Case: 20-30728 Document: 00516291557 Page: 1 Date Filed: 04/22/2022
United States Court of Appeals
for the Fifth Circuit United States Court of Appeals
Fifth Circuit
FILED
April 22, 2022
No. 20-30728
Lyle W. Cayce
Clerk
United States of America,
Plaintiff—Appellee,
versus
Oliver Pierre,
Defendant—Appellant.
Appeal from the United States District Court
for the Eastern District of Louisiana
No. 2:17-CR-132-2
Before Smith, Elrod, and Oldham, Circuit Judges.
Per Curiam:*
Oliver Pierre pleaded guilty to conspiring to traffic at least 280 grams
of cocaine. In exchange, the government dropped a less serious charge and
agreed not to pursue a sentencing enhancement. In hindsight, it is clear that
the sentencing enhancement could not have applied to Pierre even if the
government had pursued it. So, Pierre gave up his right to stand trial to avoid
*
Pursuant to 5th Circuit Rule 47.5, the court has determined that this
opinion should not be published and is not precedent except under the limited
circumstances set forth in 5th Circuit Rule 47.5.4.
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No. 20-30728
a punishment that could never have come. Because he has shown that the
district court committed plain error by accepting a plea based on an illusory
benefit, we VACATE the district court’s judgment and the plea and
REMAND for further proceedings consistent with this opinion.
I.
In the spring of 2014, local law enforcement began investigating the
drug trafficking activities of a person called “B.P.” The officers purchased
cocaine base from B.P. three times in April of that year for quantities totaling
about ten grams. The DEA collected more information and by the next year
learned that one of B.P.’s suppliers was named James Bickham. They
purchased cocaine from B.P. three more times for quantities totaling about
twenty-five grams. The DEA officers soon intercepted phone calls between
B.P. and Bickham and learned that the two of them hoped to make a drug deal
in Houston. Specifically, they discussed having a courier, Pierre, assist them
in the deal.
The officers staked out B.P.’s home at the scheduled time. They
followed B.P. to a gas station, where he parked next to Pierre. Pierre tossed
two bags of cocaine base into B.P.’s car, and the two of them drove away
separately. The officers stopped and detained B.P. and recovered 156.1
grams of cocaine base.
Pierre was indicted for conspiring to traffic 280 grams or more of
cocaine base (Count 1) and distributing 28 grams or more of cocaine base
(Count 2). He was assigned counsel in late 2017 and over a year later
successfully moved for the appointment of new counsel. Eventually a plea
agreement was reached. Under it, Pierre pleaded guilty to Count 1. In return,
the government agreed to request dismissal of Count 2 and agreed that it
would not charge Pierre as a multiple offender under 21 U.S.C. § 851—a
2
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provision which, Pierre was told, would have raised his mandatory minimum
sentence from ten years to fifteen years.1
At Pierre’s re-arraignment, the district court read Count 1 of the
indictment, which charged that Pierre conspired “to distribute and possess
with the intent to distribute 280 grams or more of cocaine base . . . in violation
of [21 U.S.C. § 841(a)(1), (b)(1)(A)] . . . .”2 It then explained that for him to
be convicted of Count 1, the government would have to prove beyond a
reasonable doubt that: (1) two or more persons reached an agreement to
possess and distribute cocaine base; (2) Pierre knew of the agreement’s
unlawful purpose; and (3) Pierre willfully joined the agreement. At that point
the court did not specifically explain that the government would have to
prove that Pierre’s participation in the conspiracy foreseeably involved the
280-gram quantity.
The factual basis for the plea provided by the government contained
the facts surrounding the incident described above. It also included a
stipulation for the purposes of sentencing that Pierre had participated in the
trafficking of at least 280 grams, but less than 840 grams, of cocaine base.
Pierre affirmed that the information pertaining to him was true.
The presentence report also noted that both the government and
Pierre stipulated to the 280- to 840-gram quantity for the purposes of
sentencing. But it likewise specifically noted Pierre’s role as courier for “at
least 156.1 grams of crack cocaine,” and that Pierre was a “minor participant
in any criminal activity.” The criminal history portion of the presentence
1
The government also agreed not to bring “any other charges in the Eastern
District of Louisiana arising from [Pierre’s] violations of the Federal Controlled Substances
Act prior to October 8, 2015,” as long Pierre provided the details of those crimes.
2
Because this charge was based on an alleged conspiracy, Pierre was also charged
under 21 U.S.C. § 846.
