FILED

U.S. COURT OF APPEALS

ELEVENTH CIRCUIT

JULY 21, 2006

THOMAS K. KAHN

CLERK

[PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

________________________

No. 05-13205

________________________

D. C. Docket No. 04-00111-CR-ORL-31-JGG

UNITED STATES OF AMERICA,

Plaintiff-Appellant,

versus

AARON ERIC WILLIAMS,

Defendant-Appellee.

________________________

Appeal from the United States District Court

for the Middle District of Florida

_________________________

 (July 21, 2006)

Before BLACK, PRYOR and COX, Circuit Judges.

BLACK, Circuit Judge:
2

The Government appeals Aaron Eric Williams’ 204-month sentence

imposed for possessing crack cocaine with intent to distribute, in violation of 21

U.S.C. § 841(a)(1). We conclude the district court erred in mitigating Williams’

sentence based on (1) its generalized disagreement with Congress’s policy of

punishing crack cocaine offenders more severely than powder cocaine offenders

through the 100-to-1 crack-to-powder drug quantity ratio, (2) its generalized

disagreement with the Guidelines career offender enhancement, U.S.S.G. § 4B1.1,

and (3) its belief that the Government manipulated Williams’ sentence by

arranging to purchase crack cocaine instead of powder cocaine. We further

conclude that these errors are not harmless because Williams has failed to meet his

burden of showing that, considering the record as a whole, the errors did not have

a substantial effect on the court’s choice of sentence. We, therefore, vacate the

sentence as unreasonable and remand for the district court to sentence Williams

based on the individualized facts and circumstances of Williams’ case bearing

upon the sentencing considerations enumerated in 18 U.S.C. § 3553(a). 

I. BACKGROUND

In April 2003, a confidential informant told Drug Enforcement

Administration (DEA) agents and Osceola County Sheriff’s Deputies that

Williams was selling crack cocaine from his home in Kissimmee, Florida. Based
Williams sold the undercover agent 4.6 grams of crack cocaine in April, 10.1 grams of 1

crack cocaine in May, and 20.1 grams of crack cocaine in July.

3

on this tip, DEA agents initiated a sting operation to purchase crack cocaine from

Williams with the help of the confidential informant. In three separate

transactions in April, May, and July of 2003, an undercover DEA agent purchased

a total of 34.8 grams of crack cocaine from Williams. A grand jury subsequently

1

indicted Williams for one count of possessing crack cocaine with intent to

distribute, in violation of § 841(a)(1) and (b)(1)(C), and two counts of possessing

five or more grams of crack cocaine with intent to distribute, in violation of

§ 841(a)(1) and (b)(1)(B)(iii). On the day of trial, but before the jury was

empaneled, the Appellant filed a notice pursuant to § 851(a) of its intent to rely on

Williams’ prior felony drug convictions to seek enhanced punishment. On

February 1, 2005, the jury found Williams guilty of all three counts in the

indictment, making specific findings of the drug quantities involved in each

transaction.

At the sentencing hearing, the district court adopted, without objection, the

facts and Guidelines calculation set out in Williams’ presentence investigation

report (PSI). According to the PSI, Williams has an extensive criminal history,

which began in 1991, when he was sixteen years old. His scored criminal history
All references to the Sentencing Guidelines refer to the Guidelines effective 2

November 1, 2004.

4

includes five convictions for possession of crack cocaine (two of which were

committed with the intent to sell), four convictions for offenses involving

possession of marijuana, one conviction for possession with intent to sell MDMA

(a controlled substance also known as Ecstasy), and two convictions for battery of

two women, one of whom was pregnant at the time. As a result, Williams had a

total of 22 criminal history points, well above the 13 points needed to place him in

the highest criminal history category, category VI. 

The PSI calculated Williams’ base offense level at 28, pursuant to U.S.S.G.

§ 2D1.1(c)(6). Williams’ multiple prior felony convictions for drug offenses 2

qualified him as a career offender under § 4B1.1(a). Because the statutory

maximum for his offenses was life imprisonment, see 21 U.S.C. § 841(b)(1)(B),

§ 4B1.1 enhanced Williams’ offense level to 37, see U.S.S.G. § 4B1.1(b)(A). 

Williams’ advisory Guidelines range was, therefore, 360 months to life

imprisonment. 

The district court sentenced Williams to 204 months’ incarceration on all

counts, to run concurrently. The district court explained its choice of sentence at

the sentencing hearing and in its subsequent “Memorandum Sentencing Opinion,”
5

which is published at United States v. Williams, 372 F. Supp. 2d 1335 (M.D. Fla.

2005). In explaining the sentence, the district court purported to track the

sentencing factors outlined in 18 U.S.C. § 3553(a). 

At the sentencing hearing, the district court expressed “concern about the

discrepancy between powder and crack cocaine”—referring to Congress’s policy

of punishing crack cocaine offenders more severely than powder cocaine

offenders—and viewed the cocaine sentencing disparity as bearing on “the nature

and circumstances of the offense.” See id. § 3553(a)(1). The district court

suggested the harsher penalties for crack offenses “smacks of discrimination

against blacks, African-Americans.” It said crack cocaine and powder cocaine are

“the same drug” with the same effects and that the different form of the drug “has

never justified the substantial disparity in sentences.” The court also condemned

the DEA’s conduct in investigating Williams, characterizing the sting operation as

“basically set up by the Government to snare Mr. Williams.” The district court

stated, without elaboration, that this was also relevant to “the nature and

circumstances of the offense.”

