United States Court of Appeals

For the First Circuit

No. 21-1511

UNITED STATES OF AMERICA,

Appellee,

v.

SAMUEL ARCE-AYALA, a/k/a Brócoli, a/k/a Broco, aka Vegetal,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Francisco A. Besosa, U.S. District Judge]

Before

Barron, Chief Judge,

Lipez and Montecalvo, Circuit Judges.

Rafael F. Castro Lang for appellant. 

Ricardo A. Imbert-Fernández, Assistant United States

Attorney, with whom W. Stephen Muldrow, United States Attorney, 

Mariana E. Bauzá-Almonte, Assistant United States Attorney, Chief, 

Appellate Division, and David C. Bornstein, Assistant United 

States Attorney, were on brief for appellee. 

January 17, 2024
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LIPEZ, Circuit Judge. Pursuant to a negotiated 

agreement, appellant Samuel Arce-Ayala pled guilty to federal 

charges related to drug trafficking and possession of a firearm. 

Arce-Ayala says he understood that this plea agreement guaranteed 

his federal sentence would reflect "credit" for the prison time he 

served for related non-federal criminal convictions. Statements

from his lawyer and the district court reinforced his belief. Yet,

after entering a guilty plea, Arce-Ayala discovered such credit 

could not reduce his sentence below the applicable mandatory

minimum terms of imprisonment. He then moved to withdraw his plea

before sentencing, but the district court denied the motion and 

sentenced him to the mandatory minimum prison terms for his charged

offenses. 

On appeal, Arce-Ayala argues the district court should 

have permitted him to withdraw his guilty plea because, not 

understanding the consequences of his plea, it was unknowing. 

Agreeing with his position, we vacate Arce-Ayala's criminal 

judgment of conviction. 

I.

A. Federal Indictment and Prior Commonwealth Criminal Convictions

Arce-Ayala was a leader, drug point owner, and enforcer 

for "Los Menores," a violent drug trafficking organization in 
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Puerto Rico.1 As a drug point owner, Arce-Ayala supervised the 

purchase, sale, and distribution of narcotics at certain public 

housing projects controlled by the organization. As an enforcer, 

Arce-Ayala would carry and use firearms to protect Los Menores' 

drug trafficking activities. In December 2017, a federal grand 

jury indicted Arce-Ayala along with 103 other individuals on 

charges related to their participation in Los Menores.

Specifically, Arce-Ayala was charged with conspiring to possess 

with the intent to distribute controlled substances in violation 

of 21 U.S.C. §§ 84l(a)(l), 846, and 860 ("Count I"), and with 

possessing a firearm in furtherance of a drug trafficking crime in 

violation of 18 U.S.C. § 924(c)(l)(A) ("Count II"). 

Arce-Ayala was no stranger to the criminal justice 

system by the time he was charged federally. About five years 

before this federal indictment, the Commonwealth of Puerto Rico 

convicted Arce-Ayala on two counts of attempted second-degree 

murder and three firearms offenses.2 These Commonwealth 

convictions stemmed from an incident in June 2011, when Arce-Ayala 

shot two individuals to "further the drug trafficking activities 

1 Our description of the relevant facts is mainly based on 

the unchallenged portions of the plea agreement, the change-ofplea colloquy, the presentence investigation report, and the 

sentencing hearing. 

2 The parties describe this conviction as a "local conviction" 

or a "state case." We refer to it as a "Commonwealth conviction."
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of [Los Menores]." Both victims survived the attack.3 In September 

2012, Arce-Ayala was sentenced to eight years in prison for these 

Commonwealth convictions. 

While still serving his Commonwealth sentence, ArceAyala was charged with the federal offenses at issue here. He 

ultimately served sixty-four months in Commonwealth custody before 

being transferred to a federal facility due to the present charges. 

B. The Plea Agreement and Change-of-Plea Hearing

Although Arce-Ayala initially pled not guilty to his 

federal charges, he entered a plea agreement with the government 

on June 5, 2020. Under the agreement, Arce-Ayala would plead 

guilty to both Count I and Count II of the indictment. Several 

provisions in the agreement governed the sentence the parties would 

recommend to the district court.

To start, the parties noted the applicable minimum and 

maximum penalties for each offense. The statutory minimum term of 

imprisonment for Count I, the drug trafficking conspiracy charge, 

was 120 months, while the maximum prison sentence was life in 

prison. See 21 U.S.C. §§ 841 (b)(l)(A), 860. The statutory 

minimum prison sentence for Count II, the firearms charge, was 

3 The record provides few further details about the incident. 

Nevertheless, both parties agree the Commonwealth offenses were 

"relevant conduct" in relation to Arce-Ayala's federal drug 

trafficking conspiracy charge. 
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sixty months, while the maximum was a life term. See 18 U.S.C. 

§ 924(c)(l)(A).