3
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report identified five prior state convictions, and Pierre’s sentencing range
was thus calculated as 120 to 137 months. The district court sentenced Pierre
to the statutory minimum 120 months. Pierre appealed the judgment and
sentence to this court, arguing for the first time that the district court erred
by accepting his guilty plea and that he was unconstitutionally deprived of
effective assistance of counsel.
II.
Pierre argues that his plea was not knowing and voluntary and thus
should be vacated because, among other things, it was conditioned on the
government agreeing not to pursue a sentencing enhancement under a
provision that could not apply to him. We agree with Pierre and hold that
that the district court plainly erred by accepting his plea under these
circumstances.
A.
Pierre argues that the district court erred by accepting his guilty plea.
Because he raises this challenge for the first time on appeal, we review for
plain error. See United States v. Hicks, 958 F.3d 399, 401 (5th Cir. 2020);
United States v. Hughes, 726 F.3d 656, 659 (5th Cir. 2013). Under the plain
error standard, Pierre must show (1) an error, (2) that is clear or obvious, and
(3) that affected his substantial rights. United States v. Trejo, 610 F.3d 308,
319 (5th Cir. 2010). When challenging the acceptance of a guilty plea,
specifically, he must demonstrate “a reasonable probability” that he would
not have pleaded guilty without the error. Hicks, 958 F.3d at 401–02. And
“[i]n making this determination, we may consult the whole record on
appeal.” United States v. Reyes, 300 F.3d 555, 559 (5th Cir. 2002). Finally, if
Pierre satisfies each criterion, we may vacate the judgment if the error
“seriously affect[s] the fairness, integrity or public reputation of judicial
4
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proceedings.” United States v. Young, 470 U.S. 1, 15 (1985) (quoting United
States v. Atkinson, 297 U.S. 157, 160 (1936)).
B.
Pierre argues that his guilty plea was not knowing and voluntary
because it was induced by the government’s promise not to pursue a
sentencing enhancement under a provision which could not have applied to
him.3 The government concedes that the sentencing enhancement provision
could not have applied but argues that Pierre cannot satisfy the plain error
standard because he cannot show that there is a reasonable probability he
would not have pleaded guilty without the error. We agree with Pierre.
A guilty plea must be knowing and voluntary. Parke v. Raley, 506 U.S.
20, 28 (1992). “That is so because a guilty plea constitutes a waiver of three
constitutional rights: the right to a jury trial, the right to confront one’s
accusers, and the privilege against self-incrimination.” Id. at 29. A guilty
plea is not sufficiently voluntary if it is induced by “deception, an
unfulfillable promise, or misrepresentation . . . .” United States v. Amaya, 111
F.3d 386, 389 (5th Cir. 1997). “A plea of guilty that is based on the fear of a
non-existent penalty can be neither knowing nor intelligent, and this flaw
colors the fundamental fairness of the entire proceeding.” Kennedy v.
Maggio, 725 F.2d 269, 273 (5th Cir. 1984).
Under this standard, Pierre’s plea was not knowing and voluntary, so
the district court erred by accepting it. His guilty plea was induced in part by
3
The dissenting opinion attempts to cabin such a challenge to a collateral action
under 28 U.S.C. § 2255 instead of in a direct appeal. But we regularly consider involuntary-
plea claims on direct appeal, and we will not depart from our standard practice here. See,
e.g., United States v. Diaz, 989 F.3d 390, 392–94 (5th Cir. 2021); United States v. Scott, 857
F.3d 241, 244–46 (5th Cir. 2017); United States v. Washington, 480 F.3d 309, 315–16 (5th
Cir. 2007).
5
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the government’s promise not to charge him as a multiple offender “having
at least one prior felony drug conviction, which would have resulted in a
mandatory sentence of at least fifteen (15) years” under 21 U.S.C.
§§ 841(b)(1)(A) and 851. The current version of § 841(b)(1)(A) explains that
a defendant’s mandatory minimum sentence may be increased from ten to
fifteen years if he has a “prior conviction for a serious drug felony.” A
“serious drug felony” is one described in 18 U.S.C. § 924(e)(2) for which the
defendant served a term of imprisonment of over a year and for which the
defendant’s release from imprisonment occurred within fifteen years of the
current offense. 21 U.S.C. § 802(57). And 18 U.S.C. § 924(e)(2)(A)(ii)
limits the provision to offenses which, “under State law, involv[e]
manufacturing, distributing, or possessing with intent to manufacture or
distribute, a controlled substance . . . [and] for which a maximum term of
imprisonment of ten years or more is prescribed by law.”
