the possibility of revocation 

under section 3583(k). The Court noted that, critically, the mandatory minimum here 

“comes into play only as a result of additional judicial factual findings” by a preponderance.

Finally, the Court made clear that its holding is limited to the “unusual” section 3583(k) 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 2

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

provision and does not address whether all supervised released proceedings comport with 

Apprendi/Alleyne. 

Justice Breyer issued a concurring opinion. He agreed with the dissent that the role 

of the judge in a supervised-release proceeding is consistent with traditional parole. He also 

stated that Apprendi/Alleyne should not broadly apply to the supervised-release context.

However, he concurred in the judgment that section 3583(k) is unconstitutional because its 

provisions closely resemble the punishment of new criminal offenses without granting a defendant the rights that attend a new criminal prosecution.

Justice Alito issued a dissenting opinion joined by Chief Justice Roberts and Justices 

Thomas and Kavanaugh. The dissent stated that Justice Breyer’s opinion, which was narrower than the plurality’s, represented the Court’s holding. See Marks v. United States, 

430 U.S. 188, 193 (1977). The dissent rejected the plurality opinion’s analogy between section 3583(k) and the mandatory minimum in Alleyne, cautioning that the plurality’s reasoning suggests the Sixth Amendment right to a jury trial applies to any supervised-release 

revocation proceeding. The dissent argued that Congress did not intend that supervised release be treated differently from parole for Sixth Amendment purposes. Thus, a parole revocation proceeding was not a “criminal prosecution” within the scope of the Sixth Amendment, and revocation did not result in a new sentence. 

United States v. Davis, 139 S. Ct. 2319 (2019).

The Supreme Court struck down the residual clause in 18 U.S.C. § 924(c)(3)(B)’s 

“crime of violence” definition as unconstitutionally vague. Davis followed and relied on 

Johnson v. United States, 135 S. Ct. 2551 (2015), and Sessions v. Dimaya, 138 S. Ct. 1204 

(2018), which had invalidated similar residual clauses. 

In Johnson, the Court had struck down the Armed Career Criminal Act (ACCA)’s residual clause which, under the categorical approach, required courts to determine the conduct involved in the “ordinary case” of an offense and measure that against an indeterminate “serious” degree of risk. Those two features in combination made the clause impossible 

to apply and violated due process. Similarly, Dimaya held that a straightforward application of Johnson invalidated section 16(b)’s residual clause, because it used the same flawed 

“ordinary case” approach.

Davis involved section 924(c)(3)(B)’s residual clause, which was identically worded to 

the clause in Dimaya. Given Johnson and Dimaya, the Court stated that section 924(c)’s residual clause would also be void for vagueness if the categorical approach applied to it. But 

if the clause permitted a conduct-based approach looking to the facts of the specific case, it 

would be valid. Davis thus focused on whether section 924(c)(3)(b) requires a categorical approach. The Court examined the text, context, and history of section 924(c)(3)(B), noting its 

use of language like “offense” and “by its nature” as well as its similarity and historical connection with the residual clause in section 16(b). Based on those factors, the Court held that 

section 924(c)(3)(B) requires the categorical approach and is therefore invalid.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 3

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

The Court rejected the government’s argument that under the canon of constitutional avoidance, the Court must adopt any “fairly possible” reading to avoid holding a statute unconstitutional and thus a conduct-based approach must apply. In rejecting that argument, the Court noted that it has never invoked that canon to expand the reach of a statute 

and that doing so would risk violating due process and the separation-of-powers and conflict 

with the rule of lenity.

Justice Kavanaugh wrote a dissenting opinion joined by Justices Thomas and Alito 

and joined in part by Chief Justice Roberts. The dissent argued that the statute should be 

read with a conduct-based approach and is thus constitutional. The dissent emphasized the 

distinction between section 924(c), which involves presently charged conduct, and the 

ACCA and section 16, which involve prior offenses. Given this distinction, the dissent reasoned, a conduct-based approach under section 924(c) would not require minitrials relitigating past convictions, nor would it implicate the Sixth Amendment, as a jury would have 

found the requisite level of risk of physical force for the conviction. The dissent also argued 

that the text of the statute supports a conduct-based approach but, even if the text is ambiguous, constitutional avoidance militates in favor of applying that approach. Finally, the 

dissent highlighted policy concerns regarding violent conduct that may go unpunished under the majority’s decision.

Stokeling v. United States, 139 S. Ct. 544 (2019).

The Supreme Court held that robbery offenses that require force sufficient to overcome a victim’s resistance qualify as violent felonies under the elements clause of the 

Armed Career Criminal Act (ACCA) enhancement.

Stokeling pleaded guilty to possessing a firearm and ammunition as a felon. At sentencing, U.S. Probation recommended imposing the ACCA enhancement based, in part, on 

the defendant’s 1997 Florida conviction for robbery. The district court held that his conviction was not an ACCA predicate and imposed a sentence below the ACCA’s 15-year mandatory minimum. The Eleventh Circuit reversed, holding that Florida robbery is a violent felony under the ACCA’s elements clause, which requires the use, attempted use, or threatened use of “physical force.”

The Supreme Court agreed with the Eleventh Circuit, holding that Florida robbery, 

which requires force sufficient to overcome a victim’s resistance, is “physical force” under 

the elements clause. The Court focused on the common law understanding of “force” that 

was sufficient to distinguish robbery from simple theft, citing a treatise which stated that 

overcoming a victim’s resistance is enough to make a taking a robbery, however slight the 

resistance. Based on the amendment history of the ACCA, the Court concluded Congress 

intended to incorporate this common-law understanding of robbery in the ACCA. The Court 

noted that to hold otherwise would disqualify the majority of state law definitions of robbery at the time of the ACCA’s enactment. 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 4

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

The Court stated that defining “physical force” to include force sufficient to overcome 

a victim’s resistance comports with Johnson v. United States, 559 U.S. 133 (2010), which 

held that Florida battery did not require the degree of force necessary to satisfy the elements clause. The Court rejected Stokeling’s argument that Johnson defined “physical 

force” as so substantial as to exclude the force in Florida robbery. The Court confirmed that 

“physical force” means force “capable of” causing physical pain or injury—not, as Stokeling 

urged the Court, force “reasonably expected to cause” physical pain or injury. The Court explained that Stokeling’s proposed definition was impractical and inconsistent with common 

law and the text of Johnson. And because “force capable of causing physical pain or injury”

includes the amount of force necessary to overcome a victim’s resistance, Florida robbery 

qualifies as a violent felony.

Justice Sotomayor wrote a dissenting opinion joined by the Chief Justice and Justices Ginsburg and Kagan, questioning the majority’s reading of Johnson and “physical 

force.” The dissent stated that, read in the context of Johnson’s entire opinion, “capable of 

causing physical pain or injury” means a heightened degree of force that Florida robbery 

does not satisfy. The dissent pointed to Florida robbery cases involving minimal force and 

resistance, such as a pickpocket attempting to pull free after the victim caught his arm and 

a purse snatcher whose victim instinctively held onto the strap of her purse for a moment.

Thus, the dissent argued, Florida robbery can be committed with force that is no greater 

than that discussed in Johnson and is therefore not categorically the kind of violent offense 

that makes an offender more likely to be dangerous with a gun and deserving of the significant sentencing enhancement in the ACCA.

Rosales-Mireles v. United States, 138 S. Ct. 1897 (2018).

The Supreme Court held that a miscalculation affecting a defendant’s sentencing 

guideline range will, in the ordinary case, seriously affect the fairness, integrity, or public 

reputation of judicial proceedings, and thus will warrant relief under plain error review. 

Rosales-Mireles pleaded guilty to illegal re-entry. The presentence report mistakenly 

counted one of his prior convictions twice in calculating his criminal history score, resulting 

in an incorrect guideline range of 77 to 96 months. The correct range was 70 to 87 months.

He did not object to the error and was sentenced to 78 months of imprisonment. On appeal, 

he argued for the first time that his guideline range was incorrect, which was reviewed for 

plain error under Federal Rule of Criminal Procedure 52(b) because he had not objected in 

the district court. The Fifth Circuit denied relief, ruling that because his 78-month sentence 

fell within the correct guideline range, he could not satisfy the fourth prong of plain error 

review under United States v. Olano, 507 U.S. 725 (1993), which requires that the error seriously affect the fairness, integrity, or public reputation of judicial proceedings. The Fifth 

Circuit held that to satisfy that prong, such an error must “shock the conscience.”

The Supreme Court disagreed, holding that the Fifth Circuit’s “shock the conscience”

standard was improperly narrow and unsupported by Rule 52(b) and Olano. The Court 

stated that errors need not amount to a “powerful indictment” of the judicial system or call 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 5

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

into question the competence or integrity of the district judge. The Court explained that an 

error resulting in a higher guideline range usually will warrant relief because it establishes 

a reasonable probability that a defendant will serve a prison sentence that is longer than 

necessary to achieve the purposes of incarceration. The Court stated that guideline errors 

particularly undermine judicial proceedings because of the judge’s role in calculating the 

guideline range and that the public legitimacy of the justice system relies on procedures 

that are “neutral, accurate, consistent, trustworthy, and fair,” with mechanisms for error 

correction. Correcting the error here, the Court added, required only an inexpensive resentencing proceeding. However, the Court noted that the fourth prong of plain error review is 

a case-specific inquiry so there may be countervailing factors in some cases that preserve 

the integrity of the proceeding despite the error. 

Justice Thomas wrote a dissenting opinion joined by Justice Alito, arguing that 

while the “shock the conscience” test was wrong, the fourth prong of plain error review 

should be reserved for errors determined to be particularly egregious after a case-specify inquiry. Thus, the dissent argued, the majority should not have created a rebuttable presumption that guideline errors will ordinarily satisfy the fourth prong of plain error review.

The dissent argued that a proper case-specific inquiry here shows that Rosales-Mireles did 

not satisfy the fourth prong. The dissent emphasized that the guidelines are advisory and 

that purely procedural errors that likely did not affect the substantive outcome do not satisfy the fourth prong. 

Koons v. United States, 138 S. Ct. 1783 (2018).

The Supreme Court affirmed the denial of the defendants’ motions for sentence reductions under 18 U.S.C. § 3582(c)(2), where the high end of the guideline ranges at their 

original sentencings fell below the applicable mandatory minimum, and the defendants received sentences below the mandatory minimum based on substantial assistance departures. 

Koons involved five defendants who had pled guilty to drug trafficking offenses carrying mandatory minimum sentences and had been sentenced below the mandatory minimum for substantial assistance to the government. Significantly, their guideline ranges fell 

entirely below the mandatory minimum. Following Amendment 782, a retroactive drug 

guideline amendment which lowered base offense levels for certain drug quantities, they 

sought to have their sentences further reduced. The district court and 8th Circuit held that 

they were ineligible for retroactive resentencings under section 3582(c)(2) because each defendant had received a sentence based on his mandatory minimum and not “based on a sentencing range that has subsequently been lowered by the Sentencing Commission.”

The Supreme Court unanimously agreed with the lower courts, holding that the defendants were not eligible for sentence reductions under the retroactive guideline amendment because their sentences were “based on” their mandatory minimums and substantial 

assistance. The Court rejected the defendants’ argument that their sentences were “based 

on” the guidelines because the district court was first required to calculate their guideline 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 6

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

ranges and then use the substantial assistance guidelines to determine whether, and to 

what extent, to reduce the sentence. The Court noted that what matters is the role the 

guideline range played in the selection of the eventual sentence, not its role in the initial 

calculation. 

The Court stated that for a sentence to be “based on” a lowered guideline range, the 

range must have played a relevant part in the framework used by the sentencing judge in 

imposing the sentence. The Court noted that at each original sentencing, the district court 

calculated the offender’s guideline range, but then discarded that range in favor of the mandatory minimum sentence because the minimum was higher than the high end of the guideline range. Only after it had discarded the guideline range did the district court proceed to 

consider the substantial assistance factors—and only the substantial assistance factors—to 

arrive at its final sentence. The Court indicated that this approach was consistent with 

§§1B1.1(a)(8) and 5G1.1(b). Because the guideline ranges were necessarily discarded, the 

Court reasoned that the defendants’ sentences were not “based on” the subsequently reduced guideline ranges.

Hughes v. United States, 138 S. Ct. 1765 (2018).

The Supreme Court held that a sentence entered under a Federal Rule of Criminal 

Procedure 11(c)(1)(c) (“Type-C”) plea, in which the government and defendant agree to a 

specific sentence or sentencing range, will generally be “based on” the guidelines, and the 

defendant will be eligible for resentencing if the guidelines are retroactively amended. 

Hughes had received a Type-C plea for a 180-month sentence, which the district 

court accepted after calculating his guideline range as 188 to 235 months. Soon after, the 

guidelines were retroactively amended so that his new guideline range would be 151 to 

188 months. He filed a motion for a sentence reduction under 18 U.S.C. § 3582(c)(2), which 

the district court denied and the Eleventh Circuit affirmed. Both courts held that under 

Justice Sotomayor’s concurrence in Freeman v. United States, 564 U.S. 522 (2011), he was 

ineligible for a sentence reduction because his plea agreement did not expressly rely on a 

guideline range. 

The Supreme Court disagreed with the lower courts, holding that in the ordinary 

case, a defendant is eligible for a sentence reduction even if he entered a Type-C plea agreement. The Court reasoned that a sentence imposed pursuant to a Type-C plea agreement is 

not an exception to the general rule that the guidelines form the basis of a defendant’s ultimate sentence. The Court also emphasized §6B1.2(c), which sets the procedure courts use 

in deciding whether to accept C pleas. The Court noted that a court “may not accept the 

agreement unless it is satisfied that ‘(1) the agreed sentence is within the applicable guideline range; or (2)(A) the agreed sentence is outside the applicable guideline range for justifiable reasons . . . .’ ” Thus, the Court reasoned that C pleas, like ordinary sentences, use “the 

guideline range [a]s both the starting point and a basis for the ultimate sentence.” The majority stated that its interpretation was the most consistent with the Sentencing Reform 

Act’s concern with avoiding unwarranted disparity. The majority determined that, because 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 7

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

of the role the guidelines inherently play in a decision whether to accept a C plea, disparate 

access to retroactive amendments would not be proper.

Justice Sotomayor joined the majority opinion in its entirety but authored a concurrence explaining her change in opinion from Freeman to Hughes. Justice Sotomayor did not 

disavow her Freeman concurrence’s analysis but indicated that her decision to join the majority was driven by the confusion in the lower courts stemming from the prior concurrence.

Chief Justice Roberts wrote a dissenting opinion joined by Justices Thomas and 

Alito, arguing that a sentence from a Type-C plea agreement is not based on the guidelines.

The dissent argued that a judge is not deciding a sentence in a Type-C plea but is merely 

imposing the sentence brought forth by the parties. The dissent stated that, notwithstanding the requirement of a guideline calculation, the only decision that a judge makes in the 

C plea context is whether to accept or reject a plea. Moreover, the dissent rejected the majority’s disparity arguments, arguing that such defendants had bargained for specific concessions and a specific sentence chosen without judicial discretion.

Sessions v. Dimaya, 138 S. Ct. 1204 (2018).

The Supreme Court held that the residual clause in 18 U.S.C. § 16, which defines a 

“crime of violence” and is incorporated by reference in the Immigration and Nationality 

Act’s mandatory removal provisions, is void for vagueness. The Court concluded that section 16’s residual clause possessed the same flaws as the Armed Career Criminal Act’s residual clause, which the Court invalidated in Johnson v. United States, 135 S. Ct. 2551 

(2015).

In 2010, the government sought to deport Dimaya, a lawful permanent resident, after his second conviction for first-degree residential burglary under California law. The government contended that Mr. Dimaya was deportable as an “aggravated felon” because his 

convictions were “crimes of violence” under section 16(b). Section 16(b)’s residual clause, on 

which the government relied, defines a “crime of violence” as “any other offense that is a felony and that, by its nature, involves a substantial risk that physical force against the person or property of another may be used in the course of committing the offense.” Dimaya 

unsuccessfully challenged his deportation before the Board of Immigration Appeals and appealed to the Ninth Circuit. Relying on Johnson, the Ninth Circuit ruled in Dimaya’s favor.

The Supreme Court affirmed, concluding that section 16(b) suffered from the same “fatal 

features” of the ACCA’s residual clause.

The Court observed that the clause creates “uncertainty” about both “how to estimate the risk posed by a crime” and “the level of risk that makes a crime ‘violent.’ ” It also 

rejected the government’s emphasis on the textual distinctions between section 16(b) and 

the ACCA’s residual clause, observing that “[e]very offense that could have fallen within 

ACCA’s residual clause might equally fall within §16(b). Finally, the Court concluded that 

precedent established that removal statutes should be held to the same exacting vagueness 

standard as criminal provisions. 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 8

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice Gorsuch concurred, observing that the standard adopted by the majority 

should not be limited to criminal statutes or statutes resulting in deportation. Chief Justice 

Roberts dissented, joined by Justices Kennedy, Thomas, and Alito, concluding that the 

clause is constitutional “even under the standard applicable to criminal laws.” Justice 

Thomas also filed a separate dissenting opinion, expressing doubts about whether the voidfor-vagueness doctrine is consistent with the original meaning of the Due Process Clause 

and opining that the clause “might not apply to laws governing the removal of aliens.”

Honeycutt v. United States, 137 S. Ct. 1626 (2017).

The Supreme Court held that 21 U.S.C. § 853(A)(1) (Criminal forfeitures) does not 

allow joint and several liability for forfeiture judgments. The Court held that, under the 

statute, forfeiture is limited to “the defendant who initially acquired the property and who 

bears responsibility for its dissipation.” Honeycutt’s case involved conspiracy to distribute a 

product used in methamphetamine production. Because Honeycutt had “no ownership interest” in the relevant property and “did not personally benefit” from the relevant sales, the 

Court held that he never obtained any tainted property as a result of the crime and forfeiture was not required.

Dean v. United States, 137 S. Ct. 1170 (2017). 

The Supreme Court held that 18 U.S.C. § 924(c) does not prevent a sentencing court 

from considering a mandatory sentence imposed under that provision when determining 

the sentence for the underlying predicate offense.

Dean was convicted on numerous charges related to the robberies, including two 

counts of violating 18 U.S.C. § 924(A), which establishes mandatory sentences for defendants who used a firearm in furtherance of a crime of violence. The parties agreed that a 

guidelines range of 84–105 months’ imprisonment on the non-section 924 counts was appropriate. Dean requested that the district court sentence below the guideline range because 

the section 924(c) counts carried mandatory five- and 25-year prison sentences to run consecutively. The district court indicated that there was no room for modification. The Eighth 

Circuit agreed. The Supreme Court reversed, rejecting the government’s contention that 

sentencing courts should not consider the effect of other sentences until it is deciding 

whether sentences should run consecutively or concurrently.

The Supreme Court explained that a sentencing court may use the full breadth of 

the factors at 18 U.S.C. § 3553(a) to determine an appropriate sentence for each offense in a 

multicount case, and that nothing in the text of section 924(c) prohibits a court from considering that statute’s mandatory sentences when calculating the sentence for the predicate 

offense. Neither the fact that the mandatory sentence must be imposed “in addition to” the 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 9

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

punishment for the predicate offense, nor the fact that the additional sentence must be imposed “consecutively” to the sentence for the predicate offense, affects the sentencing court’s 

discretion to consider the mandatory minimum when calculating each individual sentence.

Beckles v. United States, 137 S. Ct. 886 (2017).

The Supreme Court decided that the advisory sentencing guidelines are not subject 

to constitutional challenge under the void-for-vagueness doctrine.

Beckles had been sentenced as a “career offender” under §4B1.1(a) because his offense involved possession of a sawed-off shotgun, and such an offense qualified as a “crime 

of violence” under §4B1.2(a). He filed a post-conviction motion to vacate his sentence, arguing that §4B1.2(a)’a “residual clause” was unconstitutionally vague. The Eleventh Circuit 

affirmed the denial of his motion, distinguishing the ACCA’s residual clause from the identical clause in the guidelines. The Supreme Court affirmed, holding that the sentencing 

guidelines, including §4B1.2(a)’s residual clause, are not subject to vagueness challenges 

under the Constitution’s Due Process Clause.

The Court distinguished between the ACCA’s residual clause, which fixes sentences 

for certain defendants, and the advisory guidelines. The guidelines do not fix the permissible range of sentences, the Court noted, but instead guide the exercise of a court’s discretion 

in choosing an appropriate sentence within the statutory range. The Court also noted that 

Congress has long permitted district courts wide discretion over sentencing. “If a system of 

unfettered discretion is not unconstitutionally vague,” it reasoned, then a system of guided 

discretion could not be, either. The Court cautioned that its holding did not render the advisory guidelines immune from all constitutional scrutiny, or even render “sentencing procedure[s]” entirely “immune from scrutiny under the Due Process Clause.”

Justice Kennedy concurred, emphasizing that “some other explication of the constitutional limitations,” instead of the vagueness doctrine, would be necessary to challenge arbitrariness in sentencing. Justice Ginsburg concurred in the judgment only, noting she 

would deny Beckles’ petition because he could not show that the guidelines residual clause 

was vague as applied to him, and would not reach the question of whether the advisory 

guidelines were generally subject to void-for-vagueness challenges. Justice Sotomayor 

agreed with Justice Ginsburg about the proper resolution of the case, and therefore also 

concurred in the judgment only. She also wrote separately to note that the advisory guidelines had an anchoring affect on sentences and therefore implicated the concerns of the 

vagueness doctrine.

Mathis v. United States, 136 S. Ct. 2243 (2016).

The Supreme Court decided that the “categorical approach” to evaluating predicate 

convictions at federal sentencing requires that a sentencing court look only to the elements 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 10

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

of the statute of conviction, even if the statute enumerates various factual means of committing one of the listed elements. 

Mathis was convicted of being a felon in possession of a firearm and received an enhanced sentence under the Armed Career Criminal Act (“ACCA”) based on his prior convictions under Iowa’s burglary statute. Unlike generic burglary, which requires unlawful entry 

into a “building or other structure,” the Iowa statute includes unlawful entry into “any 

building, structure, [or] land, water, or air vehicle.” The sentencing court applied the modified categorical approach. The Eighth Circuit affirmed, acknowledging that the Iowa statute swept more broadly than the generic statute, but noting that, even if “structures” and 

“vehicles” were not separate elements but alternative means of fulfilling a single element, a 

sentencing court could still use the modified categorical approach to see which crime the defendant had been convicted of. The Supreme Court reversed, holding that a defendant’s sentence cannot be enhanced by a conviction under a statute when one of the statute’s specified 

means creates a match with the generic offense, even though the broader component would 

not.

Relying on decisions of the Iowa Supreme Court, the Court held that the burglary 

statute’s list of places does not set out alternative elements, but rather alternative means of 

fulfilling a single locational element. Accordingly, elements of Iowa’s burglary law are 

broader than those of generic burglary and Mathis’s prior convictions could not give rise to 

ACCA’s sentence enhancement. The Court cited the ACCA’s text as well as the Sixth

Amendment’s requirement that a jury, not a judge, find facts that increase the maximum 

penalty for an offense. It instructed that the first task for sentencing courts faced with alternatively phrased statutes is to “determine whether its listed items are elements or 

means.” If the alternatives are means of committing the offense, the court cannot apply the 

modified categorical approach to determine which of the statutory alternatives was at issue 

in the earlier prosecution.

Justice Kennedy concurred, emphasizing that the categorical approach should not be 

justified by the Sixth Amendment concerns raised in Apprendi v. New Jersey, 530 U. S. 466 

(2000), which he believes was wrongly decided. Justice Thomas also concurred, arguing that

the ACCA is unconstitutional in its entirety because necessarily requires a court to find the 

existence (and nature of) prior convictions. Justice Breyer dissented, joined by Justice Ginsburg, opining that there is no relevant difference between a federal judge looking to judicial 

records to determine which of multiple alternative elements a defendant had committed, 

and which of multiple alternative means a defendant had committed. Justice Alito also dissented, noting that the opinion would prove difficult to apply because the distinction between elements and means is seldom relevant “in the real world.”