The agreement then set out the applicable sentencing 

range under the United States Sentencing Guidelines 

("Guidelines"). Starting with Count I, the parties agreed ArceAyala's Total Offense Level was thirty-one.4 Assuming a criminal 

history category of one, Arce-Ayala's Guidelines sentencing range

for Count I was between 108 and 135 months.5 As to Count II, the 

agreement noted the guideline sentence is "the minimum term of 

imprisonment required by statute." See U.S.S.G. § 2K2.4(b). The

statute charged under Count II, as mentioned, carries a sixtymonth mandatory minimum term of imprisonment. See 18 U.S.C. 

§ 924(c)(l)(A). 

Next, the parties agreed to recommend certain sentences 

for each charge. As to Count I, they agreed to recommend the 

statutory minimum prison sentence of 120 months; as for Count II, 

4 To reach a Total Offense Level of thirty-one, the parties 

first stipulated that the amount of cocaine distribution

attributable to Arce-Ayala was between five and fifteen kilograms. 

Such an amount corresponded to a Base Offense Level of thirty under 

the Drug Quantity Table in U.S.S.G. § 2D1.1. A two-level 

enhancement applied due to Arce-Ayala's conduct taking place in a 

"Protected Location" under U.S.S.G. § 2D1.2(a)(1). And an 

additional two-level enhancement applied because Arce-Ayala, as a 

leader of Los Menores, acted in an "Aggravating Role" under 

U.S.S.G. § 3B1.1(c). Finally, he received a three-level deduction 

for acceptance of responsibility under U.S.S.G. § 3E1.1. 

5 The parties did not stipulate to Arce-Ayala's criminal 

history category. 
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they agreed to recommend the statutory minimum prison sentence of 

sixty months, which would be served consecutively to the sentence 

imposed from Count I.6

These recommendations were followed by the "relevant 

conduct" provision at issue in this appeal. The parties agreed 

Arce-Ayala's Commonwealth convictions for attempted murder (and 

the accompanying firearms offenses) involved "relevant conduct to 

the case of reference and that in the instant case, the sentence 

of imprisonment shall be imposed pursuant to U.S.S.G. § 5G1.3 and 

§ 5K2.23."7

6 By statute, the sentence imposed under Count II had to be 

served consecutively. See 18 U.S.C. § 924(c)(l)(D)(ii) ("[N]o 

term of imprisonment imposed on a person under this subsection 

shall run concurrently with any other term of imprisonment imposed 

on the person, including any term of imprisonment imposed for the 

crime of violence or drug trafficking crime during which the 

firearm was used, carried, or possessed."). 

7 U.S.S.G. § 5G1.3(b) provides that if "a term of imprisonment 

resulted from another offense that is relevant conduct to the 

instant offense of conviction," the district court shall "adjust 

the sentence for any period of imprisonment already served on the 

undischarged term of imprisonment" and order the federal sentence 

to run concurrently with the remainder of the undischarged sentence

if the court determines that such period of imprisonment will not 

be credited to the federal sentence by the Bureau of Prisons. 

"Relevant [c]onduct," for these purposes, is defined as actions 

"that were part of the same course of conduct or common scheme or 

plan as the offense of conviction." U.S.S.G. § 1B1.3(a)(2).

U.S.S.G § 5K2.23 provides that "[a] downward departure may be 

appropriate if the defendant (1) has completed serving a term of 

imprisonment; and (2) subsection (b) of § 5G1.3 . . . would have 

provided an adjustment had that completed term of imprisonment 

been undischarged at the time of sentencing for the instant 
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The parties appeared for a change-of-plea hearing on 

June 8, 2020, three days after Arce-Ayala signed the abovedescribed agreement. There, the government summarized key 

provisions of the deal. During the government's description of

the "relevant conduct" provision, the district court interjected 

to have the following colloquy with Arce-Ayala: 

THE COURT: I want to ask Mr. Arce one question. Mr. 

Arce, you heard the Prosecutor say that 

some cases in which you were convicted in the 

State Court are relevant conduct to this case 

and that your sentence would be imposed 

pursuant to certain sections of the sentencing 

guidelines. Did you hear that?

ARCE-AYALA: Yes.

THE COURT: That means, Mr. Arce, that whatever time you

spent in the State Court will be -- you will

be given credit for that time when I sentence

you in this case. Do you understand that?

ARCE-AYALA: Yes.

THE COURT: With that clarification, Mr. Arce, do you 

agree with the summary stated by the 

Prosecutor of your plea agreement? 

offense. Any such departure should be fashioned to achieve a 

reasonable punishment for the instant offense."
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ARCE-AYALA: Yes.

