*

The Honorable Gerald E. Rosen, Chief Judge of the United States District Court for the Eastern

District of Michigan, sitting by designation.

RECOMMENDED FOR FULL-TEXT PUBLICATION

Pursuant to Sixth Circuit I.O.P. 32.1(b)

File Name: 13a0196p.06

UNITED STATES COURT OF APPEALS

FOR THE SIXTH CIRCUIT _________________

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

TRAVIS R. HOGG,

 Defendant-Appellant.

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No. 11-6105

Appeal from the United States District Court

for the Middle District of Tennessee at Nashville.

No. 3:10-cr-99-1—William J. Haynes, Jr., District Judge.

Argued: July 25, 2012

Decided and Filed: July 26, 2013 

Before: COLE and COOK, Circuit Judges; ROSEN, Chief District Judge.*

_________________

COUNSEL

ARGUED: Michael C. Holley, FEDERAL PUBLIC DEFENDER’S OFFICE, Nashville,

Tennessee, for Appellant. Brent A. Hannafan, UNITED STATES ATTORNEY’S

OFFICE, Nashville, Tennessee, for Appellee. ON BRIEF: Michael C. Holley,

FEDERAL PUBLIC DEFENDER’S OFFICE, Nashville, Tennessee, for Appellant.

Brent A. Hannafan, UNITED STATES ATTORNEY’S OFFICE, Nashville, Tennessee,

for Appellee.

1
No. 11-6105 United States v. Hogg Page 2

_________________

OPINION

_________________

ROSEN, Chief District Judge.

I. INTRODUCTION

Defendant/Appellant Travis R. Hogg was charged in a two-count indictment with

possession with intent to distribute fifty grams or more of crack cocaine and possession

with intent to distribute an unspecified quantity of cocaine. On March 21, 2011,

Defendant pled guilty to a lesser included variant of the first of these offenses,

possession with intent to distribute five grams or more of crack cocaine, and he was

sentenced to a 188-month term of imprisonment on September 13, 2011.

Defendant now appeals the district court’s denial of two motions to withdraw his

guilty plea. The first of these motions rested upon newly-discovered evidence

concerning criminal charges brought against the lead detective in Defendant’s case. In

the second motion, Defendant argued that the district court violated Fed. R. Crim. P.

11(b)(1)(H)-(I) by incorrectly advising him of the statutory penalty range for the lesser

included offense to which he pled guilty. Beyond these challenges to the district court’s

rulings, Defendant contends for the first time on appeal that the Government offered him

an inducement to plead guilty that was not included in his written plea agreement.

While this case was pending on appeal, and after the parties had completed their

briefing, the Supreme Court issued its ruling in Dorsey v. United States, __ U.S. __, 132

S. Ct. 2321, 2326 (2012), holding that defendants who are sentenced after the August 3,

2010 effective date of the Fair Sentencing Act of 2010 (“FSA”), Pub. L. No. 111-220,

124 Stat. 2372, are entitled to the benefit of the “new, more lenient” statutory penalties

set forth in this enactment for crack cocaine offenses. Dorsey overrode the law of this

Circuit as it stood at the time Defendant was sentenced, which held that the courts should

apply the statutory penalty provisions in effect at the time a defendant committed his

offense. See United States v. Carradine, 621 F.3d 575, 580 (6th Cir. 2010).
No. 11-6105 United States v. Hogg Page 3

Understandably, then, the district court in this case failed to anticipate the ruling in

Dorsey, and instead advised Defendant of the pre-FSA statutory penalty range for the

lesser included offense to which he pled guilty.

This post-plea development calls to mind two maxims that arguably might guide

us in deciding this appeal. First, the Government urges us to apply the principle of “no

harm, no foul,” contending that Defendant received precisely the 188-month sentence

for which he bargained, and that this sentence is readily justified, even under the postFSA sentencing regime, by the over fifty grams of crack cocaine for which Defendant

admitted responsibility in his plea agreement. Next, we are tempted to caution

Defendant to “be careful what you wish for,” because in exchange for the 188-month

plea deal he now wishes to spurn, he received (i) the opportunity to plead guilty to an

offense involving significantly less crack cocaine than he admitted responsibility for in

his plea agreement, (ii) the dismissal of the second count of the indictment, and

(iii) apparent freedom from the prospect that the Government might pursue charges

arising from a second incident occurring after his initial arrest.

As we discuss below, however, while these maxims carry an undeniable

commonsense appeal, our precedents compel us to chart a different course under the

unique facts and procedural posture of this case. Indeed, we find ourselves drawn

toward yet a third well-known expression — namely, that “no good deed goes

unpunished” — because despite the district court’s commendable effort to address the

potential impact of the FSA at Defendant’s plea hearing, neither the court nor counsel

correctly anticipated the effect of this new enactment on the statutory penalty range for

the offense to which Defendant agreed to plead guilty. In light of this error — or

perhaps lack of clairvoyance — and the resulting Rule 11 violation in the advice given

to Defendant at his plea hearing, we find that Defendant should have been permitted to

withdraw his guilty plea, and we REVERSE and REMAND to the district court for

further proceedings consistent with this ruling.
No. 11-6105 United States v. Hogg Page 4

1

As discussed below, Defendant has since produced affidavits from these individuals denying

that they made the statements attributed to them in Detective Edwards’ search warrant affidavit.

2

The Government has not brought any charges arising from the drugs found during Defendant’s

March 10, 2010 arrest. Defendant contends on appeal that the Government promised during plea

bargaining to refrain from prosecuting him for his conduct on this occasion, but that this promise was

erroneously omitted from the parties’ plea agreement.

II. FACTUAL AND PROCEDURAL BACKGROUND

A. Defendant’s Arrest

On September 2, 2009, officers of the Wilson County Sheriff’s Department went

to a residence at 2404a Phillips Road in Lebanon, Tennessee to execute an arrest warrant

for domestic assault against Defendant Travis Hogg. After knocking on the front door,

the officers arrested Defendant as he attempted to leave the residence through the back

door. Defendant confessed to one of the officers, Detective John Edwards, that he had

been smoking marijuana when the officers arrived at his home.

Following Defendant’s arrest, Detective Edwards applied for a warrant to search

the Phillips Road residence, citing Defendant’s admission to marijuana use and the

purported statements of two of Defendant’s acquaintances that Defendant lived at this

address and possessed or sold narcotics at this location.1 Upon obtaining the requested

search warrant, Detective Edwards and other officers searched the Phillips Road

residence and found just over 55 grams of crack cocaine, approximately 167 grams of

powder cocaine, and multiple weapons.

While on bond, Defendant was arrested on March 10, 2010 at his mother’s house

pursuant to an unrelated, outstanding arrest warrant, with Detective Edwards again

among the officers present on this occasion. Defendant gave his consent to search the

premises, and also showed Detective Edwards where he kept marijuana, cocaine, and

digital scales at his mother’s home.2

 The day after this arrest, Defendant gave a

statement in which he admitted to selling drugs but denied that the cocaine found in the

Phillips Road residence back in September of 2009 belonged to him.
No. 11-6105 United States v. Hogg Page 5

3

The Government agreed to dismiss the second count of the indictment upon Defendant’s

sentencing for this lesser included crack cocaine offense.

B. Defendant’s Indictment and Guilty Plea

On April 28, 2010, a federal grand jury returned a two-count indictment charging

Defendant with possession with intent to distribute fifty grams or more of crack cocaine

and possession with intent to distribute an unspecified amount of cocaine. On March 21,

2011, Defendant entered into a plea agreement under Fed. R. Crim. P. 11(c)(1)(C) that

called for him to “enter a voluntary plea of guilty to a lesser included offense of the

charge in Count One of the indictment” — namely, possession with intent to distribute

five grams or more of crack cocaine. (R. 21, Plea Agreement at ¶ 3, PageID 36.)3

 The

plea agreement recited the parties’ agreement and understanding that the statutory

penalty range for this lesser included offense was “not . . . less than five years nor more

than forty years [of] imprisonment.” (Id. at ¶ 4.) The parties further agreed to a

recommended advisory sentencing range under the U.S. Sentencing Guidelines of

188 to 235 months of imprisonment, and the plea agreement called for the district court

to impose a sentence of 188 months’ imprisonment. (Id. at ¶¶ 10(c), 11, PageID 42-43.)

As the factual basis for his guilty plea, Defendant acknowledged in the agreement (i) that

he “did unlawfully, knowingly, and intentionally possess with intent to distribute

50 grams or more of a mixture and substance containing a detectable amount of cocaine

base, that is, crack cocaine,” (ii) that the controlled substances seized from the Phillips

Road residence in connection with his September 2, 2009 arrest included approximately

167 grams of powder cocaine and 55.2 grams of cocaine base, and (iii) that, for purposes

of determining relevant conduct under the Sentencing Guidelines, “the total amount of

cocaine base for which he is responsible is between at least 50 grams but less than

150 grams.” (Id. at ¶¶ 8(a),(f),(g), PageID 38-40.) 