Pierre had three prior convictions for possessing a controlled
substance. As the government concedes, those offenses “do not include the
necessary elements of manufacturing, distributing, or possessing with intent
to do so,” so they do not provide a basis for the § 841(b)(1)(A) enhancement.
And Pierre’s one conviction for distribution carries a maximum sentence of
less than ten years.4 So, Pierre’s plea was induced by the promise of an
illusory benefit and thus was not sufficiently knowing and voluntary.
4
The sentencing enhancement would have applied to Pierre under the previous
version of that provision. Before 2018, § 841(b)(1)(A) provided for an enhanced mandatory
minimum sentence of 20 years and simply applied to “felony drug offense[s],” which
included any drug offense “punishable by imprisonment for more than one year.” 21
U.S.C. § 802(44). This change to the statute was made after Pierre was indicted but before
he pleaded guilty. Presumably, that is the reason this error was made and neither the
district court nor the parties caught it initially.
6
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This error flatly contradicted the applicable statutory language of the
sentencing enhancement provision, and so was “clear or obvious.” Cf. Trejo,
610 F.3d at 319. To prove that any error was “clear or obvious,” a defendant
need not identify a past decision of this court directly holding in the
defendant’s favor on the exact same issue. Instead, our rule is that a
defendant must show that the “error is clear under existing law.” United
States v. Dunigan, 555 F.3d 501, 506 (5th Cir. 2009) (quoting United States v.
Maturin, 488 F.3d 657, 663 (5th Cir. 2007)). An undisputed contradiction of
statutory language is an error that is clear under existing law. United States
v. Aderholt, 87 F.3d 740, 744 (5th Cir. 1996) (“The error is evident from a
plain reading of the statute and thus, is obvious.”). There is no dispute that
the sentencing enhancement provision could not have applied to Pierre, and
the parties agree on that point. Thus, prongs one and two of the plain error
analysis are satisfied. See Trejo, 610 F.3d at 319 (identifying prongs one and
two of the plain error analysis as (1) whether an error occurred, and (2)
whether the error was clear or obvious).
But Pierre must also show that absent the error there is a reasonable
probability that he would not have pleaded guilty. Hicks, 958 F.3d at 401–02.
He has made this showing because the promise not to seek the inapplicable
sentence enhancement was the primary benefit he was to receive in exchange
for pleading guilty to Count 1. If applicable, the enhancement would have
increased his mandatory minimum sentence by fifty percent, from ten years
to fifteen years. Avoiding that enhancement is a substantial benefit and,
indeed, the presentence report described it as the “[i]mpact” of the plea
agreement. Moreover, as Pierre points out, he and his counsel participated
in plea negotiations for quite a long time, and Pierre only agreed to plead
guilty after the government offered not to seek the enhancement. The plea’s
timing does not prove a direct causal relationship between the government’s
promise and Pierre’s plea, but it certainly weighs in Pierre’s favor; it suggests
7
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that the promise made a difference for his decision. And, finally, Pierre
conceivably could have prevailed at trial had he chosen to proceed. Certainly
we cannot determine at this stage what additional evidence against him the
government might have gathered if proceedings continued towards trial. But
it is likely that the promise not to pursue a substantially enhanced sentence
played a significant role in his decision to plead guilty.
Of course, in exchange for Pierre’s guilty plea to Count 1, the
government also agreed to move to dismiss Count 2. At the surface level,
then, Pierre had another incentive to plead guilty besides the promise not to
seek the inapplicable sentence enhancement. But the surface is as deep as
that additional benefit goes. Count 2 charged Pierre with distributing twenty-
eight grams or more of cocaine base. That crime is less serious than the
Count 1 offense5 and in this case is based on the same conduct as that to which
the alleged conspiracy was aimed; thus, had Pierre been convicted of both
Count 1 and Count 2, the Count 2 conviction likely would have been
subsumed by Count 1 for the purposes of sentencing. See U.S.S.G. § 3D1.2
cmt. 4 (“When one count charges a conspiracy or solicitation and the other
charges a substantive offense that was the sole object of the conspiracy or
solicitation, the counts will be grouped together under [U.S.S.G.
§ 3D1.2(b)].”). And if at trial Pierre had been convicted on Count 2 only,
that offense carries a lower sentencing range than Count 1. See 21 U.S.C.