In considering “the seriousness of the offense” and the need for the sentence

“to provide just punishment,” see id. § 3553(a)(2)(A), the district court disagreed

with what it called the “compounding effects” of the Guidelines, which it said
6

causes “incongruity and unjust results.” The district court was referring to the

interplay between the Guidelines career offender enhancement, U.S.S.G. § 4B1.1,

and the enhanced statutory maximum provided in 21 U.S.C. § 841(b)(1)(B) for

offenders with at least one prior felony drug conviction. The enhanced offense

levels set out in § 4B1.1(b) for career offenders vary depending on the statutory

maximum for the offense of conviction. See U.S.S.G. § 4B1.1(b). Because

Williams had a prior conviction for a felony drug offense, his statutory maximum

sentence under § 841(b)(1)(B) increased from 40 years’ imprisonment to life

imprisonment. See 21 U.S.C. § 841(b)(1)(B). The § 841(b)(1)(B) “enhancement”

had the corresponding effect under § 4B1.1(b) of increasing Williams’ offense

level from 28 to 37. The district court saw the interaction between § 841(b)(1)(B)

and § 4B1.1(b) as a “totally inappropriate way to consider the individual nature of

an offense or a defendant’s individual background” and stated it was “not going to

do it.”

With respect to the “history and characteristics of the defendant,” see id.

§ 3553(a)(1), the district court noted Williams’ “long history of criminal conduct”

and stated Williams was, therefore, “going to be spending a bunch of time in

prison.” Turning to the need for the sentence “to afford adequate deterrence,” see
7

id. § 3553(a)(2)(B), the district court opined that sending a “petty drug dealer” like

Williams to prison for 30 years was not the way to deter the illegal drug trade.

In its subsequent “Memorandum Sentencing Opinion,” the district court

again addressed the cocaine sentencing disparity. The district court stated it was

“mindful of the substantial criticism” the disparity had garnered and that evidence

suggested the disparity had a “discriminatory impact on African Americans of

whom Williams is one.” Williams, 372 F. Supp. 2d at 1339 n.8. The district

court’s disdain for the disparity factored into its choice of sentence in another way

as well. Echoing its earlier statement that the DEA had snared Williams, the

district court concluded a Guidelines sentence would not “promote respect for the

law,” see id. § 3553(a)(2)(A), because the DEA arranged a sting purchase of crack

cocaine instead of powder cocaine to obtain a longer prison sentence. Williams,

372 F. Supp. 2d at 1339. Without referring to any facts in the record, the district

court found that a powder cocaine sale would have been consistent with Williams’

prior drug sales. Id. To highlight the injustice it perceived in the Government’s

decision to purchase crack cocaine from Williams, the district court compared

Williams’ Guidelines range with the range applicable to defendants who, though
The advisory Guidelines range for a defendant convicted of selling 34.8 grams of powder 3

cocaine with a criminal history category of VI is 37 to 46 months’ imprisonment. See U.S.S.G.

§ 2D1.1(c)(13); ch. 5, pt. A. Notably, the district court did not compare Williams’ sentence to

the range applicable to a career offender convicted of selling 34.8 grams of powder cocaine: 262

to 327 months’ imprisonment. See 21 U.S.C. § 841(b)(1)(C); U.S.S.G. § 4B1.1(b); ch. 5, pt. A.

8

not career offenders, have a criminal history category of VI and are convicted of

selling the same quantity of powder cocaine. Id.

3

The district court then explained, as it did at the sentencing hearing, that a

Guidelines sentence was inappropriate for another reason, namely its disagreement

with the career offender provision in § 4B1.1. Id. According to the district court,

Williams’ past criminal conduct was already accounted for in his category VI

criminal history. Id. The “layering of Chapter 4 enhancements,” the district court

reasoned, “results in a double-compounding effect, increasing Williams’ minimum

guideline sentence . . . in light of the same criminal conduct.” Id. The district

court stated this “arbitrary compounding results in a guideline sentence much

greater than that necessary” to achieve the sentencing goals enumerated in

§ 3553(a). Id. 

Finally, the district court explained that although “Williams is a low-level

drug dealer . . . convicted of selling relatively small amounts of crack cocaine,” the

“substantial term” of 204 months’ incarceration was warranted by “the

circumstances (crack versus powder cocaine) and Williams’ long history of selling
9

illegal drugs.” Id. The Appellant subsequently appealed Williams’ sentence as

unreasonable.

II. STANDARD OF REVIEW

Our review of sentences after United States v. Booker, 543 U.S. 220, 125 S.

Ct. 738 (2005), has two components. First, we consider challenges to the district

court’s calculation of the advisory Guidelines range. Second, we review the

sentence for reasonableness. See United States v. Williams, 435 F.3d 1350, 1353

(11th Cir. 2006) (determining whether the district court correctly calculated the

Guidelines range before evaluating the reasonableness of the sentence).

A. Guidelines Calculation

“[A]s was the case before Booker, the district court must calculate the

Guidelines range accurately.” United States v. Crawford, 407 F.3d 1174, 1179

(11th Cir. 2005). We review the district court’s interpretation of the Guidelines de

novo and accept its factual findings unless clearly erroneous. United States v.

Jordi, 418 F.3d 1212, 1214 (11th Cir. 2005). An error in the district court’s

calculation of the advisory Guidelines range warrants vacating the sentence, unless

the error is harmless. See United States v. Scott, 441 F.3d 1322, 1329 (11th Cir.

2006) (applying harmless error review to Guidelines miscalculation). A
The § 3553(a) sentencing factors include the nature and circumstances of the offense and 4

the history and characteristics of the defendant; the need for the sentence to reflect the

seriousness of the offense, promote respect for the law, and provide just punishment for the

offense; the need to deter crime, protect the public, and provide the defendant with educational or

vocational training, or medical care; the kinds of sentences available; the Sentencing Guidelines

range; pertinent policy statements of the Sentencing Commission; the need to avoid unwarranted

sentencing disparities; and the need to provide restitution to victims. 18 U.S.C. § 3553(a);

United States v. Winingear, 422 F.3d 1241, 1246 (11th Cir. 2005).

10

Guidelines miscalculation is harmless if the district court would have imposed the

same sentence without the error. See id.

