Court Opinion

ID: 8208843
Source: CourtListenerOpinion
Date Created: 2022-09-23 18:00:27.863225+00
Date Added: 2024-06-11T16:41:35.765403
License: Public Domain

United States Court of Appeals
                     For the First Circuit

No. 17-2134

                    UNITED STATES OF AMERICA,

                            Appellee,

                               v.

                            JOHN DOE,

                      Defendant, Appellant.

          APPEAL FROM THE UNITED STATES DISTRICT COURT
               FOR THE DISTRICT OF MASSACHUSETTS

       [Hon. George A. O'Toole, Jr., U.S. District Judge]

                             Before

                    Lynch, Lipez, and Howard,
                         Circuit Judges.

     Allison Koury for appellant.
     Alexia R. De Vincentis, Assistant United States Attorney,
with whom Andrew E. Lelling, United States Attorney, was on brief,
for appellee.

                       September 23, 2022
            HOWARD, Circuit Judge.        On May 17, 2016, defendant-

appellant John Doe pled guilty to one count of being a felon in

possession of a firearm, in violation of 18 U.S.C. § 922(g)(1).

Shortly before sentencing, Doe moved to withdraw his guilty plea,

arguing that his counsel was constitutionally ineffective and

therefore, that his plea was unknowing and involuntary.               The

district court denied the motion, and Doe appeals that denial.         He

has also argued for the first time on appeal there was a "fatal

omission" in his plea colloquy, and that the indictment in this

case should be dismissed because it did not allege that he knew

that he was not permitted to possess a firearm, as required by the

Supreme Court's recent decision in Rehaif v. United States, 139 S.

Ct. 2191 (2019).

            On October 18, 2017, Doe was sentenced to fifteen years

of incarceration, followed by three years of supervised release.

The district court made clear during sentencing that it adopted

the Sentencing Guideline calculation recommended by the probation

office in the Presentence Investigative Report ("PSR").         The PSR

in   turn   identified   three   predicate   convictions   --   two   for

possession with intent to distribute cocaine and one for assault

with a dangerous weapon.    Because Doe had at least three predicate

offenses, the district court found, he was subject to a mandatory

minimum incarcerative sentence of fifteen years under the Armed

Career Criminal Act ("ACCA"). The district court also denied Doe's

                                  - 2 -
request to stay sentencing and hold an evidentiary hearing in light

of his allegation that the government breached its obligations

under a cooperation agreement by failing to file substantial

assistance motions under U.S.S.G. § 5K1.1 and 18 U.S.C. § 3553(e).

Doe additionally appeals his classification as an armed career

criminal and the district court's failure to conduct an evidentiary

hearing before proceeding with sentencing.

          For the reasons discussed below, we affirm both Doe's

conviction and sentence.

               I.    CHALLENGES TO THE PLEA AND CONVICTION

          We        begin   with   Doe's   challenges   to   his    plea   and

conviction.    Doe argues, as he did in the district court, that his

decision to plead guilty was not knowing or voluntary because it

was predicated on his belief that trial counsel had filed a motion

in federal court to suppress the firearms at issue.                He further

asserts that the plea was not knowing or voluntary because trial

counsel was constitutionally ineffective in failing to file a

motion in state court to vacate at least one of his qualifying

predicate convictions. He also argues for the first time on appeal

that the district court's failure to inform him specifically that

he faced a mandatory minimum sentence violated Rule 11's core

concerns and rendered his plea invalid.            Finally, Doe contends

that, in the wake of the Supreme Court's decision in Rehaif, 139

S. Ct. 2191, the indictment in this case failed to allege an

                                     - 3 -
essential element of the offense charged and therefore must be

dismissed.

              Only Doe's ineffective assistance claim was raised in

the district court in the motion to withdraw the guilty plea.

Consequently, this is the only basis that we may review for an

abuse of discretion, rather than for plain error.                    See United

States   v.    Isom,   580   F.3d   43,   52   (1st   Cir.   2009)   ("As   [the

defendant] moved to withdraw his guilty plea prior to sentencing,

we review the denial of the motion for abuse of discretion . . .

[and] [t]he district court's factfinding supporting its denial of

the motion . . . only for clear error."); see also United States

v. Castro-Gómes, 233 F.3d 684, 686–87 (1st Cir. 2000) (same).

              Doe's preserved ineffective assistance claim, however,

cannot be resolved in this direct appeal.              We have consistently

held that "fact-specific claims of ineffective assistance cannot

make their debut on direct review of criminal convictions, but,

rather, must originally be presented to, and acted upon by, the

trial court" in the post-conviction context.                 United States v.

Negrón-Narváez, 403 F.3d 33, 40 (1st Cir. 2005) (quoting United

States v. Mala, 7 F.3d 1058, 1063 (1st Cir. 1993)); see also United

States v. Rosario-Cólon, 431 F. App'x 4, 5 (1st Cir. 2011) ("[A]

collateral proceeding brought under 28 U.S.C. § 2255, and not

direct appeal, is usually the proper vehicle for a claim of

ineffective assistance of counsel.").            We may make an exception,

                                     - 4 -
however, "for cases in which trial counsel's ineffectiveness is

manifestly apparent from the record." United States v. Wyatt, 561

F.3d 49, 52 (1st Cir. 2009).

          Though it was raised below, Doe's claim cannot be decided

purely on the record before us.       To be sure, Doe filed several

affidavits in the district court stating that he believed his

original counsel had sought to suppress the firearms at issue and

that this belief affected his decision to plead guilty.           His

successor counsel represented that the motion to suppress would

have been meritorious.   Beyond this, however, there is nothing in

the record that sheds light on the actual substance of these

hypothetical motions that should have been filed; nor is there any

meaningful way for us to evaluate the claim that prior counsel was

constitutionally    ineffective     because   he   failed   to   seek

suppression.   Doe's claim of ineffective assistance therefore is

not "manifestly apparent from the record" and must be reserved for

future collateral proceedings.     Id.

          Our review on direct appeal is limited to Doe's challenge

to the sufficiency of his plea colloquy under Rule 11 and to the

indictment under Rehaif, 139 S. Ct. 2191.      Because neither claim

was presented to the district court, we review each claim only for

plain error.   See United States v. Dominguez Benitez, 542 U.S. 74,

76 (2004) ("Because the claim of Rule 11 error was not preserved

by timely objection, the plain-error standard . . . applies, with

                                  - 5 -
its requirement to prove effect on substantial rights, . . .

