United States Court of Appeals 

for the Fifth Circuit 

No. 20-30728 

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opinion should not be published and is not precedent except under the limited 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. 

United States Court of Appeals 

Fifth Circuit 

FILED 

April 22, 2022 

Lyle W. Cayce 

Clerk 

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2 

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 

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3 

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. 

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4 

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 

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5 

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 involuntaryplea 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). 

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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. 

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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 

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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 twentyeight 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). 

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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. 

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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 

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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.”). 

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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 

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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. AlvaradoCasas, 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 otherwisegenerous 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 

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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 AlvaradoCasas—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 nosentencing-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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15 

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-sentencingenhancement 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 multicount 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 mandatoryminimum 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. 

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