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
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HOWARD, Circuit Judge. On May 17, 2016, defendantappellant 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 
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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 
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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, 
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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 
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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 
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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 
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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). 
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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 
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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-ofstatus 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 
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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 scienterof-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.").
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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
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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 
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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 
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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, 

1 Subsequent 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.

 
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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 
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"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 
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. . . 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 
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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).
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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 
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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 
- 22 -

("[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 
- 23 -

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 
- 24 -

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

testify or appear in court, and that his name "never appeared on 
- 25 -

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 twohour 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."). 
- 26 -

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-
- 27 -

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.

6 The 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."
- 28 -

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 
- 29 -

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 
- 30 -

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 burdenshifting 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: 

7 Despite the disjunctive language of Alegría, even if the 

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. 
- 31 -

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 
- 32 -

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 --
- 33 -

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. 
- 34 -

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 
- 35 -

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 
- 36 -

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 postsentencing 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 
- 37 -

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 
- 38 -

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.