[meaning]    the    defendant      is   obligated       to    show   a   reasonable

probability that, but for the error, he would not have entered the

plea."); United States v. Dawn, 842 F.3d 3, 5 (1st Cir. 2016)

(same).

                     A.    Rule 11 and the Plea Colloquy

            On appeal, Doe focuses his challenge to his conviction

on his contention that his plea colloquy was facially invalid

because of a "fatal omission" that rendered his guilty plea

unknowing and involuntary.

            Doe is correct that Rule 11 of the Federal Rules of

Criminal Procedure requires the district court to "address the

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

and determine that the defendant understands . . . any mandatory

minimum penalty" he may face.           Fed. R. Crim. P. 11(b)(1)(I).          This

requirement,       like    the   others   codified       in    Rule 11(b)(1),      is

intended to ensure that "(1) the plea is voluntary; (2) that the

defendant understands the charge to which he has pled guilty; and

(3) that the defendant knows the consequences of his guilty plea."

Castro-Gómez, 233 F.3d at 687 (holding that these are the "'core'

concerns of Rule 11(c)") (Rule 11 was subsequently amended in 2002

to explicitly include the list of requirements in the text of

subsection (b)).      Even in cases where a mandatory minimum sentence

"is   not   finally       determined    until   after    the    plea     process   is

                                        - 6 -
complete," the district court is obligated under Rule 11 to inform

the defendant of at least the possibility of a mandatory minimum

sentence. United States v. Santo, 225 F.3d 92, 98 (1st Cir. 2000).

And, the court's failure to do so renders the plea colloquy

"imperfect."   Castro-Gomez, 233 F.3d at 687 (citing Santo, 225

F.3d at 98).

          The record reveals that the district court satisfied

this requirement.   During the plea colloquy, the district court

inquired of Doe whether he had read the plea agreement and had

discussed it with his counsel.   The court went on to say that "if

you look at Section 2 [of the plea agreement], it summarizes the

penalties you become exposed to on conviction of this offense that

you're pleading guilty to, and it includes the possibility of a

minimum mandatory sentence of 15 years."      Doe responded in open

court that he understood this.   Whether the district court could

have been more persistent in its inquiry of Doe with respect to

his understanding of the penalties he faced, we cannot say that

the plea colloquy in this case was deficient, especially in the

absence of any objection by counsel, either contemporaneously or

in Doe's later motion to withdraw his plea.

          Even if the plea colloquy was facially "imperfect,"

however, Doe must still show that, had the district court informed

him that he faced a possible mandatory minimum sentence of fifteen

years, he would not have pled guilty.   See Dominguez Benitez, 542

                              - 7 -
U.S. at 76.   He cannot make such a showing here, especially because

the plea agreement specifically states that Doe faced a mandatory

minimum sentence of fifteen years and that the government would

recommend an incarcerative sentence of fifteen years.    During the

plea colloquy, Doe confirmed in open court that he had read the

plea agreement multiple times and had discussed the agreement and

its implications with counsel before agreeing to plead guilty.

Moreover, Doe was advised by the PSR that he faced a mandatory

minimum sentence of fifteen years of incarceration because he had

been classified as an armed career criminal.      And, Doe had the

opportunity to (and in fact did) object to this classification

prior to sentencing.

          Read in conjunction, the plea agreement, the transcript

of the plea colloquy, and the PSR make clear that Doe was fully

aware of the potential mandatory minimum penalty that he faced and

still chose to proceed and plead guilty.      Doe therefore cannot

carry his burden of establishing plain error.     See United States

v. Romero-Galindez, 782 F.3d 63, 67–68 (1st Cir. 2015) (holding

that the defendant could not show that the district court's failure

to advise him of the statutory maximum and minimum penalties was

plainly erroneous because he was "made aware of the mandatory

minimum and maximum imprisonment term during plea negotiations, as

evidenced by the plea agreement" and because the penalties were

correctly reflected in the PSR).

                                - 8 -
                        B.     Rehaif and the Indictment

              Second,    Doe    contends      that   the   indictment    should    be

dismissed because it failed to adequately allege that he knew that

he was not permitted to possess a firearm at the time of the

offense.      See Hamling v. United States, 418 U.S. 87, 117 (1974)

("[A]n indictment is sufficient if it . . . contains the elements

of the offense charged and fairly informs a defendant of the charge

against which he must defend.").

              In Rehaif v. United States, the Supreme Court made clear

that "[t]o convict a defendant [for a firearm offense under 18

U.S.C. § 922(g)], the government must show that the defendant knew

he possessed a firearm and also that he knew he had the relevant

status when he possessed it."               139 S. Ct. at 2194.     The knowledge

requirement of section 922(g), the Court held, applies to all

material elements of the offense, meaning the government had to

allege and prove that a defendant knew that he was prohibited from

carrying a firearm.           Id. at 2196.     Because the indictment does not

clearly state that he knew he was barred from possessing a firearm,

Doe argues, it is facially deficient and should be dismissed.

The government has not contested the indictment's deficiency, so

we   assume    that     it,    in   fact,    fails   to    adequately   allege    the

essential elements of the charged offense.

              This does not, however, mean that the indictment must be

dismissed.      "[D]efects in indictments [including the omission of

                                        - 9 -
a material element of the charged offense] are not jurisdictional

and thus are subject to waiver."    United States v. Urbina-Robles,

817 F.3d 838, 842 (1st Cir. 2016) (citing United States v. Cotton,

536 U.S. 625, 630 (2002)).     And Doe waived his right to challenge

the sufficiency of the indictment by pleading guilty.      Id.; see

also United States v. Burghardt, 939 F.3d 397, 402 (1st Cir. 2019).

          Moreover, Doe did not argue in his original briefing

that the deficiency in his indictment rendered his plea unknowing

and involuntary because he was not properly advised of the charges

against him.   He was not barred by his guilty plea from raising

this argument, see Urbina-Robles, 817 F.3d at 842, and his failure

to do so until much later, in a letter filed under Fed. R. App. P.

28(j), means that the argument is waived.      See United States v.

Dávila-Félix, 667 F.3d 47, 51 n.5 (1st Cir. 2011).