At Defendant’s March 21, 2011 plea hearing, the district court and counsel

addressed the possible impact of the FSA on the statutory penalty range for the offense

to which Defendant was pleading guilty. In particular, the district court noted the

parties’ statement in the plea agreement that Defendant faced a “five-year mandatory
No. 11-6105 United States v. Hogg Page 6

4

Detective Edwards subsequently pled guilty to a federal charge of obstructing an official

proceeding, and was sentenced to a 220-month term of imprisonment by the U.S. District Court for the

Middle District of Tennessee.

minimum sentence” and a “maximum possible penalty [of] 40 years,” but the court

further advised Defendant that depending “in large part about whether the Fair

Sentencing Act passed in 2010 applies to your case,” it was “possible that the statutory

maximum penalty is life imprisonment and that there is a ten-year mandatory minimum

sentence.” (R. 33, Plea Hearing Tr. at 15-16, PageID 129-30; see also id. at 20-21,

PageID 134-35.) Counsel for both the Government and Defendant stated their views that

the 5-to-40-year statutory sentencing range stated in the plea agreement was accurate,

but they agreed that it was prudent “out of [an] abundance of caution” to inform

Defendant that he might instead be facing a statutory penalty range of ten years to life

imprisonment. (Id. at 9-12, PageID 123-26.) At the conclusion of the plea hearing, the

district court accepted both Defendant’s guilty plea and the plea agreement.

C. Defendant’s First Motion to Withdraw His Guilty Plea

Just a few days after the court accepted Defendant’s guilty plea, Detective

Edwards was arrested and charged by state authorities with property theft, and he was

later charged in a federal criminal complaint with attempting to sell confidential

investigative information to the targets of a federal drug investigation.4 In light of these

developments, Defendant filed an April 8, 2011 motion to withdraw his guilty plea,

arguing that the “newly emerging evidence” of Detective Edwards’ legal troubles would

improve his prospects at trial by “undermin[ing] the credibility of the key witness

against him.” (R. 23, Defendant’s 4/8/2011 Motion to Withdraw Plea at 1, PageID 49.)

Defendant also submitted affidavits from two of the individuals cited in Detective

Edwards’ affidavit for the warrant to search the Phillips Road residence, denying that

they had made the inculpatory statements attributed to them by Detective Edwards.

Following a June 20, 2011 hearing, the district court denied Defendant’s motion.

Specifically, in a July 12, 2011 memorandum and order, the district court observed that

Defendant had not asserted his innocence as a ground for withdrawing his guilty plea,
No. 11-6105 United States v. Hogg Page 7

but instead had maintained that “because Edwards’s credibility has been tarnished by the

charges against him, the Government lacks a strong enough case to convict Defendant.”

(R. 40, 7/12/2011 Mem. Op. at 8, PageID 368.) Yet, in light of the facts admitted by

Defendant in his plea agreement — including, most notably, his admission that “he did

unlawfully, knowingly, and intentionally possess[] with intent to distribute 50 grams or

more of crack cocaine” — the court found that Defendant’s guilt of the charge to which

he pled had been established beyond a reasonable doubt, regardless of any developments

that might have called Detective Edwards’ credibility into question. (Id.) As additional

grounds for denying Defendant’s motion, the district court pointed to (i) the “months of

negotiations” that led to Defendant’s plea agreement, (ii) the benefits gained by

Defendant through this agreement, (iii) Defendant’s extensive familiarity with the

criminal justice system, and (iv) Defendant’s knowledge prior to his plea that his

acquaintances disputed the statements attributed to them in Detective Edwards’ search

warrant affidavit. (Id. at 9-11, PageID 369-71.)

D. Defendant’s Second Motion to Withdraw His Guilty Plea

On August 22, 2011, Defendant filed a second motion to withdraw his guilty

plea, contending that the district court had violated Fed. R. Crim. P. 11(b)(1)(H)-(I) by

misinforming him as to the applicable statutory penalty range for the offense to which

he had pled guilty. As noted in this motion, while the district court and counsel had

considered at the March 21, 2011 plea hearing whether this penalty range might be

affected by the FSA, “no one present considered the best-possible-case

scenario” — namely, that the FSA would govern Defendant’s sentence, resulting in a

statutory penalty range of zero to twenty years for a drug offense involving at least five

grams but less than 28 grams of crack cocaine. (R. 47, Defendant’s 8/22/2011 Second

Motion to Withdraw Plea at 4, PageID 399.) Defendant further observed that with this

lower statutory maximum of twenty years, his offense level under the applicable career

offender provision of the U.S. Sentencing Guidelines, U.S.S.G. § 4B1.1, would be

decreased from 34 to 32, resulting in an advisory Sentencing Guideline range of 151 to

188 months rather than the 188-to-235-month range set forth in his plea agreement. (See
No. 11-6105 United States v. Hogg Page 8

id.) If these effects of the FSA had been accurately disclosed to him, Defendant asserted

that he would not have accepted the Government’s offer of a 188-month sentence — an

offer which, as Defendant noted, was at the top of the post-FSA Sentencing Guideline

range and “only about four years short of the [post-FSA] statutory maximum of 240

months” — and he contended that the failure to make these disclosures violated Rule 11

and warranted the withdrawal of his guilty plea. (Id. at 4-5, 8-10, PageID 399-400, 403-

05.)

In a September 8, 2011 memorandum and order, the district court denied

Defendant’s motion. In so ruling, the district court pointed to the decision in Carradine,

621 F.3d at 580, in which this Court held that the FSA lacked any statement of

congressional intent that would overcome the usual presumption that a criminal

defendant should be subject to the “penalties in place at the time the crime was

committed.” Although Carradine did not squarely address the applicability of the FSA

to a defendant who committed his crime before the statute’s enactment but is sentenced

after its effective date, the district court noted that a number of district courts in this

Circuit had read Carradine as foreclosing the availability of the FSA’s more lenient

penalties in this situation, and it concluded, consistent with this authority, that Defendant

had been accurately advised as to the applicable statutory penalty range in his plea

agreement and at the plea hearing. (See R. 52, 9/8/2011 Mem. Op. at 12-14, PageID

520-22.) Alternatively, even if the FSA were to govern Defendant’s sentencing, the

district court found that Defendant still would be subject to the same 5-to-40-year

statutory penalty range disclosed in his plea agreement and at the plea hearing, in light

of his admission in his plea agreement to a quantity of crack cocaine (55.2 grams) that

exceeded the 28-gram threshold that continued to trigger a 5-to-40-year penalty range

in the wake of the FSA’s enactment. (See id. at 14-16, PageID 522-24.) Accordingly,

the district court found no violation of Rule 11 in Defendant’s plea agreement or at his

plea hearing, and thus concluded that there were no grounds for allowing Defendant to

withdraw his plea.
No. 11-6105 United States v. Hogg Page 9

5

A different standard would govern our review of the district court’s denial of Defendant’s first

motion to withdraw his guilty plea, as that motion did not rest on any Rule 11 violation, nor did Defendant

challenge the voluntariness of his plea in that motion. We need not consider the merits of the district

court’s resolution of this motion, however, in light of our determination that Defendant should have been

permitted to withdraw his guilty plea on the grounds identified in his second motion.

Following this ruling, the district court conducted a September 9, 2011

sentencing hearing. In the course of this hearing, Defendant reasserted his contention

that the correct statutory penalty range for the offense to which he pled guilty was zero

to twenty years of imprisonment, but the district court overruled this objection for the

reasons given in its ruling on Defendant’s second motion to withdraw his guilty plea.

(See R. 60, Sentencing Hearing Tr. at 7-8, PageID 595-96.) Upon resolving this and

other matters raised by the parties, the district court sentenced Defendant to the 188-

month term of imprisonment called for in his Rule 11(c)(1)(C) plea agreement. This

appeal followed, with Defendant challenging the district court’s denial of his two

motions to withdraw his guilty plea, and also arguing that his plea agreement

erroneously omitted a promise of leniency made by the Government in the course of the

parties’ plea negotiations.

III. ANALYSIS

A. The Standards Governing This Appeal

In his second motion to withdraw his guilty plea, Defendant argued that his plea

was not knowing, voluntary, and intelligent in light of the district court’s purported

failure to comply with the dictates of Rule 11(b)(1)(H)-(I) during the course of the plea

hearing. Assuming that Defendant is able to establish this claimed violation — a point

challenged by the Government — we review such a violation of Rule 11 for harmless

error. See Fed. R. Crim. P. 11(h); see also United States v. Martin, 668 F.3d 787, 791

(6th Cir. 2012). Under the plain language of the Rule itself, a “variance from the

requirements of this rule is harmless error if it does not affect substantial rights.” Fed.