B. Reasonableness

If the Guidelines calculation is correct, or if the miscalculation is harmless,

we consider whether the sentence is reasonable. When reviewing a sentence for

reasonableness, we must evaluate whether the sentence achieves the purposes of

sentencing as stated in 18 U.S.C. § 3553(a). United States v. Talley, 431 F.3d 4

784, 788 (11th Cir. 2005). This evaluation must be made having “regard for . . .

the factors to be considered in imposing a sentence, as set forth in [§ 3553(a)]; and

. . . the reasons for the imposition of the particular sentence, as stated by the

district court pursuant to the provisions of section 3553(c).” Booker, 543 U.S. at

261, 125 S. Ct. at 765 (quoting 18 U.S.C. § 3742(e)(3) (1994)); see also Williams,

435 F.3d at 1355 (stating that “when reviewing for reasonableness, we must

consider both the § 3553(a) factors and the reasons given by the district court”). 
We realize a sentence could be alleged to be unreasonable on grounds other than length. 5

Here, the Government contests only the length of Williams’ sentence, so we confine our

discussion to length. Our opinion should not be read to foreclose other possible challenges to the

reasonableness of the terms of a sentence.

11

The party challenging the sentence bears the burden of establishing the sentence is

unreasonable in light of the § 3553(a) factors. Talley, 431 F.3d at 788.

In order to tailor our reasonableness standard of review to the issues in this

case, we must first identify the challenges Appellant makes to the reasonableness

of Williams’ sentence. First, Appellant argues the sentence is unreasonable,

regardless of length, because it resulted from the district court’s consideration of

impermissible factors. Second, Appellant contends in the alternative that, even if

Williams’ sentence was not affected by legal errors, the length of the sentence is

unreasonable because the record does not support a deviation from the Guidelines

range.

1. Reasons for the Sentence

With respect to Appellant’s first argument, we agree that a sentence can be

unreasonable, regardless of length, if the district court’s selection of the sentence 5

was substantially affected by its consideration of impermissible factors. This is so,

because our reasonableness inquiry is not confined to reviewing whether there are

facts and circumstances found in the record that would justify the length of the
12

sentence imposed. See United States v. Webb, 403 F.3d 373, 383 (6th Cir. 2005)

(“[R]eview for reasonableness is not limited to the length of the sentence.”

(quotation omitted)). The reasons given by the district court for its selection of a

sentence are important to assessing reasonableness. United States v. JimenezBeltre, 440 F.3d 514, 519 (1st Cir. 2006) (en banc) (stating the emphasis in

reviewing the reasonableness of a sentence “will be on the provision of a reasoned

explanation, a plausible outcome and—where these criteria are met—some

deference to different judgments by the district judges on the scene”). A sentence

based on an improper factor fails to achieve the purposes of § 3553(a) and may be

unreasonable, regardless of length. United States v. Moreland, 437 F.3d 424, 434

(4th Cir. 2006) (“A sentence may be substantively unreasonable if the court relies

on an improper factor or rejects policies articulated by Congress or the Sentencing

Commission.”).

Because the party challenging the sentence bears the burden of

demonstrating that the sentence is unreasonable, the party challenging the sentence

bears the initial burden of establishing that the district court considered an

impermissible factor at sentencing. Whether a factor is impermissible is a

question of law that we will review de novo. See United States v. Robinson, 935

F.2d 201, 203 (11th Cir. 1991) (“The application of the law to sentencing issues is
13

subject to de novo review.”). If such an error exists and was preserved for appeal,

we will vacate the sentence and remand, unless the error is harmless. See 28

U.S.C. § 2111; Fed. R. Crim. P. 52(a). The party defending the sentence has the

burden of establishing the error was harmless. See, e.g., United States v.

Mathenia, 409 F.3d 1289, 1291-92 (11th Cir. 2005).

In considering whether an error is harmless, we apply our traditional

harmless error standard: “A ‘non-constitutional error is harmless if, viewing the

proceedings in their entirety, a court determines that the error did not affect the

sentence, ‘or had but very slight effect.’ If one can say ‘with fair assurance . . .

that the sentence was not substantially swayed by the error,’ the sentence is due to

be affirmed even though there was error.” Id. at 1292 (quoting United States v.

Hornaday, 392 F.3d 1306, 1315-16 (11th Cir. 2004) (quoting Kotteakos v. United

States, 328 U.S. 750, 762, 763, 66 S. Ct. 1239, 1246, 1248 (1946))); see also

United States v. Williams, 503 U.S. 193, 203, 112 S. Ct. 1112, 1120-21 (1992)

(holding that once the party challenging the sentence shows the district court

relied on an invalid factor at sentencing, “a remand is appropriate unless the

reviewing court concludes, on the record as a whole, that the error was harmless,

i.e., that the error did not affect the district court’s selection of the sentence

imposed”); United States v. Paley, 442 F.3d 1273, 1278 (11th Cir. 2006) (stating a
14

district court’s misinterpretation of the Guidelines is harmless if the district court

would have imposed the same sentence absent the error); United States v. Jones, 1

F.3d 1167, 1171 (11th Cir. 1993) (“A sentencing error is harmless if the record as

a whole shows that the error did not affect the district court’s selection of the

sentence imposed.”). Consistent with this standard, a district court’s consideration

of an impermissible factor at sentencing is harmless if the record as a whole shows

the error did not substantially affect the district court’s selection of the sentence

imposed. 

If the error is not harmless, we will go no further, and will vacate the

sentence and remand for the district court to impose a sentence based on the

individualized facts and circumstances of the defendant’s case bearing upon the

sentencing considerations enumerated in § 3553(a). If, on the other hand, the

party defending the sentence is successful in showing the error did not

substantially affect the district court’s selection of the sentence, we must then

resolve whether the sentence is reasonable in light of the § 3553(a) factors and the

reasons given by the district court.

In sum, to succeed on a claim that an impermissible factor affected the

sentence, the party challenging the sentence has the initial burden of establishing

that the district court considered an impermissible factor in fashioning the
15

sentence. If we conclude after a de novo review that the district court considered

an impermissible factor at sentencing, and if the error was preserved, the burden

shifts to the party defending the sentence to show, based on the record as a whole,

that the error is harmless, i.e., that the error did not substantially affect the court’s

choice of sentence. If the error is not harmless, we will vacate the sentence as

unreasonable and remand for the district court to resentence the defendant based

on the individualized facts and circumstances of the defendant’s case bearing upon

the sentencing considerations enumerated in § 3553(a). If the error is harmless,

we will review the sentence for reasonableness in light of the § 3553(a) factors

and the reasons given by the district court.