          Even if it had not been waived, this argument would be

subject only to plain error review, because it was never presented

to the district court.    To succeed, then, Doe would have had to

show that "he would have insisted on going to trial [rather than

pleading guilty] . . . if he had been told of the scienter-of-

status element" of § 922(g).    United States v. Burghardt, 939 F.3d

397, 403 (1st Cir. 2019).    In other words, Doe would have had to

"make a specific showing of prejudice" arising from the district

court's failure to inform him of an element of the crime to which

he was pleading guilty.   United States v. Antonakopoulos, 399 F.3d

                                - 10 -
68, 77 (1st Cir. 2005) (citing United States v. Olano, 507 U.S.

725, 735 (1993)); but see, generally, United States v. Gary, 954

F.3d   194, 198 (4th Cir. 2020) (holding, contrary to the First,

Second, Fifth, Sixth, Seventh, Eighth, and Eleventh Circuits, that

a district court's failure to inform a defendant of the scienter-

of-status element of § 922(g) during a plea colloquy constituted

structural error and rendered a guilty plea void).            Doe cannot

make such a showing here.      During his plea colloquy, Doe agreed

with the government's summary of the case against him, including

the fact that Doe told police that he "had traveled in interstate

commerce with the weapons and that he knew he should not have had

those weapons."

          Even if, contrary to our conclusion in Burghardt, we

were free to agree with the Fourth Circuit that this kind of error

could be structural, Doe has waived any challenge to his guilty

plea on this basis.    See United States v. Zannino, 895 F.2d 1, 17

(1st Cir. 1990) ("[I]ssues advanced in a perfunctory manner,

unaccompanied   by   some   effort   at   developed   argumentation,   are

deemed waived."); Jackson v. Bartow, 930 F.3d 930, 934 (7th Cir.

2019) ("[T]he consequence of a 'structural' error is that it is

not subject to harmless error review . . . but such errors can

still be waived.").

                                 - 11 -
                   II.    CHALLENGES TO THE SENTENCE

           In addition to challenging his conviction itself, Doe

challenges his classification as an armed career criminal and the

resulting fifteen-year mandatory minimum sentence.           He also argues

that the district court should have conducted an evidentiary

hearing prior to sentencing to determine whether the government

had   breached   its    obligations   under   the   plea   and   cooperation

agreements by failing to file substantial assistance motions under

U.S.S.G. § 5K1.1 and 18 U.S.C. § 3553(e).

           We conclude that, even if Doe's challenge to the ACCA

classification is not precluded by the appeal waiver in his plea

agreement, his classification as an armed career criminal is

appropriate under our precedent.         Although his challenge to the

government's failure to file substantial assistance motions falls

outside the scope of the appeal waiver, we nevertheless conclude

that the district court did not err in declining to hear evidence

before sentencing.

                       A. Waiver of Appellate Rights

           We consider first whether, in light of the waiver of

appellate rights contained in the plea agreement, Doe is entitled

to a merits review of his challenges to his sentence.               We have

consistently held that written waivers of appellate rights are

valid and enforceable as long as "(1) the written plea agreement

clearly delineates the scope of the waiver; (2) the district court

                                  - 12 -
inquired specifically at the plea hearing about any waiver of

appellate rights; and (3) the denial of the right to appeal would

not constitute a miscarriage of justice." United States v. Edelen,

539 F.3d 83, 85 (1st Cir. 2008) (citing United States v. Teeter,

257 F.3d 14, 25 (1st Cir. 2001)).           As a general rule, a waiver of

appellate rights will not bar a defendant from arguing that his

guilty plea was not knowing and voluntary, meaning the waiver of

appellate rights only implicates Doe's challenge to his sentence

and not to the plea itself.         See Isom, 580 F.3d at 43.           The waiver

in this case also does not bar a challenge to either the conviction

or sentence that is predicated on a claim of ineffective assistance

of   counsel    or     prosecutorial    misconduct,   meaning      it    does   not

foreclose      Doe's     argument   with    respect   to     the   government's

obligations under the cooperation agreement.

            However,      the   appellate   waiver    does   appear      to   apply

broadly to all other challenges to the sentence, including to Doe's

classification as a career offender for purposes of ACCA.                     By its

terms, the waiver of appellate rights prevents Doe from challenging

"any sentence of imprisonment of 210 months or less . . . even if

the Court's Guidelines analysis is different from that set forth

in his plea agreement."          Doe's mandatory sentence stemming from

his classification as an armed career criminal seems to fall within

the plain meaning of this provision.             There is also no dispute

that the district court inquired specifically about the waiver of

                                       - 13 -
appellate rights during the plea colloquy.                Doe's ACCA claim

therefore    merits    substantive       consideration    only   if     certain

conditions are met, and then only if a failure to do so would

constitute a "miscarriage of justice."           Teeter, 257 F.3d at 25.

In this connection, Doe "faces a steep challenge" because "the

miscarriage of justice reservation is to be applied sparingly and

without undue generosity."             Edelen, 539 F.3d at 87 (internal

quotations and citations omitted).           "The appropriateness of the

exception    turns    on   our   consideration     of    several      factors,"

including "the clarity of the alleged error, its character and

gravity," prejudice to the government, and "the extent to which

the defendant acquiesced in the result."                Id. (quoting United

States v. Pratt, 533 F.3d 34, 37 (1st Cir. 2008)).

            We do not need to consider the miscarriage of justice

factors, however.      Assuming arguendo that Doe's ACCA claim is not

barred by his waiver of appellate rights in the plea agreement,

the claim fails on the merits in any event.

                       B. The ACCA Classification

            Doe focuses his challenge to his classification as an

armed career criminal on his contention that his prior convictions

for possession with intent to distribute cocaine are not proper

ACCA   predicates     because    the    Massachusetts    drug    distribution

statute, Mass. Gen. Laws ch. 94C, § 32A, is not a "serious drug

                                   - 14 -
offense" for purposes of ACCA.1   In particular, he argues that the

Massachusetts statute is overbroad because, unlike the federal

Controlled Substances Act ("CSA"), it criminalizes "dispensing,"

in addition to "manufactur[ing], distributing, or possessing with

intent to manufacture or distribute a controlled substance."           See

18 U.S.C. § 924(e)(2)(A)(ii).     As a consequence, Doe argues, the

Massachusetts statute criminalizes conduct that is not within the

"generic guidelines offense."