R. Crim. P. 11(h). The Government bears the burden of establishing the harmlessness

of a Rule 11 violation. See United States v. Vonn, 535 U.S. 55, 62-63, 122 S. Ct. 1043,

1048 (2002).5
No. 11-6105 United States v. Hogg Page 10

6

As noted earlier, defense counsel was somewhat equivocal on this point, opining that Defendant

was subject to a mandatory statutory minimum of “at least five years based on his plea,” but agreeing with

the district court’s suggestion that Defendant should be advised in the alternative that the statutory penalty

range for the offense to which he pled guilty might be ten years to life imprisonment. (Id. at 9-11, PageID

123-25.)

As we have recognized, however, a defendant surrenders the comparative benefit

of harmless error review, and instead must satisfy the more demanding plain error

standard, if he fails to timely object to a claimed Rule 11 violation. See Martin, 668 F.3d

at 791. In that event, “the tables are turned on demonstrating the substantiality of any

effect on a defendant’s rights: the defendant who sat silent at trial has the burden to

show that his ‘substantial rights’ were affected.” Vonn, 535 U.S. at 62-63, 122 S. Ct. at

1048. More specifically, if a defendant “seeks reversal of his conviction after a guilty

plea, on the ground that the district court committed plain error under Rule 11, [he] must

show a reasonable probability that, but for the error, he would not have entered the plea.”

United States v. Dominguez Benitez, 542 U.S. 74, 83, 124 S. Ct. 2333, 2340 (2004). The

defendant then has the “further burden,” under plain error review, to “persuade the court

that the error seriously affected the fairness, integrity or public reputation of judicial

proceedings.” Vonn, 535 U.S. at 63, 122 S. Ct. at 1048 (internal quotation marks,

alteration, and citations omitted).

At oral argument, the Government suggested that Defendant must meet the more

stringent plain error standard because his counsel not only failed to object to any claimed

Rule 11 error in the course of the plea hearing, but to the contrary agreed with the district

court’s determination that the offense to which Defendant was pleading guilty was

subject to a 5-to-40-year statutory penalty range. (See R. 33, Plea Hearing Tr. at 9,

PageID 123.)6

 Yet, the Government failed to argue in its brief on appeal that the plain

error standard should apply, but instead asserted that Rule 11’s harmless error provision

governs our review of the district court’s denial of Defendant’s second motion to

withdraw his guilty plea. (See Appellee’s Br. at 47 (citing Fed. R. Crim. P. 11(h).)

Arguably, then, the Government has forfeited the opportunity for plain error review of

Defendant’s claim of a Rule 11 violation at his plea hearing. See United States v.

Rodriguez, 664 F.3d 1032, 1035 (6th Cir. 2011) (reviewing de novo a challenge to a
No. 11-6105 United States v. Hogg Page 11

Sentencing Guideline determination “because the Government has not asked us to apply

the plain-error standard in light of [the defendant’s] failure to object below”); United

States v. Williams, 641 F.3d 758, 763 (6th Cir. 2011) (“[W]e will not apply the plainerror standard unless requested to do so by one of the parties.”). See generally Hunter

v. United States, 160 F.3d 1109, 1113 (6th Cir. 1998) (confirming that “as with any other

argument, the government can forfeit a waiver argument by failing to raise it in a timely

fashion”).

At any rate, the Government’s acknowledgment of the harmless error standard

in its appellate brief is understandable, because Defendant preserved his entitlement to

this more favorable standard of review by expressly claiming a Rule 11 violation in the

course of the district court proceedings. Although, as noted, he and his counsel did not

identify this purported Rule 11 error at the first available opportunity, the plea hearing,

Defendant’s second motion to withdraw his guilty plea rested squarely on the contention

that the district court violated Rule 11(b)(1)(H)-(I) by “misinform[ing] [him] as to the

statutory penalty range for the offense to which he pled guilty.” (R. 47, Defendant’s

8/22/2011 Second Motion to Withdraw Plea at 1, PageID 396.) The district court, in

turn, explicitly addressed Defendant’s claim of a Rule 11 violation in its opinion denying

this motion. (See R. 52, 9/8/2011 Mem. Op. at 10-11, 14-15, PageID 518-19, 522-23.)

This was sufficient to secure harmless error review of this claim. Under the

express language of Fed. R. Crim. P. 52(b), plain error review is required if an issue was

“not brought to the court’s attention.” Here, however, Defendant unequivocally

advanced his Rule 11 challenge in the lower court proceedings and gave the district court

an opportunity to rule on this matter. Likewise, our precedents do not demand strict

contemporaneity in complaining of purported defects in plea proceedings, but instead

hold that plain error review is avoided so long as a defendant raises a claim of Rule 11

error in the course of the district court proceedings and prior to sentencing. See, e.g.,

United States v. Lalonde, 509 F.3d 750, 759 (6th Cir. 2007) (“We review violations of

Rule 11 for plain error if the defendant did not object before the district court.”); United

States v. Murdock, 398 F.3d 491, 496 (6th Cir. 2005) (construing the Supreme Court’s
No. 11-6105 United States v. Hogg Page 12

7

We note that a number of other circuits also would apply harmless error review under the

circumstances presented here, where a defendant did not raise any objections at his plea hearing but then

moved prior to sentencing to withdraw his guilty plea on the basis of a purported Rule 11 violation. See,

e.g., United States v. Ortiz-Garcia, 665 F.3d 279, 285 (1st Cir. 2011); United States v. Gray, 581 F.3d 749,

752-53 (8th Cir. 2009); United States v. Hairston, 522 F.3d 336, 341 (4th Cir. 2008); United States v.

Harrington, 354 F.3d 178, 183 (2d Cir. 2004); United States v. Powell, 354 F.3d 362, 367 (5th Cir. 2003);

United States v. Fernandez, 205 F.3d 1020, 1027-28 (7th Cir. 2000).

Vonn decision as “instruct[ing] us to review violations of Rule 11 for plain error if the

defendant did not object before the district court”); United States v. Syal, 963 F.2d 900,

903, 905-07 (6th Cir. 1992) (reviewing a Rule 11 violation for harmless error, where the

defendant raised his Rule 11 claim in a motion to withdraw his guilty plea brought prior

to sentencing); United States v. Payton, No. 08-1628, 380 F. App’x 509, 512 (6th Cir.

June 9, 2010) (reviewing a claim of an unknowing and involuntary plea for plain error

“[b]ecause [the defendant] did not object at his Rule 11 plea hearing or otherwise seek

to withdraw his plea before the district court”); cf. Martin, 668 F.3d at 791 & n.1 (noting

that the defendant’s statements at his sentencing, “[l]iberally construed,” could “qualify

as a timely objection” that triggered harmless error review of a claimed Rule 11

violation). See generally United States v. Gibbs, 182 F.3d 408, 431 (6th Cir. 1999)

(holding that the harmless error standard applies so long as the defendant “brought the

issue . . . to the attention of the district court”).7 Accordingly, having cleared away the

procedural underbrush and determined that the harmless error standard of Rule 11(h)

governs our review, we now proceed to the even more challenging and nuanced

substantive issues raised by this appeal.

B. Defendant Must Be Permitted to Withdraw His Guilty Plea Due to the

Incorrect Statement of the Statutory Penalty Range Made to Him in His

Plea Agreement and at the Plea Hearing, Where This Misstatement Affected

Defendant’s Substantial Rights by Changing the Calculus Under Which He

Weighed and Accepted the Government’s Plea Offer.

1. In the Wake of the Supreme Court’s Decision in Dorsey, the District

Court Violated Rule 11 by Misinforming Defendant of the Statutory

Penalty Range for the Offense to Which He Pled Guilty.

Under Rule 11(b)(1), before a district court may accept a guilty plea, it must

“inform the defendant of, and determine that the defendant understands,” a number of
No. 11-6105 United States v. Hogg Page 13

rights and other pertinent considerations, including “any maximum possible penalty,

including imprisonment, fine, and term of supervised release,” and “any mandatory

minimum penalty.” Fed. R. Crim. P. 11(b)(1)(H)-(I). In his second motion to withdraw

his guilty plea, Defendant contended that the district court violated these Rule 11

provisions by misinforming him of the statutory penalty range he faced for the offense

to which he pled guilty. Although the penalty range set forth in Defendant’s plea

agreement and identified by the district court at Defendant’s plea hearing was correct

under the then-current law of this Circuit, we agree that this penalty range must now be

viewed as mistaken in light of the Supreme Court’s supervening decision in Dorsey, __

U.S. __, 132 S. Ct. 2321, with the result that Rule 11 was violated in the course of taking

Defendant’s guilty plea.