§ 841(b)(1)(A)(iii), (b)(1)(B)(iii); 21 U.S.C. § 846. In other words, it is
unlikely that a Count 2 conviction would have affected his guidelines range
for sentencing. The government therefore conveyed little (if any) benefit by
5
The Count 1 offense to which Pierre pleaded guilty, conspiracy to traffic 280
grams or more of cocaine base, carries a standard sentencing range of 10 years to life
imprisonment. 21 U.S.C. § 841(b)(1)(A)(iii); 21 U.S.C. § 846. The Count 2 offense,
distributing 28 grams or more of cocaine base, carries a standard sentencing range of 5 to
40 years imprisonment. 21 U.S.C. § 841(b)(1)(B)(iii).
8
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dismissing the Count 2 charge in exchange for his guilty plea to Count 1,
leaving as the primary “benefit” the illusory promise not to pursue an
inapplicable sentencing enhancement.6
It is true that Pierre was ultimately sentenced to the statutory
minimum for the Count 1 offense to which he pleaded guilty. That means
that if he had not pleaded guilty, and then had proceeded to trial and been
convicted on either count, he could have been sentenced to a longer term.
But, contrary to the government’s position, Pierre nonetheless could have
been prejudiced by the misconception about the applicability of the
sentencing enhancement. When reviewing the acceptance of a guilty plea for
plain error, the question is not whether the plea likely caused the defendant
to be issued a longer sentence, but whether there is a reasonable probability
that absent the error the defendant would not have entered the plea. United
States v. Dominguez Benitez, 542 U.S. 74, 83 (2004). Pierre has shown that
the core benefit he received from the guilty plea was the government’s
promise not to charge him as a multiple offender. Thus, there is a reasonable
probability that he would not have entered the plea if he understood that the
benefit was illusory. Under Dominguez Benitez, he has satisfied the third
element of plain error review.
6
The government also agreed not to bring “any other charges in the Eastern
District of Louisiana arising from [Pierre’s] violations of the Federal Controlled Substances
Act prior to October 8, 2015,” as long Pierre provided the details of those crimes. The
statute of limitations applicable to such offenses is five years. 18 U.S.C. § 3282(a). Because
Pierre pleaded guilty in June of 2019, the government’s promise could have applied only to
an offense committed between mid-2014 and early October of 2015. The record does not
show that the government was in a position to charge Pierre with any such offense. Thus,
it is unlikely that the promise gave Pierre a significant benefit. Notwithstanding this
additional promise the government made, there is still a reasonable probability that the
illusory promise not to pursue the sentencing enhancement affected Pierre’s decision to
plead guilty.
9
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Finally, Pierre must show that the error seriously affects the fairness,
integrity, or public reputation of judicial proceedings. Young, 470 U.S. at 15.
If he does, we “may then exercise [our] discretion to notice the error.”
United States v. Serna-Villarreal, 352 F.3d 225, 231 (5th Cir. 2003). Under
our precedent, we conclude that Pierre has satisfied this criterion. The right
to a jury trial is one of the primary constitutional safeguards for fairness and
integrity in judicial proceedings. Thus, as we have explained, “[t]he integrity
of the plea bargaining system is ‘vital to our national system of criminal
justice,’” and “[m]aintaining that integrity requires diligently policing its
failure to function properly.” United States v. Palmer, 456 F.3d 484, 491 (5th
Cir. 2006) (quoting United States v. Ashburn, 20 F.3d 1336, 1347 (5th Cir.
1994)).
When a plea is induced by the government’s promise of an illusory
benefit, and so the defendant forgoes a fundamental right because he wrongly
believes doing so will bring him a substantial benefit, the criminal justice
system has “fail[ed] to function properly.” See Palmer, 456 F.3d at 491. In
this case Pierre lost the opportunity to pursue a more favorable outcome in a
manner consistent with his fundamental rights—either by going to trial or by
negotiating a different plea agreement founded on accurate assumptions—so
we exercise our discretion to vacate the judgment and his plea.7
7
We consider this case appropriate for us to exercise our discretion under prong
four of the plain error analysis in part because Pierre could potentially negotiate a
significantly more favorable plea deal if given the chance. If, for example, he pleaded guilty
to participating in the trafficking of anything less than the 280-gram quantity of cocaine
base, he would face a five-year mandatory minimum sentence instead of a ten-year
mandatory minimum. Compare 21 U.S.C. § 841(b)(1)(A), (b)(1)(A)(iii), with id.