          To    determine    whether     a   conviction      under     the

Massachusetts   drug   distribution    statute   qualifies   as   an   ACCA

predicate, we use the categorical approach, which requires that we

look "only to the statutory definitions of the prior offenses,"

and not to the particular facts underlying the conviction.           Taylor

v. United States, 495 U.S. 575, 600 (1990); see also Mathis v.

United States, 136 S. Ct. 2243 (2016).       In doing so, Doe argues,

     1Subsequent to the oral argument in this appeal, Doe argued
that, after Borden v. United States, 141 S.Ct. 1817 (2021), his
Massachusetts conviction for assault with a dangerous weapon is no
longer a proper ACCA predicate. In Borden, the Court held that
ACCA's elements clause does not "include[] offenses criminalizing
reckless conduct." Id. at 1827 (plurality). We have previously
held that, in Massachusetts, assault with a dangerous weapon cannot
be committed recklessly. See United States v. Hudson, 823 F.3d
11, 17 (1st Cir. 2016) ("[U]nder Massachusetts decisional law an
[Assault with a Dangerous Weapon] conviction requires that the use
or threat of physical force be intentional.") (citing Commonwealth
v. Porro, 939 N.E.2d 1157, 1163–64 (Mass. 2010)). We see no reason
to deviate from our precedent.

                                - 15 -
we determine whether a state conviction is for a "serious drug

offense" by comparing the state offense to its common-law or

federal counterpart; in other words, we apply the same approach

that we use when deciding whether a prior conviction qualifies as

one of the enumerated offenses in ACCA's definition of a "violent

felony."   Mathis, 136 S. Ct. at 2248 ("ACCA defines the term

'violent felony' to include any felony, whether state or federal,

that 'is burglary, arson, or extortion.' . . . To determine whether

a prior conviction is for generic burglary (or other listed crime)

courts . . . focus solely on whether the elements of the crime of

conviction sufficiently match the elements of generic burglary.").

           Contrary    to   Doe's     argument,   the   Supreme   Court

specifically disavowed this approach and held that "[t]he 'serious

drug offense' definition requires only that the state offense

involve the conduct specified in the federal statute; it does not

require that the state offense match certain generic offenses."

Shular v. United States, 140 S. Ct. 779, 781 (2020).       Instead, we

ask only whether the elements of the prior state conviction

"necessarily entail one of the types of conduct identified in

§ 924(e)(2)(a)(ii),"    namely      manufacturing,   distribution,   or

possession with intent to distribute a controlled substance.         Id.

at 784 (citing Kawashima v. Holder, 565 U.S. 478 (2012)) (emphasis

in original); see also United States v. McKenney, 450 F.3d 39, 43–

44 (1st Cir. 2006) ("[T]he word 'involving' [in the definition of

                                 - 16 -
"serious drug offense"] has expansive connotations, [meaning] it

must be construed as extending the focus of § 924(e) beyond the

precise offenses of distributing, manufacturing, or possessing,

and as encompassing as well offenses that are related to or

connected with such conduct." (quoting, inter alia, United States

v. King, 325 F.3d 110, 113 (2d Cir. 2003) (cleaned up)).             To be

sure, Shular does not suggest that "all offenses bearing any sort

of     relationship   with   drug    manufacturing,      distribution,   or

possession with intent to manufacture or distribute will qualify

as predicate offenses under ACCA."           McKenney, 450 F.3d at 45.   But

it would go     too far to say that a state statute that adds

"dispensing" to the categories of prohibited conduct no longer

defines an offense that "necessarily entail[s] one of the types of

conduct identified in § 924(e)(2)(a)(ii)."           Shular, 140 S. Ct. at

784.

            Further supporting our conclusion is the fact that the

Massachusetts Supreme Judicial Court ("SJC") has narrowed the

definition of the word "dispense" to apply only to conduct covered

by the federal CSA.      Commonwealth v. Brown, 925 N.E.2d 845, 856

n.14 (Mass. 2010) (citing United States v. Badia, 490 F.2d 296,

298, n.4 (1st Cir. 1973), and concluding that the Massachusetts

legislature "intended the same when it included 'dispense' in the

drug statutes").      Under Massachusetts law, "the threshold element

of unlawful dispensing is the issuance of an invalid prescription

                                    - 17 -
. . . i.e., one issued without a legitimate medical purpose and

not in the usual course of the physician's professional practice."

Brown, 925 N.E.2d at 854-55 (emphasis added) (citing Commonwealth

v. Comins, 356 N.E.2d 241, 247 (Mass. 1976)).             Consequently, only

a physician may "dispense"; everyone else "distributes."                    See

Comins, 356 N.E.2d at 247.        And, the SJC has concluded that "there

is no space in the definition of 'dispense' for a physician acting

outside his or her role as a physician, or for a patient acting

outside   his   or   her   role   as    a   patient,"   meaning   a   physician

"unlawfully dispenses" a controlled substance only in a narrow set

of circumstances -- such as when a physician has allowed his

license to lapse.     Brown, 925 N.E.2d at 856-57 and n.14.