Count One of the two-count indictment in this case charged Defendant

with possession with intent to distribute 50 grams or more of crack cocaine. Under the

express terms of his plea agreement, Defendant “agree[d] to enter a voluntary plea of

guilty to a lesser included offense of the charge in Count One of the

indictment” — namely, “the crime of possessing with intent to distribute 5 grams or

more of cocaine base.” (R. 21, Plea Agreement at ¶ 3, PageID 36.) Under the applicable

statutory provision at the time Defendant committed this offense in September of 2009,

the drug offense to which Defendant agreed to plead guilty, involving five or more but

less than fifty grams of crack cocaine, triggered a statutory sentencing range of five to

forty years of imprisonment, see 21 U.S.C. § 841(b)(1)(B)(iii) (2009), and Defendant’s

plea agreement recited this sentencing range, (see R. 21, Plea Agreement at ¶ 4, PageID

36). Upon the enactment of the FSA in 2010, however, the penalty provisions of

§ 841(b)(1) have been amended with respect to crack cocaine offenses, with the statute

now providing that a drug offense must involve at least 28 grams of crack cocaine in

order to subject a defendant to the five-to-forty-year sentencing range set forth at

§ 841(b)(1)(B).

As the district court and the parties correctly recognized at Defendant’s March

21, 2011 plea hearing, the enactment of the FSA had a potential impact on the district
No. 11-6105 United States v. Hogg Page 14

8

Interestingly, in its discussion of the potential impact of the FSA, the district court appeared to

anticipate the Supreme Court’s decision in Dorsey, opining that “the intent of Congress was for the Fair

Sentencing Act to be applied to all sentences that were imposed after the act was passed.” (Id. at 9, PageID

123.) As noted earlier, however, this view ran counter to the law of this Circuit at the time, which held

that the FSA lacked any expression of congressional intent that would overcome the usual rule that a

defendant should be subject to the penalties in place at the time he committed his offense. See Carradine, 621 F.3d at 580.

court’s obligation under Rule 11(b)(1)(H)-(I) to inform Defendant of the statutory

penalty range for the offense to which he was pleading guilty. (See R. 33, Plea Hearing

Tr. at 4-5, 8-9, PageID 118-19, 122-23.) In particular, the district court observed that

the FSA had the effect of “lower[ing] the sentence” for certain crack cocaine offenses,

and it decided that the “safest course of action,” in light of the uncertain state of the law

in the wake of the FSA’s enactment, was to advise Defendant of the two alternative

statutory penalty ranges he faced if “the new act applies” or if it “does not apply.” (Id.

at 9-12, PageID 123-26.)8

 In carrying out this chosen course of action, however, the

district court elected to advise Defendant that he potentially faced either (i) the five-toforty-year statutory penalty range identified in his plea agreement, or (ii) an increased

statutory penalty range of ten years to life imprisonment. (See id. at 11-12, 15-16,

PageID 125-26, 129-30.)

Regrettably, judges do not have a crystal ball, and this advice turned out to be

inaccurate. While the district court was forced to speculate as to the potential impact of

the FSA, we have the benefit of hindsight — namely, the Dorsey decision, which was

not available to the district court — that enables us to ascertain the correct statutory

penalty range for the offense to which Defendant pled guilty. In Dorsey, __ U.S. at __,

132 S. Ct. at 2326, the Supreme Court held that the FSA’s “more lenient penalty

provisions apply to offenders who committed a crack cocaine crime before August 3,

2010, but were not sentenced until after August 3.” Because Defendant was not

sentenced until September of 2011, well after the effective date of the FSA, the district

court should have applied the § 841(b)(1) penalty provisions as amended by the FSA in

computing Defendant’s statutory penalty range and advising him of this range at the plea

hearing. More specifically, for the drug offense to which Defendant agreed to plead

guilty, involving “five grams or more of cocaine base,” (R. 21, Plea Agreement at ¶ 3,
No. 11-6105 United States v. Hogg Page 15

9

As noted earlier, the parties had already completed their appellate briefing before Dorsey was

issued, and neither side sought leave to file supplemental briefs addressing the impact of this Supreme

Court decision. Thus, the parties’ respective positions on this point must be gleaned largely from their

contentions at oral argument.

PageID 36), Defendant should have been advised that he was subject to the statutory

penalty range for drug offenses involving less than 28 grams of cocaine base — i.e., zero

to twenty years of imprisonment, see 21 U.S.C. § 841(b)(1)(C) (2011). Because he was

instead informed that he faced a five-to-forty-year statutory sentencing range, and

perhaps even a higher range of ten years to life imprisonment, we conclude that this

advice violated Rule 11(b)(1)(H)-(I) as an inaccurate statement of the statutory penalty

range for the offense to which Defendant pled guilty.

In resisting this conclusion at oral argument,9

 the Government first suggested that

Defendant remains ineligible for the zero-to-twenty-year statutory penalty range

established under the FSA for drug offenses involving less than 28 grams of crack

cocaine, in light of his admissions in his plea agreement (i) that he “unlawfully,

knowingly, and intentionally possess[ed] with intent to distribute 50 grams or more of

a mixture and substance containing a detectable amount of cocaine base,” and (ii) that,

“for the purpose of determining the applicable advisory sentencing range under the

United States Sentencing Guidelines, . . . the total amount of cocaine base for which he

is responsible is between at least 50 grams but less than 150 grams.” (R. 21, Plea

Agreement at ¶¶ 8(a),(g), PageID 38, 40.) As we noted at the outset, this argument

amounts to a claim of “no harm, no foul” — in the Government’s view, Defendant

cannot complain about a five-to-forty-year statutory penalty range when the drug

quantity to which he has admitted would trigger this elevated range even in the wake of

Dorsey.

Although this argument has some superficial appeal, we find that it unduly

discounts the important role of Rule 11 in ensuring that a defendant is fully informed of

the consequences of his guilty plea. Defendant’s admissions to particular quantities of

crack cocaine appear in an entirely separate portion of the plea agreement from the

paragraph that describes the five-grams-or-more offense to which Defendant agreed to
No. 11-6105 United States v. Hogg Page 16

10Incidentally, and as the district court observed in its opinion denying Defendant’s second

motion to withdraw his plea, (see R. 52, 9/8/2011 Mem. Op. at 15-16, PageID 523-24), Defendant’s

admission to a drug quantity of 50 grams or more of crack cocaine also served to avoid any possible

concern under Apprendi v. New Jersey, 530 U.S. 466, 120 S. Ct. 2348 (2000), that Defendant’s sentence

might exceed the maximum statutory penalty to which Defendant was subject in light of the facts to which

he admitted upon entering his guilty plea. Regardless of the pre- or post-FSA state of the law, Defendant’s

188-month term of imprisonment falls below the lowest possible statutory maximum (twenty years) that

could possibly apply in light of the facts admitted by Defendant in his plea agreement and at the plea

hearing. Thus, the district court correctly recognized that “this action does not involve any Apprendi

issues.” (R. 52, 9/8/2011 Mem. Op. at 16, PageID 524.) While this absence of an Apprendi violation is

irrelevant to our inquiry whether there was a Rule 11 violation at Defendant’s plea hearing, we consider

below the extent to which the principles of Apprendi might inform the question whether this Rule 11 error

was harmless.

plead guilty, and they serve wholly distinct purposes. Specifically, it is evident from the

plea agreement itself that Defendant’s admissions to quantities of between fifty and 150

grams of crack cocaine were intended to establish a factual basis for his guilty plea, and

to demonstrate to the district court how the parties determined Defendant’s relevant

conduct under the Sentencing Guidelines and arrived at a recommended advisory

sentencing range of 188 to 235 months of imprisonment. Although these recitations

served their intended purposes,10 the Government has failed to identify a basis in the law

for us to give double duty to these admissions, allowing us to read the five-grams-ormore charge to which Defendant agreed to plead guilty, coupled with these other terms

of the plea agreement, as effectively demonstrating Defendant’s knowing and voluntary

decision to plead guilty to a 28-grams-or-more offense under the post-FSA version of

§ 841(b)(1)(B).