§ 841(b)(1)(B), (b)(1)(B)(iii). Such a charge would also correspond to a lower base offense
level. Compare U.S.S.G. § 2D1.1(c)(5), with U.S.S.G. § 2D1.1(c)(6). With all else equal,
those changes could reduce Pierre’s guidelines minimum sentence to 92 months (a
sentence nearly twenty-five percent shorter than the 120-month sentence he received) and
10
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* * *
Thus, the district court plainly erred when it accepted Pierre’s guilty
plea that was induced by a promise not to pursue a sentencing enhancement
that could not have applied. We therefore VACATE the district court’s
judgment and the plea and REMAND to the district court for further
proceedings consistent with this opinion.8
his guidelines maximum to 115 months (which is less than the 120-month sentence he
received).
8
Pierre also argues that his plea was not knowing and voluntary because the district
court failed to follow the requirements of Rule 11 of the Federal Rules of Criminal
Procedure. He claims, first, that the district court failed to properly advise him of the
nature of the charge against him as required by Rule 11(b)(1)(G). Relatedly, he claims that
the court erred by accepting his guilty plea without a sufficient factual basis for the drug
quantity as required by Rule 11(b)(3). Because we vacate the judgment entered on his guilty
plea and remand for further proceedings, we need not address these alternative arguments
for vacating.
For the same reason, we decline to address Pierre’s argument that he was deprived
of effective assistance of counsel. But we note that rarely will we consider such claims on
direct appeal. See United States v. Gulley, 526 F.3d 809, 821 (5th Cir. 2008) (“[T]he
‘general rule in this circuit is that a claim of ineffective assistance of counsel cannot be
resolved on direct appeal when the claim has not been raised before the district court since
no opportunity existed to develop the record on the merits of the allegations.’”
(quoting United States v. Higdon, 832 F.2d 312, 313–14 (5th Cir. 1987))); United States v.
Gordon, 346 F.3d 135, 136 (5th Cir. 2003) (“[A] § 2255 motion is the preferred method for
raising a claim of ineffective assistance of counsel.”).
11
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Andrew S. Oldham, Circuit Judge, dissenting:
Pierre bears the burden of showing plain error in this court. That
means he must establish “(1) that the district court committed an error
(2) that is plain and (3) affects his substantial rights and (4) that failure to
correct the error would ‘seriously affect the fairness, integrity or public
reputation of judicial proceedings.’” United States v. Sanchez-Hernandez, 931
F.3d 408, 410 (5th Cir. 2019) (quoting Johnson v. United States, 520 U.S. 461,
467 (1997)). Pierre cannot make that showing as to the third or fourth prongs.
I therefore respectfully dissent.
One overarching procedural problem afflicts the majority’s analysis:
Pierre is raising his involuntary-plea claim, not by way of a 28 U.S.C. § 2255
motion, but on direct appeal. That matters because a § 2255 motion would
allow the district court to “grant a prompt hearing” on Pierre’s claim and to
“determine the issues and make findings of fact and conclusions of law with
respect thereto.” 28 U.S.C. § 2255(b) (emphasis added). That factfinding
mechanism is crucial for claims, like ineffective-assistance-of-counsel claims,
that are predicated on facts outside the trial record. For that very reason,
“the general rule in this circuit is that a claim of ineffective assistance of
counsel cannot be resolved on direct appeal when the claim has not been
raised before the district court since no opportunity existed to develop the
record on the merits of the allegations.” United States v. Gulley, 526 F.3d 809,
821 (5th Cir. 2008) (quotation omitted); see also Massaro v. United States, 538
U.S. 500, 504 (2003) (“[I]n most cases a motion brought under § 2255 is
preferable to direct appeal for deciding claims of ineffective assistance.”);
ante, at 11 n. 8 (citing this rule favorably). Pierre’s involuntary-plea claim, no
less than his ineffective-assistance claim, turns on facts that he has not proved.
Both claims turn on who said what and when in the plea negotiations between
his lawyer and the prosecutor. The majority simply assumes that Pierre’s
12
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assertions are true and then vacates his conviction based on nothing more
than his assertions. There is zero basis in law or logic for that approach.
I.