Torres v. Lynch, 136 S. Ct. 1619 (2016).

The Supreme Court held that a state offense counts as an “aggravated felony” under 

the Immigration and Nationality Act when it has every element of a listed federal crime except one requiring a connection to interstate or foreign commerce.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 11

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Torres immigrated to the United States as a child and is a lawful permanent resident of this country. In 1999, he pleaded guilty to third degree attempted arson under New 

York law. Later, the government initiated removal proceedings. An immigration judge rejected his request for cancellation of removal on the basis of his prior “aggravated felony”

conviction. The term “aggravated felony” is defined in Section 1101(a)(43), which provides a 

long list of offenses, including 21 different subparagraphs enumerating 80 different crimes.

The Board of Immigration Appeals (BIA) affirmed the denial after determining that the 

New York statute matched the federal arson statute “element-for element with one exception: The New York law does not require a connection to interstate commerce.” It reasoned 

that the commerce element was merely jurisdictional. The Second Circuit denied Torres’ petition for review of the BIA’s ruling. The Supreme Court affirmed, concluding courts using 

the categorical approach can ignore the “jurisdictional element” of a federal criminal statute 

when deciding whether a state offense is “described in” the federal statute.

The Court reasoned that Section 1101(a)(43) “declares the source of criminal law irrelevant,” because it provides that the term aggravated felony applies to a listed offense 

whether in violation of federal or state law. The Court also held that “a settled practice of 

distinguishing between substantive and jurisdictional elements of federal criminal laws”

supported its reading of Section 1101(a)(43).

Justice Sotomayor dissented, joined by Justices Breyer and Thomas. She observed

that “until today, the Court has always required the state offense to match every element of 

the listed ‘aggravated felony.’ ”

Molina-Martinez v. United States, 136 S. Ct. 1338 (2016).

The Supreme Court held that a court of appeals cannot categorically require additional evidence to establish that an error in guidelines calculation prejudiced a defendant.

The Court noted that when a district court applies an incorrectly calculated guideline 

range, a defendant has typically been prejudiced by the error, even if the sentence imposed 

was within the range later found to be correct on appeal.

Molina-Martinez pleaded guilty to illegal reentry after deportation. The Guidelines 

range calculated in his presentence report was 77 to 96 months. The district court, with little explanation, sentenced him to the low end of what it believed to be the applicable guidelines range —77 months. On appeal, Molina-Martinez argued for the first time that the probation office and the district court miscalculated his guidelines range, which should have 

been 70 to 87 months, and noted that his 77-month sentence would have been in the middle 

of the correct range, not at the bottom. The Fifth Circuit agreed that the district court’s 

guidelines range was incorrect but found that Molina-Martinez could not satisfy 

Rule 52(b)’s requirement that the error affect his substantial rights. The Supreme Court reversed and remanded, holding that a court of appeals cannot categorically require additional evidence to establish that an error in guidelines calculation prejudiced a defendant.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 12

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

The Court observed that the Sentencing Guidelines establish the essential framework for sentencing proceedings and noted that courts “must begin their analysis with the 

Guidelines and remain cognizant of them throughout the sentencing process.” It also cited 

Sentencing Commission statistics confirming that the guidelines inform the district court’s 

determination of an appropriate sentence. It relied on several of the Commission’s publications to show that sentences are closely linked to the applicable guideline range in most 

cases. The Court added that the government could rebut the presumption of error in “unusual circumstances,” such as when the sentencing judge made it clear that the sentence 

rested on factors outside the guidelines.

Justice Alito, joined by Justice Thomas, wrote a separate opinion, concurring in part 

and concurring in the judgment. Justice Alito disagreed with the Court’s statement —which 

he characterized as dicta— that “most” defendants who can show an error in guidelines application will thereby be able to demonstrate a reasonable probability of prejudice, as required to establish plain error.

Welch v. United States, 136 S. Ct. 1257 (2016).

The Supreme Court held that that its 2015 decision in Johnson v. United States, 

135 S. Ct. 2551 (2015), which invalidated the “residual clause” of the Armed Career Criminal Act (“ACCA”), applies retroactively to cases on collateral review. 

Welch filed an initial section 2255 motion challenging whether a prior conviction 

qualified as a predicate “violent felony” under ACCA’s residual clause. The district court denied the petition, and the Eleventh Circuit denied a certificate of appealability (“COA”) 

prior to the Supreme Court’s decision in Johnson. The Supreme Court vacated and remanded the decision, holding that the rule in Johnson should be retroactively available.

Applying the framework under Teague v. Lane, 489 U.S. 288 (1989), for determining 

whether a rule applies to cases on collateral review the Court concluded that Johnson’s rule 

was “substantive” rather than a “watershed rule of criminal procedure,” and should be applied retroactively. The Court explained that “a rule is substantive rather than procedural 

if it alters the range of conduct or the class of persons that the law punishes,” rather than 

“regulat[ing] only the manner of determining the defendant’s culpability.” Because Johnson

“changed the substantive reach of” ACCA, thereby “altering the range of conduct or the 

class of persons” that the statute punishes, it was a substantive decision.

Justice Thomas filed a dissenting opinion. He argued that the Court should not have 

ruled on a claim that was never brought before a lower court in Welch’s section 2255 petition. He also contended that the Johnson decision was not substantive, because it did not 

preclude the government from enhancing sentences based on the prior commission of violent felonies — it found only that a particular means of doing so was unconstitutionally 

vague — and it did not narrow the statute’s reach.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 13

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Johnson v. United States, 135 S. Ct. 2551 (2015).

The Supreme Court held unconstitutionally vague the “residual clause,” 18 U.S.C. 

§ 924(e)(2)(B)(ii), of the Armed Career Criminal Act (“ACCA”). Accordingly, the Court reversed the defendant’s increased sentence due to ACCA. 

Johnson pleaded guilty to being a felon in possession of a firearm, pursuant to 

18 U.S.C. § 922(g). The government sought an enhanced sentence under ACCA, which imposes a mandatory minimum 15-year prison term on a felon-in-possession defendant with 

three prior convictions for a “violent felony,” a term defined in the residual clause to include 

any felony that “involves conduct that presents a serious potential risk of physical injury to 

another.” 18 U.S.C. § 924(e)(2)(B)(ii). The district court and the Eighth Circuit agreed that 

Johnson’s prior state conviction for unlawful possession of a short-barreled shotgun met 

this definition (it was undisputed that Johnson had two other qualifying convictions). The 

Supreme Court reversed and remanded, finding that imposing an increased sentence under 

ACCA’s residual clause violates the Due Process Clause. 

The Court found that two features of the residual clause combined to make it unconstitutionally vague. First, the Court’s precedents applying the “categorical approach,” in 

which the sentencing court pictures the kind of conduct that the crime involves in “the ordinary case” instead of applying a real-world factual inquiry, leaves too much uncertainty and 

speculation to the residual clause application. Second, the residual clause leaves too much 

uncertainty about how much risk it takes for a crime to qualify as a violent felony. In particular, the clause’s reference to offenses that “otherwise” pose the necessary risk suggests a 

link to the four “enumerated offenses” listed just before the residual clause, but the nature 

of that link is confusing and causes additional uncertainty. A court is left to determine in 

what sense a particular offense poses a risk comparable to burglary, arson, extortion, or the 

use of explosives, even though those offenses themselves appear to involve varying, and uncertain, levels of risk. 

The Court rejected the argument that the residual clause is constitutional merely 

because “some conduct clearly falls within the provision’s grasp,” electing instead to strike 

down the language altogether. The Court also made clear that other laws using terms like 

“substantial risk” are not touched by this opinion because they generally involve an assessment of risk related to real conduct, not an “idealized ordinary case.”

The Court also rejected the argument that the doctrine of stare decisis barred it from 

finding ACCA’s residual clause unconstitutionally vague. While some prior opinions such as 

Sykes v. United States, 555 U.S. 122 (2009), and James v. United States, 550 U.S. 192 

(2007), had briefly opined the clause was not vague, they had done so without full briefing 

or argument, and thus did not constrain the Court. Moreover, the Court found, continued 

adherence to those decisions would undermine, rather than promote, the goals of evenhandedness, predictability, and consistency served by stare decisis. 

Justices Kennedy and Thomas concurred in the judgment only, each stating separately their view that the residual clause was not unconstitutionally vague but also that 

Johnson’s offense did not qualify as a violent felony. 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 14

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice Alito dissented, defending the residual clause because of stare decisis and because the residual clause is not unconstitutionally vague in his view. Justice Alito also argued for abandoning the traditional, elements-based categorical approach, in favor of a conduct-based inquiry, solely for application of ACCA’s residual clause. Under either approach, 

he maintained that Johnson’s prior conviction did qualify as a violent felony under the residual clause.

Paroline v. United States, 572 U.S. 434 (2014).

The Supreme Court held that mandatory restitution for offenses that involve the 

sexual exploitation of children and child pornography, pursuant to 18 U.S.C. § 2259, is 

proper only to the extent that the defendant proximately caused the victim’s losses. The 

Court maintained that even mere possessors of child pornography cause proximate harm to 

the victims. Id. Because child pornography victims suffer “continuing and grievous harm as 

a result of [knowing] that a large, indeterminate number of individuals have viewed and 

will in the future view images of the sexual abuse she endured[,]” all persons who reproduce, distribute, or possess child pornography play a part in this tragedy and are liable for 

restitution. Id. However, the Supreme Court further addressed the more difficult task of determining the appropriate amount of restitution—i.e. how much of the victim’s losses are 

attributable to the defendant’s conduct. 

The defendant was convicted of possessing child pornography and admitted to possessing a total of 150–300 images, two of which were images of the victim at issue. The victim sought $3.4 million in damages, and the Fifth Circuit sitting en banc held that each defendant who possessed the victim’s images should be made liable for the victim’s entire loss 

of $3.4 million from the trade in her images. In vacating and remanding, the Court, by a 5-4 

vote, held that there is a general proximate cause requirement for all losses under section 2259, and that “where it can be shown both that a defendant possessed a victim’s images and that a victim has outstanding losses caused by the continuing traffic in those images but where it is impossible to trace a particular amount of those losses to the individual 

defendant” through the more traditional but-for causal inquiry, the court “should order restitution in an amount that comports with the defendant’s relative role in the causal process 

that underlies the victim’s general losses.”

The Court provided further guidance to district courts by enumerating factors to 

consider in determining the amount of restitution: the victim’s total losses caused by traffic 

in her images, the number of past criminal defendants who contributed to those losses, reasonable predictions of the number of future offenders likely to be caught and convicted for 

contributing, an estimate of the broader number of offenders involved, whether the defendant reproduced or distributed the images, whether the defendant had any connection to the 

initial production of the images, and how many images of the victim the defendant possessed. In the case of a “possessor like Paroline” who played a relatively small part in the 

victim’s overall losses, the Court held that the amount would “not be severe” but would also 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 15

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

not be “a token or nominal amount.” However, the Court declined to “prescribe a precise algorithm” and urged the courts to use “discretion and sound judgment.”

Abramski v. United States, 573 U.S. 169 (2014).

In a 5-4 opinion, the Supreme Court resolved a circuit split, holding that a straw 

buyer made a material false statement in violation of 18 U.S.C. § 922(a)(6) when he represented himself as the actual transferee/buyer of a firearm on the sales record. Although 

Abramski was purchasing a firearm on behalf of his uncle, Abramski answered “Yes,” affirming that he was the “actual buyer” of the firearm on the form used and maintained by 

federally licensed firearms dealers for gun sales. The Fourth Circuit held that regardless of 

whether the straw buyer or the actual buyer can legally obtain a handgun, answering the

“actual buyer” inquiry falsely does constitute a material misrepresentation. The Supreme 

Court affirmed, reasoning that “the identity of the actual purchaser of a firearm is a constant that is always material to the lawfulness of a firearm acquisition under § 922(a)(6).”

United States v. Castleman, 572 U.S. 157 (2014).

The Supreme Court held that a defendant could be convicted for illegally possessing 

a firearm if he had a prior conviction of “intentionally or knowingly caus[ing] bodily injury 

to” a family member because that offense constituted a “misdemeanor crime of domestic violence.” See 18 U.S.C. § 921(a)(33)(A)(ii); 18 U.S.C. § 922(g)(9). In particular, the Court held 

that the domestic violence offense did involve “the use or attempted use of physical force” as 

required by section 922(g)(9). The Court interpreted its prior opinion in Johnson v. United 

States, 559 U.S. 133 (2010), to require it to conclude that the common law definition of 

“force” applied to this statute. The Court then applied the modified categorical approach 

discussed in Descamps v. United States, 570 U.S. 254 (2013), to conclude that the prior conviction did involve such force.

Justice Scalia concurred in part and concurred in the judgment, disagreeing with the 

Court that the broader definition of “force” should apply but concluding that the defendant’s 

prior conviction also qualified under a narrower definition. Justice Alito, joined by Justice 

Thomas, also concurred in the judgment, expressing their view that Johnson was wrongly 

decided.

Burrage v. United States, 571 U.S. 204 (2014).

The Supreme Court held that a defendant who distributes drugs cannot receive an 

enhanced penalty when a victim suffers death or serious bodily injury as a result of using 

the drugs unless the victim’s use of the drugs is a but-for cause of the death or injury, at 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 16

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

least where the use of the drug was not independently sufficient to cause the death or injury.

The victim in the case died following an extended drug binge involving a mixture of 

several drugs, only one of which he had purchased from the defendant. Expert testimony 

showed that the drug purchased from the defendant contributed to the victim’s death, but 

not that the use of that drug alone would have caused the death. The Court determined 

that this type of causation does not meet the standard required by 21 U.S.C. § 841(b)(1)(C), 

which provides for an enhanced sentence if the death or bodily injury “results from” the 

drug distributed by the defendant. The Court stated that this statute required actual causation for the enhanced penalty to apply.

Justice Ginsburg, joined by Justice Sotomayor, concurred in the judgment on the basis of the rule of lenity.

Descamps v. United States, 570 U.S. 254 (2013).

The Supreme Court held that, when evaluating whether a prior state conviction constitutes “burglary” within the meaning of the Armed Career Criminal Act (“ACCA”), a federal sentencing court may not apply the modified categorical approach to a non-divisible 

state statute of conviction.

Descamps argued that his California burglary conviction did not count as ACCA burglary because the California statute did not contain all the elements of generic burglary; 

specifically, California’s burglary statute does not require that a defendant’s initial entry 

into a building be unlawful. The district court and court of appeals accepted the government’s argument that the “modified-categorical approach” allowed the court to examine certain documents, including the original state-court plea colloquy, in order to determine that 

Descamps had in fact committed conduct that would constitute generic ACCA burglary. The 

Ninth Circuit’s holding deepened a circuit split over whether the modified categorical approach, in which such documents may be consulted, applies only to statutes that are “divisible” into multiple, alternative possible elements, any of which suffice for commission of the 

offense, or also, as here, to a statute that is “indivisible” but overbroad, encompassing a 

broader array of conduct than the generic offense.

The Court reversed, finding that its existing precedent “all but resolve[d] this case.”

The Court stated that it had long emphasized that courts should “look only to the statutory 

definitions” of offenses, and focus on the “elements, not facts” underlying a particular conviction, but that in a “narrow range of cases” courts could look beyond the statute of conviction to such documents as the “charging paper and jury instructions” to determine when 

ACCA was satisfied. That range of cases consisted of “statute[s] with alternative elements,”

such as burglary statutes applying to both automobiles and dwellings. This analysis became 

known as the modified categorical approach. In Shepard v. United States, the Court held 

that the purpose of the modified categorical approach was only to determine what “version”

of the statute a defendant had pled guilty to. For that reason, “the only way” the Court had 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 17

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

ever endorsed the use of the modified categorical approach was to evaluate statutes with 

alternative elements.

Justice Kennedy wrote a separate concurring opinion, emphasizing his concern that 

a defendant pleading guilty to a state criminal offense will not typically be thinking of the 

possibility of “later consequences under ACCA,” and finding “troubling” the proposition that 

inadvertent admissions might later lead to significant sentencing enhancements.

Justice Thomas concurred in the judgment only, and wrote separately to reaffirm his 

view that ACCA violates the Sixth Amendment because it permits courts to find facts increasing the sentence that could be imposed on a defendant.

Justice Alito dissented. He stated that he would give “ACCA a more practical reading,” and hold that “when it is clear that a defendant necessarily admitted or the jury necessarily found” that a defendant committed generic burglary, a prior conviction should 

qualify.

Alleyne v. United States, 570 U.S. 99 (2013).

The Supreme Court held that facts that increase a mandatory minimum penalty are 

elements that must be submitted to a jury and found beyond a reasonable doubt. The opinion overruled Harris v. United States, 536 U.S. 545 (2002), in which the Court held that judicial factfinding that increases the mandatory minimum sentence but does not affect the 

maximum penalty is permissible under the Sixth Amendment. The Alleyne Court concluded 

that Harris is inconsistent with Apprendi v. New Jersey, 530 U.S. 466 (2000), and with the 

original meaning of the Sixth Amendment.

The Court held that the Sixth Amendment, in conjunction with the Due Process 

Clause, requires that each element of a crime be proven to the jury beyond a reasonable 

doubt. Shortly after Apprendi, the Court decided Harris, which involved the same statutory 

provision and issue before the Court in Alleyne. The Harris Court declined to apply Apprendi to facts that altered only the mandatory minimum sentence, and not the maximum 

penalty. Harris reasoned that such facts do not implicate the Sixth Amendment, because 

the verdict “authorized the judge to impose the minimum with or without the finding.” Such 

a finding was not “essential” to the defendant’s punishment and merely limited the sentencing judge’s “choices within the authorized range.”

The Alleyne Court relied on the logic of Apprendi to overrule the holding in Harris.

The Court concluded that the definition of “elements” necessarily includes facts that not 

only increase the maximum penalty, but also those that increase the minimum, because 

both affect the sentencing range to which a defendant is exposed. The Court stated, “[i]t is 

impossible to dissociate the floor of a sentencing range from the penalty affixed to the 

crime.” Increasing the legally prescribed floor indisputably aggravates the punishment and 

“heightens the loss of liberty associated with the crime”, because the government can invoke the mandatory minimum to require a harsher punishment than would have resulted 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 18

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

otherwise. “This reality demonstrates that the core crime and the fact triggering the mandatory minimum sentence together constitute a new, aggravated crime, each element of 

which must be submitted to the jury.”

Justice Sotomayor filed a concurring opinion, which Justices Ginsburg and Kagan 

joined, discussing in more detail the question of when the Court should overrule existing 

precedent. Justice Breyer filed a separate concurring opinion in which he discussed his vote 

in Harris and expressed continuing disagreement with the holding in Apprendi. However, 

Justice Breyer acknowledged that “Apprendi has now defined the relevant legal regime for 

an additional decade” and stated that “the law should no longer tolerate the anomaly that 

the Apprendi/Harris distinction creates.”

Chief Justice Roberts, with whom Justices Scalia and Kennedy joined, dissented.

The Chief Justice argued that increasing the mandatory minimum penalty does not affect 

the defendant’s right to a jury trial under the Sixth Amendment, but rather affects the role 

of the sentencing judge by limiting discretion. Here, because the jury’s verdict authorized a 

sentence of anywhere between five years to life in prison, “[n]o additional finding of fact 

was ‘essential’ to any punishment within the range.” The resulting sentence was within the 

discretion of the judge, and “entirely consistent with Apprendi.”

Justice Alito filed a separate dissenting opinion, stating that the Court should not 

overrule “well-entrenched precedent” so easily.

Peugh v. United States, 569 U.S. 530 (2013).

In a 5-4 decision, the Supreme Court held that the Ex Post Facto Clause of the constitution prohibits a court from sentencing a defendant pursuant to a guideline that produces a higher range than the guideline in effect at the time the defendant committed the 

offense, despite the fact that the guidelines themselves are advisory. To determine whether 

an ex post facto violation occurred, the Court analyzed whether, post-Booker, an increased 

guideline range “presents a sufficient risk of increasing the measure of punishment attached to the covered crimes.” The Court concluded that three features of the system together presented sufficient “procedural hurdles” to imposing a sentence outside the guidelines to trigger the Ex Post Facto Clause. These features are: (1) the requirement that sentencing courts properly calculate the guidelines; (2) the possibility that appellate courts 

may apply a presumption of reasonableness when reviewing within guideline sentences; 

and (3) the fact that courts of appeal may review a sentence more closely the farther it varies from the guideline range.

Because the Court’s ex post facto jurisprudence has proceeded on a case-by-case basis rather than setting forth a definitive test, the Court compared the federal system to the 

Florida guideline system it had previously held did present a sufficient risk in Miller v. 

Florida, and acknowledged that “the federal system’s procedural rules establish gentler 

checks on the sentencing court’s discretion than Florida’s did.” Nonetheless, the Court concluded that the federal rules “impose a series of requirements on sentencing courts that 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 19

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

cabin the exercise of [] discretion.” The Court noted that there was “considerable empirical 

evidence indicating that the Sentencing Guidelines have the intended effect of influencing 

the sentences imposed by judges,” noting that “[i]n less than one-fifth of cases since 2007 

have district courts imposed above- or below-Guidelines sentences absent a Government 

motion” and that “the Sentencing Commission’s data indicate that when a Guidelines range 

moves up or down, offenders’ sentences move with it.”

Justice Sotomayor, joined by Justices Ginsburg, Breyer, and Kagan, also stated that 

the Ex Post Facto Clause does not simply protect a defendant’s “reliance interest” in a particular set punishment knowable by the defendant before commission of the offense; “[i]t 

also reflects principles of fundamental justice.” The Court then disagreed with the Government’s argument that, after Booker, “the Guidelines are just one among many persuasive 

sources a sentencing court can consult, no different from a policy paper,” stating that “[i]t is 

simply not the case that the Sentencing Guidelines are merely a volume that the district 

court reads with academic interest in the course of sentencing.” Although courts may consider the newer, higher version of the guidelines, the higher version “will have the status of 

one of many reasons a district court might give for deviating from the older Guidelines, a 

status that is simply not equivalent for ex post facto purposes.” Finally, the Court stated 

that its Ex Post Facto Clause holding did not undermine the Sixth Amendment remedial 

holding in its Booker line of cases, emphasizing the distinction between the Sixth Amendment and Ex Post Facto Clause inquiries and concluding that “[t]he Booker remedy was designed, and has been subsequently calibrated, to exploit precisely this distinction: it is intended to promote sentencing uniformity while avoiding a Sixth Amendment violation. In 

light of the statistics invoked by petitioner [regarding the rate of variances], it appears so 

far to be achieving this balance.”

Justice Thomas, joined by Chief Justice Roberts and Justices Scalia and Alito, dissented based on the view that the advisory guidelines “merely influence[] the exercise of the 

sentencing judge’s discretion” within the broader statutory ranges. Justice Thomas alone 

also stated that application of the Ex Post Facto Clause should be limited to increases in 

statutory penalties.

Dorsey v. United States, 567 U.S. 260 (2012).

In a 5-4 decision, the Supreme Court held that the Fair Sentencing Act’s (FSA) more 

lenient mandatory minimum sentencing provisions, which reduced the crack-to-powder cocaine sentencing disparity from 100-to-1 to 18-to-1, applied to offenders who committed cocaine offenses prior to the FSA’s effective date but were sentenced after that date. The issue 

was framed as one of congressional intent: whether Congress intended the FSA to apply 

retroactively by virtue of the Sentencing Reform Act (SRA), which says that “regardless of 

when the offender’s conduct occurs, the applicable Guidelines are the ones ‘in effect on the 

date the defendant is sentenced,’ ” or whether an 1871 saving statute, which provides that 

no new criminal statute may change penalties “unless the repealing Act shall so expressly 

provide,” governed to preclude retroactivity. 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 20

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

In holding that there was “indicia of clear congressional intent” to apply the FSA’s 

new minimum penalties, the Court said it was convinced by six considerations. First, despite its “expressly provide” language (which the FSA did not do), the saving statute permits Congress to apply a new act’s more lenient penalties to pre-FSA offenders because 

“one Congress cannot bind a later Congress” and it remains free to express its intentions as 

it chooses. Second, Congress must have been aware of the SRA’s “background principle” directing judges to apply the guidelines in effect at the time of sentencing when it passed the 

FSA. Third, language in the FSA implies that Congress intended to follow the SRA’s background principle to achieve consistency with other guideline provisions. Fourth, applying 

the prior drug law’s mandatory minimums to pre-FSA offenders sentenced post-FSA “would 

create disparities of a kind that Congress enacted the [SRA] and the [FSA] to prevent.”