The district court then asked a variety of questions to 

determine whether Arce-Ayala had entered a knowing and voluntary

plea agreement. During this exchange, the district court explained

it could impose a sentence that was "either more severe or even 

less severe than the sentence [Arce-Ayala] may anticipate, or even 

the sentence being recommended in the plea agreement." Separately, 

the district court stated, "even after [Arce-Ayala's] sentencing 

guideline range has been determined, [the court would] have the 

authority to depart from those guidelines and impose a sentence on 

[him] that is either more severe or less severe than the sentence 

called for by the guidelines." 

The court ultimately found Arce-Ayala competent to enter

an informed plea and that his guilty plea was knowing and 

voluntary. After accepting Arce-Ayala's plea, the court scheduled 

his sentencing for October 6, 2020. 

C. Defense Counsel's Mistake of Law 

Problems arose between the parties in the months 

following Arce-Ayala's guilty plea. In September 2020, ArceAyala's trial counsel, Ián Terón-Molina, learned the "relevant 

conduct" provision in the plea agreement could not provide ArceAyala with credit for his time served in Commonwealth custody. In

sharing his mistake with Arce-Ayala, Terón-Molina explained that 

if he were to receive credit for his Commonwealth sentence, his 
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federal sentence would fall below the statutory mandatory minimum. 

And, contrary to their earlier assumptions, neither U.S.S.G. 

§ 5G1.3(b) nor U.S.S.G. § 5K2.23 permitted the district court to 

sentence Arce-Ayala below the mandatory minimum.

Terón-Molina's belated understanding of the law was 

correct. Generally, "sentencing guidelines cannot be employed to 

impose a sentence below an applicable statutory mandatory 

minimum." United States v. Ramirez, 252 F.3d 516, 518–19 (1st 

Cir. 2001) (citing Melendez v. United States, 518 U.S. 120, 126-

27 (1996)). After all, "mandatory minimums are imposed by 

Congress," so "only Congress -- through the enactment of another 

statute -- can authorize downward departures from them." United 

States v. Moore, 918 F.3d 368, 370 (4th Cir. 2019). With that in 

mind, our court has so far found only two ways for a district court 

to sentence below a statutory mandatory minimum. "First, if a 

defendant provides substantial assistance the government may move 

for a below-minimum sentence pursuant to 18 U.S.C. § 3553(e) or 

Federal Rule of Criminal Procedure 35(b). Second, the court may 

sentence below a mandatory minimum if a defendant has been 

convicted of a qualifying drug trafficking offense and meets the 

requirements of the 'safety valve' provision in 18 U.S.C. 

§ 3553(f)." United States v. Candelario-Ramos, 45 F.4th 521, 525 

(1st Cir. 2022) (citations omitted). 
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Here, Arce-Ayala neither provided substantial assistance 

under 18 U.S.C. § 3553(e) nor qualified for the "safety valve" 

provision in 18 U.S.C. § 3553(f). Rather, Arce-Ayala believed the 

provisions cited in his plea agreement, U.S.S.G. § 5G1.3(b) and

U.S.S.G. § 5K2.23, would provide him "credit" for his time served 

in Commonwealth custody on related charges. But U.S.S.G. 

§ 5G1.3(b) applies only "when there is an undischarged term of 

imprisonment at the time of sentencing." Ramirez, 252 F.3d at 519 

(citing United States v. Rizzo, 121 F.3d 794, 800 (1st Cir. 1997)).

By the time Arce-Ayala scheduled his federal sentencing date, his 

Commonwealth sentence was already discharged (that is, completed), 

so § 5G1.3(b) could provide no relief.8 And while § 5K2.23 applies 

to discharged sentences, it "cannot be used to sentence below a 

mandatory minimum." Candelario-Ramos, 45 F.4th at 526 n.7; see

also Moore, 918 F.3d at 371 ("[S]everal other circuits have

[addressed this question], and each has determined that U.S.S.G. 

8 "U.S.S.G. § 5G1.3 generally allows district courts to give 

credit for time served on an undischarged sentence, provided the 

sentence arose out of relevant conduct." Moore, 918 F.3d at 371. 

"And according to some Courts of Appeals, this credit can even be 

given where a mandatory-minimum sentence is involved, 'so long as 

the total of the time served and the reduced federal sentence 

equals or exceeds the statutory mandatory minimum period.'" Id.

(quoting Ramirez, 252 F.3d at 519) (collecting cases). Our court 

has not yet resolved this question. Id. Even if there were such 

an exception for undischarged sentences, it would not have helped 

Arce-Ayala because his Commonwealth sentence was discharged by the 

time he was sentenced in this federal case. 
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§ 5K2.23 alone cannot authorize a downward departure from a 

mandatory-minimum sentence.").

D. Attempts to Withdraw the Guilty Plea

Upon learning our precedents meant that he could not 

receive credit for the relevant Commonwealth convictions that 

could bring his sentence below the mandatory minimums, Arce-Ayala

asked the district court on September 28, 2020 to postpone his 

sentencing so the parties could revisit their plea negotiations in 

light of Arce-Ayala's new understanding of the relevant law. The 

district court granted Arce-Ayala's motion in part and rescheduled

the sentencing to October 14, 2020, approximately one week after 

the initial date.

