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 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-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 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.
- 4 - 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 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 18 U.S.C.
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 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
- 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?
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, 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).
- 9 - 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.
- 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 21 U.S.C.
§ 841(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 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.
- 14 - 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
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, 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
- 15 - totality of the relevant circumstances," United States v. Nieves-
Meléndez, 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).
- 16 - 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.
- 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, 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.
- 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, 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
- 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, 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]."
- 20 - 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
- 21 - 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.
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, 63 F.3d at 61.
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, 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
- 24 - 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
- 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, 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
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, 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.
- 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 -