Fifth, not applying the FSA to these offenders “would do more than preserve a disproportionate status quo; it would make matters worse” by creating “a new disparate sentencing 

‘cliff.’ ” Sixth, “no strong countervailing consideration[s]” argued against applying the FSA.

In dissent, Justice Scalia said he would require that the “ ‘plain import of a later statute directly conflict[]’ ” with the earlier one in order to override the saving statute’s default rule; 

because the FSA was silent on the issue of retroactivity, the saving statute precluded its application.

Setser v. United States, 566 U.S. 231 (2012).

The Supreme Court held that a district court has authority to order a federal sentence be served consecutive to an anticipated (i.e., yet-to-be-imposed) state sentence. While 

on probation for a drug offense, Setser was arrested for possessing methamphetamine. Setser was indicted in state court for the possession offense, and the state moved to revoke his 

probation. Setser was also indicted in federal court for the drug possession, to which he 

pleaded guilty. At the federal sentencing, the district court imposed a 151-month sentence 

and ordered it to run consecutive to any state sentence on the probation violation, but concurrent with any state sentence for the possession charge. Setser appealed, arguing the district court lacked authority under the SRA to order a consecutive sentence and that the concurrent/consecutive decision should be made by the Bureau of Prisons (BOP) once the state 

sentence was known. While the appeal was pending, the state court sentenced Setser to five 

years’ imprisonment for the probation violation and 10 years’ imprisonment for the possession charge, both to run concurrently, effectively “thwart[ing]” the district court’s intended 

sentence.

According to the majority, in determining how state and federal sentences “fit together” under these circumstances, it is “fundamental” that the Court construe the SRA 

and related statutes “in light of ‘the common-law background against which the statues . . . 

were enacted.’ ” The Court explained that judges have long had discretion to impose sentences that will run concurrently or consecutively to other sentences, including those imposed in state proceedings, and that nothing in the SRA indicates otherwise. The Court rejected Setser’s reading of the SRA as conferring authority to impose consecutive sentences 

only when the terms are imposed simultaneously, or when the defendant is already subject 

to another, undischarged term of imprisonment. The Court based its analysis on statutory 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 21

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

interpretation and policy grounds. The Court concluded Setser’s reading of the statue was 

inconsistent with the undisputed notion that someone, either the district court or the BOP, 

must make the concurrent/consecutive decision. Further, rather than conferring specific authority on the district court (and thereby implying other, non-specified authority is withheld), the statute’s language was a “mere acknowledgment of the existence of certain preexisting authority . . . .” In addition, the Court determined that principles of federalism and 

good policy dictate that the district court, rather than BOP “employees of the same Department of Justice that conducts the prosecution,” decide whether the defendant’s term will be 

served concurrently or consecutively. Justice Breyer’s dissent focused on practical implications of the law, arguing that until the state sentence is imposed, federal judges lack valuable information necessary to make an informed concurrent/consecutive decision. 

Southern Union Co. v. United States, 567 U.S. 343 (2012). 

The Supreme Court held that the proposition established in Apprendi —that the 

Sixth Amendment reserves to juries the determination of any fact (other than the fact of 

prior conviction) that increases a criminal defendant’s maximum potential sentence— applies to criminal fines. Southern Union, a natural gas company, was tried and convicted of 

storing hazardous material without a permit in violation of the Resource Conservation and 

Recovery Act, which provides for “a fine of not more than $50,000 for each day of violation.”

At sentencing, the government argued that, consistent with the indictment and general verdict form, 762 days of violation occurred for a maximum fine of $38.1 million. Southern Union argued that this would violate Apprendi because the jury instructions allowed a conviction based on a violation of a single day and any fine imposed greater than the one-day penalty of $50,000 would require judicial factfinding prohibited by the Sixth Amendment. The 

district court imposed an $18 million fine. Although the First Circuit found that the jury 

did not necessarily find a 762-day violation, it affirmed the sentence and held that Apprendi

is inapplicable to criminal fines. 

The Court reviewed the scope of the Sixth Amendment’s jury trial right as construed 

in Apprendi. According to the Court, Apprendi’s rule is “rooted in longstanding common-law 

practice.” The Court supported this argument by providing examples in which Apprendi has 

been applied to “a variety of sentencing schemes that . . . increase a defendant’s maximum 

authorized sentence.” The Court found “no principled basis” to treat the punishments in the

examples differently than criminal fines. “Apprendi’s ‘core concern,’ ” explained the Court, 

“is to reserve to the jury ‘the determination of facts that warrant punishment for a specific 

statutory offense,’ ” and “[t]hat concern applies whether the sentence is a criminal fine or 

imprisonment or death.” The Court also found that the First Circuit incorrectly relied on 

Oregon v. Ice, which held that Apprendi does not forbid a judge from determining facts that 

authorize the imposition of consecutive sentences. The Court cited a series of cases from the 

1800s to demonstrate the “ ‘two longstanding tenets of common-law jurisprudence’ on which 

Apprendi is based: [f]irst, the ‘the truth of every accusation’ against a defendant ‘should be 

confirmed’ ” by a jury; “[a]nd second, ‘an accusation which lacks any particular fact which 

the law makes essential to the punishment is . . . no accusation within the requirements of 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 22

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

the common law . . . .’ ” Finally, the Court dismissed the government’s arguments, particularly that judicially-found facts related to fines “typically involve only quantifying the harm 

caused by the defendant’s offense . . . as opposed to defining a separate set of acts for punishment.”

In dissent, Justice Breyer argued that when a criminal fine is at issue, the Sixth 

Amendment allows a sentencing judge to determine facts relevant to the amount of the fine 

to be imposed. The dissent concludes, based primarily on the historical record and the 

Court’s earlier opinion in Ice, that the finding of this type of “particular fact” was ordinarily 

a matter for a judge and not within the jury’s domain.

DePierre v. United States, 564 U.S. 70 (2011). 

The Supreme Court resolved a circuit conflict to hold that the term “cocaine base” in 

21 U.S.C. § 841(b)(1)(A)(iii) applies to all forms of cocaine base and is not limited to “crack 

cocaine.” The term “cocaine base” defines cocaine in its chemically basic form which includes “crack cocaine” as well as coca paste and freebase. Justice Sotomayor wrote the opinion joined by all the justices (except for a discussion of legislative history which J. Scalia did 

not join). The Court observed that, because of the significant difference in penalties, Congress wanted to distinguish between powder cocaine and cocaine base products. The Court 

found that this reading of “cocaine base” was consistent with the structure of section 841(b)(1). The Court was unpersuaded by four additional arguments put forth by DePierre. The Court found that records of the congressional hearings did not show that Congress was only concerned with crack cocaine. Second, reading “cocaine base” to mean chemically basic cocaine does not lead to absurd results. Third, the fact that the Sentencing 

Guidelines defined “cocaine base” as “crack” does not require that the statutory term be interpreted the same way. Fourth, because normal rules of statutory construction made clear 

what Congress intended, the rule of lenity did not apply.

Freeman v. United States, 564 U.S. 522 (2011).

A 5-4 majority of the Supreme Court held that the defendant, William Freeman, was 

eligible for a sentence reduction under 18 U.S.C. § 3582(c)(2) after pleading guilty to drug 

and firearm charges under a Federal Rule of Criminal Procedure 11(c)(1)(C) plea agreement 

(“Type C agreement”). The five justices who formed the majority split, however, on the reasons the defendant was so eligible.

Under a Type C agreement, the parties agree that a specific sentence or sentencing 

range is the appropriate disposition of the case and the agreement binds the court once the 

court accepts it. In 2005, Freeman pleaded guilty under a Type C agreement specifying a 

sentence of 106 months’ imprisonment, the bottom of the applicable guideline range. The 

Sentencing Commission later amended the guidelines to lower the base offense level for 

drug-trafficking offenses involving crack, and made those amendments retroactive. In light 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 23

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

of those amendments, the petitioner filed a motion for a sentence reduction under 18 U.S.C. 

§ 3582(c)(2), which allows a defendant to move for a reduction in a term of imprisonment if 

he or she “has been sentenced to a term of imprisonment based on a sentencing range that 

has subsequently been lowered by the Sentencing Commission.” The district court, consistent with existing circuit precedent, denied the motion on the grounds that the defendant 

was ineligible for a sentence reduction because the sentence was imposed pursuant to a 

Type C agreement. The Sixth Circuit affirmed.

A plurality of the court concluded that Freeman is eligible for a sentence reduction 

as a result of a retroactively-applicable guideline amendment because the district judge, in 

accepting such a plea agreement, had an “independent obligation to exercise its discretion”

in imposing the sentence, and part of that exercise was consideration of the guidelines, including the crack cocaine guideline that was subsequently amended and given retroactive 

effect. As a result, the sentence was “based on” that guideline, and 18 U.S.C. § 3582(c)(2) 

permits the sentence to be reduced. Justice Sotomayor concurred in the judgment, but did 

so after finding that the Type C agreement at issue “expressly use[d] a Guidelines sentencing range applicable to the charged offense to establish the term of imprisonment,” and that 

because it did, the sentence was “based on” the crack cocaine guideline. 

The dissent wrote that a sentence imposed pursuant to a Type C agreement is not 

“based on” the guidelines in any way, but instead is based on the parties’ agreed recommendation. As a result, the dissent argued, no defendant who is sentenced pursuant to a Type C 

agreement is eligible for a sentence reduction under 18 U.S.C. § 3582(c)(2). The dissent also 

criticized Justice Sotomayor’s approach as being difficult for lower courts to apply.

McNeill v. United States, 563 U.S. 816 (2011).

The Supreme Court unanimously held that, when determining whether “an offense 

under State law” is a “serious drug offense” for purposes of the ACCA, the sentencing court 

should consult the “maximum term of imprisonment” applicable to the defendant’s offense 

at the time of the state conviction. Under the ACCA, a felon unlawfully in possession of a 

firearm is subject to a 15-year minimum prison sentence if he has three prior convictions 

for a “violent felony” or “serious drug offense.” As relevant here, “serious drug offense” is defined as “an offense under State law . . . for which a maximum term of imprisonment of ten 

years or more is prescribed by law.” The district court found that the ACCA sentencing enhancement applied to the defendant based in part on drug trafficking crimes he committed 

when they carried a maximum 10-year prison term, even though the legislature had subsequently reduced the maximum sentence. The Fourth Circuit affirmed.

The Supreme Court affirmed for three reasons. First, it held that “the plain text of 

ACCA requires a federal sentencing court to consult the maximum sentence applicable to a 

defendant’s previous drug offense at the time of his conviction for that offense.” The Court 

noted that the issue of the maximum penalty for a past offense is “a backward-looking question” that can only be answered by “consult[ing] the law that applied at the time of that 

conviction.” Second, the Court discussed the “broader context of the statute as a whole,” and 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 24

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

how the Court had in other cases looked to the historical statute of conviction when determining whether the defendant was convicted of a “violent felony” under the ACCA. Finally, 

the Court pointed out that absurd results would follow from adopting McNeill’s position, including situations where a prior conviction would “disappear” for ACCA purposes if a state 

revised its definition of an offense after it was committed.

Pepper v. United States, 562 U.S. 476 (2011).

In a 7-1 decision with several concurrences, the Supreme Court held that “when a 

defendant’s sentence has been set aside on appeal, a district court at resentencing may consider evidence of the defendant’s postsentencing rehabilitation and that such evidence may, 

in appropriate cases, support a downward variance from the now-advisory Federal Sentencing Guidelines.” Pepper had pleaded guilty to methamphetamine distribution conspiracy

and was sentenced to 24 months’ imprisonment, well below the 97-to-121-month guideline 

range. Pepper’s sentence was appealed and remanded to the district court, which imposed 

the same 24-month sentence based on explicit evidence of Pepper’s postsentencing rehabilitation, including his recovery from drug addiction, enrollment in college, and full-time employment. The government re-appealed and the Eighth Circuit concluded that postsentencing rehabilitation was an impermissible factor to consider in granting a downward variance 

from the advisory guideline range. Pepper was resentenced to a 65-month prison term and 

appealed.

Justice Sotomayor explained that over the history of federal sentencing reform, sentencing courts have been permitted to consider the widest possible breadth of information 

about a defendant. Although the SRA constrained the discretion of district courts in various 

ways, the Court’s cases since United States v. Booker made the formerly mandatory system 

effectively advisory. Therefore, district courts could now consider evidence of postsentencing rehabilitation to support a downward variance from the guidelines. As support for this 

conclusion, the Court noted that the SRA made no distinction between an initial sentencing 

and any subsequent resentencing on remand, and postsentencing rehabilitation is relevant 

to many of the statutory SRA factors. Because this conclusion conflicted with 18 U.S.C. 

§ 3742(g)(2), which precludes a court on resentencing from imposing a sentence outside the 

guidelines range except upon a “ ‘ ground of departure’ that was expressly relied upon in the 

prior sentencing,” the Court invalidated it as inconsistent with Booker. Similarly, even 

though the guidelines expressly preclude a district court from considering postsentencing 

rehabilitation, the majority opinion made clear that a district court “may in appropriate 

cases impose a non-Guidelines sentence based on a disagreement with the Commission’s 

views,” especially “where, as here, the Commission’s views rest on wholly unconvincing policy rationales not reflected in the sentencing statutes Congress enacted.” Finally, the court 

resolved a second question presented in Pepper by concluding that, at re-sentencing, a court 

is not bound by the law of the case to apply a departure percentage applied at the initial 

sentencing.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 25

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice Breyer and Justice Alito concurred in separate opinions on the principal issue in the case but each cautioned courts not to disregard the guidelines unreasonably. Justice Alito also dissented in part to the extent he believes sentencing judges must still give 

significant weight to guidelines provisions and policy statements. Justice Thomas also dissented because of his ongoing belief that the Booker remedy cannot be meaningfully applied 

and therefore he would defer to the judgment of Congress and the Commission that evidence of postsentencing rehabilitation may not be considered.

Sykes v. United States, 564 U.S. 1 (2011) (overruled by Johnson v. United States, 

135 S. Ct. 2551 (2015)).

A six-Justice majority resolved a circuit split to hold that an Indiana state crime of 

felony vehicle flight qualifies as a “violent felony” under the ACCA, 18 U.S.C. § 924(e). That 

section defines a “violent felony” as one punishable by more than one year of imprisonment 

and that “(i) has as an element the use, attempted use, or threatened use of physical force 

against the person of another; or (ii) is burglary, arson, or extortion, involves use of explosives, or otherwise involves conduct that presents a serious potential risk of physical injury 

to another.” The latter clause beginning with “otherwise” is known as the “residual clause.”

Under the Court’s “categorical approach” to the residual clause, the Court determines 

whether the “elements of the offense are of the type that would justify its inclusion within 

the residual provision,” without looking to the actual facts disclosed by the record of conviction. The question thus presented was whether Indiana’s prohibition on flight from an officer by driving a vehicle fell within the residual clause because, as a categorical matter, it 

presented a serious potential risk of physical injury to another.

The Supreme Court affirmed Sykes’s sentence. It described the dangers inherent in 

vehicular flight from law enforcement and the risk of violence associated with such conduct, 

citing statistics to build its argument that the risk of physical danger from vehicular flight 

was greater than the dangers of two of the enumerated offenses of burglary and arson. The 

Court distinguished other cases on the level of risk inherent in the felony at issue, as well 

as the fact that it required offenders to act “knowingly or intentionally.” Finally, the Court 

observed that Congress chose to frame the ACCA in general and qualitative terms that require courts to evaluate the risks posed by different offenses.

Justice Thomas concurred in the judgment. Justice Scalia dissented with a broad 

criticism of the Court’s recent residual clause jurisprudence starting in 2007, suggesting 

that the vagueness of the ACCA meant it was time to limit it to the named violent crimes 

and allow Congress to add additional crimes as it sees fit. Justice Kagan, joined by Justice 

Ginsburg, questioned the majority’s interpretation of the Indiana statute and argued that 

simple vehicular flight was not a violent felony under the ACCA.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 26

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Tapia v. United States, 564 U.S. 319 (2011).

The Supreme Court held that the SRA precludes a sentencing court from imposing 

or lengthening a prison term in order to promote a criminal defendant’s rehabilitation.

Alejandra Tapia was convicted of alien smuggling, among other things. She was sentenced 

to a term of 51 months’ imprisonment, at least in part because the district court apparently 

wanted to ensure that she served a prison term to qualify for and complete the Bureau of 

Prison’s 500-hour Residential Drug Abuse Program. The Ninth Circuit affirmed the sentence.

The Supreme Court reversed. Writing for a unanimous court, Justice Kagan began

with the text of 18 U.S.C. § 3582(a), which instructs courts to “recognize[e] that imprisonment is not an appropriate means of promoting correction and rehabilitation.” According to

the Court, this language clearly commands a district court to “consider the specified rationales of punishment except for rehabilitation, which it should acknowledge as an unsuitable 

justification for a prison term.” Moreover, the Court explains, the “context of § 3582(a) puts 

an exclamation point on this textual conclusion.” For one thing, because 28 U.S.C. § 994(k) 

similarly directs the Sentencing Commission to ensure the guidelines reflect the inappropriateness of imposing a sentence for rehabilitation purposes, “Congress ensured that all 

sentencing officials would work in tandem to implement the statutory determination” to 

preclude courts from considering rehabilitation in imposing or lengthening prison terms.

And “[e]qually illuminating” is “the absence of any provision granting courts the power to 

ensure that offenders participate in prison rehabilitation programs,” in contrast to a sentencing court’s power to order appropriate treatment in imposing probation or supervised 

release. The Court also found the legislative history supported the textual interpretation, 

and rejected various other arguments of the amicus curiae, who was appointed to defend 

the Ninth Circuit’s judgment. In the opinion’s final section, Justice Kagan stated that a 

sentencing court commits no error by discussing options for prison rehabilitation or urging 

the BOP to place an offender in a prison treatment program. What it may not do, however, 

is “impose or lengthen a prison sentence to enable an offender to complete a treatment program or otherwise promote rehabilitation.” Finally, in a brief concurrence, Justice Sotomayor (joined by Justice Alito) agreed with the Court that section 3582(a) precludes sentencing courts from considering rehabilitation when imposing or lengthening a prison sentence but was skeptical that the court did so in Tapia’s case.

Abbott v. United States, 562 U.S. 8 (2010).

In this case, the Supreme Court resolved a circuit split on the interpretation of 

18 U.S.C. § 924(c)’s “except” clause, holding that “a defendant is subject to a mandatory, 

consecutive sentence for a section 924(c) conviction, and is not spared from that sentence by 

virtue of receiving a higher mandatory minimum on a different count of conviction.” Section 924(c) requires imposition of at least 5 years’ imprisonment to be served consecutively 

for using or carrying a firearm in furtherance of a crime of violence or drug trafficking 

crime “[e]xcept to the extent that a greater minimum sentence is otherwise provided by this 

subsection or by any other provision of law.” This latter phrase is commonly referred to as 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 27

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

the “except” clause. Defendants Abbott and Gould were each convicted of gun and drug 

crimes, and each were sentenced to a 5-year term of imprisonment on the section 924(c) offense to run consecutively to the terms of imprisonment they received for their other offenses, each of which carried higher mandatory minimums. The Third and Fifth Circuits 

affirmed their respective sentences on direct appeal; the Second and Sixth Circuits adopted, 

however, a contrary interpretation of the “except” clause. 

The Supreme Court affirmed their sentences, holding that a defendant is subject to 

consecutive mandatory minimum sentences for both the predicate offense and the section 924(c) offense, even if the predicate offense carries a greater mandatory minimum than 

the section 924(c) offense. Although the defendants argued that the “except” clause meant 

that they could not be sentenced to consecutive mandatory minimum terms under section 

924(c) because they were also subject to other, higher mandatory minimums, the Court felt 

that this interpretation would “undercut” the congressional purpose of imposing additional 

punishments for possessing a firearm, as many defendants subject to section 924(c)’s fiveyear mandatory minimum are also subject to lengthier mandatory minimums for their 

predicate offenses. The Court also noted other “anomalies” that rendered the defendants’

interpretation implausible, as in the case of defendants who sell enough drugs or have an 

extensive enough criminal history to trigger high mandatory minimums and therefore 

would manage to avoid being punished at all for the section 924(c) offense. After reviewing 

the “except” clause in its textual context, the Supreme Court concluded that “Congress intended the ‘except’ clause to serve simply as a clarification of section 924(c), not as a major 

restraint on the statute’s operation.” Finally, the Court noted that the rule of lenity was inapplicable because, “[a]lthough the clause might have been more meticulously drafted,” the 

defendants’ interpretation of the statute reflected an implausible reading of congressional 

purpose. 

Dillon v. United States, 560 U.S. 817 (2010).

The Supreme Court, in a 7-1 opinion with Justice Alito recused, considered what the 

impact of its Booker decision should be on sentence reductions under 18 U.S.C. § 3582(c)(2).

The Court concluded that Booker does not apply to proceedings under section 3582(c)(2) and 

that U.S.S.G. §1B1.10 is binding on courts reducing sentences under that provision.

The Court began its analysis of the case by addressing the petitioner’s argument 

that proceedings under section 3582(c)(2) are “resentencing” proceedings, concluding that 

the plain language of the statute does not support this characterization. The Court also 

noted that the statute only applies to those prisoners whose guideline range was subsequently reduced by the Commission. These two factors, the Court concluded, demonstrate 

Congress’s intent that such proceedings not be complete resentencings. The Court went on 

to state, however, that “[t]he substantial role Congress gave the Commission with respect to 

sentence-modification proceedings further supports this conclusion,” stating that both 

28 U.S.C. §§ 994(o) and (u) “constrain[]” a district court’s power under section 3582(c)(2).
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 28

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

The statute, the Court stated, requires a two-step approach in such cases: in the first 

step, the court must “follow the Commission’s instructions in §1B1.10 to determine the prisoner’s eligibility for a sentence modification and the extent of the reduction authorized.” In 

the second step, the court must “consider any applicable § 3553(a) factors and determine 

whether, in its discretion, the reduction authorized by reference to the policies relevant at 

step one is warranted in whole or in part under the particular circumstances of the case.”

The Court further stated: “Because reference to § 3553(a) is appropriate only at the second 

step of this circumscribed inquiry, it cannot serve to transform the proceedings under 

§ 3582(c)(2) into plenary resentencing proceedings.”

The Court held that section 3582(c)(2) proceedings do not implicate the Sixth 

Amendment right at issue in Booker because they “represent[] a congressional act of lenity 

intended to give prisoners the benefit of later enacted adjustments to the judgments reflected in the Guidelines.” The Court also held that the remedial Booker opinion does not 

apply to section 3582(c)(2) proceedings, rejecting the Ninth Circuit’s opinion in United 

States v. Hicks, 472 F.3d 1167, 1170 (9th Cir. 2007). The Court again distinguished section 3582(c)(2) proceedings from other sentencing proceedings, concluding that “requiring 

courts to honor §1B1.10(b)(2)’s instruction not to depart from the amended Guidelines 

range at [section 3582(c)(2)] proceedings will create none of the confusion or unfairness that 

led us in Booker to reject the Government’s argument for a partial fix.”

The Court finally addressed Dillon’s argument that the district court should have 

corrected his criminal history calculation, holding that because §1B1.10(b)(1) instructs the 

court to leave other guideline application decisions unchanged, the district court correctly 

declined to do so.