Over the next few months, Arce-Ayala made several more 

requests to postpone his sentencing date. During that time, TerónMolina tried to persuade the government to amend the plea 

agreement. He proposed that Arce-Ayala could accept 

responsibility for more than 3.5 kilograms but less than 5 

kilograms of cocaine, which would decrease his base offense level 

by two points, see U.S.S.G. § 2D1.1(c)(1)(6), while also removing 

the 120-month mandatory minimum requirement under 21 U.S.C. 

§ 841(b)(1)(A)(ii). To compensate for these adjustments, TerónMolina suggested Arce-Ayala could accept a four-level enhancement 

-- instead of a two-level enhancement -- for his leadership role 

in Los Menores. He believed this proposal "would set the 
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sentencing range higher in the proposed amendment than the original 

plea but would permit the [application of] credit for time served 

for the local case" because "it lowered the mandatory minimum to 

five years." By pitching a lower applicable mandatory minimum

(that is, five years instead of ten years for Count I), TerónMolina sought to give the court latitude to credit Arce-Ayala for 

the time he served in Commonwealth custody. The government 

rejected such a proposal. 

On February 26, 2021, Arce-Ayala filed a pro se motion 

requesting an evidentiary hearing to address "violations of the 

plea agreement." He argued that the government's refusal to credit 

his time served in the Commonwealth cases violated the plea 

agreement. Additionally, Arce-Ayala asserted that Terón-Molina 

provided ineffective assistance of counsel in negotiating the plea 

agreement. And because he was not adequately informed of the 

consequences of pleading guilty, Arce-Ayala claimed his plea did 

not comply with Federal Rule of Criminal Procedure 11.9 On May 5, 

2021, the district court denied the motion in a text order stating: 

"The government did not violate the plea agreement." 

9 Before accepting a guilty plea, Federal Rule of Criminal 

Procedure Rule 11(b)(1) requires a district court to address the 

defendant "personally in open court" and "inform the defendant of, 

and determine that the defendant understands," among other things, 

the rights they are waiving by pleading guilty. For example, Rule 

11(b)(1)(I) requires a court to establish that the defendant 

understands "any mandatory minimum penalty." 
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On May 26, 2021, Arce-Ayala, through Terón-Molina, moved 

for leave to withdraw his plea agreement on the same grounds raised 

in the pro se motion. The district court, again, denied ArceAyala's motion in a one-sentence order, this time with no 

explanation. Two weeks later, on June 10, 2021, Arce-Ayala filed 

a pro se motion to remove Terón-Molina as counsel and to request 

the appointment of new counsel before his sentencing hearing. The 

district court denied this motion, too, with no explanation.

E. Sentencing 

Arce-Ayala appeared before the district court for 

sentencing on June 21, 2021. In his sentencing memorandum, ArceAyala requested a sentence of 120 months for Count I and sixty 

months for Count II to be served consecutively, but also asked the 

court to reduce his sentence by sixty-four months to account for 

the time he served in Commonwealth custody. During the sentencing 

hearing, Terón-Molina began his presentation on behalf of ArceAyala by reincorporating the arguments raised in the motions to 

withdraw the guilty plea. The court again denied those motions. 

In his own statement to the court, Arce-Ayala reiterated that he 

pled guilty on the understanding that he would receive credit for

his Commonwealth sentence.

The government recommended a 120-month prison sentence

as to the drug trafficking conspiracy charge (Count I) and sixty

consecutive months as to the firearms charge (Count II). But with 
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respect to Arce-Ayala's prior Commonwealth convictions, the 

government argued the "relevant conduct" provision of his plea 

agreement meant those offenses would not factor into his criminal 

history category, which remained at Category I. The district court 

calculated the Guideline range for Count I as between 120 to 135 

months. The district court noted the Guidelines sentence for Count 

II was the "minimum term of imprisonment required by statute," 

which was sixty months under 18 U.S.C. § 924(c)(l)(A). The 

district court then sentenced Arce-Ayala to 120 months as to the 

drug trafficking conspiracy offense and sixty months as to the 

firearms offense to be served consecutively.

Arce-Ayala now appeals his conviction.

II.

A defendant may withdraw a guilty plea before sentencing 

if he can show "a fair and just reason for requesting the 

withdrawal." See Fed. R. Crim. P. 11(d)(2)(B). This standard is

"liberal," United States v. Gardner, 5 F.4th 110, 114 (1st Cir. 

2021) (quoting United States v. Kobrosky, 711 F.2d 449, 454 (1st 

Cir. 1983)), and "permissive," id. (quoting United States v. 