2. Unreasonable Length of the Sentence 

Appellant argues that even if the district court considered only permissible

sentencing factors, the length of Williams’ sentence is unreasonable because the

facts and circumstances of Williams’ case do not warrant any deviation from the

advisory Guidelines range. In essence, Appellant contends that, assuming the

sentence is based on only permissible factors, the district court nevertheless made

a clear error of judgment in weighing those factors in Williams’ case.

We review the length of a sentence for reasonableness in light of the facts

and circumstances of the defendant’s case reflecting the sentencing considerations
16

in § 3553(a). Talley, 431 F.3d at 788. “Review for reasonableness is deferential.” 

Id. And we must bear in mind “that there is a range of reasonable sentences from

which the district court may choose.” Id. The weight to be accorded any given

§ 3553(a) factor is a matter committed to the sound discretion of the district court. 

See United States v. Fernandez, 443 F.3d 19, 32 (2d Cir. 2006). We will not

substitute our judgment in weighing the relevant factors because “[o]ur review is

not de novo.” Talley, 431 F.3d at 788. 

The district court’s choice of sentence, however, is not unfettered. When

reviewing the length of a sentence for reasonableness, we will remand for

resentencing if we are left with the definite and firm conviction that the district

court committed a clear error of judgment in weighing the § 3553(a) factors by

arriving at a sentence that lies outside the range of reasonable sentences dictated

by the facts of the case. See United States v. Martin, __ F.3d __, No. 05-16645,

2006 WL 1889902, at *10-13 (11th Cir. July 11, 2006) (concluding a seven-day

sentence for a multi-billion-dollar securities fraud was unreasonable); United

States v. Crisp, __ F.3d __, No. 05-12304, 2006 WL 1867754, at *6 (11th Cir.

July 7, 2006) (vacating a sentence as unreasonable because of the district court’s

unjustified reliance on a single § 3553(a) factor to the detriment of the others);

Moreland, 437 F.3d at 436 (concluding the district court committed “‘a clear error
17

of judgment by arriving at a sentence outside the limited range of choice dictated

by the facts of the case’”) (quoting United States v. Hawk Wing, 433 F.3d 622, 631

(8th Cir. 2006)); United States v. Smith, 440 F.3d 704, 708 (5th Cir. 2006)

(holding a non-Guidelines sentence may be unreasonable where it “represents a

clear error of judgment in balancing the sentencing factors”); United States v.

Sebastian, 436 F.3d 913, 915 (8th Cir. 2006) (holding a sentence may be

unreasonable if the district court “commits a clear error in judgment in weighing

the sentencing factors”).

III. DISCUSSION

A. Guidelines Calculation

The first step in our review is to determine whether the district court

properly interpreted and applied the Guidelines to Williams’ case to arrive at a

correct calculation of Williams’ advisory Guidelines range. See Williams, 435

F.3d at 1353. There is no dispute about the district court’s Guidelines calculation. 

The district court accurately calculated Williams’ advisory Guidelines range using

an enhanced offense level of 37 and criminal history category of VI,

corresponding to an advisory Guidelines range of 360 months to life

imprisonment. Moreover, the district court expressly considered the properly

calculated Guidelines range in imposing a non-Guidelines sentence. 
18

B. Reasonableness

1. Reasons for the Sentence

Appellant argues the district court committed multiple legal errors in

applying the § 3553(a) factors to Williams’ case. Specifically, Appellant contends

the district court erred in three ways: (1) it rejected Congress’s policy of

punishing crack cocaine offenders more severely than powder cocaine offenders;

(2) it refused to sentence Williams as a career offender, thereby rejecting

Congress’s policy of punishing recidivist drug offenders more severely; and (3) it

erroneously concluded the Government engaged in sentencing manipulation by

arranging to purchase crack cocaine instead of powder cocaine and erred in

factoring this conclusion into Williams’ sentence. According to Appellant, these

impermissible considerations affected the district court’s choice of sentence,

rendering the sentence unreasonable, regardless of length. Because these

contentions present questions of law as to the proper considerations at sentencing,

we will review de novo whether the district court considered improper factors in

fashioning Williams’ sentence.
Section 841 refers to “cocaine base,” and the Sentencing Guidelines define cocaine base 6

to mean crack cocaine. See U.S.S.G § 2D1.1(c), n.D. 

Similarly, § 841(b)(1)(A) sets the sentencing range for offenses involving 50 grams or 7

more of crack cocaine or 5 kilograms or more of powder cocaine at ten years to life in prison. If

the defendant has at least one prior conviction for a felony drug offense, § 841(b)(1)(A) requires

a sentence between 20 years and life in prison.

19

a. Impermissible Considerations Affecting the Sentence

i. The Cocaine Sentencing Disparity

Under 21 U.S.C. § 841 and § 2D1.1 of the Sentencing Guidelines, a

defendant convicted of an offense involving “cocaine base” (i.e., crack cocaine)6

faces a longer possible sentence than a defendant convicted of an offense

involving the same amount of powder cocaine, a chemically-similar substance. 

This disparity is commonly referred to as the “100-to-1” ratio, so named because

of the relative quantities of each drug required to trigger the mandatory sentencing

ranges in § 841(b). For example, § 841(b)(1)(B) provides that offenses involving

5 grams or more of crack cocaine or 500 grams or more of powder cocaine call for

sentences in the range of 5 to 40 years’ imprisonment. Where the defendant has at

least one prior conviction for a felony drug offense, § 841(b)(1)(B) enhances the

sentencing range to ten years to life in prison. Congress enacted harsher penalties 7

for crack cocaine than for powder cocaine based on its conclusion that crack

cocaine poses a greater threat to society. Specifically, Congress found crack
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cocaine (1) has a more rapid onset of action, (2) is more potent, (3) is more

addictive, (4) is less expensive than powder cocaine, (5) has widespread

availability, (6) more highly correlates with the incidence of violence and other

crimes, (7) is more likely to have physiological effects, and (8) is more likely to

attract users who are young or especially vulnerable. See United States v. Byse, 28

F.3d 1165, 1169 (11th Cir. 1994) (quoting United States v. Thurmond, 7 F.3d 947,

953 (10th Cir. 1993)); U.S. Sentencing Comm’n, Special Report to the Congress:

Cocaine and Federal Sentencing Policy 118 (1995). The Sentencing Commission

adopted the same 100-to-1 crack-to-powder cocaine ratio in establishing the Drug

Quantity Table in U.S.S.G. § 2D1.1(c), which sets the offense levels for drug

offenses. For example, § 2D1.1(c)(6) designates offense level 28 for offenses

involving 20 to 35 grams of crack cocaine or 2 to 3.5 kilograms of powder

cocaine.