The legal standard for our prong-three prejudice inquiry is
undisputed. We must ask whether there is “a reasonable probability that, but
for the error, [the defendant] would not have entered the plea.” United States
v. Dominguez Benitez, 542 U.S. 74, 83 (2004) (in the context of Federal Rule
of Criminal Procedure 11); see also United States v. Reyes, 300 F.3d 555, 558
(5th Cir. 2002) (“Rule 11 ensures that a guilty plea is knowing and
voluntary.”). So Pierre must show a “reasonable probability” that, if the
district court had noticed the plea involved an unfulfillable promise, he
wouldn’t have pleaded guilty to Count 1 (the conspiracy charge). See
Dominguez Benitez, 542 U.S. at 83; United States v. Hicks, 958 F.3d 399, 401
(5th Cir. 2020).
That’s tough to do. Consider, for example, United States v. Alvarado-
Casas, 715 F.3d 945 (5th Cir. 2013). In that case, the district court had
wrongly told the defendant that, if he pleaded guilty, “he faced a maximum
of ten years of imprisonment.” Id. at 953–54. His counsel told him the same
thing. Id. at 954. In fact, his maximum exposure was twice that—twenty years.
Ibid. After the defendant pleaded guilty, he was in fact sentenced to 190
months—“70 months greater than the 10-year maximum possible prison
sentence of which his counsel and the district court advised him.” Id. at 954
(quotation omitted). Despite all of that, this court held the defendant failed
to show prejudice. See id. at 954–55 (considering, inter alia, the otherwise-
generous plea agreement, the fact that the PSR did not share the court’s
error, and the defendant’s failure to show he had been ready to go to trial);
see also United States v. Molina, 469 F.3d 408, 412 (5th Cir. 2006) (holding
the third prong unsatisfied and explaining the defendant did not “direct this
13
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court to any portion of the record supporting the proposition that the
maximum sentence for count three affected his plea decision. Because [the
defendant] has not satisfied his burden, we affirm his conviction.”).
The majority opinion holds Pierre has shown “that absent the error
there is a reasonable probability that he would not have pleaded guilty.” See
ante, at 7–10. The majority gives five main reasons for that holding. Each of
those reasons, naturally, focuses on the Government’s promise not to seek
an inapplicable sentencing enhancement. At no point does the majority
acknowledge that it is climbing uphill against precedents like Alvarado-
Casas—nor does it acknowledge that the absence of a § 2255 factual hearing
renders Pierre incapable of making the required showing in this case.
I reproduce the majority’s stated reasons for that holding here, in my
own order. (1) The PSR described the Government’s meaningless promise
as the plea agreement’s “impact.” Id. at 8. (2) Pierre and his first lawyer had
been negotiating with the Government for a long time, and Pierre “only
agreed to plead guilty after the government offered not to seek the
enhancement.” Ibid. (citing only Pierre’s brief in support). (3) “Pierre
conceivably could have prevailed at trial had he chosen to proceed.” Ibid. But
see ibid. (acknowledging that “we cannot determine at this stage what
additional evidence against him the government might have gathered if
proceedings continued towards trial”). (4) “If applicable, the enhancement
would have increased his mandatory minimum sentence by fifty percent,
from ten years to fifteen years.” Ibid. And finally, (5), the other promises in
Pierre’s plea agreement went only as deep as the “surface,” so when the no-
sentencing-enhancement promise turned out to be empty, Pierre got little out
of the deal. See id. at 8–9. So goes the reasoning.
The first three reasons aren’t probative at all. (1) I’m not sure what
the majority means by its quotation of the “impact” phrase in the PSR. Is the
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idea that Pierre must have relied on the PSR to understand what the plea deal
entailed, and that the PSR framed the deal as being solely about the
sentencing enhancement? If so, that’s descriptively inaccurate: Elsewhere,
the PSR acknowledged the Government’s other two promises, which I
address in more detail below. And it makes little sense to treat the PSR’s
characterization of the plea agreement as more probative than the agreement
itself—which clearly made three promises, not just one.
Reason (2) is baseless because the record says nothing about the inner
workings of the plea negotiations. The record shows that Pierre and the
Government repeatedly, and successfully, asked the district court to push
back the trial date while they hammered out a plea agreement. The record
shows that, in December 2018, Pierre wrote the district judge a letter asking
for new counsel, and that he got his wish in February 2019. And the record
shows that the parties notified the court of their plea agreement a few months
later, in June 2019. That’s it. That’s all the record shows.