Merritt, 755 F.3d 6, 9 (1st Cir. 2014)), but not toothless, see

Merritt, 755 F.3d at 11 ("[L]iberal allowance is not to be confused 

with automatic allowance."). Indeed, a defendant does not have 

"an unfettered right to retract a guilty plea." United States v. 
- 15 -

Flete-Garcia, 925 F.3d 17, 24 (1st Cir. 2019) (quoting Merritt, 

755 F.3d at 9).

To determine whether a defendant has shown a "fair and 

just reason" to withdraw a guilty plea, courts typically consider: 

"(1) whether the original plea was knowing, intelligent, and 

voluntary and in compliance with Rule 11, (2) the strength of the 

reason for withdrawal, (3) the timing of the motion to withdraw, 

(4) whether the defendant has a serious claim of actual innocence, 

(5) whether the parties had reached (or breached) a plea agreement, 

and (6) whether the government would suffer prejudice if 

withdrawal is permitted." Gardner, 5 F.4th at 114 (first citing 

United States v. Dunfee, 821 F.3d 120, 127 (1st Cir. 2016) (per 

curiam), then citing United States v. Tilley, 964 F.2d 66, 72 (1st 

Cir. 1992)).10 Yet district courts must ultimately look to "the 

10 Whether courts should consider the presence or absence of 

government prejudice as part of an initial inquiry remains an open 

question in our circuit. In some cases, we have instructed

district courts to consider prejudice to the government only after 

the defendant makes a threshold showing of a fair and just reason 

for withdrawal. See, e.g., Flete-Garcia, 925 F.3d at 24; Merritt, 

755 F.3d at 9; United States v. Todd Isom, 85 F.3d 831, 834-35 

(1st Cir. 1996). In other cases, we have suggested the presence 

or absence of prejudice to the government should be considered 

holistically, as a relevant factor to be weighed against the others 

in determining whether a fair and just reason for withdrawal 

exists. See Dunfee, 821 F.3d at 127; compare Gardner, 5 F.4th at 

118-19 & n.9 (considering these factors holistically), with id. at 

122 (Lynch, J., dissenting) (arguing that a court may consider 

prejudice only if the totality of the other factors weighs in favor 

of withdrawal). 

We need not resolve this conflicting authority here because 

under the circumstances presented both approaches lead to the same 
- 16 -

totality of the relevant circumstances," United States v. NievesMeléndez, 58 F.4th 569, 574 (1st Cir. 2023) (quoting Flete-Garcia, 

925 F.3d at 24), so these six considerations do not represent an 

"exclusive list of reasons that might allow withdrawal of a plea," 

id. (quoting Gardner, 5 F.4th at 114). 

The first consideration -- whether the plea was knowing, 

intelligent, and voluntary and in compliance with Rule 11 -- holds 

special weight for good reason. See United States v. Derrick Isom, 

580 F.3d 43, 52 (1st Cir. 2009) (noting that the "most important" 

factors to consider are whether a guilty plea was knowing, 

intelligent, and voluntary). Due process requires a voluntary and 

knowing waiver of the constitutional entitlement to trial. See

McCarthy v. United States, 394 U.S. 459, 466 (1969). Hence, 

district courts must determine that a defendant understands the 

consequences to pleading guilty, see Fed. R. Crim. P. 11(b)(1), 

while also evaluating whether a guilty plea is voluntary and not 

the result of force, threats, or promises beyond a plea agreement, 

see Fed. R. Crim. P. 11(b)(2). 

As part of this inquiry, we have distilled three "core 

concerns" of Rule 11: (1) "a lack of coercion," (2) "the 

defendant's understanding of the charges against him," and (3) 

"the defendant's 'knowledge of the consequences of the guilty 

outcome. See United States v. Fonseca, 49 F.4th 1, 7 n.5 (1st 

Cir. 2022) (declining to resolve this split in precedent).
- 17 -

plea.'" United States v. Williams, 48 F.4th 1, 6 (1st Cir. 2022) 

(quoting United States v. Cotal-Crespo, 47 F.3d 1, 4 (1st Cir. 

1995)). A failure to satisfy any one of these core concerns 

"requires that the guilty plea be set aside." Todd Isom, 85 F.3d 

at 835 (citing United States v. Gray, 63 F.3d 57, 60 (1st Cir.

1995)). 

Given the fact-intensive nature of plea withdrawal

inquiries, we trust these decisions to the sound discretion of 

district courts. See United States v. Caramadre, 807 F.3d 359, 

370 (1st Cir. 2015). We review the denial of a motion to withdraw 

a guilty plea for abuse of such discretion. See United States v. 

Adams, 971 F.3d 22, 38 (1st Cir. 2020) (citing United States v. 

Dávila-Ruiz, 790 F.3d 249, 251 (1st Cir. 2015)). 

III. 

This case turns on the third "core concern" of Rule 11. 