In dissent, Justice Stevens set forth his view that Booker’s remedial opinion should 

apply to section 3582(c)(2) proceedings, conceding that “[a]s a matter of textual analysis, divorced from judicial precedent, it is certainly reasonable for the Court to find that the Commission can set mandatory limits on sentence reductions under § 3582(c)(2)” but disagreeing that this analysis is sufficient to decide the case. Justice Stevens expressed his view 

that “[t]he only fair way to read the Booker majority’s remedy is that it eliminated the mandatory features of the Guidelines—all of them.” Additionally, Justice Stevens expressed his 

view that the majority’s decision raises separation-of-powers and delegation concerns.

Johnson v. United States, 559 U.S. 133 (2010).

The Supreme Court, in a 7-2 decision, held that the petitioner’s prior conviction under Florida law for the felony offense of battery by “[a]ctually and intentionally touch[ing]”

another person did not constitute a violent felony for purposes of the ACCA.

The defendant’s ACCA sentencing enhancement was based, in part, on a 2003 conviction for battery in violation of Fla. Stat. § 784.03(1). The government may prove a battery under that statute “in one of three ways . . . . It can prove that the defendant ‘[i]ntentionally caus[ed] bodily harm,’ that he ‘intentionally str[uck]’ the victim, or that he merely 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 29

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

‘[a]ctually and intentionally touche[d]’ the victim.” In determining whether the battery conviction was a “violent felony” for the purpose of the ACCA, the Supreme Court applied the 

“modified categorical approach,” whereby the court may “determine which statutory phrase 

was the basis for the conviction by consulting the trial record.” In this case, the record did 

not provide a basis for this determination. Therefore, the Court was required to determine 

whether a conviction for the least of the acts enumerated in the Florida battery statute (actually and intentionally touching another person) had as an element the use of force 

against the person of another.

The Court held that it does not. First, the Court held that it was bound by the Florida Supreme Court’s interpretation of the elements of the battery statute, and that that 

court had held that “the element of ‘actually and intentionally touching’ . . . is satisfied by 

any intentionally physical contact, ‘no matter how slight.’ ” The Court went on to reason 

that, absent a definition within the ACCA of “physical force,” it must give the term its ordinary meaning, and that the ordinary meaning of “force” “suggest[s] a degree of power that 

would not be satisfied by the merest touching.” The Court then held that although force was 

an element of common law battery (which itself encompassed “even the slightest offensive 

touching”), in the context of §924(e)(1)(B)(i), “physical force” must mean “violent force—that 

is, force capable of causing physical pain or injury to another person.”

In his dissent, Justice Alito, joined by Justice Thomas, argued that the Court should 

look to the traditional, common law definition of battery, which includes the element of 

physical force. Since battery may encompass even slight touching, Alito reasoned, slight 

touching must therefore involve the element of physical force, and battery under the Florida statute must be a violent felony.

United States v. O’Brien, 560 U.S. 218 (2010).

The Supreme Court unanimously held that, under 18 U.S.C. § 924(c), which prohibits the use of a firearm in relation to or in furtherance of a crime of violence, the fact that 

the firearm is a machine gun is an element of the offense that must be proved to a jury. The 

Court considered this issue in an earlier case, Castillo v. United States, 530 U.S. 120 (2000), 

interpreting an earlier version of the statute, and held that the machine gun provision was 

an element of the offense. The Court reconsidered the issue in light of changes made to section 924(c) in 1998.

In this case, the defendant was charged with the attempted robbery of an armored 

car. Among the weapons recovered by authorities was a pistol that allegedly operated as a 

fully automatic weapon. The defendant disputed whether this pistol was in fact a machine 

gun. Under 18 U.S.C. § 924(c), the defendant would be subject to a 30-year mandatory minimum sentence if the gun were determined to be a machine gun. The district court ruled 

that the machine gun provision of section 924(c) was an element of the offense. The First 

Circuit affirmed, basing its decision on Castillo. The First Circuit held that even though 

Castillo had been decided using an earlier version of the statute, the changes to the statute 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 30

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

simply amounted to breaking up a lengthy sentence into subparagraphs that were easier to 

read, and the changes in no way altered the meaning of the statute. 

The Supreme Court did not interpret the statute anew, but rather asked only if the 

analysis of Castillo must change in light of the 1998 restructuring of the statute. In Castillo, the Court examined five factors to determine whether Congress intended the machine 

gun provision to be an element or a sentencing factor: (1) language and structure, (2) tradition, (3) risk of unfairness, (4) severity of the sentence, and (5) legislative history. The Court 

held that the main effect of the 1998 changes “was to divide what was once a lengthy principal sentence into separate subparagraphs.” This change, the Court held, would change the 

analysis only as to the first Castillo factor. The Court described the 1998 version as making 

three main changes to the statute, two of which it called substantive and the last structural. The substantive changes were: 1) what were once mandatory sentences became mandatory minimum sentences; and 2) the revised statute added the word “possesses” to “uses 

or carries,” and added mandatory minimums for the acts of brandishing and discharging 

the firearm. The third change, which the Court called structural, consisted of moving the 

machine gun provision from the main paragraph of the statute to a separate subsection.

The Court held that this change “does not provide a clear indication that Congress meant to 

alter its treatment of machineguns as an offense element.” Rather, the Court determined, 

Congress more likely sought to break up a lengthy paragraph before adding the substantive 

changes.

As for the other Castillo factors, the Court held that the second—legal tradition and 

past congressional practice—was unaffected by the 1998 changes, noting that “[s]entencing 

factors traditionally involve characteristics of the offender—such as recidivism, cooperation 

with law enforcement or acceptance of responsibility . . . . Characteristics of the offense itself are traditionally treated as elements, and the use of a machinegun under §924(c) lies 

closest to the heart of the crime at issue.” The Court rejected the government’s argument 

that the SRA, and thus the sentencing guidelines, treat possession of a firearm as a sentencing factor, and that whether a firearm is a machine gun should likewise be treated as a 

sentencing factor. The Court pointed out that the SRA was enacted before the original section 924(c) was enacted, and thus would already have been considered in Castillo. Next, the 

court held that the third Castillo factor, potential unfairness, was not changed by the 

1998 amendments. The Castillo court noted that a judge might not be aware of which 

among many firearms a jury had determined a defendant had used in the course of a crime, 

and that thus a judge’s sentencing determination could be at odds with a jury’s factfinding.

The Court in the present case held that this holding of Castillo remained unaffected. The 

Court further held that the restructuring of the statute had no effect on the fourth factor in 

Castillo, the potential severity of the sentence. In each instance, the shift from a mandatory 

minimum of five years to one of thirty years represents “a drastic, sixfold increase that 

strongly suggests a separate substantive crime.” The fifth Castillo factor was legislative 

history, and in both Castillo and the present case, the Court held that the legislative history was “of little help” in resolving the question presented. Given that four out of five Castillo factors were unaffected, and that there was no strong support for changing the analysis of the first factor, the Court reached the same conclusion that it had in Castillo: whether 

the firearm possessed or used under 18 U.S.C. § 924(c) was a machine gun is an element of 

the offense and not a sentencing factor.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 31

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice Stevens authored a concurring opinion, in which he wrote that the principles 

of Apprendi should apply with equal force to statutes that trigger mandatory minimums.

Stevens contended that a preferable solution to the issue presented “would be to recognize 

that any fact mandating the imposition of a sentence more severe than a judge would otherwise have discretion to impose should be treated as an element of the offense.” This would 

mean overruling the Court’s earlier holdings in McMillan v. Pennsylvania, 477 U.S. 79 

(1986) and Harris v. United States, 536 U.S. 545 (2002). Justice Thomas concurred in the 

judgment. Justice Thomas cited his own dissent in Harris, writing, “it is ultimately beside 

the point whether as a matter of statutory interpretation [the machinegun enhancement] is 

a sentencing factor . . . . [A]s a constitutional matter, because it establishes a harsher range 

of punishments, it must be treated as an element of a separate, aggravated offense that is 

submitted to a jury and proved beyond a reasonable doubt.”

Chambers v. United States, 555 U.S. 122 (2009).

The Supreme Court, in a 9-0 decision, reversed the Seventh Circuit’s opinion upholding the district court’s conclusion that the defendant’s prior offense of failure to report for 

periodic incarceration qualified as a “violent felony” for purposes of the ACCA. Justice 

Breyer authored the opinion; Justice Alito wrote a separate concurring opinion, in which 

Justice Thomas joined.

The ACCA, 18 U.S.C. § 924(e), requires a 15-year minimum term of imprisonment if 

an individual convicted of being a felon in possession of a firearm has three prior convictions “for a violent felony or a serious drug offense, or both . . . .” The issue before the district court was whether the defendant’s prior conviction for failing to report to a penal institution qualified as a “violent felony” as that term is used in the ACCA because it “otherwise 

involve[d] conduct that presents a serious potential risk of physical injury to another.” The 

district court held that the failure to report was a type of escape, which qualified as a violent felony under the ACCA. The Seventh Circuit affirmed this classification, and the Supreme Court granted review in light of conflicting case law on this point among the circuits.

The Court reaffirmed the use of the categorical approach in applying the ACCA, 

stating that “[t]he nature of the behavior that likely underlies a statutory phrase matters in 

this respect.” The Court referred back to its opinion in Shepard v. United States, 544 

U.S. 13 (2005), in which it examined a Massachusetts statute that combined various breaking and entering offenses into one section and “found that the behavior underlying, say, 

breaking into a building, differs so significantly from the behavior underlying, say, breaking into a vehicle, that for ACCA purposes a sentencing court must treat the two as different crimes.” The Court took a similar approach to the Illinois statute at issue, separating 

the “failure to report” sections of the statute from the sections involving escape from secured custody or from the physical custody of a law enforcement officer on one hand, and 

the failure to abide by conditions of home detention on the other. For ACCA purposes, then, 

the Court said, the Illinois statute involved “at least two separate crimes”: escape from se-
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 32

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

cured custody or physical custody of a law enforcement officer, which would qualify as a violent felony; and failure to report, which would not qualify as a violent felony. The Court further observed that the statute (1) “lists escape and failure to report separately (in its title 

and its body);” and (2) “places the behaviors in two different felony classes (Class Two and 

Class Three) of different degrees of seriousness.”

As so defined, the Court held that the crime of failure to report does not qualify as a 

violent felony under the ACCA:

Conceptually speaking, the crime amounts to a form of inaction, a far cry from the 

“purposeful, ‘violent,’ and ‘aggressive’ conduct” potentially at issue when an offender 

uses explosives against property, commits arson, burgles a dwelling or residence, or 

engages in certain forms of extortion. [Begay v. United States, 553 U.S. 137, 146

(2008)] (slip op., at 7). While an offender who fails to report must of course be doing 

something at the relevant time, there is no reason to believe that the something 

poses a serious potential risk of physical injury. Cf. James [v. United States], 550 

U.S. [192], at 203–204. To the contrary, an individual who fails to report would seem 

unlikely, not likely, to call attention to his whereabouts by simultaneously engaging 

in additional violent and unlawful conduct. 

In so holding, the Court rejected the government’s argument “that a failure to report 

reveals the offender’s special, strong aversion to penal custody” and that this aversion suggests that this presents a serious potential risk of physical injury. The Court disagreed, citing a Commission report that it said “helps provide a conclusive, negative answer” to the 

question of whether this connection exists. The Court discussed the information provided in 

the report, concluding that it “strongly supports the intuitive belief that failure to report 

does not involve a serious potential risk of physical injury.” As a result, the Court reversed 

the Seventh Circuit’s judgment and remanded the case.

Justice Alito, joined by Justice Thomas, wrote a separate concurring opinion, noting 

a continuing disagreement with the use of the categorical approach in these cases, but recognizing the precedential value of earlier cases on the issue. Additionally, Justice Alito emphasized the view that action from Congress is required to properly address the issue.

Spears v. United States, 555 U.S. 261 (2009).

The Supreme Court, in a 5-4 per curiam opinion, granted certiorari and summarily 

reversed and remanded this crack cocaine case to the Eighth Circuit Court of Appeals. Justice Kennedy disagreed with this approach, preferring to grant review and schedule the 

case for oral argument. Justice Thomas dissented without comment, and Chief Justice Roberts, joined by Justice Alito, wrote a dissenting opinion.

The defendant was convicted of conspiring to distribute crack and powder cocaine; in 

determining his sentence, the district court declined to impose a sentence within the guideline range, concluding that the 100:1 crack to powder ratio inherent in that range produced 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 33

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

too long a sentence. Instead, the district court determined what the defendant’s guideline 

range would be if the drug guideline contained a 20:1 crack to powder ratio, and imposed a 

sentence near the middle of that range. The en banc Eighth Circuit, prior to the Supreme 

Court’s opinion in Kimbrough, held that this sentence was unreasonable because, in its 

view, 18 U.S.C. § 3553(a) and Booker did not permit district courts to substitute a different 

ratio. The Supreme Court concluded that this decision was inconsistent with its opinion in 

Kimbrough.

Discussing Kimbrough, the Supreme Court explained that it “holds that with respect 

to the crack cocaine Guidelines, a categorical disagreement with and variance from the 

Guidelines is not suspect.” In fact, the Court said, this “was indeed the point of Kimbrough: 

a recognition of district courts’ authority to vary from the crack cocaine Guidelines based on 

policy disagreement with them, and not simply based on an individualized determination 

that they yield an excessive sentence in a particular case.” It necessarily follows from this 

authority, the Court held, that a district court also has authority to substitute “a different 

ratio which, in his judgment, corrects the disparity.” The Court noted that, in this case, the 

election of the 20:1 ratio “was based upon two well-reasoned decisions by other courts, 

which themselves reflected the Sentencing Commission’s expert judgment that a 20:1 ratio 

would be appropriate in a mine-run case.”

Chief Justice Roberts, in dissent, expressed disagreement with the Court’s decision 

to summarily reverse the Eighth Circuit’s opinion, though acknowledging that the majority’s holding “may well” follow from Kimbrough.

Begay v. United States, 553 U.S. 137 (2008).

The Supreme Court, in a 6-3 opinion, held that a conviction for felony driving under 

the influence (DUI) is not a “violent felony” that can trigger the mandatory 15-year minimum under the ACCA. Justice Breyer wrote for the majority, in which Chief Justice Roberts and Justices Stevens, Kennedy, Souter, and Ginsburg joined. Justice Scalia, writing 

separately, concurred in the judgment; Justice Alito, joined by Justices Souter and Thomas, 

dissented.

The Court was asked to construe the “residual clause” of 18 U.S.C. § 924(e)(2)(B)(ii), 

which defines a “violent felony” as, inter alia, a crime punishable by more than one year’s 

imprisonment that “is burglary, arson, or extortion, involves use of explosives, or otherwise 

involves conduct that presents a serious potential risk of physical injury to another.” The 

petitioner challenged the enhancement of his sentence on the basis of the prior DUI, arguing that the “otherwise” clause of the above provision was not intended to encompass DUI.

The government argued that, because DUI presents a serious potential risk of physical injury to another, it falls within the scope of the statute and therefore qualified the petitioner 

for the enhanced sentence. The district court accepted the government’s view of the statute 

and applied the enhancement, and the court of appeals upheld the sentence.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 34

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

The Supreme Court concluded that the lower courts had erroneously construed the 

statute, holding that a prior conviction for DUI should not expose a defendant to the 15-

year mandatory minimum. The Court began with the presumption that “the lower courts 

were right in concluding that DUI involves conduct that ‘presents a serious potential risk of 

physical injury to another.’ ” The Court then faced the issue of why Congress included the 

enumerated offenses (burglary, arson, extortion, and offenses involving “use of explosives”) 

in the provision. The Court rejected the government’s argument that the examples were intended “to demonstrate no more than the degree of risk sufficient to bring a crime within 

the statute’s scope,” concluding that “the examples are so far from clear in respect to the degree of risk each poses that it is difficult to accept clarification in respect to degree of risk as 

Congress’ only reason for including them.” Rather, the Court concluded, “we should read 

the examples as limiting the crimes . . . to crimes that are roughly similar, in kind as well 

as in degree of risk posed, to the examples themselves.” The Court held that the legislative 

history of the ACCA supported this conclusion. Applying this standard, the Court concluded 

that DUI does not sufficiently resemble the enumerated crimes to bring it within the ambit 

of the statute. The most significant distinction, according to the Court, is the fact that DUI 

offenses are essentially strict liability crimes, whereas the enumerated offenses typically 

involve “purposeful, violent, and aggressive conduct . . . [which] makes it more likely that 

an offender, later possessing a gun, will use that gun deliberately to harm a victim.”

In a separate concurrence, Justice Scalia followed the analysis set forth in his dissent in James v. United States, a case from the prior term in which the Court addressed 

whether attempted burglary fell within the statute. Under this analysis, Justice Scalia concluded that, without further evidence, he could not find that DUI “pose[s] at least as serious 

a risk of physical injury to another as burglary” and that the rule of lenity therefore required the conclusion that the defendant’s sentence could not be enhanced under the ACCA.

In dissent, Justice Alito argued that the text of the statute requires only the analysis 

of whether the offense in question presents a serious risk of physical injury to another, and 

concluded that the DUI in this case did pose such a risk.

Greenlaw v. United States, 554 U.S. 237 (2008). 

The Supreme Court, in a 7-2 opinion, held that an appeals court was not permitted 

to order an increase in a defendant’s sentence where the government did not appeal the 

sentence. Justice Ginsburg wrote for the majority, in which Chief Justice Roberts and Justices Scalia, Kennedy, Souter and Thomas joined. Justice Breyer wrote separately, concurring in the judgment. Justice Alito dissented; Justice Stevens joined the dissent in full and 

Justice Breyer joined it in part.

The petitioner was convicted of seven counts of an eight-count indictment arising out 

of his participation in a crack cocaine trafficking scheme. The charges included two section 924(c) counts; the district court, in direct contravention of prior Supreme Court precedent, held over government objection that the second count was not considered a “second or 

subsequent conviction” because the two counts were charged in the same indictment. As a 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 35

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

result, the district court erroneously imposed a sentence of 442 months’ imprisonment, 

which fell below the required mandatory minimum of 622 months’ imprisonment. Nevertheless, the defendant appealed the sentence; in defending the sentence, the government noted 

that the sentence was erroneously low, but did not file a cross-appeal of the error. The 

Eighth Circuit, relying on the “plain error” rule set forth in Fed. R. Crim. P. 52(b), vacated 

the sentence and remanded to the district court with instructions that it impose the statutorily mandated sentence. The defendant then sought rehearing and rehearing en banc, and 

the petitions were summarily denied. The defendant and the United States agreed that the 

appeals court erred in vacating and remanding the sentence; therefore, the Court invited an 

amicus brief in support of the Eighth Circuit’s position.

The majority opinion began by noting the general “principle of party presentation”

that characterizes the United States’ adversary system in which courts “rely on the parties 

to frame the issues for decision” and themselves play “the role of neutral arbiter of matters 

the parties present.” Derived from this principle is the “cross-appeal rule,” which the Court 

described as an “unwritten but longstanding rule” that “an appellate court may not alter a 

judgment to benefit a nonappealing party.” The Court noted the split among the circuits regarding the question of whether this rule is “jurisdictional,” and therefore not subject to exception, or a “rule of practice” to which courts may create exceptions. As in previous cases, 

the Court declined to resolve the circuit split, concluding that resolving the issue was not 

necessary to deciding the case at bar.

The Court discussed 18 U.S.C. § 3742(b), which provides that the government may 

not proceed with an appeal of a criminal case “without the personal approval of the Attorney General, the Solicitor General, or a deputy solicitor general designated by the Solicitor 

General.” The Court concluded that “[i]t would severely undermine Congress’ instruction 

were appellate judges to ‘sally forth’ on their own motion . . . to take up errors adverse to 

the Government when the designated Department of Justice officials have not authorized 

an appeal from the sentence the trial court imposed.” The Court said that “[t]hat measure 

should garner the Judiciary’s full respect.” The Court then addressed the relationship between Fed. R. Crim. P. 52(b) and the cross-appeal rule, concluding that no plain-error exception to the cross-appeal rule existed where the error was to the detriment of the government in a criminal appeal.

The Court then rejected the arguments of amicus supporting the Eighth Circuit’s position. In so doing, the Court discussed at some length the argument that 18 U.S.C. § 3742, 

the part of the SRA dealing with appellate review standards, supports the Eighth Circuit’s 

judgment. The argument relies on a comparison of section 3742(f)(1) and (f)(2); the former 

sets the standard of review for “sentences imposed ‘in violation of law’ and Guideline application errors” and the latter sets the standard of review for “sentences ‘outside the applicable Guideline range.’ ” For sentences outside the range, the provision specifies that remand 

is proper “only where a departure from the Federal Sentencing Guidelines harms the appellant;” for sentences that are “imposed ‘in violation of law’ ” or that result from an erroneous 

guideline application, no limit is specified. “The inference amicus draws from this distinction is that Congress intended to override the cross-appeal rule for sentences controlled by 

§ 3742(f)(1), i.e., those imposed ‘in violation of law’ (or incorrectly applying the Guidelines), 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 36

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

but not for Guideline departure errors, the category covered by § 3742(f)(2).” The Court rejected this interpretation, instead concluding that, since the cross-appeal rule was well-settled at the time of the SRA, “Congress was aware of the cross-appeal rule, and framed 

§ 3742 expecting that the new provision would operate in harmony with the ‘inveterate and 

certain’ bar to enlarging judgments in favor of an appellee who filed no cross-appeal.” In 

support of its interpretation, the Court noted that earlier crime control legislation had included a specific exception to the cross-appeal rule, which was repealed by the SRA. Additionally, the Court noted that “the construction proposed by amicus would draw a puzzling 

distinction between incorrect applications of the Sentencing Guidelines . . . and erroneous 

departures from the Guidelines.” Finally, the Court supported its application of the crossappeal rule by discussing what it called the “auxiliary” roles of the Federal Rules of Appellate Procedure in ensuring “fair notice and finality” to permit strategic decisions in appellate litigation.

The Court concluded by distinguishing its holding in this case from what it viewed 

as proper treatment of “sentencing package cases” in which a defendant successfully attacks his sentence on one or some of the multiple counts, and the appellate court vacates 

“the entire sentence on all counts so that, on remand, the trial court can reconfigure the 

sentencing plan to assure that it remains adequate to satisfy the sentencing factors in 

18 U.S.C. § 3553(a).” This procedure, the Court said, “is not at odds with the cross-appeal 

rule” and “simply ensures that the sentence ‘will suit not merely the offense but the individual defendant.’ ”

In concurring in the judgment, Justice Breyer expressed the view that the Eighth 

Circuit had authority to vacate the sentence, but that its decision to do so in this case was 

an abuse of discretion because the decision was “based solely on the obviousness of the 

lower court’s error,” a standard which is explicitly disapproved by prior Supreme Court 

precedent.

In dissent, Justice Alito expressed the view that the cross-appeal rule is not jurisdictional but rather a rule of practice, and therefore subject to exceptions. Further, Justice 

Alito argued that application of the rule in this instance is not as important to the interests 

of justice as the majority believed it is, and would in fact “disserve[] . . . the interest of the 

Judiciary and the public in correcting grossly prejudicial errors of law that undermine confidence in our legal system.” Because the parties did not brief the issue of whether, if the 

Eighth Circuit did have such authority, it abused its discretion in the case at bar, Justice 

Alito noted that he would affirm without reaching the question.

Irizarry v. United States, 553 U.S. 708 (2008).

The Supreme Court, in a 5-4 opinion, held that a district court was not required to 

provide advance notice to the parties when imposing a sentence that represents a variance 

from the guideline range. Justice Stevens delivered the opinion of the Court, in which Chief 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 37

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice Roberts and Justices Scalia, Thomas, and Alito joined. Justice Thomas filed a concurring opinion. Justice Breyer filed a dissent, in which Justices Kennedy, Souter, and 

Ginsburg joined. 