           Violation of the Massachusetts drug distribution statute

is therefore categorically a "serious drug offense" and Doe's two

                                       - 18 -
prior convictions under this statute were properly characterized

as ACCA predicates.2   3

                   C. The Cooperation Agreement

          Finally, Doe challenges the district court's decision to

proceed with sentencing despite argument from defense counsel that

the government had failed to honor the terms of the cooperation

agreement.   At the outset, we note that this challenge to his

     2 Doe also argues that his 1994 conviction in Waltham district
court does not qualify as a predicate offense under the First Step
Act. Passed in 2018, the First Step Act amended the definition of
"serious drug felony" in the CSA to apply only to convictions that
were within "15 years of the commencement of the instant offense."
21 U.S.C. § 802.    However, the First Step Act only applies to
offenses that "[were] committed before the date of enactment . . .
if the sentence for the offense has not been imposed as of such
date of enactment [here, December 21, 2018]."      First Step Act,
Pub. L. 115-391 § 401 (passed December 21, 2018); see also United
States v. Wiseman, 932 F.3d 411, 417 (6th Cir. 2019) ("[T]he First
Step Act is largely forward-looking and not retroactive.").
Because Doe was sentenced in 2017, before the First Step Act went
into effect, it does not apply here.
     3 After oral argument, Doe filed a pro se submission citing a
recent Seventh Circuit opinion which held that the Illinois
statutory definition of cocaine was "categorically broader than
the federal definition" because its definition of cocaine included
"optical, positional and geometric isomers," see United States v.
Ruth, 966 F.3d 642, 647 (7th Cir. 2020), cert. denied, 141 S. Ct.
1239 (2021), where the federal definition of cocaine includes only
its "optical and geometric isomers,"      21 U.S.C. § 812.     Doe
mistakenly argues that the Massachusetts statute suffers from the
same defect. We review this entirely new argument for plain error.
See United States v. Figuereo, 404 F.3d 537, 540 n.3 (1st Cir.
2005). Unlike Illinois, Massachusetts's relevant statute does not
reference any isomers. See Mass. Gen. L. c. 94c § 31. Based on
this distinction and with the briefing and record before us, we
cannot say that any potential error was clear or obvious.      See
United States v. Mastera, 435 F.3d 56, 61 (1st Cir. 2006).

                              - 19 -
sentence falls outside the scope of the waiver of appellate rights

contained within the plea agreement.          Indeed, the appellate waiver

specifically reserves to Doe the right to challenge his sentence

on the basis of prosecutorial misconduct.

            The cooperation agreement between Doe and the government

specifies    that   Doe      would    provide    "complete   and      truthful

information" to law enforcement about certain individuals and

testify against those individuals if asked to do so.           In exchange,

the Agreement stated that if the "Defendant provide[d] substantial

assistance in the investigation or prosecution of another person,"

the government "w[ould] file a motion under U.S.S.G. § 5K1.1 to

recommend that the Court impose a sentence below the advisory

Guideline    range";   "if     the   U.S.     Attorney   determines    it   is

appropriate," the government will "also file a motion under 18

U.S.C. § 3553(e) to enable the Court to impose a sentence below

the statutory mandatory minimum."             However, the Agreement also

specified that "[t]he determination whether Defendant had provided

substantial assistance rests solely in the discretion of the U.S.

Attorney," who would make the decision "based on the truthfulness

and value of Defendant's assistance."

            At sentencing, Doe argued to the district court that it

did not have sufficient information to proceed with sentencing and

asked the court to hear evidence on whether the government had

breached its obligations under the cooperation agreement.                   In

                                     - 20 -
essence,    Doe     argued,      the   government    "is   in    breach      of   the

[cooperation] agreement by inducing this individual to agree to a

harsh sentence and then pulling it out from under him," especially

because Doe did "everything the government asked him to do."                      The

district court denied the request for an evidentiary hearing.                      We

review its denial for abuse of discretion.                      United States v.

Alegría, 192 F.3d 179, 189 (1st Cir. 1999).

            Under the Sentencing Guidelines, the government has the

power, but not the obligation, to file a motion on behalf of a

defendant     who    has    "provided     substantial      assistance        in   the

investigation or prosecution of another person who has committed

an offense," asking the court to vary downward from the guidelines.

U.S.S.G. § 5K1.1; see also Wade v. United States, 504 U.S. 181,

185 (1992).      If the government also files a motion under 18 U.S.C.

§ 3553(e), as it agreed to consider here, the court may also vary

downward    from    any    statutory     mandatory    minimums.         18    U.S.C.

§ 3553(e) ("Upon motion of the Government, the court shall have

the authority to impose a sentence below a level established by

statute as a minimum sentence so as to reflect a defendant's

substantial      assistance      . . .");   see     also   Melendez     v.    United

States,    518    U.S.    120,   130   (1996).      However,     both   18    U.S.C.

§ 3553(e) and U.S.S.G. § 5K1.1 are permissive, not mandatory;

unless the government agrees explicitly to file such motions, the

decision to file them is discretionary.                Wade, 504 U.S. at 185

                                       - 21 -
("[W]e see no reason why courts should treat a prosecutor's refusal

to   file    a    substantial-assistance        motion    differently     from    a

prosecutor's other decisions . . . .").

             Whether there was an abuse of discretion by the district

court in not holding an evidentiary hearing should be viewed in

context.         Our   cases   make   clear   that   there   are   only   certain

scenarios in which a defendant can challenge the government's

exercise of its discretion to file substantial assistance motions.

United States v. Sandoval, 204 F.3d 283, 286 (1st Cir. 2000).                    One

is where the government's decision not to file was based "on some

constitutionally impermissible factor (say, race or religion), or

is 'not rationally related to [some] legitimate Government end.'"

Id. (quoting Wade, 504 U.S. at 185–86); see also United States v.

Moore, 225 F.3d 637, 641 (6th Cir. 2000).                Another is where "the

government explicitly undertakes to make, or to consider making,

such a motion."         Sandoval, 204 F.3d at 286.         Neither scenario is

presented here.

             Doe has not argued that the government's failure to file

substantial assistance motions was not rationally related to some

legitimate government purpose or that the decision was premised on

his race, religion, sex, or membership in any other protected

group.      Instead, his argument is that the government promised to

consider making substantial assistance motions and that it acted

in bad faith by failing to file such motions.                      The argument

                                       - 22 -
proceeds that the court abused its discretion by not holding an

evidentiary hearing on the issue of the government's good faith.

See Alegría, 192 F.3d at 188 (stating that a government promise to

file a substantial assistance motion "carried with it an obligation

to evaluate the appellant's assistance in good faith (although the

'sole   discretion'   language       in   which   the    promise   was   couched

informed the nature of the obligation)").

           "[A] party seeking an evidentiary hearing must carry a

fairly heavy burden of demonstrating a need for special treatment."

Id. at 188 (quoting United States v. McGill, 11 F.3d 223, 225 (1st

Cir. 1993)).      After the government offers "facially adequate

reasons"   explaining   why     a    defendant    "failed     to   achieve    the

substantial assistance benchmark," the defendant must "make[] a

substantial threshold showing that the government acted in bad

faith" to warrant an evidentiary hearing.               Id. at 187-88.