Arce-Ayala argues that the district court and his defense 

attorney's statements misled him into believing he would "receive 

credit" for his time served in Commonwealth custody on related 

charges.11 Because he pled guilty on the mistaken assumption that 

he would receive such credit regardless of the applicable mandatory 

11 Arce-Ayala also alleges the prosecutors "knew that [he] 

would not be able to receive the 64-month credit," but took 

advantage of his and his lawyer's "lack of knowledge of the law" 

to "induce him to accept the Plea Agreement." We need not reach 

that issue here. 
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minimum terms, Arce-Ayala contends he "did not know the 

consequences of his guilty plea," thus implicating a "core concern" 

of Rule 11.12 

A. The District Court's Comments 

During the change-of-plea hearing, the district court 

emphasized that Arce-Ayala was "convicted in the State Court" for 

offenses involving "relevant conduct to this case." Beyond simply 

stating that factual predicate, the district court sought to 

clarify the legal effect of the "relevant conduct" provision in 

Arce-Ayala's plea agreement. That is, the district court told 

Arce-Ayala the provision "mean[t] . . . [he] will be given credit" 

for "whatever time [he] spent in the State Court" when sentenced 

in this case (emphasis added). 

12 We summarily reject the government's forfeiture contention. 

Arce-Ayala, the government asserts, "forfeited the argument that 

the district court should have let him withdraw his guilty plea" 

because Arce-Ayala only asked the district court for leave to 

"withdraw from his plea agreement, but not his plea." Plea 

agreements and pleas are, of course, distinct. See Gardner, 5 

F.4th at 114. Even though Arce-Ayala conflated the two at times, 

the record makes clear he moved to withdraw his guilty plea in 

addition to his plea agreement. At the sentencing hearing, for 

example, Terón-Molina reiterated that Arce-Ayala sought to 

"withdraw the plea agreement and the plea of guilty" (emphasis 

added). And in his motions below, Arce-Ayala consistently cited 

Federal Rule of Criminal Procedure 11, which governs both plea 

agreements and the acceptance of guilty pleas by a court. Finally, 

the government even admits that, when it opposed his request for 

relief in the district court, it "treated Arce-Ayala's pro se

motion as a motion to withdraw his guilty plea . . . ." In light 

of this record, the government's forfeiture argument borders on 

the frivolous. 
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Arce-Ayala could have reasonably interpreted the 

district court's remark as a guarantee that he would receive credit 

for his time served in state custody. The comment that he would 

be "given credit" contained no conditions or reservations. Nowhere 

did the district court qualify its statement by noting, 

notwithstanding such credit, the statutory minimums represented an 

absolute floor for his term of imprisonment.

Separately, the district court noted it "ha[d] the 

authority to depart from th[e] guidelines and impose a sentence on 

[Arce-Ayala] that is either more severe or less severe than the 

sentence called for by the guidelines" (emphasis added). Of 

course, this comment simply explains the advisory nature of the 

sentencing guidelines under United States v. Booker, 543 U.S. 220, 

245 (2005). But we cannot assume a reasonable person, having heard 

the other remarks from the district court, would be able to 

distinguish this comment about the advisory nature of the 

sentencing guidelines from the mandatory nature of statutory 

minimum sentences.

To be sure, the district court noted that, as to Count 

I, Arce-Ayala could not be sentenced to "anything less than ten 

years." Still, that statement is difficult to square with the 

district court's explanation that it could impose a sentence that 

was "either more severe or even less severe than the sentence 

[Arce-Ayala] may anticipate, or even the sentence being 
- 20 -

recommended in the plea agreement" (emphasis added). After all, 

the sentence recommended in the plea agreement was the sum of the 

mandatory minimum terms, so one could interpret the district 

court's remark as conveying an ability to impose a sentence less 

severe than the mandatory minimums. 

We have addressed similarly misleading statements on 

several occasions. In United States v. Hernandez-Wilson, 186 F.3d 

1 (1st Cir. 1999), for example, we vacated a conviction based on

the defendant's misunderstanding of his eligibility for the safety 

valve provision in 18 U.S.C. § 3553(f). Id. at 6. There, the 

district court "represented to [the defendant] that his criminal 

history made him eligible for sentencing under the safety valve." 

Id. But because the defendant committed the offense at issue while 

on probation, his criminal history category was too high to qualify

for the safety valve provision. Id. at 4. In fact, the defendant 

could not "be sentenced to anything less than . . . the statutory 

mandatory minimum sentence for the crime to which [he] was pleading 

guilty." Id. We set aside the defendant's guilty plea because it 

was "induced at least in part by an inaccurate representation by 

the court about the consequences of his plea." Id. at 6.