Petitioner Richard Irizarry pleaded guilty to one count of making a threatening interstate communication, in violation of 18 U.S.C. § 875(c). Irizarry admitted to sending a 

number of e-mails threatening to kill his ex-wife and her new husband, and that his emails 

were intended to be true threats to kill or injure them. The PSR described the threatening 

emails and added that the petitioner had asked another inmate to kill his ex-wife’s new 

husband. As possible grounds for departure, the PSR stated that Irizarry’s criminal history 

category might not adequately reflect his past criminal conduct or the likelihood that he 

would commit other crimes. The government noted in its response to the PSR that it intended to call Irizarry’s ex-wife as a witness at the sentencing hearing. At the hearing, Irizarry’s ex-wife testified regarding incidents of domestic violence, the basis for the restraining order against Irizarry, and the threats he had made against her and her family. A special agent of the FBI also testified, describing documents recovered from Irizarry’s car indicating that he intended to find his ex-wife and their children. And Irizarry’s cellmate testified that Irizarry “was obsessed with the idea of getting rid of” his ex-wife’s husband. Irizarry also testified. After listening to the witnesses and hearing from counsel, the district 

court concluded “that the maximum time that [the defendant] can be incapacitated is what 

is best for society, and therefore the guideline range . . . is not high enough.” The court varied upward from the Guidelines range, and sentenced Irizarry to the statutory maximum 

term of imprisonment. The court’s decision was based on its determination, after hearing 

Irizarry’s ex-wife testify at the sentencing hearing, that Irizarry “will continue . . . in this 

conduct regardless of what this court does and regardless of what kind of supervision he’s 

under.” Following the court’s imposition of sentence, Irizarry objected, stating that he 

“didn’t have notice of [the court’s] intent to upwardly depart.” The court overruled this objection, finding that notice was not required now that the U.S. Sentencing Guidelines are 

advisory. The Court of Appeals for the Eleventh Circuit affirmed, holding that Rule 32(h) 

did not apply in this case because the above-Guidelines sentence was a variance, not a departure.

The Supreme Court granted certiorari and affirmed, holding that Rule 32(h) does 

not apply to a variance from a recommended Guidelines range. The Court’s holding rests on 

its decision in Booker, “which invalidated the mandatory features of the Guidelines.” According to the Court, “[t]he due process concerns that motivated the Court to require notice 

in a world of mandatory Guidelines no longer provide a basis for this Court to extend the 

rule set forth in Burns either through an interpretation of Rule 32(h) itself or through Rule 

32(i)(1)(c).”

In Burns, the Court had previously held that the text of Rule 32 required “ ‘notice of 

any contemplated departure.’ ” Justice Souter’s dissent, which argued that the text itself 

did not require notice, discussed due process concerns. The Court in this case stated that its 

decision in Burns “applied in a narrow category of cases,” namely, departures “authorized 

by 18 U.S.C. § 3553(b) which required ‘an aggravating or mitigating circumstance of a kind, 

or to a degree, not adequately taken into consideration by the Sentencing Commission in 

formulating the guidelines that should result in a sentence different from that described.’ ”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 38

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Such departures had to be based on “the sentencing guidelines policy statements, and official commentary of the Sentencing Commission.” Further, the notice requirement set forth 

in Burns “only applied to the subcategory of those departures that were based on ‘a ground 

not identified as a ground . . . for departure either in the presentence report or in a prehearing submission.’ ”

Because, post-Booker, “there is no longer a limit comparable to the one at issue in 

Burns on the variances from Guidelines ranges,” the Court held that Rule 32(h) does not 

apply to variances. The Court also voiced more practical concerns that a special notice requirement in such circumstances might “create unnecessary delay.” The Court stated that 

the proper approach to cases in which “the factual basis for a particular sentence will come 

as a surprise to a defendant or the Government” is for the “district court to consider granting a continuance when a party has a legitimate basis for claiming that the surprise was 

prejudicial.”

The dissent (written by Justice Breyer) contended that Rule 32(h) applies to section 3553(a) variances by its terms. The dissent argued that by distinguishing “departures”

from “variances” in this context, the Court is “creat[ing] a legal distinction without much of 

a difference.” According to the dissent, “[s]o-called variances fall comfortably within” the 

Guidelines’ definition of “departure.” Further, “[v]ariances are also consistent with the ordinary meaning of the term ‘departure,’ ” and “conceptually speaking, the substantive difference between” the two terms “is nonexistent.” The majority rejected this argument, stating 

that “ ‘[d]eparture’ is a term of art under the Guidelines and refers only to non-Guidelines 

sentences imposed under the framework set out in the Guidelines.”

The dissent also found the majority’s concerns about delay to be “exaggerated,” noting that in most cases in which the district court varies outside the Guidelines range, the 

PSR or the parties have identified the ground for the variance. In other cases, the parties 

might be able to address the “unconsidered” issue at the hearing without the need for a continuance. In all other cases, according to the dissent, “fairness justifies notice regardless” of 

“burdens and delay.”

United States v. Rodriquez, 553 U.S. 377 (2008).

The Supreme Court, in a 6-3 opinion, held that a previous offense for which the statutory maximum sentence was 10 years’ imprisonment only because the defendant was a repeat offender qualified as a predicate offense under the ACCA. Justice Alito, writing for 

Chief Justice Roberts and Justices Scalia, Kennedy, Thomas and Breyer concluded that the 

recidivism enhancement applied under state law should be used to calculate the “maximum 

term of imprisonment” for ACCA purposes. Justice Souter authored a dissenting opinion, 

which was joined by Justices Stevens and Ginsburg. 

In the case at bar, the defendant had two California burglary convictions and three 

convictions in Washington state for delivery of a controlled substance. The district court, in 

sentencing the defendant on a federal felon-in-possession charge, declined to apply the 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 39

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

ACCA enhancement because the defendant was subject to the ten-year maximum in Washington state only because he was a repeat offender; under that law, first offenders face only 

a statutory maximum of five years. The Ninth Circuit affirmed, noting that its holding on 

this issue was in conflict with law from the Seventh Circuit and “in tension” with precedent 

from the Fourth and Fifth Circuits. 

The Court held that the government’s interpretation of the ACCA was the correct 

one, focusing on the statute’s definition of three terms: “offense,” “law,” and “maximum 

term.” The Court said: 

The “offense” in each of the drug-delivery cases was a violation of §§69.50.401(a)(ii)–

(iv). The relevant “law” is set out in both that provision, which prescribes a “maximum term” of five years for a first “offense,” and §69.50.408(a), which prescribes a 

“maximum term” of 10 years for a second or subsequent “offense.” Thus, in this case, 

the maximum term prescribed by Washington law for at least two of respondent’s 

state drug offenses was 10 years.

The Ninth Circuit’s approach, the Court said, “contorts ACCA’s plain terms” and is “inconsistent with the way in which the concept of the ‘maximum term of imprisonment’ is customarily understood by participants in the criminal justice process.”

Addressing the respondent’s arguments, the Court rejected the argument that the 

term “offense” as used in the ACCA should be defined as the elements of the offense, of 

which a recidivism enhancement (at least of the kind in this case) is not one. The Court 

held that this reading added a limitation to the ACCA that was not part of the plain language of that statute. Additionally, the court rejected the respondent’s argument that the 

government’s reading contradicted the “manifest purpose” of the ACCA. The respondent argued that, since the sentence length was used essentially as a proxy for the seriousness of 

the offense (thus limiting application of the ACCA enhancement to those convicted of more 

serious prior offenses), including recidivism enhancements skews this measurement. The 

Court stated that “[t]his argument rests on the erroneous proposition that a defendant’s 

prior record of convictions has no bearing on the seriousness of an offense,” instead noting 

that “an offense committed by a repeat offender is often thought to reflect greater culpability and thus to merit greater punishment” and that “a second or subsequent offense is often 

regarded as more serious because it portends greater future danger and therefore warrants 

an increased sentence for purposes of deterrence and incapacitation.” Additionally, the 

Court observed that “the ACCA itself is a recidivist statute,” concluding that this fact “bolster[ed]” its reading of the statute in that “Congress must have had such provisions in mind 

and must have understood that the ‘maximum penalty prescribed by [state] law’ in some 

cases would be increased by state recidivism provisions.”

Finally, the Court rejected the respondent’s arguments that the Court’s prior decisions in LaBonte and Taylor, as well as the policy and practical implications of the government’s reading, support the respondent’s interpretation of the statute. With respect to LaBonte, the Court rejected the respondent’s argument that Congress’s decision not to make 

reference to a “category of offenders” in the ACCA as it did in 18 U.S.C. § 994(h) (which the 

Court interpreted in LaBonte) supported his interpretation of the ACCA. The Court said: 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 40

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

“Respondent does not explain how 18 U.S.C. § 924(e)(2)(A) could have easily been reworded 

to mirror 28 U.S.C. § 994(h). But in any event, the language used in ACCA, for the reasons 

explained above, is more than clear enough.” The Court similarly rejected the respondent’s 

argument that the Court’s decision in Taylor, adopting the categorical approach, supported 

his interpretation, finding “no connection . . . between the issue in Taylor . . . and the issue 

here . . . .”

In dissent, Justice Souter argued that the majority “chooses one reading of the 

[ACCA] over another that would make at least as much sense of the statute’s ambiguous 

text and would follow the counsel of a tradition of lenity in construing perplexing criminal 

laws” and that the majority’s interpretation “promises hard times for the trial courts that 

will have to make the complex sentencing calculations this decision demands.”

Cunningham v. California, 549 U.S. 270 (2007).

The Supreme Court in a 6-3 opinion struck down California’s Determinate Sentencing Law (DSL) on grounds that it violated the Sixth Amendment’s jury trial right, as interpreted by the Supreme Court in the Apprendi line of cases. The specific question presented 

in the case was: “Whether California’s Determinate Sentencing Law, by permitting sentencing judges to impose enhanced sentences based on their determination of facts not found by 

the jury or admitted by the defendant, violates the Sixth and Fourteenth Amendments.”

The Court concluded that it did, holding that the relevant statutory maximum for Sixth 

Amendment purposes under California’s DSL was the middle term sentence because a 

judge was required to find no facts beyond the jury’s verdict to impose it. In so holding, the 

Court overruled a California Supreme Court case, People v. Black, 113 P.3d 534 (Cal. 2005), 

which had determined that the DSL did not violate Blakely.

Gall v. United States, 552 U.S. 38 (2007).

In a 7-2 decision, the Supreme Court held that the abuse of discretion standard of 

review applies equally to all sentences, rejecting the form of proportionality review employed by the court of appeals in the case. Justice Stevens delivered the opinion of the 

Court, in which Chief Justice Roberts, Justices Scalia, Kennedy, Souter, Ginsburg, and 

Breyer joined. Justices Scalia and Souter filed concurring opinions, and Justices Thomas 

and Alito filed dissenting opinions.

The Court held that “while the extent of the difference between a particular sentence and the recommended Guidelines range is surely relevant, the court of appeals must 

review all sentences —whether inside, just outside, or significantly outside the Guidelines 

range— under a deferential abuse of discretion standard.” The Court further held that the 

appellate rule “requiring ‘proportion’ justifications for departures from the Guidelines range 

is not consistent with” Booker. The Court also stated: “Our explanation of ‘reasonableness’
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 41

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

review in the Booker opinion made it pellucidly clear that the familiar abuse of discretion 

standard of review now applies to appellate review of sentencing decisions.”

In reviewing the reasonableness of a sentence outside the range, the Court said, appellate courts “may therefore take the degree of variance into account and consider the extent of a deviation from the Guidelines.” An inappropriate standard of appellate review, the 

Court said, is one: “that requires ‘extraordinary’ circumstances to justify a sentence outside 

the Guidelines range.” The Court also disapproved “the use of a rigid mathematical formula 

that uses the percentage of a departure as the standard for determining the strength of the 

justifications required for a specific sentence.” The Court reasoned that such an approach 

would “come too close to creating an impermissible presumption of unreasonableness for 

sentences outside the Guidelines range.” The Court also stated that the “mathematical approach also suffers from infirmities of application” and “assumes the existence of some ascertainable method of assigning percentages to various justifications.” The Court also observed that these practices “reflect a practice . . . of applying a heightened standard of review to sentences outside the Guidelines range,” which, the Court said, “is inconsistent with 

the rule that the abuse of discretion standard of review applies to appellate review of all 

sentencing decisions —whether inside or outside the Guidelines range.”

The Court then discussed the proper analysis for sentencing courts, beginning with 

proper calculation of the guideline range, followed by consideration of the section 3553(a) 

factors, and noting that if the court determines that a sentence outside the guideline range 

is appropriate, the court “must consider the extent of the deviation and ensure that the justification is sufficiently compelling to support the degree of the variance.” The Court went 

on to state: “We find it uncontroversial that a major departure should be supported by a 

more significant justification than a minor one.” After making this determination, the 

Court said, the sentencing court must adequately explain the reasons for the sentence.

With respect to appellate review, the Court acknowledged that reviewing courts “will, of 

course, take into account the totality of the circumstances, including the extent of any variance from the Guidelines range.” In so doing, the Court said, the appellate court “may consider the extent of deviation, but must give due deference to the district court’s decision 

that the 3553(a) factors, on a whole, justify the variance. The fact that the appellate court 

might reasonably have concluded that a different sentence was appropriate is insufficient to 

justify reversal of the district court.”

The Court then concluded that, in the case at bar, the Eighth Circuit failed to give 

the proper deference to the district court’s decision, and reversed the judgment.

Justice Alito, dissenting, stated that he would hold that “a district court must give 

the policy decisions that are embodied in the Sentencing Guidelines at least some significant weight” and would therefore affirm the Eighth Circuit’s decision.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 42

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

James v. United States, 550 U.S. 192 (2007).

The Supreme Court in a 5-4 opinion upheld the Eleventh Circuit’s determination 

that a conviction for attempted burglary under Florida law is a “violent felony” under the

ACCA, 18 U.S.C. § 924(e). The issue was whether “overt conduct directed toward unlawfully entering or remaining in a dwelling, with the intent to commit a felony therein, is ‘conduct that presents a serious potential risk of physical injury to another.’ ” The Court said 

that “[t]he main risk of burglary arises not from the simple physical act or wrongfully entering onto another’s property, but rather from the possibility of a face-to-face confrontation 

between the burglar and a third party - whether an occupant, a police officer, or a bystander - who comes to investigate.” Attempted burglary, the Court said, “poses the same 

kind of risk.” The Court also noted that, because attempted burglaries that give rise to convictions are typically those that were interrupted by such a third party, attempted burglaries that are ACCA predicates may actually pose a greater risk than completed burglaries.

The Court concluded: “As long as an offense is of a type that, by its nature, presents a serious potential risk of injury to another, it satisfies the requirements of” the ACCA.

Kimbrough v. United States, 552 U.S. 85 (2007).

In a 7-2 opinion, the Court held that a sentencing judge may consider the disparity 

between the Guidelines’ treatment of crack and powder cocaine when determining a sentencing range. 

The Court summarized the history of the crack/powder disparity, noting the circumstances surrounding its inclusion in the Anti-Drug Abuse Act of 1986 (the 1986 Act) and the 

assumptions that underlay the conclusion that crack offenders should be punished significantly more severely than powder cocaine offenders. The Court observed that, in creating 

the drug guidelines, the Commission varied from its usual practice of employing an “empirical approach based on data about past sentencing practices,” instead adopting the “weightdriven scheme” used in the 1986 Act, and maintaining the 100-to-1 quantity ratio throughout the drug table. The Court then discussed the Commission’s subsequent criticisms of the 

ratio, quoting from the various Commission reports to Congress on the issue, and discussed 

Congress’s previous responses to Commission actions and recommendations. The Court finally discussed the Commission’s 2007 amendments, and observed that the Commission 

considered them “only . . . a partial remedy” for the problems caused by the disparity.

The Court then discussed the status of the relevant guidelines in light of Booker, examining the government’s arguments that “the Guidelines adopting the 100-to-1 ratio are 

an exception to the general freedom that sentencing courts have to apply the § 3553(a) factors.” The Court first rejected the government’s grounding of the proposition in the text of 

the 1986 Act, “declin[ing] to read any implicit directive into [the] congressional silence” on 

the appropriate length of sentences not dictated by the mandatory minima and maxima in 

the 1986 Act itself. The Court observed that “[d]rawing meaning from silence is particularly 

inappropriate here, for Congress has shown that it knows how to direct sentencing prac-
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 43

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

tices in express terms,” citing 28 U.S.C. § 994(h)’s direction regarding career offenders. Additionally, the Court looked to its earlier decision in Neal v. United States, 516 U.S. 284 

(1996), in which it held that the Commission’s method for calculating the weight of LSD did 

not dictate the method used for determining the applicable statutory mandatory minimum.

Next, the Court rejected the government’s argument that Congress’s 1995 disapproval of the Commission’s implementation of the 1:1 ratio in the guidelines “made clear 

that the 1986 Act required the Commission (and sentencing courts) to take drug quantities 

into account, and to do so in a manner that respects the 100:1 ratio.” The Court observed 

that “nothing in Congress’ 1995 reaction to the Commission-proposed 1-to-1 ratio suggested 

that crack sentences must exceed powder sentences by a ratio of 100 to 1. To the contrary, 

Congress’ 1995 action required the Commission to recommend a ‘revision of the drug quantity ratio of crack cocaine to powder cocaine.’ ” The Court further observed that the 2007 

amendments result in a crack/powder ratio that is not consistently 100-to-1, but that Congress did not disapprove of the amendments.

Finally, the Court rejected the government’s arguments that consideration of the 

100-to-1 ratio would result in unwarranted sentencing disparities in violation of section 

3553(a)(6). The two kinds of disparities considered were those arising from “cliffs” in the 

guideline ranges near and at the mandatory minima, and those arising from different sentencing judges’ opinions regarding the proper relationship between crack offenders and 

powder cocaine offenders. The Court observed that both are inherent in the guidelines system and that “advisory Guidelines combined with appellate review for reasonableness 

will . . . not eliminate variations between district courts, but . . . Booker recognized that 

some departures from uniformity were a necessary cost of the remedy [Booker] adopted.”

The Court finally noted that, if an unwarranted disparity arises, the district court is required to address it under section 3553(a)(6).

The Court then discussed the Commission’s ongoing role in determining sentencing 

ranges, noting that “while the Guidelines are no longer binding, closer review may be in order when the sentencing judge varies from the Guidelines based solely on the judge’s view 

that the Guidelines range ‘fails properly to reflect § 3553(a) considerations’ even in a minerun case.” The Court held that the crack cocaine guidelines “do not exemplify the Commission’s exercise of its characteristic institutional role” and noted the Commission’s opinion 

that the crack cocaine guidelines produce “disproportionately harsh sanctions.” In light of 

this, “it would not be an abuse of discretion for a district court to conclude when sentencing 

a particular defendant that the crack/powder disparity yields a sentence ‘greater than necessary’ to achieve § 3553(a)’s purposes, even in a mine-run case.”

Applying these principles, the Court concluded that the sentence in the instant case 

did not constitute an abuse of discretion, and reversed the Fourth Circuit’s order vacating 

the sentence.

In dissent, Justice Thomas expressed his continuing disagreement with the opinion 

of the Booker remedial majority, and Justice Alito wrote that he would vacate the Fourth 

Circuit’s decision and remand for reconsideration in light of Booker’s holding that a court of 

appeals may not “treat the Guidelines’ policy decisions as binding.”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 44

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Logan v. United States, 552 U.S. 23 (2007).

The Supreme Court, in a unanimous opinion, held that, under the ACCA, 18 U.S.C. 

§ 924(e)(1), a violent felony offense for which the defendant’s civil rights were never revoked 

is not excluded from qualifying as a predicate for an enhanced sentence. Such a prior offense, the Court ruled, does not fall into the category of those offenses “for which a person . . . has had civil rights restored.” 18 U.S.C. § 921(a)(20). The case addressed a circuit 

split arising out of two main cases: McGrath v. United States, 60 F.3d 1005 (2d Cir. 1995), 

holding that such convictions are not excluded, and United States v. Indelicato, 97 F.3d 627 

(1st Cir. 1996), holding the opposite. In the case at bar, the Seventh Circuit adopted the 

McGrath analysis.

The petitioner pleaded guilty in the Western District of Wisconsin to a violation of 

18 U.S.C. § 922(g)(1), the felon-in-possession statute. His sentence was enhanced pursuant 

to the ACCA, and the district court imposed the relevant 15-year mandatory minimum. The 

court based the enhancement on the petitioner’s three Wisconsin misdemeanor battery convictions, each punishable by up to three years’ imprisonment. Although these convictions 

would otherwise count as “violent felonies” for ACCA purposes pursuant to 18 U.S.C. 

§ 921(a)(20)(B), the petitioner argued that, because none of them caused the revocation of 

his civil rights, they were exempt pursuant to 18 U.S.C. § 921(a)(20). That statute excludes 

from the relevant definition of a qualifying predicate offense:

Any conviction which has been expunged, or set aside or for which a person has been 

pardoned or has had civil rights restored . . . unless such pardon, expungement, or 

restoration of civil rights expressly provides that the person may not ship, transport, 

possess, or receive firearms.

In support of his position that the term “restored” should be construed to include offenses 

for which civil rights were never revoked, the petitioner argued inter alia that the McGrath

construction would contravene the purpose of the statute and produce absurd results. He 

argued that the purpose of the statute was to expand the reach of the exemption provision 

and to permit its application to be dictated by state law. He further argued that less serious 

offenders (i.e., those whose offenses did not result in the revocation of civil rights) would receive harsher treatment than more serious offenders (i.e., those whose offenses did result in 

revocation, but whose civil rights were later restored). In response, the government relied 

largely on textualist arguments, emphasizing the plain meaning of the term “restored” and 

its implication that something never lost may not be restored.

The Supreme Court examined Congressional intent, and summarized it as follows:

Congress framed § 921(a)(20) to serve two purposes. It sought to qualify as ACCA 

predicate offenses violent crimes that a State classifies as misdemeanors yet punishes by a substantial term of imprisonment, i.e., more than two years. Congress 

also sought to defer to a State’s dispensation relieving an offender from disabling effects of a conviction. Had Congress included a retention-of-rights exemption, however, the very misdemeanors it meant to cover would escape ACCA’s reach.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 45

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

(Internal citations omitted). The Supreme Court further observed that the petitioner’s reading of the statute would also produce absurd or anomalous results, noting that Maine does 

not revoke any offender’s civil rights, and so offenders who committed the most dangerous 

offenses in Maine would receive less punishment than offenders who committed less serious 

offenses in other states. The Supreme Court also noted that Congress must have been 

aware that allowing state laws, which vary, to dictate application of the ACCA would produce some anomalous results. Ultimately, the Supreme Court held that it had “no warrant”

to move beyond the plain language of the provision and observed: “We are not equipped to 

say what statutory alteration, if any, Congress would have made had its attention trained 

on offenders who retained civil rights; nor can we recast §921(a)(20) in Congress’ stead.”

Rita v. United States, 551 U.S. 338 (2007).

The Supreme Court, in an 8-1 decision, held that courts of appeals may apply a presumption of reasonableness when reviewing a sentence imposed within the sentencing 

guideline range, and affirmed the within-guidelines sentence imposed in the case. Writing 

for the majority, Justice Breyer, joined by Chief Justice Roberts and Justices Stevens, Kennedy, Ginsburg, and Alito, emphasized the close relationship between the guidelines and 

the section 3553(a) factors.