In 1994, Congress directed the Sentencing Commission to conduct a study

of the disparities in penalties for different forms of cocaine and to make

recommendations about retaining or modifying the disparities. See Violent Crime

Control and Law Enforcement Act of 1994, Pub. L. No. 103-322, § 280006, 108

Stat. 1796, 2097 (1994). Pursuant to this directive, the Commission issued a

report to Congress in 1995 in which it agreed with Congress’s finding that “crack
The Sentencing Commission’s reports are available at http://www.ussc.gov/reports.htm.

8

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cocaine poses greater harms to society than does powder cocaine,” but concluded

“it [could not] recommend a ratio differential as great as the current 100-to-1

quantity ratio.” U.S. Sentencing Comm’n, Special Report to the Congress:

Cocaine and Federal Sentencing Policy 195-96 (1995). One reason why the 8

Commission rejected the 100-to-1 ratio was that Congress adopted it prior to the

Guidelines taking effect, and the Commission believed that many, but not all, of

the attendant additional harms of crack vis-à-vis powder cocaine (such as the

increase in violent and other crimes) are now accounted for in the Guidelines. 

Id. at 196 (“[I]f Congress believed that certain factors warranted a 100-to-1

quantity ratio and if the subsequently adopted guidelines provided a punishment

for some of those factors, then, as a logical matter, the ratio should be lowered by

an amount commensurate with the extent to which these factors are addressed by

the guidelines.”). 

The Commission subsequently proposed Guidelines amendments that would

eliminate entirely the sentencing disparity between crack and powder cocaine. 

See Notice of Submission to Congress of Amendments to the Sentencing

Guidelines, 60 Fed. Reg. 25,074, 25,076 (May 10, 1995). Although Congress

stated “the current 100-to-1 quantity ratio may not be the appropriate ratio,” it
22

rejected the Commission’s proposals because “the evidence clearly indicates that

there are significant distinctions between crack and powder cocaine that warrant

maintaining longer sentences for crack-related offenses” and “gross sentencing

disparities” would result if the proposals were to take effect without Congress

lowering the statutory mandatory minimum penalties. H.R. Rep. No. 104-272, at 4

(1995), reprinted in 1995 U.S.C.C.A.N. 335, 337; see also Federal Sentencing

Guidelines, Amendment, Disapproval, Pub. L. No. 104-38, § 1, 109 Stat. 334, 334

(1995). 

The Commission issued a second report in 1997, again at the direction of

Congress. U.S. Sentencing Comm’n, Special Report to the Congress: Cocaine and

Federal Sentencing Policy (1997). In this report, the Commission reiterated its

earlier finding that “although research and public policy may support somewhat

higher penalties for crack than for powder cocaine, a 100-to-1 quantity ratio

cannot be justified.” Id. at 2. The Commission recommended that Congress adjust

the mandatory sentencing ranges to reflect a 5-to-1 ratio. Id. Congress, however,

took no action.

In 2002, at the request of the Senate Judiciary Committee, the Commission

issued a third report on the crack-to-powder disparity. U.S. Sentencing Comm’n,

Report to the Congress: Cocaine and Federal Sentencing Policy (2002). In the
For example, the Commission pointed to studies showing the effects of prenatal crack 9

cocaine exposure were the same for powder cocaine and that the epidemic of young users and

distributors “never materialized to the extent feared.” U.S. Sentencing Comm’n, Report to the

Congress: Cocaine and Federal Sentencing Policy 93-97 (2002).

For example, the Commission stated that although studies showed harmful conduct 10

(such as violence) occurs more often in crack cocaine offenses than in powder cocaine offenses,

“it occurs in only a relatively small minority of crack cocaine offenses.” U.S. Sentencing

Comm’n, Report to the Congress: Cocaine and Federal Sentencing Policy 100 (2002). Thus, “to

the extent that the 100-to-1 drug ratio was designed to account for the harmful conduct . . . , it

sweeps too broadly by treating all crack cocaine offenders as if they committed these various

harmful acts, even though most crack cocaine offenders in fact had not.” Id. Although the

Commission recognized that “some differential in the quantity-based penalties for crack cocaine

and powder cocaine is warranted” because sentencing enhancements did not account for the fact

that “trafficking in crack cocaine is associated with somewhat greater levels of systemic crime,”

23

report, the Commission “firmly and unanimously” declared the 100-to-1 drug

quantity ratio “is unjustified and fails to meet the sentencing objectives set forth

by Congress.” Id. at 91. The Commission made four principal findings. First, it

found that current penalties exaggerate the relative harmfulness of crack cocaine.9

Id. at 93-97. Although the Commission found that crack was the most addictive

form of cocaine because of the method of ingestion, it concluded this difference

alone did not warrant the 100-to-1 ratio. Id. at 94. Second, the Commission

concluded the current penalties sweep too broadly and apply most often to lowerlevel offenders, creating disparate penalties in comparison to similar powder

cocaine offenders and overstating the culpability of most crack cocaine offenders. 

Id. at 97-100. Third, the Commission found the penalties overstate the seriousness

of most crack cocaine offenses and fail to provide adequate proportionality.10
it opined that this consideration did not justify the 100-to-1 ratio. Id. at 101-02. 