Certainly, nothing in the plea agreement itself evidences the parties’

understanding that the district court was free to look to the factual basis for Defendant’s

guilty plea and his admissions as to relevant conduct in order to determine how to advise

Defendant under Rule 11(b)(1)(H)-(I) as to the statutory penalty range he faced for the

offense to which he was pleading guilty. To the contrary, under the law as the parties

uniformly understood it at the time — i.e., with the FSA not applicable in determining

Defendant’s statutory sentencing range — the parties expressed their shared belief and

agreement that Defendant faced a five-to-forty-year statutory penalty range, (see R. 21,

Plea Agreement at ¶ 4, PageID 36), despite Defendant’s admission elsewhere in the plea

agreement to a fifty-grams–or-more crack cocaine offense that would have triggered an
No. 11-6105 United States v. Hogg Page 17

11In our view, such an understanding of the district court’s obligations under Rule 11(b)(1)(H)-(I)

would be problematic and unworkable. Presumably, if a district court were permitted to leaf through the

entirety of a plea agreement in order to find provisions that might potentially have a bearing upon the

defendant’s statutory penalty exposure, this authority would quickly transform into a duty, lest the district

court misstate the defendant’s statutory penalty range by failing to appreciate the impact of the defendant’s

admissions as to the factual basis for his plea or his relevant conduct. Should a district court, for example,

factor in relevant conduct or factual basis recitations that could potentially expose the defendant to

additional charges, even though the plea agreement does not call for the defendant to plead guilty to these

charges or perhaps even mention these additional offenses? We do not read Rule 11(b)(1)(H)-(I) as

requiring such detective work, which would threaten to place the district court in the untenable position

of a surrogate prosecutor who must determine the potential sentencing exposure arising from any criminal

conduct to which a defendant might admit anywhere in his plea agreement. Again, this potential

sentencing exposure might be relevant (as discussed below) to a harmless error inquiry, but we are hesitant

to construe Rule 11(b)(1)(H)-(I) as demanding that the district court look beyond the specific offense to

which a defendant has agreed to plead guilty in discharging its obligation to advise the defendant of his

statutory penalty range.

elevated statutory penalty range of ten years to life imprisonment under the pre-FSA

sentencing regime. Consistent with this view reflected in the plea agreement, counsel

for the Government expressly confirmed at the plea hearing that Defendant’s statutory

penalty range should be “set by the charge to which he is pleading guilty,” and not by

the relevant conduct to which he admitted elsewhere in the plea agreement. (R. 33, Plea

Hearing Tr. at 6, PageID 120.) Nowhere in the course of this appeal has the Government

identified any authority for its attempt to now retreat from this position, and to instead

contend that a district court is permitted to stray beyond the four corners of the specific

offense to which a defendant has agreed to plead guilty in determining how to advise

him of the statutory penalty range he faces for this offense.11

Alternatively, the Government suggested at oral argument that the FSA has

merely introduced a potential ambiguity into drug offenses charged by reference to the

crack cocaine quantities that triggered escalating tiers of punishment under the pre-FSA

version of § 841(b)(1) — e.g., five or fifty grams of crack cocaine, as opposed to the

28 or 280 grams of crack cocaine that now are necessary under the FSA to invoke these

same escalating penalty ranges — and that the totality of Defendant’s plea agreement

serves to resolve any such potential ambiguity here. In particular, the Government

observes that the plea agreement’s statement of the offense to which Defendant pled

guilty — “possessing with intent to distribute 5 grams or more of cocaine base,” (R. 21,

Plea Agreement at ¶ 3, PageID 36) — fails to distinguish between or exclude the

possibilities (i) that this drug offense involved at least five but less than 28 grams of
No. 11-6105 United States v. Hogg Page 18

12Presumably, the upper-bound quantity for this latter hypothetical offense would be fifty grams

of crack cocaine, as a quantity of fifty grams or more of crack cocaine would have triggered the next tier

of escalating penalty ranges under the pre-FSA version of § 841(b)(1). See 21 U.S.C. § 841(b)(1)(A)(iii)

(2009). In fact, Defendant’s plea agreement seemingly confirms this view, as it distinguishes between the

fifty-grams-or-more offense charged in Count One of the indictment and the five-grams-or-more “lesser

included offense” to which Defendant pled guilty.

13The Government further suggests in its brief on appeal that the parties essentially agreed during

their plea negotiations that Defendant “would be in no different position by pleading to an offense

involving 5 or more grams than if he was charged with and pleaded to possessing 28 or more grams.”

(Appellee’s Br. at 48.) This claimed “agreement,” however, rests on a pair of e-mail messages sent by

Assistant U.S. Attorney Brent Hannafan to defense counsel, Michael Holley. In the first, Mr. Hannafan

floats the notion that the Government could file an information charging Defendant with possession with

intent to distribute 28 grams or more of crack cocaine, and that the plea agreement could be modified to

reflect Defendant’s plea of guilty to this 28-grams-or-more offense. (See R. 55-1, 3/15/2011 E-mail,

PageID 605.) In the second, however, Mr. Hannafan abandons this proposal of filing an information

charging a 28-grams-or-more crack cocaine offense, in light of his understanding (and the Department of

Justice’s then-current position) that the FSA’s revised penalty scheme would not apply to Defendant’s

sentencing. (See R. 55-1, 3/15/2011 E-mail, PageID 606.)

Plainly, this one-sided “discussion,” in which the Government first proposed but then promptly

abandoned a plan to address the potential ambiguity introduced by Defendant’s plea to a five-grams-ormore crack cocaine offense, cannot be said to evidence any “agreement” by Defendant or his counsel that

the five-grams-or-more offense to which he pled guilty was one and the same as a 28-gram-or-more

offense under the FSA’s revised penalty scheme for crack cocaine offenses. Indeed, defense counsel made

precisely this point at Defendant’s sentencing, opining that the two e-mails sent by Mr. Hannafan reflected

a “unilateral[]” offer by the Government that it later deemed “not necessary,” with the Government

ultimately remaining content that Defendant would “just . . . plead to the five grams” referenced in the plea

agreement. (R. 60, Sentencing Hearing Tr. at 5, PageID 593.)

crack cocaine, or (ii) that this drug offense involved 28 grams or more of crack

cocaine.12 Yet, as discussed above, in identifying the factual basis for his guilty plea,

Defendant admitted that he “unlawfully, knowingly, and intentionally possess[ed] with

intent to distribute 50 grams or more of a mixture and substance containing a detectable

amount of cocaine base,” and that, for purposes of computing his advisory Sentencing

Guideline range, the “total amount of cocaine base for which he [wa]s responsible [wa]s

between at least 50 grams but less than 150 grams.” (R. 21, Plea Agreement at

¶¶ 8(a),(g), PageID 38, 40.) It follows, in the Government’s view, that the five-gramsor-more offense to which Defendant pled guilty is more accurately characterized as a 28-

grams-or-more offense under the post-FSA version of § 841(b)(1), with the result that

the district court accurately advised Defendant of the five-to-forty-year statutory penalty

range for this offense.13

This argument, clever though it may be, runs afoul of the evident intent of the

parties as expressed in Defendant’s plea agreement. Although Defendant acknowledged,

in establishing the factual basis for his plea, that he had engaged in a drug offense
No. 11-6105 United States v. Hogg Page 19

14The Government seemingly acknowledges this point in its brief on appeal, stating that despite

the parties’ agreement during their plea negotiations that “defendant possessed over 50 grams of crack as

charged in Count One of the indictment, the United States agreed he could plead to the charge of

possessing 5 or more grams of crack.” (Appellee’s Br. at 47-48.) This promise would be illusory if, as

the Government now contends, Defendant’s admission in his plea agreement to possession of over

50 grams of crack cocaine were deemed to relieve the Government of the consequences of its agreement

to accept a plea of guilty to a lower-quantity offense than Defendant’s admission would otherwise have

established.

To be sure, the parties could have negotiated over the contingency that the FSA might apply at

Defendant’s sentencing, and could have agreed that the drug quantity for the offense to which Defendant

pled guilty would trigger the same five-to-forty-year statutory penalty range regardless of whether

involving fifty grams or more of crack cocaine, he and the Government nonetheless

agreed that he would plead guilty to the “lesser included offense” of possessing with

intent to distribute five grams or more of crack cocaine. (R. 21, Plea Agreement at ¶ 3,

Page ID 36 (emphasis added).) Under the Government’s proposed reading of the plea

agreement, however, this “lesser included offense” would be deemed to involve

28 grams or more of crack cocaine, resulting in a post-FSA statutory penalty range of

five to forty years of imprisonment under the amended § 841(b)(1)(B). Yet, the offense

charged in Count One of the indictment, involving fifty grams or more of crack cocaine,

is also subject to this same post-FSA 28-grams-or-more statutory penalty range of five

to forty years of imprisonment; in order to step to the next penalty tier of ten years to life

imprisonment under the FSA, the offense would have had to involve at least 280 grams

of crack cocaine, see 21 U.S.C. § 841(b)(1)(A)(iii) (2011), but the highest crack cocaine

quantity referenced anywhere in Defendant’s plea agreement is 150 grams, (see R. 21,

Plea Agreement at ¶ 8(g), PageID 40).