First, the Court discussed the statutory provisions governing the promulgation of 

the guidelines and how those provisions mirror the factors that section 3553(a) requires 

sentencing courts to consider, noting that “the sentencing statutes envision both the sentencing judge and the Commission as carrying out the same basic § 3553(a) objectives, the 

one, at retail, the other at wholesale.” Second, the Court discussed the process that the 

Commission used to initially promulgate and subsequently amend the guidelines, concluding that the guidelines “seek to embody the § 3553(a) considerations, both in principle and 

in practice” and that they “reflect a rough approximation of sentences that might achieve 

§ 3553(a)’s objectives.” In sum, the Court said “the courts of appeals’ “reasonableness” presumption, rather than having independent legal effect, simply recognizes the real-world circumstance that when the judge’s discretionary decision accords with the Commission’s view 

of the appropriate application of § 3553(a) in the mine run of cases, it is probable that the 

sentence is reasonable.” The majority also emphasized that circuits are not required to employ a presumption when conducting reasonableness review, and that the presumption is 

applied on appeal and not by the sentencing judge. 

The majority opinion also discussed the procedural issues raised by the advisory 

guidelines scheme. Specifically, the Court (and in this it was joined by Justices Scalia and 

Thomas) examined the district court’s statement at sentencing to determine whether it 

complied with the requirement in section 3553(c) that the judge “state in open court the 

reasons for its imposition of the particular sentence.” The Court emphasized that the 

amount of detail required in such a statement would vary depending on the circumstances 

of the case, but that the district court “should set forth enough to satisfy the appellate court 

that he has considered the parties’ arguments and has a reasoned basis for exercising his 

own legal decisionmaking authority.” Further, the Court said, when imposing a within-
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 46

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

guidelines sentence, a brief explanation may be sufficient: “Unless a party contests the 

Guidelines sentence generally under §3553(a) - that is argues that the Guidelines reflect an 

unsound judgment, or, for example, that they do not generally treat certain defendant characteristics in the proper way - or argues for departure, the judge normally need say no 

more.” The Court said that, where such arguments are made, the sentencing judge will typically explain why he has rejected them; it noted again, however, that a brief explanation 

may be sufficient. The Court approved the sentencing judge’s very brief explanation in sentencing Mr. Rita, noting that the judge had clearly heard and considered the arguments relating to Mr. Rita’s military service, his health issues, and his vulnerability in prison, but 

“simply found [them] insufficient to warrant a sentence” below the guideline range. On this 

issue, the Court concluded: “Where a matter is as conceptually simple as in the case at 

hand and the record makes clear that the sentencing judge considered the evidence and arguments, we do not believe the law requires the judge to write more extensively.”

In dissent, Justice Souter argued that it is impossible, under the current system, to 

“recognize such a presumption and still retain the full effect of Apprendi in aid of the Sixth 

Amendment guarantee.” In his view, the proper resolution to the tension between the Sixth 

Amendment jury trial right and Congressional concerns about uniformity would be for Congress to “reenact the Guidelines law to give it the same binding force it originally had, but 

with provision for jury, not judicial, determination of any fact necessary for a sentence 

within an upper Guidelines subrange.” Concurring in part and concurring in the judgment, 

Justice Scalia (with whom Justice Thomas joined), criticized the Court because, he said, 

“the Court has failed to establish that every sentence which will be imposed under the advisory Guidelines scheme could equally have been imposed had the judge relied upon no facts 

other than those found by the jury or admitted by the defendant.” In his view, “reasonableness review cannot contain a substantive component at all,” but procedural reasonableness 

review can provide some sentencing uniformity. Applying this standard, Justices Scalia and 

Thomas concluded that the sentence imposed in this case was reasonable. Justice Stevens, 

joined by Justice Ginsburg, concurred, also concluding that the sentence was reasonable, 

but emphasized that the presumption was a rebuttable one and that even an outside-theguidelines sentence would be reviewed “under traditional abuse-of-discretion principles.”

Watson v. United States, 552 U.S. 74 (2007).

In a unanimous opinion, the Supreme Court held that, for purposes of 18 U.S.C. 

§ 924(c)(1)(A), a person who receives a firearm in a drugs-for-firearms transaction does not 

“use” the firearm “during and in relation to ... [a] drug trafficking crime.” The Court observed that a circuit conflict had arisen regarding the construction of the term “use” in this 

context, and reversed the Fifth Circuit’s ruling in this case, remanding for proceedings consistent with the opinion.

The Court began by noting that section 924(c)(1)(A) prescribes a mandatory minimum sentence for a defendant who “during and in relation to any crime of violence or drug 

trafficking crime[,] . . . uses or carries a firearm,” but does not define the term “uses.” The 

court further observed that it had addressed the definition of the term in two earlier cases, 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 47

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Smith v. United States, 508 U.S. 223 (1993) and Bailey v. United States, 516 U.S. 137 

(1995). In Smith, the Court held that a person who trades a firearm for drugs does “use” the 

firearm for purposes of the statute; the Watson court observed that this ruling relied mostly 

on the “ordinary or natural meaning” of the term “use” in the context of the statute. In Bailey, the Court held that possessing a firearm when the firearm was stored near the scene of 

drug trafficking did not constitute “use” for purposes of section 924(c)(1). The Watson court 

again observed that this construction relied on the “ordinary or natural” meaning of the 

term and held that the statute “requires evidence sufficient to show an active employment 

of the firearm by the defendant, a use that makes the firearm an operative factor in relation 

to the predicate offense.”

The Court observed that neither Smith nor Bailey answered the question presented 

in the case at bar, and stated: 

With no statutory definition or definitive clue, the meaning of the verb “uses” has to

turn on the language as we normally speak it; there is no other source of a reasonable inference about what Congress understood when writing or what its words will 

bring to the mind of a careful reader.

(Internal citations omitted.) The Court concluded that “regular speech would not say that”

the person in these circumstances had “used” the item received in the barter.

The Court then turned to the government’s arguments for a different construction of 

the term, rejecting each in turn. The government’s first argument asked the Court to read 

section 924(c)(1)(A) in conjunction with section 924(d), arguing that the Smith court’s observation that section 924(d) supported its reading of 924(c) means that the Court must construe the two provisions to give the same meaning to the term “use” in both sections. The 

Court rejected this reading of Smith, and concluded that the differences between the two 

provisions render section 924(d) unhelpful in this case. This is because, the Court said, 

“[section 924(d)] tells us a gun can be ‘used’ in a receipt crime, but not whether both parties 

to a transfer use the gun, or only one, or which one.” Since the two provisions operate at different levels of specificity, the Court held, construing them differently does not bring them 

into conflict.

The government’s second argument was, the Court said, essentially a policy argument; the government characterized the ordinary meaning of the statute as leading to “unacceptable asymmetry” with Smith. The Court held that if Congress concluded that the 

asymmetry was unacceptable, it could amend the statute, noting that “law depends on respect for language and would be better served by a statutory amendment . . . than by racking statutory language to cover a policy it fails to reach.”

Justice Ginsburg concurred in the judgment and wrote separately to observe that 

distinguishing between the two parties to the gun-for-drugs transaction “makes scant 

sense,” but that she joined the judgment because she had since concluded that Smith was 

wrongly decided and would overrule it, holding that the term “use” in section 924(c)(1) was 

limited to using the firearm “as a weapon, not . . . in a bartering transaction.”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 48

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Washington v. Recuenco, 548 U.S. 212 (2006).

In this 7-2 decision, the Supreme Court reversed the Supreme Court of Washington.

The Court held that failure to submit a sentencing factor to the jury is not “structural” error which always invalidates a conviction. Rather, Blakely violations may be subject to 

harmless error review.

Recuenco was convicted of second-degree assault based on the jury’s finding that he 

was armed with a “deadly weapon.” Rather than requesting the one-year enhancement corresponding to a finding of the involvement of a deadly weapon, the state sought a mandatory three-year enhancement because the defendant was armed with a firearm. Under 

Washington law, a firearm qualifies as a deadly weapon, but the jury form did not require 

the jury to make the specific finding that a firearm was used. The trial court found that the 

weapon was a firearm and imposed the higher penalty. The state conceded before the 

Washington Supreme Court that a Sixth Amendment violation occurred under Blakely. The 

Washington Supreme Court refused to apply harmless-error analysis to the Blakely error, 

vacated the sentence, and remanded for sentencing based on the deadly weapon enhancement.

In reversing the state court, the Court noted that it has repeatedly recognized that 

“commission of a constitutional error at trial alone does not entitle a defendant to automatic 

reversal. Instead, most constitutional errors can be harmless.”

Shepard v. United States, 544 U.S. 13 (2005).

The Supreme Court, in a plurality decision (5-1-2), held that a sentencing court cannot look to police reports in making a “generic burglary” decision under the ACCA.

The ACCA mandated a fifteen-year minimum sentence for any person found to have 

committed certain federal firearms violations if that person had three prior convictions for 

“violent felonies.” Congress specified that the term “violent felony” included “burglary,” and 

the Court in Taylor v. United States held that the ACCA’s use of the term “burglary” encompasses only “generic burglary.” A “burglary” was considered a “generic burglary” if 

three elements were present: “[i] unlawful or unprivileged entry into, or remaining in, [ii] a 

building or structure, [iii] with intent to commit a crime.” In Taylor, the Court stated that a 

sentencing court, in determining whether a previous trial-based conviction is for a “generic 

burglary,” can look to the statutory definition, charging documents and jury instructions.

Taylor, therefore, does not require that recidivism be proved beyond a reasonable doubt for 

the purposes of sentencing under the ACCA. The Court in Shepard, however, did not expand Taylor to allow a sentencing court to examine the police record and complaint to determine whether an earlier guilty plea to burglary counts as a “generic burglary,” and thus 

considered a “violent felony,” for the purposes of sentencing pursuant to the ACCA.

Justice Souter, delivering the opinion of the Court, except as to Part III, concluded 

that judicial inquiry under the ACCA, as to whether a guilty plea to burglary is a “violent 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 49

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

felony,” “is limited to the terms of the charging document, the terms of a plea agreement or 

transcript of colloquy between judge and defendant in which the factual basis for the plea 

was confirmed by the defendant, or to some comparable judicial record of this information.”

In Part III of the plurality opinion, Justice Souter attempted to distinguish the situation 

found in Shepard from all other situations where a jury need not find the factor of recidivism beyond a reasonable doubt. Justice Souter, joined by Justice Stevens, Justice Scalia, 

and Justice Ginsburg, explained that the fact of a prior conviction in the Shepard context 

“is too far removed from the conclusive significance of a prior judicial record” because the 

sentencing judge would have to “make a disputed finding of fact about what the defendant 

and the state judge must have understood as the factual basis of the prior plea.”

United States v. Booker, 543 U.S. 220 (2005).

The Supreme Court, in a 5-4 decision, held that any fact (other than a prior conviction) which is necessary to support a sentence exceeding the maximum authorized by the 

facts established by a plea of guilty or a jury verdict must be admitted by the defendant or 

proved to a jury beyond a reasonable doubt. “The Sixth Amendment, as construed in 

Blakely, does apply to the Sentencing Guidelines.” A separate majority determined that the 

remedy was to excise two provisions of the SRA, rendering the federal sentencing guidelines advisory.

Booker was convicted of possession with intent to distribute cocaine. The defendant’s 

criminal history and drug quantity resulted in a recommended guidelines range of 210 to 

262 months. The sentencing judge later found, by a preponderance of the evidence, that the 

defendant possessed a greater amount than the jury found and increased the defendant’s 

sentence. Booker appealed arguing that the sentence enhancement violated his Sixth 

Amendment right to a jury trial because it permitted the judge to find facts not admitted by 

the defendant nor found by the jury. The Seventh Circuit held that the sentence enhancement violated the Sixth Amendment because it limited Booker’s right to have a jury find 

facts. The court affirmed the conviction but overturned the sentence and ruled that the 

Guidelines violated the Sixth Amendment in cases where they limit the defendant’s right to 

a jury trial.

The Government raised two issues before the Supreme Court to determine “whether 

the Apprendi line of cases applies to the Sentencing Guidelines and, if so, what portions of 

the guidelines remain in effect.” The Court noted that in Apprendi it expressly declined to 

consider the Guidelines because a statute, not guidelines, was considered in that case. However in Blakely the Court stated that “there was no distinction of the constitutional significance between the federal sentencing guidelines and the Washington procedures at issue.”

“The availability of a departure in specified circumstances does not avoid the constitutional 

issue, just as it did not in Blakely itself.” The Court rejected the government’s argument 

that there would only be a Sixth Amendment violation if the final sentence exceeded the applicable statutory maximum for the offense. The Court concluded that application of the 

Federal Sentencing Guidelines violated the Sixth Amendment. Having rejected that argument, the Court answered the question of remedy “by finding the provision of the federal 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 50

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

sentencing statute that makes the Guidelines mandatory, 18 U.S.C.A. § 3553(b)(1) 

(Supp. IV), incompatible with today’s constitutional holding.”

In a separate opinion by Justice Breyer, joined by Chief Justice Rehnquist, Justice 

O’Connor, Justice Kennedy, and Justice Ginsberg, the Court concluded that “the two provisions of the [SRA] that have the effect of making the Guidelines mandatory must be invalidated in order to allow the statute to operate in a manner consistent with congressional intent.” The Court concluded that 18 U.S.C.A. §§ 3553(b)(1) and 3742(e), which depend upon 

the Guidelines’ mandatory nature, must be severed and excised. “So modified, the Federal 

Sentencing Reform Act of 1984 . . . makes the Guidelines effectively advisory.” With this 

modification, the sentencing courts would be required to consider Guidelines ranges, but 

also be permitted to tailor the sentence in light of other statutory concerns.

Four dissenting opinions (dissenting in part) were filed. Justice Stevens dissented in 

part, joined by Justice Souter and Justice Scalia, who joined except for Part III and footnote 

17 of the dissenting opinion. Justice Stevens addressed the Court’s decision to excise and 

sever the two statutory provisions which made the application of the Guidelines mandatory.

Justice Stevens asserted that the Court’s decision to do so represented a policy choice that 

Congress had considered and decisively rejected. “While it is perfectly clear that Congress 

has ample power to repeal these two statutory provisions if it so desires, this Court should 

not make that choice on Congress’ behalf.” Justice Stevens recognized the Court’s action as 

an “extraordinary exercise of authority” that violated “the tradition of judicial restraint that 

has heretofore limited our power to overturn validly enacted statutes.”

Justice Scalia wrote a dissent, dissenting in part to the excision of the provision governing appellate review of sentences, 18 U.S.C. § 3742(e), which had, as its sole purpose, enabling the appellate courts to enforce conformity with the Guidelines. Justice Scalia asserted that “if the Guidelines are no longer binding, one would think that the provision designed to ensure compliance with them would, in its totality, be inoperative.”

Justice Thomas’s dissent concluded that the presumption of severability had not 

been overcome in Booker. According to Justice Thomas, the question remains “whether the 

unconstitutional application of certain statutory provisions and guidelines applied to 

Booker are severable from the constitutional applications of the same provisions to other 

defendants.”

Justice Breyer wrote a dissent, joined by Chief Justice Rehnquist, Justice O’Connor, 

and Justice Kennedy, disagreeing with the Court’s conclusion requiring a jury, not a judge, 

to find sentencing facts. Justice Breyer stated that he found “nothing in the Sixth Amendment that forbids a sentencing judge to determine (as judges at sentencing have traditionally determined) the manner or way in which the offender carried out the crime of which he 

was convicted.” “The upshot is that the Court’s Sixth Amendment decisions —Apprendi, 

Blakely, and today’s— deprive Congress and state legislatures of authority that is constitutionally theirs.”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 51

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Blakely v. Washington, 542 U.S. 296 (2004).

The Supreme Court, in a 5-4 decision, held that the defendant’s sentence violated his 

Sixth Amendment right to a jury trial, because the sentencing judge increased his sentence 

above the prescribed guideline range based on an aggravating factor found by the judge and 

not admitted by the defendant in his guilty plea. The State of Washington charged defendant Ralph Blakely with first-degree kidnaping. Blakely pleaded guilty to second-degree kidnaping for which the statutory maximum sentence was ten years of imprisonment. Under 

the state’s sentencing guidelines, the “standard sentencing range” or presumptive sentence 

for the kidnaping charge was 49 to 53 months. Under the Washington guidelines, the sentencing court must impose a sentence within the standard sentencing range, unless the 

court finds aggravating or mitigating circumstances by a preponderance of the evidence 

that justify an “exceptional sentence.” After conducting a sentencing hearing, the judge 

found that Blakely acted with deliberate cruelty, one of the specified statutory aggravating 

factors, and sentenced Blakely to 90 months of imprisonment. The Supreme Court found 

that this increase beyond the presumptive range was unconstitutional.

The Court held that any fact, other than a prior conviction, that raises the penalty 

beyond the prescribed statutory maximum must be submitted to a jury and proved beyond 

a reasonable doubt.” The Court defined “statutory maximum” as the “maximum sentence a 

judge may impose solely on the basis of the facts reflected in the jury verdict or admitted by 

the defendant.” In other words, the Court said, “the relevant ‘statutory maximum’ is not the 

maximum sentence a judge may impose after finding additional facts, but the maximum he 

may impose without any additional findings” beyond what the jury found in its verdict or 

what was admitted by the defendant. The majority did not address the application of the 

case to the federal sentencing guidelines.

Three dissenting opinions were filed. Justice O’Connor wrote a dissent joined by Justice Breyer in its entirety, and by Chief Justice Rehnquist and Justice Kennedy, except as 

to the section addressing the possible impact on the federal guidelines. Justice O’Connor 

warned that the majority’s opinion may bring an end to 20 years of sentencing reform. Prior 

to the enactment of the Washington guidelines, there was unguided discretion that resulted 

in racial disparity and a general lack of uniformity in sentencing. The new system “placed 

meaningful restraints on discretion” and eliminated parole. Justice O’Connor noted that the 

sentencing system sought uniformity, transparency, and accountability, and that it had 

largely met those goals. Justice O’Connor also wrote of the far-reaching impact the decision 

could have on other states’ sentencing guideline systems and the federal sentencing guidelines. 

Justice Kennedy wrote a brief separate dissent joined by Justice Breyer. Justice 

Kennedy described sentencing as a collaborative process between the legislatures and the 

courts. Justice Kennedy cited Mistretta v. United States, 488 U.S. 361 (1989), as recognizing 

that this interchange among the branches of government “is consistent with the Constitution’s structural protections.”

Justice Breyer also wrote separately in dissent joined by Justice O’Connor. Justice 

Breyer stated that this holding “threatens the fairness of our traditional criminal justice 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 52

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

system” and distorts historical sentencing practices. Justice Breyer concluded that, as a result of this opinion, legislatures will have several options for sentencing systems in the future, but that these alternative approaches are problematic because they shift power to the 

prosecutor, they lack uniformity, or they are too complex and expensive to implement.

Lastly, Justice Breyer questioned whether it will be possible to distinguish the federal sentencing guidelines from the Washington system. 

Leocal v. Ashcroft, 543 U.S. 1 (2004).

In this unanimous opinion, the Supreme Court reversed the Eleventh Circuit’s decision in Le v. United States Attorney General, 196 F.3d 1352 (11th Cir. 1999), which held 

that a conviction under the Florida DUI statute qualified as a crime of violence. In doing so, 

the Court resolved a split among the circuits on the question of whether state DUI offenses 

similar to Florida’s, which either require only a showing of negligence or do not have a mens 

rea requirement, can qualify as a crime of violence. The petitioner, a Haitian citizen, was a 

lawful permanent resident of the United States convicted under Florida law of DUI and 

causing serious bodily injury. He was ordered deported after his DUI conviction was classified as a “crime of violence” under 18 U.S.C. § 16 and therefore deemed an “aggravated felony” under the Immigration and Nationality Act (INA). The Supreme Court disagreed.

“Many states have enacted similar statutes, criminalizing DUI causing serious bodily injury or death without requiring proof of any mental state, or, in some states, appearing to 

require only proof that the person acted negligently in operating the vehicle.” “The critical 

aspect of § 16(a) is that a crime of violence is one involving the “use . . . of physical force 

against the person or property of another.” “The key phrase in § 16(a) —the ‘use . . . of physical force against the person or property of another’— most naturally suggests a higher degree of intent than negligent or merely accidental conduct.” The Court concluded that petitioner’s DUI offense, a third-degree felony, did not require proof of any particular mental

state and thus would not qualify as a “crime of violence” under sections 16(a) or (b). However, the Court did conclude that an underlying offense requiring proof of a reckless use of 

force would qualify as a crime of violence under 18 U.S.C. § 16.

Schriro v. Summerlin, 542 U.S. 348 (2004).

The Supreme Court held that Ring v. Arizona, 536 U.S. 584 (2002), did not apply 

retroactively to death penalty cases already final on direct review, because it was a procedural rule rather than a substantive rule and because Ring did not announce a watershed 

rule of criminal procedure. When the Supreme Court announced Ring, it established a new 

rule that applied to all criminal cases still pending on direct review. The Court held that 

Ring established a procedural rule because it allocated decisionmaking authority by demanding that a jury rather than a judge make findings regarding aggravating factors in 

death penalty cases. However, new rules of procedure generally do not apply retroactively 

to cases already final on direct review. The exception is that “watershed rules of criminal 

procedure” that implicate the fundamental fairness and accuracy of the criminal proceeding 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 53

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

will be applied retroactively. The Court did not find that this was a watershed rule because 

judicial factfinding did not so seriously diminish the accuracy of the proceeding so at to create an impermissibly large risk of punishing conduct inappropriately.

Justice Breyer filed a dissenting opinion joined by Justices Stevens, Souter, and 

Ginsberg. The dissenters view the right to have jury sentencing in the capital context as 

both a “fundamental aspect of constitutional liberty and also significantly more likely to 

produce an accurate assessment of whether death is the appropriate sentence.” Justice

Breyer states that juries are more capable of making community-based value judgments 

that are important in death penalty cases, that retroactivity assures more uniformity 

among similarly situated defendants, that death is different so greater accuracy is needed, 

and that giving this rule retroactive effect would not inordinately burden the criminal justice system because of the small number of prisoners affected (approximately 110 persons 

on death row). 

Harris v. United States, 536 U.S. 545 (2002) (overruled by Alleyne v. United States, 

570 U.S. 99 (2013)).

The Supreme Court, in a 5-4 decision, held that as a matter of statutory construction, that “brandishing” is a sentencing factor to be determined by the judge. This case represents the Court’s continued effort in distinguishing between offense elements and sentencing enhancements. In reaching its holding, the Court reiterated that the rule announced in Apprendi v. New Jersey, 530 U.S. 466 (2000), accords with its prior decision in 

McMillan v. Pennsylvania, 477 U.S. 79 (1986). In Apprendi, the Court stated that any fact, 

other than a prior conviction, that increases the penalty for a crime beyond the prescribed 

statutory maximum must be submitted to a jury and proved beyond a reasonable doubt. Apprendi, 530 U.S. at 490. McMillan established that statutory provisions that subject defendants to increased mandatory minimum penalties are sentencing factors that may be determined by the sentencing judge through a preponderance of the evidence.

Harris was arrested for selling illegal narcotics out of his pawnshop with an unconcealed semiautomatic pistol at his side. He was charged with violating federal drug and 

firearm laws, including 18 U.S.C. § 924(c). In drafting the indictment, the Government proceeded on the assumption that section 924(c)(1)(A) sets forth a single crime and that brandishing is a sentencing factor, to be determined by the judge. Thus, brandishing was not 

charged in the indictment. Harris was found guilty after a bench trial. The presentence report recommended a seven-year minimum sentence because he had brandished the firearm.

The district court agreed and sentenced Harris accordingly and the Fourth Circuit affirmed.

The Supreme Court first considered the statutory construction of 8 U.S.C. § 924(c) 

which begins with a principal paragraph listing the basic elements of the offense of carrying 

or using a gun during and in relation to a violent crime or drug offense. The statute then 

lists subsections that explain how the defendant shall be sentenced. Finding that this struc-
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 54

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

ture sufficiently delineates between the offense elements and sentencing factors (which traditionally involve special features of the manner in which the basic crime was perpetrated), 

the Court held that Congress did not intend brandishing to be an offense element.