24

Id. at 100-02. Fourth, the Commission found that the current penalties impact

minorities most severely, fostering disrespect for the criminal justice system. Id.

at 102-03. Based on these findings, the Commission recommended that Congress

revise the mandatory sentencing range for crack and powder cocaine to implement

a 20-to-1 drug quantity ratio. Id. at 107. The Commission also asked Congress for

guidance in changing the Guidelines structure to better target the most serious

drug offenders. Id. at 108. Again, Congress did not act on the Commission’s

recommendations. 

With this background in mind, we turn to the district court’s treatment of the

cocaine sentencing disparity. The district court disapproved of the severity of

Congress’s disparate treatment of crack cocaine offenders relative to powder

cocaine offenders. At sentencing, the district court expressed its belief that the

disparity “smacks of discrimination” and that the difference between crack cocaine

and powder cocaine “has never justified the substantial disparity in sentences.”

Even though the district court did not completely reject Congress’s policy of

imposing harsher penalties on crack offenders, it took into account its personal

disagreement with Congress’s judgment as to how much harsher the penalties for
See also United States v. Miller, 450 F.3d 270, 275 (7th Cir. 2006) (agreeing with 11

Pho and Eura).

25

crack offenders should be. To the extent the district court did so, it considered an

impermissible factor in fashioning Williams’ sentence.

The First Circuit’s decision in United States v. Pho, 433 F.3d 53 (1st Cir.

2006), and the Fourth Circuit’s decision in United States v. Eura, 440 F.3d 625

(4th Cir. 2006), are particularly instructive. The district courts in both cases 11

categorically rejected the 100-to-1 drug quantity ratio because they believed it

overstated what the penalties ought to be for crack cocaine offenders relative to

powder cocaine offenders. Pho, 433 F.3d at 58-59; Eura, 440 F.3d at 631-32. In

sentencing the defendants below the advisory Guidelines range, the district courts

failed to mention any facts concerning the defendants as individuals that would

have warranted non-Guidelines sentences, but instead relied on the general

inequities they perceived existed in the 100-to-1 ratio. Pho, 433 F.3d at 64; Eura,

440 F.3d at 634. The First and Fourth Circuits vacated the sentences, concluding

that district courts are bound by Congress’s policy judgments concerning the

appropriate penalties for federal offenses. Pho, 433 F.3d at 62-63; Eura, 440 F.3d

at 633-34. Both courts held that sentences must be based on individualized

aspects of the defendant’s case that fit within the § 3553(a) factors, and not on
Post-Booker, we have rejected a defendant’s challenge to the reasonableness of his 12

sentence predicated on the disparity between crack and powder cocaine. See United States v.

Marlin, 147 F. App’x 122, 124 (11th Cir. 2005) (unpublished opinion). 

26

generalized disagreement with congressional sentencing policy. Pho, 433 F.3d at

64-65; Eura, 440 F.3d at 634.

We agree with the First and Fourth Circuit’s conclusions. Congress’s

decision to punish crack cocaine offenders more severely than powder cocaine

offenders is plainly a policy decision. It reflects Congress’s judgment that crack

cocaine poses a greater harm to society than powder cocaine. We have repeatedly

held Congress’s disparate treatment of crack cocaine offenders is supported by a

rational basis. See, e.g., Byse, 28 F.3d at 1168-71 (rejecting equal protection

challenge that the crack-to-powder cocaine disparity constitutes intentional race

discrimination); United States v. Sloan, 97 F.3d 1378, 1383-84 (11th Cir. 1996)

(holding the sentencing disparity is supported by a rational basis). The 100-to-1 12

drug quantity ratio not only reflects Congress’s policy decision that crack

offenders should be punished more severely, but also reflects its choice as to how

much more severe the punishment should be. Federal courts are not at liberty to

supplant this policy decision. See Pho, 433 F.3d at 62-63; Eura, 440 F.3d at 633;

see also Mistretta v. United States, 488 U.S. 361, 364, 109 S. Ct. 647, 650-51

(1989) (“Congress, of course, has the power to fix the sentence for a federal crime,
27

and the scope of judicial discretion with respect to a sentence is subject to

congressional control.” (internal citation omitted)). Although the two drugs may

be chemically similar, their effect on society is not the same, and it is not for the

courts to say just how much worse crack cocaine is than powder cocaine. This is

simply an impermissible sentencing consideration. As the Seventh Circuit aptly

put it: “§ 3553(a) . . . does not include a factor such as ‘the judge thinks the law

misguided.’” Miller, 450 F.3d at 275.

Williams, however, asserts that the crack versus powder cocaine sentencing

disparity is a valid consideration under § 3553(a)(6), which requires courts to

consider “the need to avoid unwarranted sentence disparities among defendants

with similar records who have been found guilty of similar conduct.” Several

district courts that have addressed the issue agree with Williams’ position. See,

e.g., United States v. Fisher, __ F. Supp. 2d __, 2005 WL 2542916, at *8-9

(S.D.N.Y. Oct. 11, 2005); United States v. Smith, 359 F. Supp. 2d 771, 781 (E.D.

Wis. 2005). Powder cocaine offenders, however, have not been found guilty of

similar conduct in any relevant sense. Congress has determined that crack

offenders and powder offenders are not similarly situated, and that the disparities

caused by its choice of the 100-to-1 drug quantity ratio are warranted. See Pho,

433 F.3d at 64 (“Congress plainly believed that not all cocaine offenses are equal
28

and that trafficking in crack involves different real conduct than trafficking in

powder. . . . Clearly, then, Congress intended that particular disparity to exist, and

federal courts are not free to second-guess that type of decision.”). The district

court’s rejection of the 100-to-1 drug quantity ratio, therefore, cannot be justified

under § 3553(a)(6).

Williams also contends the district court did not impermissibly usurp

Congress’s policy judgment because Williams was sentenced within the statutory

range. He argues the 100-to-1 ratio embedded in the Guidelines is not Congress’s

policy, but the Sentencing Commission’s policy, one the Commission has

unanimously rejected. He suggests that the district courts can exercise their

sentencing discretion to reject the advisory crack cocaine Guidelines without

running afoul of Congress’s policy judgment. 