As we have recognized, plea agreements must be interpreted in accordance with

ordinary contract principles, with the intent of the parties ascertained primarily through

the chosen wording of their agreement, and with any ambiguities construed against the

Government. See United States v. Moncivais, 492 F.3d 652, 662 (6th Cir. 2007); Smith

v. Stegall, 385 F.3d 993, 999 (6th Cir. 2004). In order to give meaning and effect to the

parties’ statement in the plea agreement that Defendant would be permitted to plead

guilty to a “lesser included offense,” the charge to which Defendant pled guilty must be

viewed as a less severe variant of the fifty-grams-or-more offense charged in the

indictment, with a correspondingly reduced statutory penalty range.14 The only way to
No. 11-6105 United States v. Hogg Page 20

Defendant was entitled to the benefit of this new enactment. In fact, and as noted above, the Government

evidently proposed such a solution at one point in the parties’ plea negotiations. The plea agreement

ultimately arrived at by the parties includes no such provision, however, and we are not at liberty to

construe its silence on this point in favor of the Government.

achieve this intended result, as expressed by the parties through their agreement that

Defendant would plead guilty to “a lesser included offense of the charge in Count One

of the indictment,” (R. 21, Plea Agreement at ¶ 3, PageID 36), is to construe the offense

to which Defendant pled guilty as involving between five and 28 grams of crack cocaine

— an offense which, in the wake of the FSA, is subject to a statutory penalty range of

zero to twenty years of imprisonment. Because Defendant was not advised of this

penalty range at his plea hearing, we conclude that Rule 11 was violated.

2. The District Court’s Rule 11 Violation Was Not Harmless.

Having concluded that the district court failed (albeit understandably) to

anticipate the Supreme Court’s ruling in Dorsey and accurately advise Defendant of the

post-FSA statutory penalty range for the offense to which he pled guilty, we next must

consider whether this Rule 11 violation was harmless — that is, whether this error did

“not affect [Defendant’s] substantial rights.” Fed. R. Crim. P. 11(h). We have explained

that “a plea that is not voluntary is undoubtedly an impairment of a defendant’s

substantial rights,” and that “[f]or a plea to be voluntary, the defendant must understand

the direct consequences of a plea, which includes the maximum and minimum sentences

that may be imposed.” Martin, 668 F.3d at 792. Nonetheless, flaws in a district court’s

advice to a defendant regarding his sentencing exposure do not necessarily render the

defendant’s guilty plea involuntary and affect his substantial rights, so long as “the

defendant reasonably could be said to have understood the consequences of his plea

regardless of any omission or misinformation provided by the district court.” Martin,

668 F.3d at 793.

Our prior case law provides considerable guidance in resolving the harmless

error inquiry presented here. Most notably, in Pitts v. United States, 763 F.2d 197, 199

(6th Cir. 1985), the district court mistakenly informed the defendant while taking his

guilty plea that he faced a maximum possible sentence of 25 years of imprisonment and
No. 11-6105 United States v. Hogg Page 21

a $25,000 fine, when in fact his maximum sentencing exposure was fifteen years’

imprisonment and a $20,000 fine. We remanded for an evidentiary hearing to

“determine whether [the defendant] would not have pleaded guilty but for the

misstatement,” emphasizing that the district court had made “affirmative misstatements

of the maximum possible sentence,” and observing that “[n]umerous cases have held that

misunderstandings of this nature invalidate a guilty plea.” Pitts, 763 F.2d at 201

(collecting cases). In so ruling, we rejected the Government’s appeal to the defendant’s

plea agreement as mitigating the harm from the misinformation he was given:

Although the government argues that the presence of the plea agreement

in this case renders [the district court’s] misadvice insignificant, the

effect of the plea agreement may have been to exacerbate the problem.

When considering a plea agreement, a defendant might well weigh the

terms of the agreement against the maximum sentence he could receive

if he went to trial. When the maximum possible exposure is overstated,

the defendant might well be influenced to accept a plea agreement he

would otherwise reject.

763 F.2d at 201 (footnote omitted).

Similarly, in United States v. Stubbs, 279 F.3d 402, 405 (6th Cir. 2002),

abrogated on other grounds by Harris v. United States, 536 U.S. 545, 122 S. Ct. 2406

(2002), the defendant pled guilty to a violation of 18 U.S.C. § 924(o), and his plea

agreement provided that he was subject to a mandatory term of sixty months’

imprisonment to be served consecutive to the sentence imposed for his other offenses.

We held that this mandatory consecutive sixty-month sentence resulted from a mistaken

application of a different statutory provision, 18 U.S.C. § 924(c), and that “[i]f

Defendant had been properly sentenced under § 924(o), he would not have been subject

to a mandatory minimum sentence and there would not have been a requirement that the

sentence be served consecutive to any other sentence[] imposed.” Stubbs, 279 F.3d at

410. We then concluded, in accordance with Pitts and other decisions, that this mistake

served to invalidate the defendant’s guilty plea:

The record reveals that neither Defendant, his counsel nor the district

court was aware that Defendant was not subject to a mandatory

consecutive minimum 60-month sentence under § 924(o). There is no
No. 11-6105 United States v. Hogg Page 22

15Under comparable circumstances, other circuits have held that a district court’s misstatement

of the statutory penalty range faced by a defendant could not be deemed harmless error under Rule 11, but

instead provided grounds for permitting the defendant to withdraw his guilty plea. See, e.g., Hairston, 522

F.3d at 341 (finding that the misinformation provided to the defendant at his plea hearing “completely

changed the sentencing calculus,” where the defendant had been advised “when he pleaded guilty that his

best-case scenario was a thirty-year prison term,” but he then “learned at sentencing that his best-case

scenario in fact was a forty-five-year prison term”); Harrington, 354 F.3d at 185-86 (noting that the district

court had “informed the defendant that a mandatory minimum sentence applied when one did not,” and

explaining that “[b]ecause a mandatory minimum sentence represents such a strong inducement to plea[d],

where a defendant has been informed . . . that he is facing such a sentence, that information is

presumptively significant in the defendant’s decision-making”); United States v. Santo, 225 F.3d 92, 100

(1st Cir. 2000) (finding that the defendant was entitled to withdraw his guilty plea after being misinformed

of a five-year statutory minimum sentence rather than the ten-year minimum that actually applied, where

the defendant “reasonably could have expected from the information given, including in particular the

inaccurate five-year minimum, that he might receive a significantly lighter punishment than the fourteenyear sentence he eventually received”); Fernandez, 205 F.3d at 1030 (finding that a Rule 11 violation was

not harmless where the defendant never was “alerted to the mandatory minimum sentences applicable in

his case,” and thus his “decision to plead guilty could not have been fully informed [by] the penalties he

faced”); United States v. Guerra, 94 F.3d 989, 995 (5th Cir. 1996) (observing that because of the district

court’s Rule 11 violation, the defendant “did not know that going to trial would only put him at risk of half

the possible sentence he was informed he would face,” and concluding that this misinformation left the

defendant “unaware of the true nature of the options he faced” as he elected to plead guilty).

record evidence which demonstrates that Defendant was aware of the

true nature of the crime charged and the proper statutory consequences

of his guilty plea.

Furthermore, it is reasonably probable that but for the

misinformation as to Defendant’s proper statutory sentence, Defendant

would not have pleaded guilty. Here, Defendant was ready to proceed

to trial when his counsel suggested that he plead guilty. Moreover,

Defendant had moved to withdraw his guilty plea based in part on the

ground that his counsel had not properly informed him of the nature of

the charge against him, albeit for a different reason. It is therefore

reasonably probable that had Defendant known that he was not subject

to a mandatory consecutive 60-month sentence, but rather was subject to

a sentence of up to twenty years that could be served concurrent to any

other sentence[] received, Defendant would not have pleaded guilty.

279 F.3d at 412 (citation omitted).15

In contrast, we have determined on other occasions that a district court’s

misstatement of a defendant’s sentencing exposure was harmless because the defendant

had notice through other sources of the correct statutory penalty range. In Martin, 668

F.3d at 790, 793, for example, the district court initially stated at the defendant’s plea

hearing that each of the two offenses to which he was pleading guilty carried a five-year

statutory minimum sentence, but the court then proceeded to direct the defendant’s

attention to a passage in his plea agreement that “unequivocally stated correctly” that he
No. 11-6105 United States v. Hogg Page 23

faced an overall mandatory minimum sentence of 32 years’ imprisonment. We found

that despite this “minimally conflicting information” provided by the district court

regarding the defendant’s minimum sentence, the defendant’s statements at the plea and

sentencing hearings “amply demonstrate[d] that [the defendant] adequately understood

the direct consequences of his plea at the time of his plea hearing.” Martin, 688 F.3d at

793-94.

Likewise, in United States v. Ospina, 18 F.3d 1332, 1334 (6th Cir. 1994), the

district court correctly advised the defendant of a five-year mandatory term of

imprisonment, but then misleadingly “used discretionary rather than mandatory language

in discussing whether the sentence would run consecutively” to a state prison sentencing

the defendant was then serving. We concluded that any resulting Rule 11 violation was

harmless, where the “defendant knew before pleading guilty that he could be sentenced

to a five-year term of imprisonment to be served upon completion of his state term of

imprisonment,” he “raised no objection” to a provision in his presentence report

disclosing a “statutory mandate of a 5 years consecutive sentence,” and his counsel

acknowledged at sentencing that the defendant was aware “that he pled guilty to a fiveyear mandatory consecutive sentence.” Ospina, 18 F.3d at 1334; see also Williams v.