After examining several important recent decisions, the Court ultimately concluded 

that subjecting defendants to increased mandatory minimum penalties via preponderance 

of the evidence does not violate Apprendi. The Court noted that Apprendi said that “any 

fact that would extend a defendant’s sentence beyond the maximum authorized by the 

jury’s verdict would have been considered an aggravated crime . . . by those who framed the 

Bill of Rights.” The Court concluded that facts increasing the mandatory minimum (but not 

extending the sentence beyond the statutory maximum) are different in that “the jury has 

authorized the judge to impose the minimum with or without the [fact] finding” at sentencing.

Ring v. Arizona, 536 U.S. 584 (2002).

The Supreme Court, in a 7-2 decision, held that the Sixth Amendment entitles defendants in capital cases to a jury determination of any aggravating factors that increase 

their maximum punishment from life imprisonment to death. The Court overruled its prior 

decision in Walton v. Arizona, 497 U.S. 639 (1990), which had upheld the Arizona state capital sentencing scheme. In Ring, the jury found the defendant guilty of first-degree felony 

murder. The sentencing judge then conducted a sentencing hearing and found the existence 

of aggravating factors beyond a reasonable doubt, and sentenced the defendant to death.

The Supreme Court noted that the defendant could not receive the death penalty unless the 

court found the existence of at least one aggravating factor beyond a reasonable doubt; 

therefore, such a finding increases the maximum punishment from life imprisonment to 

death. The Court held that, because Arizona’s enumerated aggravating factors operate as 

the “functional equivalent of an element of a greater offense,” the Sixth Amendment requires that they be found by a jury.

Justice Scalia filed a concurring opinion, joined by Justice Thomas. Justice Scalia 

noted that he never agreed with the line of cases beginning with Furman v. Georgia, 

408 U.S. 238 (1972), that invalidated the death penalty and caused states to enact death 

penalty schemes with aggravating factors. His concurrence in this case was based on the 

holding of Apprendi that the jury must find facts that are used to increase the sentence beyond what is authorized by the jury’s verdict.

Justice Kennedy filed a brief concurrence noting that he still believed Apprendi was 

wrongly decided, but that Apprendi and Walton cannot stand together. Justice Breyer filed 

an opinion concurring in the judgment but not the opinion of the majority because he believes that jury sentencing in capital cases is mandated by the Eighth Amendment and not 

by the Sixth Amendment analysis of the majority (Justice Breyer dissented in Apprendi).

Justice Breyer discussed the continued difficulty of justifying capital punishment and concluded that the “danger of unwarranted imposition of the penalty cannot be avoided” unless 

a jury makes the determination.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 55

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Justice O’Connor, joined by Chief Justice Rehnquist, filed a dissenting opinion. Justice O’Connor stated that the decision in Apprendi “was a serious mistake.” Justice O’Connor did not agree that the Constitution requires that any fact that increases the maximum 

penalty must be treated as an element and found by a jury. Justice O’Connor also discussed

the increase in habeas filings and the disruption of the criminal justice system caused by 

Apprendi.

United States v. Cotton, 535 U.S. 625 (2002).

The Supreme Court, in a unanimous decision, held that defects in an indictment do 

not automatically require reversal of a conviction or sentence. The respondents were 

charged with conspiring to distribute and to possess with intent to distribute a “detectable”

amount of powder and cocaine base. The respondents were later convicted and received a 

sentence based on the district court’s drug quantity finding of at least 50 grams of cocaine 

base. The district court did not sentence the defendants under 21 U.S.C. § 841(b)(1)(C), 

which would have provided a statutory maximum penalty of 20 years, but instead implicated the enhanced penalties of 21 U.S.C. § 841(b) which provided a sentence up to life imprisonment. Two of the respondents were sentenced to 30 years of imprisonment, while 

those remaining received life imprisonment.

The respondents argued on appeal that the court was deprived of jurisdiction because the indictment was defective due to the omission of a fact that enhanced the statutory 

maximum. They further argued that their sentences were invalid under Apprendi because 

the issue of drug quantity was neither alleged in the indictment nor before the jury. The 

Fourth Circuit reviewed for plain error and held that the district court had no jurisdiction 

to sentence based on information not contained in the indictment. The Supreme Court reversed the holding of the Fourth Circuit and noted that the reasoning of the Fourth Circuit 

was based on Ex parte Bain, 121 U.S. 1 (1887), a nineteenth century case that addresses 

the jurisdiction of the courts to interpret a revised indictment. 

The Court here overruled Bain and held that (1) a defective indictment does not by 

its nature deprive a court of jurisdiction, and (2) the omission from a federal indictment of a 

fact that enhances the statutory maximum sentence does not justify a Court of Appeals’ vacating the enhanced sentence, even though the defendant did not object in the trial court.

Buford v. United States, 532 U.S. 59 (2001).

The Supreme Court, in a unanimous decision, held that the appellate court properly 

reviewed the district’s court’s “functional consolidation” decision deferentially in light of the 

fact-bound nature of the decision, the comparatively greater expertise of the district court, 

and the limited value of uniform Court of Appeals precedent. The Court reviewed the standard of review that applies when determining whether an offender’s prior convictions are 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 56

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

consolidated, thus “related,” for the purposes of sentencing. The defendant pleaded guilty to 

armed bank robbery, a crime of violence, but he also had five prior state convictions, four of 

which were robberies. The four bank robberies were considered related because the court 

found that the robberies had been the subject of a single criminal indictment and the defendant had pleaded guilty to all four at the same time in the same court. The fifth conviction was for a drug crime. The defendant argued that all five priors, including the drug 

crime, were related because they were “functionally consolidated,” without the entry of a 

formal order of consolidation, because the sentencing judge was the same, and all five cases 

were sentenced at the same time in a single proceeding. The government disagreed, stating 

that the drug offense was handled by a different judge, a different state prosecutor, and 

with a separate judgement. The district court ruled against the defendant and held that the 

drug case was unrelated to the robbery cases and had not been consolidated for sentencing, 

either formally or functionally. The Seventh Circuit stated that in this case “the standard of 

appellate review may be dispositive” and elected to review the district court’s decision “deferentially” rather than “de novo.”

Apprendi v. New Jersey, 530 U.S. 466 (2000).

In a 5-4 decision, the Supreme Court found unconstitutional a New Jersey statute 

that increased the maximum penalty of the defendant’s weapon possession offense from 10 

to 20 years based on the trial court’s finding by a preponderance of evidence that the defendant committed a “hate crime.” “Other than the fact of a prior conviction, any fact that 

increases the penalty for a crime beyond the prescribed statutory maximum must be submitted to a jury, and proved beyond a reasonable doubt.”

The Court addressed the issue of whether constitutional protections of due process 

and rights to notice and jury trial entitled the defendant to have a jury, not a judge, decide 

bias beyond a reasonable doubt. The Court rejected the State’s three primary arguments 

that (1) the biased purpose was a traditional sentencing factor of motive; (2) McMillan authorizes a court to find a traditional sentencing factor by a preponderance of evidence; and 

(3) under Almendarez-Torres, a judge may sentence beyond the maximum. Merely labeling 

a provision a sentencing factor is not dispositive: “The defendant’s intent in committing a 

crime is perhaps as close as one might hope to come to a core criminal offense ‘element.’ ”

Recognizing that application of the statute could potentially double the defendant’s sentence, the Court rejected the State’s reliance on McMillan: “When a judge’s finding based on 

a mere preponderance of the evidence authorizes an increase in the maximum punishment, 

it is appropriately characterized as ‘a tail which wags the dog of the substantive offense.’ ”

In rejecting the State’s reliance on Almendarez-Torres, the Court distinguished the recidivist provision from the “biased purpose inquiry, [which] goes precisely to what happened in 

commission of the offense.” The Court further asserted that “there is a vast difference between accepting the validity of a prior judgment of conviction entered in a proceeding in 

which the defendant had . . . the right to require the prosecutor to prove guilt beyond a reasonable doubt, and allowing the judge to find the required fact under a lesser standard of 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 57

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

proof.” The Court also noted that “it is arguable that Almendarez-Torres was incorrectly decided, and that a logical application of our reasoning today should apply if the recidivist issue were contested,” but that revisiting that decision was not necessary to resolve the case.

In a concurring opinion, Justice Thomas, joined by Justice Scalia, asserted that “the 

Constitution requires a broader rule than the Court adopts . . . . If a fact is by law the basis 

for imposing or increasing punishment —for establishing or increasing the prosecution’s entitlement— it is an element.”

Justice O’Connor, joined by the Chief Justice, Justice Kennedy, and Justice Breyer 

dissented, finding that the majority’s “increase in maximum penalty rule” is “unsupported 

by history and case law” and rests on a “meaningless formalism.” The dissent asserted that 

the majority was overruling McMillan, and that as a result there will be a significant impact on state and federal determinate sentencing schemes. “The actual principle underlying 

the Court’s decision may be that any fact (other than prior conviction) that has the effect, in 

real terms, of increasing the maximum punishment beyond an otherwise applicable range 

must be submitted to a jury and proved beyond a reasonable doubt. The principle would 

thus apply not only to schemes . . . under which a factual determination exposes the defendant to a sentence beyond the prescribed statutory maximum, but also to all determinatesentencing schemes in which the length of a defendant’s sentence within the statutory 

range turns on specific factual determinations.”

Castillo v. United States, 530 U.S. 120 (2000).

The Supreme Court, in an 8-1 decision, held that a statute prohibiting the use or 

carrying of a “firearm” in relation to a crime of violence that subsequently increased the 

penalty when the weapon used or carried was a “machinegun,” used the word “machinegun”

and similar words to state an element of a separate, aggravated crime. The Court stated 

that the statute’s structure strongly favored the “new crime” interpretation. The Court further stated that the structure of the statute seems to suggest that the difference between 

the act of using or carrying a “firearm” and the act of using or carrying a “machinegun” is 

both substantive and substantial—a conclusion that supports a “separate crime” interpretation. Finally, the Court determined that the length and severity of an added mandatory 

sentence that turns on the presence or absence of a “machinegun” (or any of the other listed 

firearm types) weighs in favor of treating such offense-related words as referring to an element. The Court noted that these considerations make this a stronger “separate crime” case 

than either Jones v. United States or United States v. Almendarez-Torres—cases in which 

the Court was closely divided as to Congress’s likely intent. The Court concluded that Congress intended the firearm type-related words used in section 924(c)(1) to refer to an element of a separate, aggravated crime.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 58

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

United States v. Johnson, 529 U.S. 53 (2000).

The Supreme Court, in a unanimous decision, held that under 18 U.S.C. § 3624(e), a 

supervised release term does not commence until an individual “is released from imprisonment.” Therefore, the length of supervised release is not reduced by excess time served in 

prison. The defendant had two of his convictions declared invalid, pursuant to Bailey v. 

United States, 516 U.S. 137 (1995), and had served 24 months extra prison time. The defendant was released from prison, but a three-year term of supervised release was yet to be 

served on the remaining convictions. The defendant filed a motion to reduce his supervised 

release term by the amount of extra prison time he served. The district court denied the relief, explaining that supervised release commenced upon respondent’s actual release from 

incarceration, not before. The Sixth Circuit reversed and held that his supervised release 

term commenced not on the day he left prison, but when his lawful term of imprisonment 

expired. The Supreme Court, in its decision to reverse the Sixth Circuit, resolved a circuit 

split over whether the excess prison time should be credited to the supervised release term.

Compare United States v. Blake, 88 F.3d 824 (9th Cir. 1996) (supervised release commences 

on date defendants should have been released, not dates of actual release) with United 

States v. Jeanes, 150 F.3d 483 (5th Cir. 1998) (supervised release cannot run during any period of imprisonment); United States v. Joseph, 109 F.3d 34 (1st Cir. 1997) (same); United 

States v. Douglas, 88 F.3d 533 (8th Cir. 1996) (same). The Supreme Court examined the 

text of section 3624(e) which states: “[t]he term of supervised release commences on the day 

the person is released from imprisonment.” The Court concluded that the ordinary commonsense meaning of release is to be freed from confinement. The Court found additional 

support in 18 U.S.C. § 3583(a) which authorizes the imposition of a “term of supervised release after imprisonment.” Furthermore, the objectives of supervised release would be unfulfilled if excess prison time were to offset and reduce terms of supervised release. Congress intended supervised release to assist individuals in their transition to community life.

United States v. Johnson, 529 U.S. 694 (2000).

The Supreme Court resolved a split in the circuits by holding that post-revocation 

penalties relate to the original offense, and under the Ex Post Facto Clause, a law “burdening private interests” cannot be applied to a defendant whose original offense occurred before the effective date of the statute. Absent a clear indication by Congress that a statute 

applies retroactively, a statute takes effect the day it is enacted.

In the case below, the Sixth Circuit held that application of section 3583(h) (explicitly authorizing reimposition of supervised release upon revocation of supervised release) 

did not violate the Ex Post Facto Clause even though the defendant’s original offense occurred in 1993, a year before the statute was enacted. The lower court held that revocation 

penalties punish a defendant for the conduct leading to the revocation, not the original offense. Thus, because the statute was enacted before the defendant violated his supervised 

release, there was no ex post facto violation. United States v. Johnson, 181 F.3d 105 

(6th Cir. 1999). The government disavowed the position taken by the lower court of appeal, 

and “wisely so” opined the Supreme Court “in view of the serious constitutional questions 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 59

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

that would be raised by construing revocation and reimprisonment as punishment for the 

violation of the conditions of supervised release.”

In addition to making the determination that ex post facto analysis for revocation 

conduct relates to the date of the original offense, the Supreme Court found that no ex post 

facto analysis was necessary in the defendant’s case because Congress gave no indication 

that section 3583(h) applied retroactively. The statute could not be applied to the defendant 

because it did not become effective until after the defendant committed the original offense.

Nevertheless, the version of section 3583(e)(3) in effect at the time of the original offense 

authorized a court to reimpose a term of supervised release upon revocation. Congress’s unconventional use of the term “revoke” rather than “terminate” would not preclude additional supervised release, and this reading is consistent with congressional sentencing policy.

Jones v. United States, 526 U.S. 227 (1999).

The Supreme Court held that 18 U.S.C. § 2119, the federal carjacking statute, establishes three separate offenses, each of which must be charged in the indictment, proven beyond a reasonable doubt, and submitted to a jury for its verdict. The Court’s decision emphasizes the features of the carjacking statute that distinguish it from the illegal re-entry 

statute that was the focus of Almendarez-Torres v. United States, 523 U.S. 224 (1998). According to the Supreme Court, the structure of the statute and the legislative history indicate that Congress intended that the jury determine the facts which control the statutory 

sentencing range. To hold otherwise would raise serious constitutional issues.

Mitchell v. United States, 526 U.S. 314 (1999).

The Supreme Court, in a 5-4 decision, held that a defendant could plead guilty, assert the privilege against self-incrimination at the sentencing hearing, and not have a judge 

draw an adverse inference from the defendant’s sentence. The defendant had refused to testify at a sentencing hearing about her involvement in a cocaine conspiracy. The judge sentenced the defendant to ten years’ imprisonment, stating that he drew a negative inference 

from the defendant’s refusal to discuss the details of the crime. The Third Circuit affirmed 

the district court’s decision, but the Supreme Court reversed. The Supreme Court held that 

neither the defendant’s guilty plea nor her statements at a plea colloquy functioned as a 

waiver of her right to remain silent at sentencing. Furthermore, the Court held that the defendant should have been allowed to remain silent without it being held against her. The 

Court relied on Griffin v. California, 380 U.S. 609 (1995), in which the Court held that it 

was constitutionally impermissible for the prosecutor or judge to comment on a criminal defendant’s refusal to testify. The majority concluded that there is no reason not to apply this 

rule to sentencing hearings. 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 60

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Almendarez-Torres v. United States, 523 U.S. 224 (1998).

In a 5-4 decision, the Supreme Court resolved a circuit conflict, affirming the Fifth 

Circuit’s opinion holding that 8 U.S.C. § 1326(b)(2) is a penalty provision which authorizes 

an enhanced penalty for a recidivist; it does not define a separate crime. The Fifth Circuit 

had joined the First, Third, Fourth, Seventh, Eighth, Tenth, and Eleventh Circuits in holding that subsection (b)(2) is a penalty provision, in opposition to the Ninth Circuit’s opinion 

that the subsection constituted a separate crime. Subsection (a) of section 1326 prohibits an 

alien who once was deported to return to the United States without special permission, and 

it authorizes a prison term of up to two years. Subsection (b)(2) authorizes a prison term of 

up to 20 years for a deported alien under subsection (a) whose initial deportation “was subsequent to a conviction for commission of an aggravated felony.” The petitioner pleaded 

guilty to violating section 1326, admitting that he had unlawfully returned to the United 

States following deportation, and that such initial deportation was subsequent to three convictions for aggravated felonies. Inasmuch as subsection (b)(2) is a penalty provision, the 

Government is not required by the Constitution or the statute to charge the earlier aggravated felony convictions in the indictment.

Edwards v. United States, 523 U.S. 511 (1998).

The Supreme Court, in a unanimous decision, affirmed the Seventh Circuit’s opinion 

that the sentencing guidelines require the sentencing judge, not the jury, to determine both 

the amount and kind of drugs at issue in a drug conspiracy. The defendant had been 

charged under 18 U.S.C. §§ 841 and 846 with conspiracy to possess with intent to distribute 

mixtures containing cocaine and cocaine base (“crack”), and the jury had returned a general 

verdict which did not specify the object of the conspiracy. The petitioners argued that the 

drug statutes and the Constitution required the judge to assume that the jury had convicted them of a conspiracy involving the lesser object, cocaine. The Supreme Court stated 

that it was of no consequence whether the conviction was based solely on cocaine, because 

the Guidelines instruct the sentencing judge to sentence a drug conspiracy based on the offender’s relevant conduct, under USSG §1B1.3. Relevant conduct requires the sentencing 

court to base the sentence on not only the conduct which constitutes the offense of conviction, but also conduct that is “part of the same course of conduct or common scheme or plan 

as the offense of conviction.” See USSG §1B1.3(a)(2). The Court noted that the statutory 

and constitutional claims were not implicated in this case, inasmuch as the sentences imposed were “within the statutory limits of a cocaine-only conspiracy.”

Muscarello v. United States, 524 U.S. 125 (1998).

The Supreme Court, in a 5-4 decision, held that the phrase “carries a firearm” in 

18 U.S.C. § 924(c) applies to a person who knowingly possesses and conveys a firearm in a 

vehicle—including in a locked glove compartment or in the trunk of the car—in relation to a 

drug trafficking offense. In affirming the decisions of the First and Fifth Circuits, the Court 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 61

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

noted that the Federal Circuit Courts of Appeals have unanimously concluded that the 

word “carry” “is not limited to the carrying of weapons directly on the person but can include their carriage in a car.” The Court examined the legal question of whether Congress 

intended to limit the scope of the word “carry” to instances in which a gun is carried “on the 

person,” and concluded that “neither the statute’s basic purpose nor its legislative history 

support circumscribing the scope of the word ‘carry’ by applying an ‘on the person’ limitation.” The Court addressed the dissent’s argument that the rule of lenity should be applied 

because there is ambiguity in the statute. In disagreeing with the dissent, the majority 

noted that for the rule of lenity to apply, a court must conclude that there is “grievous ambiguity or uncertainty” in the statute, such that the court could make “no more than a guess 

as to what Congress intended.”

United States v. Gonzales, 520 U.S. 1 (1997).

The Supreme Court, in a 7-2 decision, held that the provisions of 18 U.S.C. § 924(c) 

mandating an additional five-year term of imprisonment that “shall [not] . . . run concurrently with any other term of imprisonment” means any other term of imprisonment, 

whether it be state or federal. The Court reversed the decision of the Court of Appeals for 

the Tenth Circuit, which had delved into legislative history to support its conclusion that 

the statute must have been limited to cases involving prior federal sentences. The Tenth 

Circuit had split from other circuit courts of appeals which had addressed the issue. The 

Supreme Court held that there was no ambiguity in the text of the statute, and “no basis in 

the text for limiting section 924(c) to federal sentences.”

United States v. LaBonte, 520 U.S. 751 (1997).

The Supreme Court, in a 6-3 decision, resolved a split among the Courts of Appeals, 

deciding that Amendment 506, promulgated by the Sentencing Commission, amending 

commentary to USSG §4B1.1, the career offender guideline, is “at odds with the plain language of [28 U.S.C.] § 994(h).” In 28 U.S.C. § 994(h), Congress directed the Commission to 

“assure” that prison terms for categories of offenders who commit a third felony drug offense or crime of violence be sentenced “at or near the maximum term authorized” by statute. The Supreme Court held that by the language “maximum term authorized,” Congress 

meant the maximum term available for the offense of conviction, including any applicable 

statutory sentencing enhancements. The enhanced penalty, from 20 to 30 years’ imprisonment, is brought before the court by the prosecutor by filing a notice under 21 U.S.C. 

§ 851(a)(1). The amendment to §4B1.1’s commentary at Application Note 2 had provided 

that the unenhanced statutory maximum should be used, in part because the unenhanced 

statutory maximum “represents the highest possible sentence applicable to all defendants 

in the category,” because section 851(a)(1) notices are not filed in every applicable case. The 

Supreme Court responded that “Congress surely did not establish enhanced penalties for 

repeat offenders only to have the Commission render them a virtual nullity.” “[T]he phrase 

‘at or near the maximum term authorized’ is unambiguous and requires a court to sentence 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 62

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

a career offender ‘at or near’ the ‘maximum’ prison term available once all relevant statutory sentencing enhancements are taken into account.” The judgment of the First Circuit 

was reversed. The Commission’s amended commentary was at odds with the plain language 

of statute at 28 U.S.C. § 994(h), and “must give way.” Cf. Stinson v. United States, 508 U.S. 

36, 38 (1993) (guidelines commentary “is authoritative unless it violates the Constitution or 

a federal statute”).

United States v. Watts, 519 U.S. 148 (1997).

The Supreme Court ruled that “a jury’s verdict of acquittal does not prevent the sentencing court from considering conduct underlying the acquitted charge, so long as that conduct has been proved by a preponderance of the evidence.” The Court granted the Government’s petition pursuant to Supreme Court Rule 12.4, and issued this per curiam opinion 

resolving a split in the Circuit Courts of Appeals by reversing the Ninth Circuit’s holding in 

United States v. Watts, 67 F.3d 790 (9th Cir. 1995), and United States v. Putra, 78 F.3d 

1386 (9th Cir. 1996). Only the Ninth Circuit had refused to permit consideration of acquitted conduct. The Court held that the guidelines did not alter the sentencing court’s discretion granted by statute at 18 U.S.C. § 3661, which provides that “[n]o limitation shall be 

placed on the information concerning the background, character, and conduct of a person 

convicted of an offense which a court of the United States may receive and consider for the 

purpose of imposing an appropriate sentence.” The Court cited Witte v. United States, 

515 U.S. 389, 402 (1995) (quoting United States v. Wright, 873 F.2d 437, 441 (1st Cir. 1989) 

(Breyer, J.)): “ ‘[V]ery roughly speaking, [relevant conduct] corresponds to those actions and 

circumstances that courts typically took into account when sentencing prior to the Guidelines’ enactment.’ ” The Supreme Court noted that Guideline §1B1.4 “reflects the policy set 

forth in 18 U.S.C. § 3661” and that the commentary to guideline §1B1.3 also provides that 

“[c]onduct that is not formally charged or is not an element of the offense of conviction may 

enter into the determination of the applicable guideline sentencing range,” and that all acts 

and omissions that were part of the same course of conduct or common scheme or plan as 

the offense of conviction (relevant conduct) must be considered whether or not the defendant had been convicted of multiple counts. The Ninth Circuit’s opinions also seemed to be 

based “on erroneous views of our double jeopardy jurisprudence,” in asserting that a jury 

verdict of acquittal “rejects” facts. See Dowling v. United States, 493 U.S. 342, 349 (1990) 

(“an acquittal in a criminal case does not preclude the Government from relitigating an issue when it is presented in a subsequent action governed by a lower standard of proof”).

Koon v. United States, 518 U.S. 81 (1996).

