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 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

- 2 - 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

(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-of- plea 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."

- 3 - 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, Arce-

Ayala 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

(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.

- 4 - sixty months, while the maximum was a life term. See

(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 Arce-

Ayala'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 sixty-

month mandatory minimum term of imprisonment. See

(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.

- 5 - 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

(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

- 6 - The parties appeared for a change-of-plea hearing on

June 8, 2020, three days after Arce-Ayala signed the above-

described 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."

- 7 - 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, Arce-

Ayala's trial counsel, Ián Terón-Molina, learned the "relevant

conduct" provision in the plea agreement could not provide Arce-

Ayala 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

- 8 - 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,

, 518–19 (1st

Cir. 2001) (citing Melendez v. United States,

, 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,

(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

(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

(f)." United States v. Candelario-Ramos,

(1st Cir. 2022) (citations omitted).

- 9 - Here, Arce-Ayala neither provided substantial assistance

under

(e) nor qualified for the "safety valve"

provision in

(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,

(citing United States v. Rizzo,

(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,

n.7; see

also Moore,

("[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,

. "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.'"

(quoting Ramirez,

) (collecting cases). Our court has not yet resolved this question.

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.

- 10 - § 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, Terón-

Molina 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

(b)(1)(A)(ii). To compensate for these adjustments, Terón-

Molina 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

- 11 - 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), Terón-

Molina 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."

- 12 - 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 Arce-

Ayala'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, Arce-

Ayala 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 Arce-

Ayala 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

- 13 - 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

(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,

(1st Cir.

2021) (quoting United States v. Kobrosky,

(1st

Cir. 1983)), and "permissive,"

(quoting United States v.

Merritt,

(1st Cir. 2014)), but not toothless, see

Merritt,

("[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.

- 14 - Flete-Garcia,

(1st Cir. 2019) (quoting Merritt,

).

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,

(first citing

United States v. Dunfee,

(1st Cir. 2016) (per

curiam), then citing United States v. Tilley,

(1st

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

10Whether 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,

; Merritt,

; United States v. Todd Isom,

(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,

; compare Gardner,

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

(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

- 15 - totality of the relevant circumstances," United States v. Nieves-

Meléndez,

(1st Cir. 2023) (quoting Flete-Garcia,

), so these six considerations do not represent an

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

(quoting Gardner,

).

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,

(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,

(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,

, 7 n.5 (1st Cir. 2022) (declining to resolve this split in precedent).

- 16 - plea.'" United States v. Williams,

(1st Cir. 2022)

(quoting United States v. Cotal-Crespo,

(1st Cir.

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

"requires that the guilty plea be set aside." Todd Isom,

(citing United States v. Gray,

(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,

(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,

(1st Cir. 2020) (citing United States v.

Dávila-Ruiz,

(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.

- 17 - 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).

12We 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,

. 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.

- 18 - 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,

(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

- 19 - 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,

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

the defendant's misunderstanding of his eligibility for the safety

valve provision in

(f).

. There, the

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

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

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.

. 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."

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."

.

Likewise, in United States v. Gray,

, 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]."

- 20 -

(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."

(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."

.

Conversely, in United States v. Bierd,

(1st

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

court misled him into pleading guilty.

. 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."

. 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.

. 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

- 21 - portion of the plea colloquy."

Furthermore, the district

court later in the same hearing "characterized the reduction as

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

misleading.

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,

.

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,

. Nor was the

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

possibility."

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,

.

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

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

- 22 - 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 Arce-

Ayala'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 [Arce-

Ayala] 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 [Arce-

Ayala]" would still lead "a reasonable person to misunderstand the

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

Rule 11's core concerns." Gray,

.

14The 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.

- 23 - 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 change-

of-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,

, 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

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

cases.'"

(brackets omitted); see also Brief for Appellee at

*6, *14-15, United States v. Candelario-Ramos,

(1st

Cir. 2022) (No. 20-1988),

(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,

(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

- 25 - 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,

(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,

(explaining the standard for assessing an infective

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

15During 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."

- 26 - 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,

, 17 n.3 (1st

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

counsel issue may be raised only under

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,

(quoting

Cotal-Crespo,

). Arce-Ayala's plea thus violated a

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

.

- 27 - 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.

- 28 -