United States, No. 00-1687, 47 F. App’x 363, 365-66, 368-69 (6th Cir. Sept. 25, 2002)

(holding that the district court had not committed plain error by erroneously stating at

a plea hearing that the defendant faced a 60-month mandatory minimum sentence, where

the defendant’s presentence report accurately disclosed the correct 84-month minimum

sentence and the defendant neither objected to this portion of the presentence report nor

moved to withdraw his plea). See generally Syal, 963 F.2d at 906 (explaining that

“[s]ubstantial rights may not be affected when a defendant makes no claim that he did

not know of the [potential penalty information omitted from the district court’s Rule 11

disclosures] and therefore cannot claim that the lack of information affected his decision

whether to enter a plea of guilty”); Pitts, 763 F.2d at 200 (noting that a plea may be

voluntary and intelligent despite the omission of required information because “[a]

defendant may learn of the information not relayed to him by the trial court from other

sources”); Gray, 581 F.3d at 754 (“Most cases in which Rule 11 violations were found
No. 11-6105 United States v. Hogg Page 24

to be harmless involve situations where the defendant was aware, or could have been

made aware, of the omitted information through other means, e.g., a plea agreement

containing the information the court omitted during the plea hearing.”).

In another series of decisions in which we have declined to provide a remedy for

a district court’s misstatement of a defendant’s sentencing exposure, we have pointed

to the absence of any indication that the defendant would have declined the

Government’s plea offer if accurately informed of the correct statutory penalty range.

In one recent case featuring facts similar to those presented here, the defendant argued

that his plea was unknowing because the district court incorrectly advised him of the preFSA five-to-forty-year statutory penalty range for his crack cocaine offense, rather than

citing the correct zero-to-twenty-year range that applied in the wake of the Supreme

Court’s Dorsey decision. See United States v. Tyus, No. 12-5614, 2013 WL 2097164,

at *1 (6th Cir. May 15, 2013). We held that the defendant’s challenge was subject to

plain error review in light of his “fail[ure] to object below” and found that the defendant

could not meet this standard, explaining that he had not “suggest[ed] that the sentencing

ranges used by the government and the district court led him to accept a plea he

otherwise would have rejected,” nor had he “claim[ed] to have pleaded guilty with the

expectation of a lower sentencing range, only to be ambushed at sentencing with a

greater sentence.” Tyus, 2013 WL 2097164, at *2.

Similarly, in United States v. Mitchell, No. 08-3126, 398 F. App’x 159, 161

(6th Cir. Oct. 7, 2010), the district court erroneously advised the defendant that two of

the counts to which he pled guilty carried statutory sentencing ranges of twenty years to

life imprisonment, when in fact only one of these offenses was subject to a statutory

minimum penalty of twenty years, while the other triggered only a ten-year mandatory

minimum sentence. We acknowledged that “where, as here, a district court overstates

the maximum potential sentence to which a defendant may be subject, the

misinformation may deprive the defendant of an understanding of the actual

consequences he faces and the true nature of the options available to him, thereby

making his plea unintelligent.” Mitchell, 398 F. App’x at 162 (citing Stubbs and Pitts).
No. 11-6105 United States v. Hogg Page 25

16It is important to emphasize that in the above-cited cases of Tyus, Mitchell, and Kennedy, we

reviewed claimed Rule 11 violations for plain error, rather than applying the harmless error standard that

governs here. Nonetheless, whether under harmless or plain error review, we must inquire whether the

error at issue affected the defendant’s substantial rights, with the “important difference” that under the

plain error standard, “[i]t is the defendant rather than the Government who bears the burden of persuasion”

as to this and the remaining elements of the standard. United States v. Olano, 507 U.S. 725, 734-35, 113

S. Ct. 1770, 1777-78 (1993); see also Vonn, 535 U.S. at 62-63, 122 S. Ct. at 1048. Thus, we believe it

appropriate to look to our decisions in Tyus, Mitchell, and Kennedy for guidance as to whether a Rule 11

error may be said to have affected a defendant’s substantial rights, so long as we are mindful not to impose

a burden on Defendant here to establish such an effect on his substantial rights.

We noted, however, that the defendant had “neither indicated that he was confused by

the district court’s misstatements nor ha[d] he attempted to withdraw his plea.” 398 F.

App’x at 162-63. Accordingly, because the defendant had not “requested the only relief

for which he would be eligible,” we rejected his challenge to the validity of his guilty

plea. 398 F. App’x at 163; see also United States v. Kennedy, No. 10-5358, 493 F.

App’x 615, 616 (6th Cir. July 20, 2012) (finding that an error in advising the defendant

of the maximum sentence he faced did not affect his substantial rights, where the

defendant “fail[ed] to maintain that he would not have pled guilty in the first place or

even that he would not plead guilty today if we remanded the case to the district court”);

United States v. Ferguson, No. 96-6029, 1997 WL 764471, at *5-6 (6th Cir. Dec. 3,

1997) (finding that the district court violated Rule 11 by failing to inform the defendant

of the maximum penalty for the four drug offenses to which he pled guilty, but

concluding that this error was harmless because the defendant “never claimed that he

would have refused the plea bargain had he been informed of the maximum possible

penalty,” nor did he “contend on appeal that this information would have altered his

decision to plead guilty”).16

Returning to the present case, we find that the outcome is governed by our prior

decisions in Pitts and Stubbs, and that this case features none of the factors cited in our

other above-cited rulings as evidencing the absence of an impairment of the defendant’s

substantial rights. In this case, as in Pitts and Stubbs, the district court materially

overstated the defendant’s sentencing exposure. In particular, Defendant was advised

that he faced a five-to-forty-year statutory penalty range, but his range for the offense

of conviction actually was zero to twenty years in the wake of the FSA and Dorsey’s

interpretation of this 2010 enactment. Moreover, this misstatement of the statutory
No. 11-6105 United States v. Hogg Page 26

penalty range had a ripple (and equally material) effect on the Sentencing Guideline

calculations set forth in Defendant’s plea agreement and used to determine his agreedupon sentence. Because the parties agreed that Defendant was subject to sentencing

under the career offender guideline, U.S.S.G. § 4B1.1, the forty-year statutory maximum

sentence disclosed in the plea agreement triggered a base offense level of 34 under

U.S.S.G. § 4B1.1(b)(2), and this, in turn, led the parties to calculate a recommended

advisory Sentencing Guideline range of 188 to 235 months of imprisonment. (See R.21,

Plea Agreement at ¶¶ 10(a)(ii),(c), PageID 41-43.) The parties then agreed to a 188-

month sentence at the bottom of this advisory range. (Id. at ¶ 11, PageID 43.) If the

parties and the district court had anticipated the Dorsey decision and correctly

understood that Defendant faced a twenty-year rather than forty-year statutory maximum

sentence, Defendant’s base offense level under the career offender guideline would have

been 32 rather than 34, see U.S.S.G. § 4B1.1(b)(3), resulting in a reduced advisory

Sentencing Guideline range of 151 to 188 months of imprisonment. (See R.47,

Defendant’s 8/22/2011 Second Motion to Withdraw Plea at 4, PageID 399.)

It seems evident to us that this is a significant change in the sentencing calculus

under which Defendant weighed the Government’s plea offer. Under the information

disclosed to Defendant in the plea agreement and at the plea hearing, he was to receive

a 188-month sentence that was less than half of the forty-year statutory maximum

sentence he faced for the offense to which he pled guilty, and that placed him at the very

bottom of the 188-to-235-month advisory Sentencing Guideline range determined by the

parties. What is more, by securing the Government’s agreement to allow him to plead

guilty to a lesser-included offense, Defendant believed he had avoided the pre-FSA

statutory penalty range of 10 years to life imprisonment he would have faced for the 50-

grams-or-more crack cocaine offense charged in the indictment, as well as the resulting

base offense level of 37 under the career offender guideline, see U.S.S.G. § 4B1.1(b)(1).