The majority simply assumes that Pierre was holding out for a better
deal all that time—and that he agreed to plead guilty only after the
Government sweetened the pot by promising not to seek the sentencing
enhancement. They act as if we know the Government had offered both to
drop Count 2 and to forego other charges all along, that Pierre was repeatedly
rejecting that offer throughout the negotiations, and that he agreed to plead
guilty only after the Government added the sentencing-enhancement
promise. But the record suggests no such thing. Maybe Pierre could prove
the Government’s promise was material. Maybe he couldn’t. But that’s why
we have § 2255 proceedings and evidentiary hearings. I am unaware of any
authority that says we can simply take the prisoner’s allegations as fact and
grant a new trial based on no evidence.
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Reason (3) is the weakest. Here, the majority indulges in pure
speculation that Pierre may have fared well if he’d decided to go to trial. As
the majority seems to acknowledge, we have no idea how strong the
Government’s case would have been if it had tried to prove Count 1. See ante,
at 7–8.
Reason (4) also does nothing. The Government promised not to seek
the sentencing enhancement, and the enhancement would’ve bumped
Pierre’s minimum sentence from 10 to 15 years. The question is: Can we infer
from the existence of the promise, res ipsa loquitur, that there’s a “reasonable
probability” Pierre wouldn’t have pleaded guilty without it? See Dominguez
Benitez, 542 U.S. at 83. The answer is no. Because the Government gave
Pierre more than one promise in exchange for his guilty plea, the mere
existence of the no-sentencing-enhancement promise doesn’t let us make
any counterfactual inferences at all.
Consider a monopsony situation where one seller (“S”) agrees to sell
a good (“G”) to one buyer (“B”) for $100. After the deal goes through, can
we infer that S wouldn’t have agreed to sell for $75? What about $50? What
about a mere $1? Nope. Without more information, the mere fact of the deal
tells us only two things: that S valued G at something less than $100, and that
B valued G at something more than $100. So we have no clue what S would’ve
done if B had offered less than $100.
We likewise have no clue who would’ve bargained for what in the
counterfactual world imagined by Pierre and the majority. The Government
offered Pierre three things in exchange for his guilty plea: the promise not to
seek the sentencing enhancement, the promise to drop the indictment’s
second charge (“Count 2”), and the promise not to prosecute Pierre for
certain crimes, on the condition that he disclose those crimes. Pierre
accepted. Does it follow that Pierre wouldn’t have accepted if the
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Government had offered only to drop Count 2? Absolutely not. We don’t
have enough information to say anything about that hypothetical. Reason (4),
like reasons (1)–(3), tells us nothing useful.
Nor does my view entail that a defendant can never satisfy the third
plain-error prong after pleading guilty. Imagine this was a § 2255 case. If so,
Pierre would have had the opportunity for a factual hearing in district court.
See 28 U.S.C. § 2255(b). Imagine that, at the hearing, Pierre showed the
Government had first offered only to drop Count 2, and Pierre refused that
offer. And suppose the Government had only then came back with a promise
to drop Count 2, paired with a promise not to seek the sentencing
enhancement. In light of those facts, we would have very strong reason to
believe Pierre wouldn’t have pleaded guilty without the no-sentencing-
enhancement promise. And the absence of such showings in the case before
us perfectly illustrates why this claim cannot be resolved without facts. Cf.
Gulley, 526 F.3d at 821 (ineffective-assistance claims generally not cognizable
on direct appeal). In all events, the mere existence of the Government’s
promise can’t answer the reasonable-probability question all by itself.
That leaves reason (5). It’s the oddest of them all. The majority
recognizes that the Government made three promises in the plea agreement:
(A) a promise to dismiss Count 2; (B) a promise not to bring future charges;
and (C) an illusory promise not to seek an inapplicable sentencing
enhancement. All agree that the value of (C) is zero. But for the majority’s
reason (5) to make sense, the value of A and B also must equal zero. Yet the
majority effectively concedes that (A) and (B) were not worth zero. The most
the majority can say is that (C) was Pierre’s “primary” benefit under the plea
agreement, and that (A) + (B) conferred “little (if any)” additional benefit
on him. See ante, at 9. All that matters, however, is that (A) + (B) conferred
some additional benefit; because they did—as the majority effectively
concedes—Pierre undisputedly benefited from his plea.
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And the majority is correct not to dispute the value of (A) + (B). As to
(A), the Government agreed to dismiss Count 2 entirely. The majority says
that might not matter because a conviction on both Counts 1 and 2 would not
affect Pierre’s Guidelines range. See id. at 8–9 (citing U.S.S.G. § 3D1.2). But
the majority ignores the fact that the sentencing court could’ve determined
the applicable range was inappropriate for a multi-count conviction and
departed accordingly. In United States v. Saldana, 427 F.3d 298 (5th Cir.