Likewise, in United States v. Gray, 63 F.3d at 57, we 

vacated a conviction where the district court mistakenly stated, 

"[t]he maximum punishment [was] ten years to life" and that "the 

matter of [the defendant's] sentence [was] up to [the court]." 
- 21 -

Id. at 60 (emphasis omitted). Those statements were incorrect:

"in fact, the mandatory minimum sentence for the crime to which 

[the defendant] pled guilty was ten years, and the court had no 

discretion over this minimum sentence." Id. (emphasis omitted).

In vacating the conviction, we explained that "the substance of 

what [the district court] communicated to [the 

defendant] . . . could have led a reasonable person to 

misunderstand the consequences of his guilty plea in th[at] 

context, thus implicating one of Rule 11's core concerns." Id. at 

61. 

Conversely, in United States v. Bierd, 217 F.3d 15 (1st 

Cir. 2000), we rejected a defendant's assertion that a district 

court misled him into pleading guilty. Id. at 21-22. During the 

change-of-plea hearing in that case, the district court suggested 

the defendant "would be entitled to a three point reduction for 

acceptance of responsibility" when "he actually was entitled to 

only a two point reduction." Id. at 21. Although the district 

court's initial comment "envisioned a three point reduction," the 

"subsequent and more important references to the reduction at the 

plea colloquy" simply provided the correct sentencing range in 

terms of months without referencing any specific point-based 

reduction. Id. at 22. In declining to invalidate the defendant's 

plea we explained that the district court's reference to a three 

point reduction was "an off-hand remark" rather than a "meaningful 
- 22 -

portion of the plea colloquy." Id. Furthermore, the district 

court later in the same hearing "characterized the reduction as 

only a possibility," so the initial comment was not necessarily 

misleading. Id.

It is true that here the text of the plea agreement 

itself did not promise Arce-Ayala "credit" for the time he served 

for relevant conduct.13 But, in reviewing that very plea agreement 

with Arce-Ayala, the district court expressed without reservation 

that Arce-Ayala would receive credit for his time served in 

Commonwealth custody when, in fact, there was "no possibility"

Arce-Ayala would receive "anything less than . . . the statutory 

mandatory minimum sentence." Hernandez-Wilson, 186 F.3d at 4. 

The district court's "credit" comment was expressed as a 

clarification of the agreement writ large. That statement was no 

mere "off-hand remark." Bierd, 217 F.3d at 22. Nor was the 

application of such credit "characterized . . . as only a 

possibility." Id. And given the district court's observation

that it could impose a sentence "less severe" than the parties'

recommendation, a reasonable person could have mistakenly assumed 

the application of such credit need not stop at a mandatory minimum 

sentence. See Gray, 63 F.3d at 61.

13 It is also worth noting that neither U.S.S.G. § 5G1.3(b) 

nor U.S.S.G. § 5K2.23 use the term "credit."
- 23 -

The government argues the plea agreement never contained

a "false promise" of credit. The "relevant conduct" provision, 

the government asserts, had two effects: (1) it ensured ArceAyala's prior convictions would not factor into his criminal 

history category;14 and (2) it guaranteed that, if Arce-Ayala's

pre-sentence report calculated a higher than expected criminal 

history category, and thus a higher sentencing range under the 

Guidelines, "he could have used [a U.S.S.G. § 5K2.23] departure to 

reduce his [Guidelines sentencing range]." The government 

contends the district court's commentary intended to explain these 

"legitimate" effects of the provision, "not the illegal one [ArceAyala] desired."

But these rationales simply suggest ways Arce-Ayala 

could have interpreted the provision without explaining how a 

reasonable person, after hearing the district court's comments, 

would have interpreted the provision. Even assuming there are 

ways to construe the provision to give it legal effect, "the 

substance of what [the district court] communicated to [ArceAyala]" would still lead "a reasonable person to misunderstand the 

consequences of his guilty plea . . . , thus implicating one of 

Rule 11's core concerns." Gray, 63 F.3d at 61. 

14 The government represents that, under U.S.S.G. § 4A1.1(a), 

Arce-Ayala would have otherwise received three criminal history 

points for his prior convictions.
- 24 -

Indeed, the government's suggested interpretations of 

the provision are not so apparent as to undermine the basis for 

Arce-Ayala's misunderstanding. First, the change-of-plea colloquy

belies the notion that the "relevant conduct" provision was only 

intended to limit Arce-Ayala's criminal history category. Before 

explaining the provision, the government said during the changeof-plea hearing that it would recommend 120 months of imprisonment 

as to Count I and sixty consecutive months as to Count II 

"regardless of [Arce-Ayala's] criminal history category." Second, 

the structure of the plea agreement weighs against the government's 

explanation because the "relevant conduct" provision is placed not 

in the "criminal history category" section, but the "sentence 

recommendation" section. 

Finally, the government's representations in a case 

against a different defendant undermine its argument in this case. 