Yet, in the wake of the FSA, this deal looks considerably less advantageous to

Defendant. The 188-month sentence imposed by the district court is not far below the

twenty-year statutory maximum for the offense to which Defendant pled guilty,
No. 11-6105 United States v. Hogg Page 27

17We acknowledge that the advisory Sentencing Guideline range presumably would have been

higher than the 151-to-188-month range identified in Defendant’s second motion to withdraw his guilty

plea, as Defendant would not have received credit for acceptance of responsibility. Defendant also would

have lost a separate benefit conferred under the plea agreement — i.e., dismissal of the second count of

the indictment — although it is not clear how much a conviction on this additional charge would have

contributed to Defendant’s overall sentencing exposure.

particularly when compared to the “discount” of well over half of the forty-year statutory

maximum disclosed by the district court and in the plea agreement. Moreover,

Defendant’s 188-month sentence sits at the upper bound of the post-FSA advisory

Sentencing Guideline range of 151 to 188 months, rather than at the lower bound of the

188-to-235-month range set forth in the plea agreement. Against this backdrop,

Defendant seemingly did not have a great deal to lose by rejecting the Government’s

plea offer and going to trial on the fifty-gram-or-more crack cocaine offense charged in

Count One of the indictment; under the FSA, the statutory penalty range for this offense

is zero to twenty years of imprisonment, and Defendant’s advisory Sentencing Guideline

range for this offense presumably would have been somewhat below this twenty-year

maximum,17 so that his resulting sentence upon conviction at trial presumably would not

have greatly exceeded (if at all) the 188-month sentence called for in the plea agreement.

As Pitts and Stubbs make clear, this sort of material overstatement of a

defendant’s sentencing exposure, as provided to Defendant in his plea agreement and

reiterated by the district court at the plea hearing, gives rise to a reasonable probability

that a “defendant might well be influenced to accept a plea agreement he would

otherwise reject.” Pitts, 763 F.2d at 201; see also Stubbs, 279 F.3d at 412. Indeed,

Defendant expressly asserted in his motion to withdraw his guilty plea that “had he been

aware of” the correct statutory penalty range of zero to twenty years, “he would not have

entered his guilty plea,” (R. 47, 8/22/2011 Second Motion to Withdraw Plea at 4-5,

PageID 399-400), and he has steadfastly maintained this position at sentencing, (R. 60,

Sentencing Hearing Tr. at 7, PageID 595), and here on appeal. Nothing in the record

casts doubt on this evidence of a reasonable probability that, but for the district court’s

Rule 11 error, Defendant would not have entered his guilty plea, and this suffices to

establish an effect upon Defendant’s substantial rights that overcomes a claim of
No. 11-6105 United States v. Hogg Page 28

18Certainly, the Government did not attempt to make a showing of harmless error in its brief on

appeal, but instead took the position that the district court committed no Rule 11 error whatsoever,

harmless or otherwise. Even after the Supreme Court issued its decision in Dorsey, the Government made

no effort to file a supplemental brief in which it advanced a claim of harmless error. Since, as observed

earlier, the Government bears the burden of demonstrating the harmlessness of a Rule 11 error that a

defendant has properly preserved, see Vonn, 535 U.S. at 62-63, 122 S. Ct. at 1048, the Government

seemingly cannot hope to carry this burden here.

harmless error. See Dominguez Benitez, 542 U.S. at 83, 124 S. Ct. at 2340; Martin,

668 F.3d at 792-93.18

Moreover, this case lacks any of the considerations that have led us to conclude

that a Rule 11 violation did not affect a defendant’s substantial rights. In contrast to

some of our above-cited decisions, see, e.g., Martin, 668 F.3d at 793; Ospina, 18 F.3d

at 1334-35, Defendant remained uninformed by any source that the district court had

erred in advising him of a five-to-forty-year statutory penalty range, and that the correct

penalty range was zero to twenty years of imprisonment. In denying Defendant’s second

motion to withdraw his guilty plea, the district court adhered to its view, as backed by

the then-current law of this Circuit, that Defendant faced a five-to-forty-year statutory

sentencing range, and Defendant’s presentence report reiterated this five-to-forty-year

penalty range. Likewise, in contrast to the circumstances presented in such cases as

Mitchell, 398 F. App’x at 162-63, and Tyus, 2013 WL 2097164, at *2, the district court’s

Rule 11 violation here cannot be discounted as having had no effect upon Defendant’s

substantial rights by virtue of any failure on his part to attempt to withdraw his guilty

plea or to insist that the correct statutory penalty range, if provided, would have led him

decline the Government’s plea offer. To the contrary, and as explained, Defendant

sought prior to sentencing to withdraw his guilty plea upon determining that he might

well have been misadvised as to the correct post-FSA statutory penalty range he faced,

and he has consistently asserted that this correct information, if provided, would have

led him to forgo a guilty plea.

This leaves only the Government’s broader contention, as advanced at oral

argument, that the harmlessness of the district court’s Rule 11 error may be

demonstrated through Defendant’s admissions in his plea agreement to drug quantities

that, even in the wake of the FSA, would suffice to trigger the five-to-forty-year
No. 11-6105 United States v. Hogg Page 29

statutory penalty range that was disclosed to Defendant in his plea agreement and at the

plea hearing. As discussed earlier, however, we fail to see how the Government’s claims

about offenses it could have proven or relevant conduct to which a defendant has

admitted for purposes of Sentencing Guideline calculations have any bearing on the

pertinent district court obligations under Rule 11(b)(1)(H)-(I) — namely, to accurately

inform a defendant of the statutory penalty range for the crime to which he is pleading

guilty. For much the same reason, we view these Government appeals to other offenses

and relevant conduct as immaterial to our determination of the harmlessness of any

deviations from these Rule 11 obligations. The requirements of Rule 11(b)(1)(H)-(I),

after all, are not designed to inform a defendant generally of the penalties he would face

for any conduct to which he has admitted, nor to advise him of the pertinent penalties

for the offenses charged in the indictment in the absence of a plea agreement. Rather,

these Rule 11 requirements are intended to ensure that the defendant is informed of the

penalty range he faces in light of the terms governing his specific agreement to plead

guilty. The task of the district court, in other words, is not to alert the defendant to the

universe of considerations that might be relevant to his plea negotiations with the

Government, but to advise him more specifically of the factors bearing on his acceptance

or rejection of the particular deal actually offered by the Government and reflected in the

parties’ plea agreement, so that he may make an informed decision whether to accept this

arrangement and plead guilty in accordance with its terms. We find that the statements

made to Defendant at the plea hearing failed to disclose all of this information, and that

this error cannot be deemed harmless under the record and circumstances presented here.

In the end, we view the Government’s argument as boiling down to the claim

that, despite the confusion engendered by the enactment of the FSA and the failure of

the parties and the district court to anticipate that this statute would govern Defendant’s

sentencing, Defendant nonetheless got a good deal that he was wise to accept. His 188-

month sentence was exactly as promised in the plea agreement, this sentence avoids any

possible Apprendi concerns as within the zero-to-twenty-year boundaries that govern in

the wake of the FSA, and his admissions in his plea agreement evidence a quantity of

crack cocaine in excess of 28 grams that would continue, under the post-FSA sentencing
No. 11-6105 United States v. Hogg Page 30

regime, to trigger the five-to-forty-year statutory penalty range disclosed in the plea

agreement. And, indeed, all of these considerations might well justify the Government’s

confidence that its plea offer to Defendant was a good one, and that Defendant might

well face a greater sentence if he insists upon withdrawing his guilty plea and proceeding

to trial. As we observed at the outset, Defendant perhaps would be well advised to heed

the maxim to “be careful what you wish for.”

Yet, while we acknowledge the pragmatic force of the Government’s position,

our precedents demand a different approach for determining whether a Rule 11 error is

harmless. As the Supreme Court has emphasized, the harmlessness inquiry must be

performed from the defendant’s perspective, and must focus on the question whether the

requirements of the Rule, if satisfied, had a reasonable probability of leading the

defendant to forgo a guilty plea and proceed to trial:

When the record made for a guilty plea and sentencing reveals evidence,

as this one does, showing both a controlled sale of drugs to an informant

and a confession, one can fairly ask a defendant seeking to withdraw his

plea what he might ever have thought he could gain by going to trial.

The point of the question is not to second-guess a defendant’s actual

decision; if it is reasonably probable he would have gone to trial absent

the [Rule 11] error, it is no matter that the choice may have been foolish.

The point, rather, is to enquire whether the omitted warning would have

made the difference required by the standard of reasonable probability .

. . .

Dominguez Benitez, 542 U.S. at 85, 124 S. Ct. at 2341. In this case, Defendant has

steadfastly maintained that he would have gone to trial if he had been correctly advised

of the post-FSA statutory penalty range governing the offense to which he pled guilty,

and the materiality of the district court’s overstatement of this range, when considered

against the backdrop of the plea offer extended by the Government and set forth in the

plea agreement, satisfies us of the reasonable probability that the district court’s Rule 11

violation could be expected to have had this impact on Defendant’s plea deliberations.

Accordingly, we hold that Defendant should have been permitted to withdraw his guilty

plea, and we remand to the district court so that he may be allowed to do so.
No. 11-6105 United States v. Hogg Page 31

IV. CONCLUSION

For the reasons set forth above, we REVERSE the decision of the district court

denying Defendant’s second motion to withdraw his guilty plea, and we REMAND for

further proceedings in accordance with this ruling.