The Supreme Court unanimously held that an “appellate court should not review the 

[district court’s] departure decision de novo, but instead should ask whether the sentencing 

court abused its discretion.” In applying this standard, the Court noted that “[l]ittle turns, 

however, on whether we label review of this particular question [of whether a factor is a 

permissible basis for departure] abuse of discretion or de novo, for an abuse of discretion 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 63

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

standard does not mean a mistake of law is beyond appellate correction.” “The abuse of discretion standard includes review to determine that the discretion was not guided by erroneous legal conclusions.” The Court divided, however, in its determination of whether the district court abused its discretion in relying on the particular factors in this case. The majority of the Court held that the Ninth Circuit erroneously rejected three of the five downward 

departure factors relied upon by the district court. The district court properly based its 

downward departure on (1) the victim’s misconduct in provoking the defendants’ excessive 

force, §5K2.10; (2) the defendants’ susceptibility to abuse in prison; and (3) the “significant 

burden” of a federal conviction following a lengthy state trial which had ended in acquittal 

based on the same underlying conduct. However, the district court abused its discretion in 

relying upon the remaining two factors, low likelihood of recidivism, and the defendants’

loss of their law enforcement careers, because these were already adequately considered by 

the Commission in USSG §§2H1.4 and 4A1.3. The judgment of the Court of Appeals for the 

Ninth Circuit was affirmed in part and reversed in part, and the case was remanded for 

further proceedings.

Melendez v. United States, 518 U.S. 120 (1996).

The Supreme Court, in a 7-2 decision, held that the district court properly concluded 

that a Government motion under USSG §5K1.1 requesting a sentence below the applicable 

guideline range did not authorize the district court to depart below the lower statutory minimum. Justice Thomas was joined by Chief Justice Rehnquist, and Justices Scalia, Kennedy, Souter, and Ginsburg. Justices O’Connor and Breyer joined in Parts I and II of the 

opinion. Justice Stevens filed an opinion concurring in the judgment. The Court noted that 

a separate government motion pursuant to 18 U.S.C. § 3553(e) is required in order for a 

court to depart below a statutory minimum. The Court rejected the argument that the Sentencing Commission had created a “unitary” motion system in promulgating the §5K1.1 policy statement. The Court agreed with the Government that “the relevant parts of the statutes [18 U.S.C. § 3553(e) and 28 U.S.C. § 994(n)] merely charge the Commission with constraining the district court’s discretion in choosing a specific sentence after the Government 

moves for a departure below the statutory minimum. Congress did not charge the Commission with ‘implementing’ § 3553(e)’s Government motion requirement, beyond adopting provisions constraining the district court’s discretion regarding the particular sentence selected.” Justice Breyer, with whom Justice O’Connor joined, filed an opinion concurring in 

part and dissenting in part, stating the view that “the Commission had the power to create 

a ‘unitary motion system.’ ”

Neal v. United States, 516 U.S. 284 (1996).

The Supreme Court, in a unanimous decision, rejected the defendant’s argument 

that the Commission’s revised system for calculating LSD sentences under the guidelines 

(.4 milligrams per dose) requires reconsideration of the method used to determine statutory 

minimum sentences. As a threshold matter, the Court was doubtful that the Commission 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 64

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

intended its new methodology to displace the actual-weight method required by Chapman 

v. United States, 500 U.S. 453 (1991). According to the Court, “principles of stare decisis require that we adhere to our earlier decision.” The Court expressed concern about overturning an earlier precedent without intervening statutory changes casting doubt on the Chapman interpretation of the statute. While the Commission, entrusted within its sphere to 

make policy judgments, can abandon one method for what it considers a better approach, 

the Court does not have the same latitude to forsake prior interpretations of statutes.

United States v. Armstrong, 517 U.S. 456 (1996).

The Supreme Court, in an 8-1 decision, held that Rule 16(a)(1)(C) of the Federal 

Rules of Criminal Procedure “authorizes defendants to examine Government documents 

material to the preparation of their defense against the Government’s case-in-chief, but not

to the preparation of selective prosecution claims.” The defendants moved for discovery or 

dismissal of the indictment, asserting that they were singled out for prosecution under the 

much more stringent statutes and sentencing guidelines in Federal Court on crack and firearms violations because they are black. In support of their motion, they offered an affidavit 

from a paralegal in the Office of the Public Defender stating that the defendant was black 

in every one of the cases prosecuted to completion during 1991 under 21 U.S.C. §§ 841 

and 846. The district court granted the discovery motion, and upon the Government’s notice 

that it would not comply, dismissed the case. To meet the threshold showing of materiality 

necessary to obtain such discovery, the defendant must “produce some evidence of differential treatment of similarly situated members of other races or protected classes.” “A selective prosecution claim asks a court to exercise judicial power over a ‘special province’ of the 

Executive.” Heckler v. Chaney, 470 U.S. 821, 832 (1985). Because the Attorney General and 

United States Attorneys have been designated by statute as the President’s delegates to 

help him discharge his constitutional duty to see that “the Laws be faithfully executed,”

they have broad discretion to enforce federal criminal laws. There is a strong presumption 

of regularity supporting a prosecutor’s decisions, and a claimant of selective prosecution 

“must demonstrate that the federal prosecutorial policy ‘had a discriminatory effect and 

that it was motivated by a discriminatory purpose.’ ” “The justifications for a rigorous 

standard for the elements of a selective-prosecution claim thus require a correspondingly 

rigorous standard for discovery in aid of such claim.”

Bailey v. United States, 516 U.S. 137 (1995).

The Supreme Court, in a unanimous opinion, held that 18 U.S.C. § 924(c)(1) “requires evidence sufficient to show an active employment of the firearm by the defendant, a 

use that makes the firearm an operative factor in relation to the predicate offense.” According to the Court, the term “use” connotes more than mere possession or storage of a firearm 

by a person who commits a drug offense.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 65

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Witte v. United States, 515 U.S. 389 (1995).

The Supreme Court, in an 8-1 decision, held that “because consideration of relevant 

conduct in determining a petitioner’s sentence within the legislatively authorized punishment range does not constitute punishment for that conduct,” a second prosecution involving that conduct “does not violate the Double Jeopardy Clause’s prohibition against the imposition of multiple punishments for the same offense.” The Court rejected the petitioner’s 

claim that his indictment for cocaine offenses violated the Double Jeopardy Clause because 

the cocaine offenses had already been considered as relevant conduct in sentencing for an 

earlier marijuana offense. The majority relied on the Court’s previous decision in Williams 

v. Oklahoma, 358 U.S. 576 (1959) specifically rejecting the claim that “double jeopardy principles bar a later prosecution or punishment for criminal activity where that criminal activity has been considered at sentencing for a second crime.” The majority further noted that 

the consideration of relevant conduct punishes the offender “for the fact that the present offense was carried out in a manner that warrants increased punishment, not for a different 

offense (which that related conduct may or may not constitute).”

Custis v. United States, 511 U.S. 485 (1994).

The Supreme Court, in a 6-3 opinion, held that with the sole exception of convictions 

obtained in violation of the right to counsel, a defendant in a federal sentencing procedure 

does not have a right to collaterally attack the validity of previous state convictions that are 

used to enhance his sentence under the ACCA. The defendant argued that his previous convictions were invalid because of ineffective assistance of counsel, because his guilty plea 

was not knowing and intelligently made, and because he had not been adequately advised 

of his rights in opting for a “stipulated facts” trial. According to the Court, “[n]one of these 

alleged constitutional violations rises to the level of jurisdictional defect resulting from the 

failure to appoint counsel at all.” The Court refused to extend the right to collaterally attack a prior conviction used for sentencing enhancement beyond the right to counsel established in Gideon v. Wainwright, 372 U.S. 335 (1963).

Nichols v. United States, 511 U.S. 738 (1994).

The Supreme Court, in a 6-3 decision, held that “consistent with the Sixth and Fourteenth Amendments of the Constitution, an uncounseled misdemeanor conviction, valid under Scott [v. Illinois, 440 U.S. 367 (1979),] because no prison term was imposed, is also valid 

when used to enhance punishment at a subsequent conviction.” The case arose when the 

district court assessed one criminal history point against the defendant for a state misdemeanor conviction—driving under the influence (DUI) — for which the defendant was fined 

but not imprisoned. The majority of the Court reaffirmed that the Sixth Amendment right 

to counsel does not attach to criminal proceedings in which imprisonment is not imposed.

The logical consequence of that holding is that if the conviction is valid, it can be relied on 

to enhance a subsequent sentence. According to the Court, reliance on such a conviction is 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 66

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

consistent with traditional sentencing practices of using a lesser standard than that for 

proving guilt. For example, consistent with due process, the defendant could have been sentenced more severely based simply on evidence of the conduct underlying the DUI. The government would only have to prove the conduct by a preponderance of evidence. Therefore, it 

must be constitutional to use a prior conviction, where that conduct has been proven beyond 

a reasonable doubt. In deciding the case, the Court overruled Baldesar v. Illinois, 446 U.S. 

222 (1980).

United States v. Granderson, 511 U.S. 39 (1994).

The Supreme Court, in a plurality decision (5-1-1-2), interpreted 18 U.S.C. § 3565(a), 

which provides that if a person on probation possesses illegal drugs “the court shall revoke 

the sentence of probation and sentence the defendant to not less than one-third of the original sentence.” The Court held that, as that term is used in 18 U.S.C. § 3565(a), “original 

sentence” refers to the original potential imprisonment range under the guidelines. Accordingly, upon revocation of probation for possession of drugs, the minimum sentence is onethird of the maximum of the original guideline range, and the maximum sentence is the 

maximum of the original guideline range. Granderson, whose original guideline range 

was 0–6 months, had received a five-year term of probation. Upon revocation for possession 

of illegal drugs, the district court sentenced him to one-third of the five years: 20 months’

incarceration. In reversing, the Eleventh Circuit invoked the rule of lenity and held that 

“original sentence” referred to the original range, which set the maximum term of imprisonment upon revocation at six months and the minimum at two months. The opinion of the 

Court of Appeals for the Eleventh Circuit was affirmed.

Deal v. United States, 508 U.S. 129 (1993).

The Supreme Court, in a 6-3 decision, upheld the defendant’s sentence under 

18 U.S.C. § 924(c) to a five-year prison term for his first conviction, and five 20-year sentences for five additional section 924(c) convictions, to be served consecutively (105 years

total). The defendant had committed six bank robberies on six different dates, using a gun 

each time, but was convicted and sentenced for all of the offenses in one proceeding. The 

Court was not persuaded by the defendant’s assertion that the language of section 924(c) 

requiring a 20-year sentence for a “second or subsequent conviction” was ambiguous and 

should be construed under the rule of lenity in his favor. The court held that the use of the 

word “conviction” refers to the finding of guilt that necessarily precedes the entry of a final 

judgment of conviction. Each subsequent conviction carried a 20-year term. This is unlike 

statutes that have been interpreted to impose an enhanced sentence for “subsequent offenses” only if the subsequent offense was committed after the sentence for the previous offense had become final. Nor could the rule of lenity be invoked based on the total length of 

the sentence, which the defendant characterized as “glaringly unjust.” Whether the defendant was convicted of six counts in one proceeding, or in six separate trials, the result mandated by the statute would be a 105-year total sentence.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 67

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Smith v. United States, 508 U.S. 223 (1993).

The Supreme Court, in a 6-3 decision, held that the exchange or barter of a gun for 

illegal drugs constitutes “use” of a firearm for purposes of the provisions of 18 U.S.C. 

§ 924(c)(1) which sets penalties for offenses where a defendant “during and in relation to 

any crime of violence or drug trafficking crime[,] uses or carries a firearm.” The Supreme 

Court agreed with the opinion of the Court of Appeals for the Eleventh Circuit that the 

plain language of the statute “imposes no requirement that the firearm be used as a 

weapon.” Rather, any use of the weapon to in any way facilitate the commission of the offense is sufficient. United States v. Smith, 957 F.2d 835, 837 (11th Cir. 1992). In United 

States v. Harris, 959 F.2d 246, 261–62 (D.C. Cir. 1992), the Court of Appeals for the District 

of Columbia Circuit so held, but the Court of Appeals for the Ninth Circuit in United States 

v. Phelps, 877 F.2d 28 (9th Cir. 1989), held that trading the gun for drugs could not constitute “use,” and the Supreme Court decided this issue to resolve the conflict among the circuits.

Stinson v. United States, 508 U.S. 36 (1993).

The Supreme Court, in a unanimous decision, held that “commentary in the Guidelines Manual that interprets or explains a guideline is authoritative unless it violates the 

Constitution or a federal statute, or is inconsistent with, or a plainly erroneous reading of, 

that guideline.” Accordingly, the Eleventh Circuit erred in concluding that commentary was 

not binding and using that as a basis for not applying an amendment to the commentary of 

§4B1.2 which stated that felon-in-possession is not included in the term “crime of violence.”

The Supreme Court concluded that guideline commentary should be treated like an 

agency’s interpretation of its own legislative rules. “According this measure of controlling 

authority to the commentary is consistent with the role the Sentencing Reform Act contemplates for the Sentencing Commission. The Commission, after all, drafts the guidelines as 

well as the commentary interpreting them, so we can presume that the interpretations of 

the guidelines contained in the commentary represent the most accurate indications of how 

the Commission deems that the guidelines should be applied to be consistent with the 

Guidelines Manual as a whole as well as the authorizing statute.” According to the Supreme Court, “Amended Commentary is binding on the federal courts even though it is not 

reviewed by Congress, and prior judicial constructions of a particular guideline cannot prevent the Commission from adopting a conflicting interpretation that satisfies the standard 

we set forth today.”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 68

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

United States v. Dunnigan, 507 U.S. 87 (1993).

The Supreme Court, in a unanimous decision, held that a sentence enhancement 

pursuant to §3C1.1 when there has been a proper determination of perjury “is not in contravention of the privilege of an accused to testify in her own behalf.” According to the Supreme Court, “the arguments made by the [Fourth Circuit] Court of Appeals to distinguish 

[United States v.] Grayson are wide of the mark.”

United States v. R.L.C., 503 U.S. 291 (1992).

The Supreme Court, in an 8-1 decision, held that 18 U.S.C. § 5037(c)(1)(B), which 

limits the sentence of a juvenile to “the maximum term of imprisonment that would be authorized if the juvenile had been tried and convicted as an adult,” refers to the maximum 

sentence that could be imposed if the juvenile were being sentenced after application of the 

sentencing guidelines. The Court’s holding does not require plenary application of the 

guidelines to juvenile proceedings. According to the Supreme Court, “a sentencing court’s 

concern with the guidelines goes solely to the upper limit of the proper guideline range as 

setting the maximum term for which a juvenile may be committed to official detention, absent circumstances that which would warrant departure under section 3553(b).” The Court 

rejected the government’s argument that the term “authorized” in section 5037(c)(1)(B) 

means the maximum term of imprisonment provided for in the statute defining the offense.

Justice O’Connor in the dissenting opinion, joined by Justice Blackmun, stated that the 

Court should have honored “Congress’ clear intention to leave settled practice in juvenile 

sentencing undisturbed.” According to the dissent, “we should wait for the Sentencing Commission and Congress to decide whether to fashion appropriate guidelines for juveniles.”

United States v. Wilson, 503 U.S. 329 (1992).

The Supreme Court, in a 7-2 decision, held that 18 U.S.C. § 3585(b) authorizes the 

Attorney General, rather than the district court, to calculate the credit toward the term of 

imprisonment for any time the defendant spent in official detention prior to the date the 

sentence commences. According to the majority opinion, the statutory language shows that 

Congress intended that the computation of the credit occur after the defendant begins his 

sentence. Thus, a district court judge cannot apply section 3585(b) at the sentencing hearing. Although section 3585(b) does not specifically refer to the Attorney General, the Court 

found that when Congress rewrote 18 U.S.C. § 3568 and changed it to its present form in 

section 3585(b) that it was likely “that the former reference to the Attorney General was 

simply lost in the shuffle.”
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 69

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

Wade v. United States, 504 U.S. 181 (1992).

The Supreme Court, in a unanimous decision, held that “federal district courts have 

authority to review a prosecutor’s refusal to file a substantial-assistance motion and to 

grant a remedy if they find that the refusal was based on an unconstitutional motive.” According to the Supreme Court, “a claim that the defendant merely provided substantial assistance will not entitle a defendant to a remedy or even discovery or an evidentiary hearing. Nor would additional but generalized allegations of improper motive.” In the instant 

case, the defendant failed to show or allege that the government refused to file the motion 

for suspect reasons such as his race or his religion. The Court noted that it did not decide 

whether §5K1.1 implements and therefore supersedes 18 U.S.C. § 3553(e) or whether the 

two provisions pose separate obstacles. The defendant also did not claim that the government-motion requirement was itself unconstitutional, or that the requirement was superseded in this case by any plea agreement by the government to file a substantial-assistance 

motion. According to the Supreme Court, the government-motion requirement in both sections 5K1.1 and 3553(e) limiting the court’s authority “gives the government a power, not a 

duty, to file a motion when a defendant has substantially assisted.”

Williams v. United States, 503 U.S. 193 (1992).

The Supreme Court, in a 7-2 decision, held that the appellate court in reviewing a 

departure decision based on both proper and improper factors, must conclude that the district court would have imposed the same sentence absent the erroneous factor, before it can 

affirm the sentence based on its independent assessment that the departure was reasonable 

pursuant to 18 U.S.C. § 3742(f)(2). According to the Supreme Court, the use of a departure 

factor which is prohibited by a policy statement can be an incorrect application of the guidelines under 18 U.S.C. § 3742(f)(1). However, a remand is not automatically required under 

section 3742(f)(1) in order to rectify an incorrect application of the guidelines. The majority 

opinion disagreed with the dissenters that the reasonableness standard of 18 U.S.C. 

§ 3742(f)(2) was the sole provision governing appellate review of departure decisions.

Braxton v. United States, 500 U.S. 344 (1991).

The Supreme Court, in a unanimous decision, acknowledges that the initial and primary task of eliminating conflicts among the circuit courts with respect to the statutory interpretation of the guidelines lies with the Commission. According to the Supreme Court, 

“in charging the Commission ‘periodically [to] review and revise’ the guidelines, Congress 

necessarily contemplated that the Commission would periodically review the work of the 

courts, and would make whatever clarifying revisions to the guidelines conflicting judicial 

decisions might suggest.” Since the Commission has the authority to “periodically review 

and revise” and the “unusual explicit power” to decide whether and to what extent its 

amendments reducing sentences will be given retroactive effect, Justice Scalia suggests 

that the court should be more “restrained and circumspect” in using its certiorari power to 
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 70

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

resolve circuit conflicts. The Supreme Court decided not to address the first issue presented 

in the case because the Commission had requested public comment on a change to §1B1.2 

which would eliminate the conflict and because the case could be decided on other grounds.

Burns v. United States, 501 U.S. 129 (1991).

The Supreme Court, in a 5-4 decision, held that “before a district court can depart on 

a ground not identified as a ground for upward departure either in the presentence report 

or in a prehearing submission by the government, Rule 32 requires that the district court 

give the parties reasonable notice that it is contemplating such a ruling.” In the instant 

case, the presentence report concluded that there were no factors warranting a departure.

Although neither party objected to the presentence report, the district court judge announced at the end of the sentencing hearing that he was making an upward departure 

from a guideline range of 30–37 months and imposing a sentence of 60 months. The Supreme Court remanded the case for further proceedings.

Chapman v. United States, 500 U.S. 453 (1991).

The Supreme Court, in a 7-2 decision, held that the statutory construction of 21 

U.S.C. § 841(b)(1)(B)(v) requires that the carrier weight be included in determining the 

lengths of sentences for trafficking in LSD, and that this construction does not violate due 

process nor is it unconstitutionally vague.

Mistretta v. United States, 488 U.S. 361 (1989).

The Supreme Court, in an 8-1 decision, upheld the SRA, which established the 

United States Sentencing Commission, against claims that it violated the doctrine of separation of powers and excessively delegated Congress’s legislative authority. The Court upheld Congress’s placement of the Commission in the Judicial Branch of government, and 

with respect to the composition of the Commission, upheld the requirement that three federal judges serve on the Commission with non-judges. The Court held that the Commission 

was an essentially “neutral endeavor” in which judicial participation is “peculiarly appropriate.” The Court also found no fault with the power of the President to appoint members 

of the Commission and remove them for cause, holding that neither power significantly 

threatened judicial independence.
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 71

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

SELECTED SUPREME COURT CASES ON SENTENCING ISSUES

Subject Matter Index

Armed Career Criminal Act, 18 U.S.C. § 924(e)

Mathis v. United States, 136 S. Ct. 2243 (2016).

Welch v. United States, 136 S. Ct. 1257 (2016).

Johnson v. United States, 135 S. Ct. 2551 (2015).

Descamps v. United States, 570 U.S. 254 (2013).

McNeill v. United States, 563 U.S. 816 (2011).

Sykes v. United States, 564 U.S. 1 (2011).

Johnson v. United States, 559 U.S. 133 (2010).

Chambers v. United States, 555 U.S. 122 (2009).

Begay v. United States, 553 U.S. 137 (2008).

United States v. Rodriquez, 553 U.S. 377 (2008).

James v. United States, 550 U.S. 192 (2007).

Logan v. United States, 552 U.S. 23 (2007).

Shepard v. United States, 544 U.S. 13 (2005).

Rehabilitation Issues

Pepper v. United States, 562 U.S. 476 (2011).

Tapia v. United States, 564 U.S. 319 (2011).

Retroactivity, 18 U.S.C. § 3582(c)

Dorsey v. United States, 567 U.S. 260 (2012). 

Freeman v. United States, 564 U.S. 522 (2011).

Dillon v. United States, 560 U.S. 817 (2010).

Sixth Amendment Issues

Alleyne v. United States, 570 U.S. 99 (2013).

Southern Union Co. v. United States, 567 U.S. 343 (2012).

Pepper v. United States, 562 U.S. 476 (2011).

Dillon v. United States, 560 U.S. 817 (2010).

Spears v. United States, 555 U.S. 261 (2009).

Gall v. United States, 552 U.S. 38 (2007). 

Kimbrough v. United States, 552 U.S. 85 (2007).

Rita v. United States, 551 U.S. 338 (2007).

Cunningham v. California, 549 U.S. 270 (2007).

Irizarry v. United States, 553 U.S. 708 (2008)

Washington v. Recuenco, 548 U.S. 212 (2006).
Selected Supreme Court Cases on Sentencing Issues (November 2019) Page 72

UNITED STATES SENTENCING SENTENCING COMMISSION COMMISSION ║ OFFICE OF THE GENERAL GENERAL COUNSEL COUNSEL

United States v. Booker, 543 U.S. 220 (2005). 

Blakely v. Washington, 542 U.S. 296 (2004).

Schriro v. Summerlin, 542 U.S. 348 (2004). 

Shepard v. United States, 544 U.S. 13 (2005).

Ring v. Arizona, 536 U.S. 584 (2002).

Apprendi v. New Jersey, 530 U.S. 466 (2000).

Nichols v. United States, 511 U.S. 738 (1994).

Supervised Release

United States v. Johnson, 529 U.S. 53 (2000).

United States v. Johnson, 529 U.S. 694 (2000).

Use of Firearm in Crime of Violence or Drug Trafficking Crime, 18 U.S.C. § 924(c)

Dean v. United States, 137 S. Ct. 1170 (2017).

Abbott v. United States, 562 U.S. 8 (2010).

United States v. O’Brien, 560 U.S. 218 (2010).

Watson v. United States, 552 U.S. 74 (2007).

Harris v. United States, 536 U.S. 545 (2002). 

Castillo v. United States, 530 U.S. 120 (2000).

Muscarello v. United States, 524 U.S. 125 (1998).

United States v. Gonzales, 520 U.S. 1 (1997).

Bailey v. United States, 516 U.S. 137 (1995).

Deal v. United States, 508 U.S. 129 (1993).

Smith v. United States, 508 U.S. 223 (1993).