Williams is incorrect in suggesting the 100-to-1 ratio embedded in the

Guidelines is merely the Sentencing Commission’s policy and not Congress’s

policy. In determining the threshold quantities for triggering the statutory

sentencing ranges in § 841(b), Congress decided on a 100-to-1 differential, and the

Sentencing Commission was left no choice but to employ the same ratio in

crafting the various Guidelines ranges within those statutory ranges. See id. at 63

(“As the Sentencing Commission recognized when it superimposed the guidelines
29

on the statutory framework, it would be illogical to set the maximum and

minimum sentences on one construct and then to use some other, essentially

antithetic construct as the basis for fashioning sentences within the range.”). 

Indeed, Congress rejected the Commission’s proposal that would have equated the

drugs for Guidelines purposes because of the gross sentencing disparities that

would result if the Guidelines did not employ the same drug quantity ratio as the

statutory scheme. See H.R. Rep. No. 104-272, at 4 (1995), reprinted in 1995

U.S.C.C.A.N. 335, 337. The same is true if instead of equating the two drugs, the

Guidelines used a different drug quantity ratio, say a 20-to-1 ratio. See Pho, 433

F3d at 63-64. If the Guidelines used a 20-to-1 ratio, a first time offender

convicted of selling 50 grams of crack cocaine (the equivalent of one kilogram of

powder cocaine in our hypothetical) would have a Guidelines range of 63 to 78

months’ imprisonment, see U.S.S.G. § 2D1.1(c)(7), but would have a mandatory

minimum sentence of 120 months’ incarceration under § 841(b)(1)(A). In

contrast, a first time offender convicted of selling 49 grams of crack cocaine (the

equivalent of 980 grams of powder cocaine in our hypothetical) would also have a

Guidelines range of 63 to 78 months’ imprisonment, but would not be subject to

the 120-month mandatory minimum. See id. § 841(b)(1)(B). In this scenario, the

difference of one gram of crack cocaine would result in a sentencing disparity of at
30

least 42 months. Thus, the statutory minimums and maximums and the Guidelines

reflect Congress’s policy decision to punish crack offenses more severely than

powder cocaine offenses by equating one gram of crack to 100 grams of cocaine. 

The same unwarranted disparities between similarly situated defendants

would result if a district court were permitted to use its discretion to disregard the

100-to-1 ratio. Thus, a district court’s rejection of the 100-to-1 ratio embedded in

the Guidelines not only countermands Congress’s policy choice, but also

undermines sentencing uniformity in direct contravention of § 3553(a)(6)’s

command that district courts seek to avoid unwarranted sentencing disparities

between similarly situated defendants. See Pho, 433 F.3d at 63-64; Eura, 440

F.3d at 633 (“[G]iving a sentencing court the authority to sentence a defendant

based on its view of an appropriate ratio between crack cocaine and powder

cocaine would inevitably result in an unwarranted disparity between similarly

situated defendants in direct contradiction to the specific mandate of 18 U.S.C.

§ 3553(a)(6).”). Of course, some disparity between similarly situated defendants

is an inevitable result of Booker. See Booker, 543 U.S. at 263, 125 S. Ct. at 766-

67 (“We cannot and do not claim that use of a ‘reasonableness’ standard will

provide the uniformity that Congress originally sought to secure.”). This

inevitable disparity, however, should only be the product of the district court’s
31

discretion in weighing individualized § 3553(a) factors in a given case, not the

consequence of the district court’s “general, across-the-board policy

considerations.” Pho, 433 F.3d at 62.

Williams is correct that a sentence below the Guidelines range in a crack

cocaine case may be reasonable, so long as it reflects the individualized, casespecific factors in § 3553(a). It may be that for some of the reasons stated in the

Sentencing Commission’s reports, the Guidelines range in a given crack case

overstates the seriousness of the particular defendant’s offense or that

individualized mitigating factors counsel against a Guidelines sentence. See Eura,

440 F.3d at 637 (Michael, J., concurring) (“While the Commission’s findings

alone cannot justify a below-guidelines sentence, in certain cases they can help

sentencing courts analyze the § 3553(a) factors and select a sentence that is

‘sufficient, but not greater than necessary’ to punish, deter, and rehabilitate the

defendant.”). But to say Congress’s choice of a 100-to-1 drug quantity ratio is

never justified is a categorical rejection of congressional policy, not an

individualized, case-specific consideration. Congress concluded the 100-to-1 ratio

is justified, and the courts have no authority to change that.

In short, the district court erred in mitigating Williams’ sentence based on

its personal disagreement with Congress’s policy decision to employ a 100-to-1,
32

crack-to-powder drug quantity ratio in punishing crack cocaine offenders more

severely than powder cocaine offenders. In so doing, the district court

impermissibly usurped Congress’s authority to set sentencing policy and failed to

properly consider § 3553(a)(6)’s directive to avoid unwarranted sentence

disparities between similarly situated defendants. We agree, moreover, with the

Fourth Circuit that “allowing sentencing courts to subvert Congress’ clearly

expressed will certainly does not promote respect for the law, provide just

punishment for the offense of conviction, or result in a sentence reflective of the

offense’s seriousness as deemed by Congress.” Id. at 633 (majority opinion).

ii. Career Offender Guideline Provision

Appellant next argues the district court erred in refusing to sentence

Williams as a career offender. There is no dispute that Williams qualified as a

career offender under U.S.S.G. § 4B1.1. At sentencing, however, the district court

stated the career offender enhancement “is a totally inappropriate way to consider

the individual nature of an offense or a defendant’s individual background” and

said it was not going to sentence Williams as a career offender. In its sentencing

memorandum, the district court again explained what it considered to be the

“arbitrary compounding” effect of the career offender enhancement. Williams,

372 F. Supp. 2d at 1339. This, too, was error.
33

In creating the Sentencing Commission and charging it with establishing

sentencing policies and practices for the federal criminal justice system, Congress

directed the Commission to:

assure that the guidelines specify a sentence to a term of

imprisonment at or near the maximum term authorized for categories

of defendants in which the defendant is eighteen years old or older

and—

(1) has been convicted of a felony that is—

(A) a crime of violence; or

(B) an offense described in section 401 of the

Controlled Substances Act (21 U.S.C. 841) . . . ; and

(2) has previously been convicted of two or more prior

felonies, each of which is—

(A) a crime of violence; or 

(B) an offense described in section 401 of the

Controlled Substances Act (21 U.S.C. 841). . . .