           Here, like in the agreement in Alegría, see id. at 186,

the government agreed to file substantial assistance motions if

Doe   provided   "substantial       assistance    in    the   investigation    or

prosecution of another person."           But it cabined that agreement by

explicitly stating that "[t]he determination whether Defendant had

provided substantial assistance rests solely in the discretion of

the U.S. Attorney."     Before sentencing, Doe alleged that he did

everything the government asked of him, that the government acted

in bad faith by failing to give a reason for its failure to file

                                     - 23 -
such motions, and requested the opportunity "to make a proffer of

what [Doe] would show and what evidence that [he] would like to

present."

             Doe also alleged, without support, that the government

was "refusing to honor the cooperation agreement and file a

[§ 5K1.1] motion . . . [because it was] alleg[ing] the defendant

breached somehow."        The government denied that allegation and

explicitly stated that it was not arguing that Doe breached either

the plea agreement or the cooperation agreement.             Rather, the

government represented that it was "just not filing a [§ 5K1.1

motion] on this matter" based on the value of the assistance Doe

provided.    Defense counsel may not get an evidentiary hearing with

unsubstantiated allegations such as these.

             The district court declined, based on that mere request,

to hold an evidentiary hearing and stated "that the government is

within its rights . . . to decline under the agreements" to file

substantial assistance motions.        It told defense counsel that he

could make a proffer after sentencing, then sentenced Doe.

             In response to the district court's willingness to hear

a proffer, the government provided further explanation as to why

it   chose    not   to   file   substantial   assistance   motions.   It

represented to the district court that Doe sat for a single, two-

hour proffer with law enforcement, that it never called Doe to

testify or appear in court, and that his name "never appeared on

                                   - 24 -
a witness list."     "At best," the government stated, "Doe's name

was mentioned to the defense in a case where they indicated that

it would be possible that they might call Doe as a potential

rebuttal witness."     Doe did not contest there was a single two-

hour proffer but did say there was some evidence that his name had

in fact appeared on a witness list.4

          The government's several representations to the court

about the reasons for its dissatisfaction with the limited nature

of Doe's assistance more than constituted a facially valid reason

for it to decide not to file substantial assistance motions.   This

is so even if one were to accept Doe's contentions5 that he did

everything that was asked of him, that he provided a fully truthful

proffer, and that his name may have in fact appeared on a witness

list resulting in retaliation.    Consequently, we cannot say that

the district court abused its discretion in declining to hold an

evidentiary hearing.

     4 He also made an argument, not pertinent to the question of
the government's reasons for not filing substantial assistance
motions, that he faced retaliation because of his cooperation.
     5 We add that even if Doe's contentions were true, that does
not lead to a conclusion that he provided substantial assistance.
See Alegría, 192 F.3d at 184 (interpreting a cooperation agreement
in light of the Sentencing Guidelines and stating that "full,
complete and truthful cooperation, in and of itself, is not
coextensive with the substantial assistance"); Sandoval, 204 F.3d
at 286 n.2 ("[C]ooperation differs significantly from substantial
assistance.").

                               - 25 -
           The arguments made by our dissenting colleague are not

supported by the record.           Contrary to the dissent's assertion, the

district   court     did     not    evince   an   erroneous    view    that     "the

government retained complete discretion to determine whether to

file a substantial assistance motion 'except under very unusual

circumstances.'"       The district court said that "the evaluation of

whether [the defendant's cooperation is] helpful enough to warrant

a reward is what the government reserves to itself," that it is

"up to the government to be satisfied," that "there's no obligation

to be satisfied," that "the usual reason given is that [the

government]     is     not     satisfied,"        that   the    "very        unusual

circumstances"       under    which    the   government    might      have    acted

impermissibly "[don't] exist here," and that "[its] ruling is that

the government is within its rights. . .                 to decline under the

agreements [to file substantial assistance motions]."                   The court

correctly recited the law.              Its statements hardly reflect an

ignorance of the law and certainly do not reflect that the court

considered the government to have unbridled discretion to refuse

to file substantial assistance motions.

           III. CONCLUSION

           For the foregoing reasons, the conviction and sentence

are affirmed.

                              -Dissenting Opinion Follows-

                                       - 26 -
             LIPEZ, Circuit Judge, dissenting in part.               I disagree

with the majority on only one issue -- its conclusion that the

district court did not err in its handling of Doe's request for an

evidentiary hearing on the government's decision not to file

substantial    assistance    motions       under    U.S.S.G.   § 5K1.1   and   18

U.S.C. § 3553(e),6 despite the government's promise to consider

doing so in the Cooperation Agreement. In my view, that conclusion

rests on a misreading of the record.                The district court never

applied the burden-shifting framework of United States v. Alegría,

192   F.3d   179   (1st   Cir.    1999),    to     Doe's   request   because   it

misapprehended the law.          Hence, I believe that the judgment must

be vacated, and the case remanded to the district court so that it

can apply that framework in determining whether Doe was entitled

to an evidentiary hearing.

      6The Sentencing Guidelines provide that, upon motion of the
government stating that the defendant has provided substantial
assistance in another criminal investigation or prosecution, a
court may sentence the defendant below the applicable guidelines
range. See U.S.S.G. § 5K1.1.     If the defendant is subject to a
mandatory minimum sentence, the government may also file a
substantial assistance motion pursuant to 18 U.S.C. § 3553(e),
which authorizes a court to impose a sentence below the applicable
mandatory minimum.   The government agreed to consider filing a
motion under both provisions in Doe's Cooperation Agreement.
During the district court proceedings, the parties referred to a
motion filed under either provision interchangeably as a "5K
motion" or a "substantial assistance motion." To avoid confusion,
I will simply refer to such motions as "substantial assistance
motions."

                                     - 27 -
                                        I.

            As the majority recognizes, Alegría similarly involved

a written agreement between the government and a defendant in which

the government promised to consider filing a motion for leniency

at   sentencing      in   exchange     for     the    defendant's     substantial

assistance.       192 F.3d at 182, 188.        The agreement in Alegría also

contained a qualification -- using language nearly identical to

that used in Doe's Cooperation Agreement -- that the decision to

file a substantial assistance motion rested in the sole discretion

of the government.           Compare Doe's Cooperation Agreement ("The

determination      whether    the    Defendant       has   provided   substantial

assistance rests solely in the discretion of the U.S. Attorney."),

with Alegría, 192 F.3d at 184 ("[T]he [government's] decision

whether to file a motion based on 'substantial assistance' . . .

rests in the sole discretion of the United States.").

