                          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
                                     _________________


                                                 X
                            Plaintiff-Appellee, -
 UNITED STATES OF AMERICA,
                                                  -
                                                  -
                                                  -
                                                      No. 11-6105
           v.
                                                  ,
                                                   >
                                                  -
                         Defendant-Appellant. -
 TRAVIS R. HOGG,
                                                 N
                    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.




         *
           The Honorable Gerald E. Rosen, Chief Judge of the United States District Court for the Eastern
District of Michigan, sitting by designation.


                                                   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 post-
FSA 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


                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.




        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.
No. 11-6105         United States v. Hogg                                             Page 5


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


        3
          The Government agreed to dismiss the second count of the indictment upon Defendant’s
sentencing for this lesser included crack cocaine offense.
No. 11-6105          United States v. Hogg                                                  Page 6


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,


        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.
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


         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


         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.
No. 11-6105             United States v. Hogg                                                       Page 10


         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


         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.)
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 plain-
error 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


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



         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).
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


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-to-
forty-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,


         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.
No. 11-6105           United States v. Hogg                                                   Page 15


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


         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.
No. 11-6105            United States v. Hogg                                                     Page 16


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-or-
more 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



         10
            Incidentally, 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.
No. 11-6105             United States v. Hogg                                                       Page 17


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


         11
            In 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.
No. 11-6105             United States v. Hogg                                                       Page 18


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-grams-
or-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

         12
            Presumably, 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.
         13
             The 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-or-
more 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.)
No. 11-6105            United States v. Hogg                                                    Page 19


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


         14
             The 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
No. 11-6105           United States v. Hogg                                                   Page 20


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


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.
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


         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

         15
             Under 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 fourteen-
year 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).
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 five-
year 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 pre-
FSA 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


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


         16
             It 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.
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 agreed-
upon 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


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



         17
            We 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.
No. 11-6105            United States v. Hogg                                                    Page 28


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


         18
             Certainly, 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.
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.