28 U.S.C. § 994(h). Section 994(h) reflects Congress’s policy that repeat drug

offenders receive sentences “at or near” the enhanced statutory maximums set out

in § 841(b). See United States v. LaBonte, 520 U.S. 751, 762, 117 S. Ct. 1673,

1679 (1997) (holding “the phrase ‘at or near the maximum term authorized’ . . .

requires a court to sentence a career offender ‘at or near’ the ‘maximum’ prison
34

term available once all relevant statutory sentencing enhancements are taken into

account”). 

Congress’s goal was not simply to punish offenders with prior criminal

histories more severely than first time offenders; Congress also wanted to target

specific recidivism, particularly repeat drug offenders. There is no question

Williams is a recidivist drug dealer. To the extent the district court believed

Williams’ prior criminal history was adequately taken into consideration in his

criminal history category of VI, it ignored Congress’s policy of targeting recidivist

drug offenders for more severe punishment. The district court, therefore, erred in

mitigating Williams’ sentence based on its disagreement with the career offender

Guidelines provision.

iii. Sentencing Factor Manipulation

Finally, Appellant argues the district court erred in mitigating Williams’

sentence based on its belief that the DEA “snared” Williams by arranging to

purchase crack cocaine from him, when a powder cocaine purchase would have

been consistent with his prior drug sales. The district court’s decision to mitigate

Williams’ sentence because of the DEA’s conduct in investigating Williams calls

to mind a claim we have referred to as “sentencing factor manipulation.” United

States v. Sanchez, 138 F.3d 1410, 1414 (11th Cir. 1998). 
35

A sentencing factor manipulation claim “‘requires us to consider whether

the manipulation inherent in a sting operation, even if insufficiently oppressive to

support an entrapment defense, . . . or due process claim, . . . must sometimes be

filtered out of the sentencing calculus.’” Id. (quoting United States v. Connell, 960

F.2d 191, 194 (1st Cir. 1992)). The claim focuses on the Government’s conduct

and “points to ‘the opportunities that the sentencing guidelines pose for

prosecutors to gerrymander the district court’s sentencing options and thus,

defendant’s sentences.’” Id. (quoting Connell, 960 F.2d at 194).

We need not decide whether a finding of sentencing factor manipulation is a

valid mitigating consideration under § 3553(a) because, even if it can be, it was

not an appropriate consideration here. There is no question Williams’ arrest and

conviction was the result of a valid sting operation, and the DEA no more

“snared” Williams or engaged in sentencing factor manipulation than in any other

sting operation. To say a district court may factor into a crack cocaine offender’s

sentence the bare fact that the Government chose to purchase crack instead of

powder cocaine, without more, would undermine Congress’s policy of punishing

crack cocaine offenders more severely and impermissibly interfere with the

executive branch’s performance of legitimate law enforcement practices. Contrary

to the district court’s conclusion, it does not promote respect for the law to imply
We note that all five of Williams’ prior felony cocaine convictions listed in the PSI 13

involved crack cocaine; two of those were convictions for possessing crack cocaine with intent to

sell.

36

Government misconduct from the mere fact that the Government chose to

purchase crack cocaine from a crack dealer instead of any other controlled

substance. To the extent the district court considered this fact as a mitigating

13

consideration, it erred as a matter of law. This is not to say that sentencing

manipulation may never be a valid consideration in sentencing. In this case,

however, it was error to mitigate Williams’ sentence based on the fact that the

DEA purchased crack cocaine from Williams instead of powder cocaine.

b. Harmless Error

Because Appellant objected to the district court’s consideration of these

impermissible factors, it is Williams’ burden under our traditional harmless error

standard to show, based on the record as a whole, that the errors did not

substantially affect the district court’s choice of sentence. See Mathenia, 409 F.3d

at 1292. Williams has failed to meet his burden. 

Williams points to nothing in the record showing the errors did not

substantially affect the district court’s choice of sentence. A review of the

sentencing transcript and the district court’s sentencing memorandum instead

shows the district court devoted the overwhelming majority of its explanation of
37

the sentence to expressing its disagreement with the cocaine sentencing disparity,

the career offender provision, and the DEA’s decision to purchase crack cocaine

from Williams. Although the record reflects that the district court also considered

individualized facts and circumstances of Williams’ case—such as the relatively

small amount of crack cocaine involved in his offenses—the district court’s

explanation of Williams’ sentence was so permeated by its consideration of

impermissible factors that we are unable to conclude the errors did not have a

substantial effect on its choice of sentence. The errors are, therefore, not harmless,

and we must vacate the sentence and remand for the district court to resentence

Williams solely on the basis of the individualized facts and circumstances of

Williams’ case bearing on the § 3553(a) factors. 

2. Unreasonable Length of the Sentence

Having concluded Williams’ sentence is unreasonable because it is based on

impermissible factors, we do not reach Appellant’s alternative argument that,

assuming the district court considered only proper factors in crafting Williams’

sentence, the length of the sentence is nevertheless unreasonable because the

record does not justify any deviation from the advisory Guidelines range. We

express no opinion as to whether there are individual facts and circumstances in

Williams’ case that would make a 204-month sentence reasonable. 
38

IV. CONCLUSION

We conclude, after a de novo review, that the district court considered

impermissible factors in crafting Williams’ sentence. Because Williams failed to

show, based on the record as a whole, that the errors did not substantially affect

the district court’s choice of sentence, we conclude the errors are not harmless. 

We, therefore, vacate Williams’ sentence as unreasonable without reaching

Appellant’s alternative argument that the record does not justify the length of the

sentence imposed. On remand, the district court must resentence Williams based

on the individual facts and circumstances of Williams’ case bearing on the

§ 3553(a) factors. We express no opinion as to what sentence the district court

should impose after properly applying the § 3553(a) factors.

VACATED AND REMANDED.