In United States v. Candelario-Ramos, 45 F.4th at 523, the United 

States Attorney's Office for the District of Puerto Rico conceded 

that it was mistaken about the interaction between a similar 

"relevant conduct" provision and mandatory minimum sentencing 

requirements. In that case, the government explained that for the 

better part of a year -- from February to November 2020 -- it "had 

not been aware of 'the Sentencing Commission's opinion in terms of 

credit that can and cannot be provided' and had 'negotiated all 

the pleas [in that case] under the mistaken understanding that the 
- 25 -

co-defendants were going to receive credit for the relevant conduct 

cases.'" Id. (brackets omitted); see also Brief for Appellee at 

*6, *14-15, United States v. Candelario-Ramos, 45 F.4th 521 (1st 

Cir. 2022) (No. 20-1988), 2021 WL 2525761 (brief of United States 

Attorney's Office for the District of Puerto Rico noting the 

government was not aware of case law prohibiting district courts 

from sentencing defendants below a mandatory minimum sentence).

Again, Arce-Ayala need only show his misinterpretation was 

reasonable. See Gray, 63 F.3d at 61 (vacating conviction where 

district court's comments "could have led a reasonable person to 

misunderstand the consequences of his guilty plea"). Given that 

the government appears to have held the same misunderstanding as 

Arce-Ayala and his legal counsel, a reasonable person could have 

made the same mistake. 

B. Defense Counsel's Comments 

We briefly note that Arce-Ayala was particularly 

susceptible to interpreting the district court's comments as 

guaranteeing him credit towards his federal sentence because his 

counsel provided him incorrect legal advice as to the effect of 

his plea. 

From the outset of negotiations, Arce-Ayala evidently

expressed dissatisfaction with the length of imprisonment 

recommended by the plea agreement. Arce-Ayala and Terón-Molina

assert they eventually "signed the plea agreement under the 
- 26 -

impression that . . . the time served for [the 

Commonwealth][c]riminal [c]ases [was] relevant conduct to the 

instant case and could be credited to the sentence imposed for the 

instant federal case." They both believed the plea agreement's 

"relevant conduct" provision memorialized such an arrangement.15

By assuming that provision could bring Arce-Ayala's sentence below 

a statutory minimum sentence, Terón-Molina's representation may 

have sunk below "the range of competence demanded of attorneys in 

criminal cases." McMann v. Richardson, 397 U.S. 759, 771 (1970). 

Terón-Molina's interpretation of such a provision was squarely 

precluded by precedent. See Ramirez, 252 F.3d at 518–19; see also

supra Section I.C. In Terón-Molina's own words, "[he] was supposed 

to know th[e] [relevant conduct] stipulation was unenforceable." 

On this basis, Arce-Ayala asserts a constitutional claim 

for ineffective assistance of counsel. Although bad legal advice 

can be a basis for invalidating a guilty plea, see Caramadre, 807 

F.3d at 371 (explaining the standard for assessing an infective 

assistance of counsel claim in the context of a plea-withdrawal 

15 During his sentencing hearing, Arce-Ayala explained: "The 

only thing that I requested from my attorneys was that they would 

obtain the relevant conduct of this indictment with the sentence 

that I was serving in state court. . . . [My] attorney expressed 

my desire to the prosecutors. Both [p]rosecutor[s] . . . accepted 

that relevant conduct be included. This you can confirm if you 

look at Section 9, paragraph 2, on page 6 of the plea. So clearly 

it is stipulated as part of the plea agreement of that being the 

relevant conduct."
- 27 -

motion), we need not reach that issue here. Instead, we identify 

Terón-Molina's incorrect legal advice only to help explain why 

Arce-Ayala lacked the requisite knowledge to enter a guilty plea. 

See United States v. Fernández-Santos, 856 F.3d 10, 17 n.3 (1st 

Cir. 2017) (rejecting argument that an ineffective assistance of 

counsel issue may be raised only under 28 U.S.C. § 2255 and 

explaining that "ineffective assistance of counsel may be a 'fair 

and just reason' to withdraw a guilty plea or may render a plea 

unknowing or involuntary") (internal citations omitted). 

In sum, Arce-Ayala was told by his defense counsel that 

the sixty-four months he spent in Commonwealth custody would be 

credited toward his federal sentence. The district court then 

seemingly confirmed that mistaken assumption through a series of 

misleading remarks. Because he did not know that the mandatory 

minimum prison sentence set an inviolable floor as to the amount 

of credit he could receive for time served on the Commonwealth 

sentences, Arce-Ayala lacked sufficient "knowledge of the 

consequences of the guilty plea." Williams, 48 F.4th at 6 (quoting 

Cotal-Crespo, 47 F.3d at 4). Arce-Ayala's plea thus violated a 

"core concern" of Rule 11 and must be set aside. See Todd Isom, 

85 F.3d at 835. 
- 28 -

IV.

We vacate the criminal judgment and remand this case to 

the district court for further proceedings. Arce-Ayala shall be 

permitted to withdraw his guilty plea.

So ordered.