            At sentencing in Alegría, the government declined to

file a substantial assistance motion.                  192 F.3d at 182.       The

defendant insisted that he was entitled to an evidentiary hearing

on whether the government had an adequate reason for its decision

not to file.      Id. at 182, 186-87.        The government argued that its

decision    was    unreviewable      because    it    had   expressly    reserved

complete discretion to decide whether to file a motion.                   Id. at

184-85.    We disagreed.      We held that when the government (1) enters

                                      - 28 -
an agreement with a defendant that specifically contemplates the

filing of a substantial assistance motion at sentencing in exchange

for the defendant's plea and cooperation, and (2) purports to

retain complete discretion as to whether to file such motion, the

government's discretion is nonetheless cabined by a requirement

that it act in good faith and supply a facially adequate reason

for its decision not to file a substantial assistance motion.                    Id.

at 187.    Otherwise, we explained, "a significant element of the

consideration for appellant's change of plea" -- the government's

promise to consider asking for leniency at sentencing -- would be

rendered "illusory."      Id. (quoting United States v. Garcia, 698

F.2d 31, 36 (1st Cir. 1983)).

           The framework spelled out in Alegría is thus clear: when

the government expressly agrees to consider filing a substantial

assistance motion and it declines to do so, and the defendant

challenges that decision, the government bears a modest burden of

production -- not persuasion -- to show that it evaluated the

defendant's    assistance     in   good    faith      by   offering   a   facially

adequate reason for its decision not to file the motion.                  Id.    That

burden exists even when the government retains complete discretion

as to whether to make that filing. Id. If the government satisfies

its burden to provide a facially adequate reason, the burden then

shifts    to   the   defendant     to     demonstrate       entitlement     to    an

evidentiary    hearing   on    the      matter   by    making   "a    substantial

                                     - 29 -
threshold showing that the government acted in bad faith."                     Id.

Such       a   showing   may    include    "persuasive    evidence   of   either

substantial assistance or bad faith."7             Id. at 189.    The defendant

must satisfy "a fairly heavy burden" to show that he is entitled

to an evidentiary hearing.            Id. at 188 (quoting United States v.

McGill, 11 F.3d 223, 225 (1st Cir. 1993)).

                                           II.

                A fair reading of the record reveals that the district

court never applied Alegría's good-faith requirement and burden-

shifting framework.            Prior to sentencing, Doe filed under seal a

Motion for Downward Departure, arguing that, even though the

government had not filed a substantial assistance motion, he was

entitled to a downward departure because the government's decision

not to file such a motion was "not rationally related to [some]

legitimate       [g]overnment      end,"    and   was   instead   based   on   the

government's unexplained determination that Doe had breached the

plea agreement.          At sentencing, in light of that motion, the

following exchange took place at sidebar:

       Despite the disjunctive language of Alegría, even if the
       7

defendant's threshold showing involves a claim of substantial
assistance, the defendant must also provide persuasive evidence
that the government's claim to the contrary involves bad faith in
order to justify an evidentiary hearing. In other words, the focus
of Alegría's burden-shifting framework is the good faith of the
government in declining to file a substantial assistance motion.
See Alegría, 192 F.3d at 188-89.

                                       - 30 -
Defense Counsel: This relates to the
government refusing to honor the cooperation
agreement and file a 5K motion and whether
the government can establish that the
defendant -- they allege the defendant
breached somehow. We don't -- I don't know
how he supposedly breached, all I know is
that the government said he breached, and
they won't file. So we need to establish
whether or not the government has an
obligation to file a 5K.
Court: I don't have the agreements in front
of me. The standard agreements usually
provide that it's at the sole discretion of
the government to make a decision to move
for a downward departure under 5K.
Defense Counsel: That may be the case, your
Honor; however, the sole discretion is to
determine whether or not a defendant
provided substantial cooperation.
Court: So --
Defense Counsel: Whether a defendant breaches
in some other manner is a question for the
Court.
Government: Let me be very clear. The
government's not alleging that he breached
the cooperation agreement in the least; the
government is just not filing a 5K on this
matter. We're not suggesting that he
breached any plea agreement.
Defense Counsel: So you induce a defendant
to sign a plea agreement and [accompanying]
cooperation agreement, and then you just
pull it out and refuse to file a 5K without
reason?
Court: Well, the usual reason given is that
they're not satisfied. It's an interesting
argument but --
Defense Counsel: Your Honor, if I may, I
would like on the record to make a proffer

                   - 31 -
of what we would show and what evidence that
we would like to present.
Court: I'll tell you what: I'll let you make
the proffer after the conclusion of the
proceedings just to protect the record,
because the ruling is that the government is
within its rights, I guess, to decline under
the agreements. I'm assuming the agreements
have the traditional language.
Government: Absolutely the standard
language. I have it at my desk.
Court: It's up to the government to be
satisfied. There's no obligation to be
satisfied.
Defense Counsel: Is the government claiming
--
Government: I'm not answering questions to
you. The court asks the questions --
Defense Counsel: This is why we need
testimony to establish it.
Court: No. I'll let you preserve the point.
I don't think it's necessary to do it any
more than we are doing it now, but I'll give
you the chance after the conclusion of the
proceedings if you want to amplify on
it. . . . [T]he evaluation of whether [the
defendant's cooperation is] helpful enough
to warrant a reward is what the government
reserves to itself. And the law is pretty
clear on that.
Defense Counsel: I'm sorry. Just -- but
that's not necessarily what they're saying.
For a Court to impose sentence with this
open issue without resolving it factually, I
think it cannot --
Court: I guess my point is that I don't
regard it as an open issue because of the
discretion the government has. They simply
say, "We've decided not to move." There's
no enforceable obligation basically --

                   - 32 -
            Defense Counsel: There is an --
            Court:   --   except   under    very   unusual
            circumstances that I might possibly imagine,
            but it doesn't exist here. But I'll let you
            preserve the argument for appellate review if
            you want. I just don't want to disrupt things.

            As the excerpted colloquy demonstrates, the district

court held the legally erroneous view that the government retained

complete discretion to determine whether to file a substantial

assistance motion "except under very unusual circumstances that

[the court] might possibly imagine," but never explained further.