2005), for example, § 3D1.2 of the Guidelines required the defendant’s
convictions be grouped together. Compare id. at 311 (explaining how the
Guidelines work and explaining, “no [multiple-convictions] adjustment was
available in this case” under the Guidelines), with ante, at 8–9 (explaining the
same in this case). But in Saldana, the district court consciously chose to
impose consecutive sentences anyway, “quadrupl[ing] the maximum
sentence allowable . . . under the Guidelines.” 427 F.3d at 308–12. We upheld
that decision as an upward departure from the Guidelines. Id. at 311–12. It’s
not my view that such upward departures are categorically permissible. But
that doesn’t matter: For a defendant facing prison, the prospect of a multi-
count conviction is a serious risk to be mitigated. The Government’s promise
to drop Count 2 didn’t just mitigate that risk for Pierre, it eliminated it
entirely. It blinks reality to dismiss the obvious benefit of (A) as basically
nothing.
As to (B), the Government promised not to bring certain charges
against Pierre in the future, so long as Pierre disclosed those offenses in full.
The majority attempts to dismiss this promise in a footnote, arguing that
“[t]he record does not show that the government was in a position to charge
Pierre with any such offense.” Ante, at 9 n. 6. But that’s not good enough:
It’s Pierre’s burden to establish plain error, including the third prong. See
Sanchez-Hernandez, 931 F.3d at 412 n. 3 (“Under prong three, it remains the
defendant’s burden (not the government’s) to prove prejudice.”). And that
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means it’s Pierre’s burden to establish the Government’s no-charge promise
was meaningless. He hasn’t done so; instead, his briefing ignored this
promise entirely. That alone is fatal to his plain-error argument. See Molina,
469 F.3d at 412 (“Moreover, [the defendant] does not direct this court to any
portion of the record supporting the proposition that the maximum sentence
for count three affected his plea decision. Because [the defendant] has not
satisfied his burden, we affirm his conviction.” (emphasis added)).
In sum: The majority’s key claim (to the extent it even makes the
claim) on the third prong is that the only benefit of the plea agreement was
the Government’s illusory promise. See ante, at 9. But the majority’s five
reasons to believe that are themselves illusory—and that’s because the
majority is substituting its own hypotheses for the factual development a §
2255(b) hearing is supposed to provide.
II.
In any event, this is not the kind of extreme case that warrants an
exercise of our discretion under the fourth plain-error prong. This prong
involves “discretion,” Henderson v. United States, 568 U.S. 266, 272 (2013),
and “a plain error affecting substantial rights does not, without more,”
satisfy this standard, United States v. Olano, 507 U.S. 725, 737 (1993). Indeed,
Rule 52(b) “authorizes the Courts of Appeals to correct only particularly
egregious errors.” United States v. Young, 470 U.S. 1, 15 (1985) (quotation
omitted).
The majority gives short shrift to one key fact: Pierre got the 10-year,
minimum sentence for his Count 1 offense—an offense he admitted under
oath. It’s not as if Pierre was sentenced under the inapplicable mandatory-
minimum of 15 years. Nor did the sentencing court impose a life sentence
(which the statute would’ve allowed). There’s nothing “particularly
egregious” about that. See ibid. (quotation omitted); cf. Alvarado-Casas, 715
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F.3d at 954–55 (denying plain-error relief partially because the Government
had dropped many charges as part of the plea agreement, which suggested
the bargain was a fair one).
The majority’s response, see ante, at 11 n.7, is to form yet another
hypothesis: that Pierre might be able to get a still better deal on remand. In
the majority’s words, “[i]f, for example, [Pierre] pleaded guilty to
participating in the trafficking of anything less than the 280-gram quantity of
cocaine base [the Count 1 offense], he would face a five-year mandatory
minimum sentence instead of a ten-year mandatory minimum.” See ibid.
What conceivable basis is there for this speculation? Pierre already got the
minimum sentence for his crime. The only way to get a better deal is to
suggest—again without a single piece of factual support—that Pierre
somehow, maybe, could’ve beaten the rap for the crime he admittedly
committed. Or perhaps the Government would’ve allowed him to plead to
something less than conspiring to traffic 280 grams or more of cocaine base.
But criminal appeals don’t turn on perhapses, would’ves, could’ves, and
maybes. We ordinarily require prisoners to prove their claims before vacating
their convictions. I would’ve followed our usual course.
I respectfully dissent.
20
United States v. Pierre
Combined Opinion