There is no support in the record for the majority's conclusion

that the district court "correctly recited the law" and determined,

in its discretion, that Doe was not entitled to an evidentiary

hearing.     To the contrary, the district court's statements make

clear that it thought that it lacked the authority to review the

government's decision.         Instead, it speculated that the "usual

reason"    the    government   gives     for   not   filing    a    substantial

assistance motion is "that they're not satisfied," but the court

did not inquire further because it concluded that, "basically,"

the government has "no enforceable obligation."                Hence, without

demanding any showing from the government (its burden of production

under Alegría), the court simply concluded that "the government

[wa]s within its rights . . . to decline [to file a substantial

assistance       motion]   under   the   agreements,"    and       proceeded   to

sentencing.

                                    - 33 -
            The post-sentencing proceedings did not, contrary to the

majority's suggestion, remedy the district court's pre-sentencing

error.     During an "addendum" to Doe's sentencing hearing, after

sentence had already been imposed, the court allowed the defense

to elaborate on Doe's objection to the government's failure to

file a substantial assistance motion for the sole purpose of

preserving the issue for appeal.              Counsel for Doe argued that the

court "did not . . . ha[ve] sufficient information with which to

impose sentence" and that the court was obligated by case law to

ask the government to provide a reason for its refusal to file a

substantial       assistance    motion     and     to    evaluate    whether     an

evidentiary hearing was warranted on the matter prior to imposing

sentence.    Counsel contended that "the government . . . decide[d],

'No, no 5K.       We don't have to.       We don't even have to give you a

reason.' I say they do and case law says they do. . . . Th[e] court

does have the ability to enforce the agreement. . . . I don't think

the court had sufficient information to impose sentence at this

time."

            Counsel for Doe also argued that it was error for the

district court effectively to conclude that the government could

"induc[e] Doe to agree to a harsh sentence" by promising to

consider    filing      a   substantial       assistance    motion    for      Doe's

cooperation and then "pull [that promise] out from under [Doe]

saying,    'No,    we   don't   have     to    file     anything'    without    any

                                    - 34 -
explanation."   Counsel argued, again for the sole purpose of

preserving the issue for appeal, that Doe was entitled to an

evidentiary hearing:

          Mr. Doe did everything, everything the
          government asked him to do.     We would have
          presented evidence that he did a good job and
          gave substantial, significant information to
          the government.     We would have presented
          evidence that the government said he, John
          Doe, hit a home run with his proffer. He did
          everything they wanted. He put his life in
          danger because of that cooperation your Honor.
          He has been attacked in jail. His wife has
          been threatened. He's in fear.

Counsel concluded: "If they [the government] say [Doe] breached,

we want to know how.     If they say he didn't breach, we want to

know why they will not file a 5K."

          The court asked if the government had anything to add.

In response, the government finally elaborated on its decision,

explaining that "Doe met with law enforcement for approximately

two hours and provided them information" but "[t]he government

chose not to use Mr. Doe."     The government emphasized that "Doe

did not testify, [he] did not appear in court. . . . [His] name

never appeared on a witness list."     The government explained that

it "chose not to utilize Mr. Doe and that's as far as it goes."

It continued, "[w]e're well within our right to do this.   We didn't

make any promises, rewards, inducements; we just chose not to use

the . . . information.    I'm not going to quantify whether it was

                              - 35 -
accurate, inaccurate.    It was just information [Doe] provided us

and we said we would consider it . . . and we chose not to use

it."

           Defense counsel responded that there was evidence that

Doe's name did in fact appear on a witness list and, apparently,

that the witness list made its way to the facility where Doe was

awaiting sentencing -- placing his life in danger.             In response,

the court simply stated, "[a]ll right," sealed the transcript, and

adjourned the proceedings.         The court said nothing about the

substance of what it had just heard.

           Remarkably, the majority reads the district court's

silence as a decision.       That is, my colleagues read the post-

sentencing record as establishing that the government provided "a

facially   valid   reason"   for    refusing   to   file   a    substantial

assistance motion, and "[c]onsequently, we cannot say that the

district court abused its discretion in declining to hold an

evidentiary hearing."

           There is a major problem with the majority's conclusion.

There is simply no indication in the record that the district court

exercised any discretion whatsoever, pre- or post-sentencing.           The

court did not weigh the issues, engage in any back and forth with

the parties, or give any indication that it was considering the

arguments presented.    It simply allowed the defendant to preserve

the record for appeal and, in fairness, it allowed the government

                                   - 36 -
to do the same.     The majority's conclusion that the district court

did anything more is unsupported by the record.

           Indeed,      in   the   offer-of-proof      sequence         that   I   have

described, the burden-shifting framework of Alegría was inverted.

Doe was compelled to make his "counter-proffer" without knowing

the   government's      reason     for    refusing   to   file      a    substantial

assistance motion.       As I noted earlier, Doe concluded his proffer

by stating,

           [o]nly after the government received [Doe's]
           assistance and the information did they
           decide, "No, no 5K.    We don't have to.    We
           don't even have to give you a reason." I say
           they do and case law says they do. If they
           say he breached, we want to know how. If they
           say he didn't breach, we want to know why they
           will not file a 5K.

Thus prompted, the government finally provided a reason.                           That

simply is not how the Alegría burden-shifting framework is supposed

to work.   See 192 F.3d at 186-89.

                                         III.

           The district court was obliged -- and failed -- (1) to

hold the government to its burden under Alegría of providing a

facially adequate reason for declining to file a substantial

assistance    motion,    and     (2)     after   considering     the     defendant's

response     to   the   government's        explanation,       to   exercise       its

discretion to consider whether Doe was entitled to an evidentiary

hearing.     The district court's failure to exercise any discretion

                                       - 37 -
was an abuse of discretion.            See In re Grand Jury Investigation,

545 F.3d 21, 25 (1st Cir. 2008) ("[A] trial court can abuse its

discretion by failing to exercise that discretion."). The district

court   made   this    error   because    of    its   misguided     view   of   the

government's unconstrained authority.             Unlike my colleagues, who

do not recognize that failure, I would vacate the judgment and

remand this case to the district court so that it can properly

determine whether Doe is entitled to an evidentiary hearing under

Alegría.

           The stakes are high in such determinations.               Cooperation

agreements     are    important   to    defendants,    and   they    assist     law

enforcement in the plea-bargaining process.              Their implementation

deserves more careful consideration than the treatment accorded by

the district court and the majority in this case.                      Hence, I

respectfully dissent.

                                       - 38 -