United States Court of Appeals

For the First Circuit

No. 22-1011

UNITED STATES OF AMERICA,

Appellee,

v.

ANTHONY MONDREZ THOMPSON,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF RHODE ISLAND

[Hon. John J. McConnell, Jr., U.S. District Judge]

Before

Barron, Chief Judge,

Lipez and Howard, Circuit Judges.

Charles W. Rankin, with whom Rankin & Sultan was on brief, 

for appellant.

Lauren S. Zurier, Assistant United States Attorney, with whom 

Zachary A. Cunha, United States Attorney, was on brief, for 

appellee.

March 10, 2023
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HOWARD, Circuit Judge. Anthony Mondrez Thompson pled 

guilty to being a felon in possession of a firearm, pursuant to a 

plea agreement in which he agreed to waive his rights to appeal 

his conviction and sentence. Despite this waiver, Thompson now 

appeals the application of two sentencing enhancements: one for 

possession of a firearm in the course of a drug trafficking crime 

and the other for possessing one or more firearms with an altered 

or obliterated serial number. Because we find his waiver of appeal 

to be valid and enforceable, we dismiss his appeal.

I.

Thompson was arrested in June 2017 following a traffic 

stop. He had twelve firearms in his vehicle, as well as 

approximately 134 grams of methamphetamine pills. He had 

previously been convicted of a federal felony offense in 2005. 

Following the 2017 arrest, he was ultimately charged with (1) being 

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

924(a)(2); (2) possession with intent to distribute 50 grams or 

more of methamphetamine under 21 U.S.C. §§ 841(a)(1),

841(b)(1)(B); and (3) possession of a firearm in furtherance of 

drug trafficking under 18 U.S.C. § 924(c)(1)(A).

In November 2020, the parties entered a plea agreement 

in which Thompson agreed to plead guilty to count 1, being a felon 

in possession of a firearm. The government agreed to move to 

dismiss the other counts, and the parties agreed to jointly 
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recommend a sentence of five to eight years of imprisonment. The 

agreement also included an appeal waiver provision that would apply 

if the district court sentenced Thompson to an incarcerative term 

of eight years or less. Thompson reserved the right, however, to 

contest the application of various sentencing enhancements in the 

district court.

Following a change of plea hearing, discussed further 

below, sentencing took place in December 2021. At sentencing, the 

district court accepted the parties' plea agreement and sentenced 

Thompson to eight years of imprisonment.

II.

On appeal, Thompson attempts to challenge the 

application of two sentencing enhancements: U.S.S.G. 

§ 2K2.1(b)(6)(B), which the district court applied for possession 

of a firearm in the course of a drug trafficking crime, and 

U.S.S.G. § 2K2.1(b)(4)(B), which the district court applied 

because one or more of the firearms had an altered or obliterated 

serial number.

The gateway issue in this appeal is whether the appeal 

waiver contained in Thompson's plea agreement is valid and 

enforceable. For the following reasons, we conclude that it is.

A waiver of appellate rights is generally valid if the 

defendant entered into the agreement "knowingly and voluntarily." 

United States v. Teeter, 257 F.3d 14, 24 (1st Cir. 2001). To make 
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this determination, we look to the "text of the plea agreement and 

the content of the change-of-plea colloquy." Id. "Appeal waivers 

in plea agreements are 'presumptively valid,' so long as: (1) the 

agreement clearly delineates the waiver's scope; (2) the district 

court specifically inquired about the waiver at the plea hearing; 

and (3) denial of the right to appeal would not constitute a 

miscarriage of justice." United States v. Betancourt-Pérez, 833 

F.3d 18, 22 (1st Cir. 2016) (citing Teeter, 257 F.3d at 23-25).

The waiver in this case provided that:

Defendant hereby waives Defendant’s right to 

appeal the conviction and sentence imposed by 

the Court, if the Court sentences Defendant to 

8 years of incarceration or less. This 

agreement does not affect the rights or 

obligations of the United States as set forth 

in 18 U.S.C. § 3742(b), and the government 

retains its right to appeal any of the Court’s 

sentencing determinations.

Thompson focuses only on the second and third Teeter

prongs. He argues (1) that the appeal waiver is unenforceable 

because the district court's colloquy with him at the change-ofplea hearing was confusing and inadequate and (2) that it would 

work a miscarriage of justice to enforce the appeal waiver 

regarding the serial number sentencing enhancement, which he 

argues is unconstitutional. We address each argument in turn.

A.

In Teeter, we held "that the district court must inquire 

specifically at the change-of-the-plea hearing into any waiver of 
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appellate rights" to ensure that the defendant "freely and 

intelligently agreed to waive [his] right to appeal." 257 F.3d at 

24. We have not prescribed mandatory language for this inquiry 

but have cautioned "that the court's interrogation should be 

specific enough to confirm the defendant's understanding of the 

waiver and [his] acquiescence in the relinquishment of rights that 

it betokens." Id. at 24 n.7. "The adequacy of such an inquiry 

'depends on the specifics of the case, including questions asked 

or statements made by the judge, characteristics of the defendant, 

and evidence that the defendant understood that he was waiving his 

right to appeal.'" United States v. Staveley, 43 F.4th 9, 14 (1st 

Cir. 2022) (quoting United States v. Morillo, 910 F.3d 1, 3 (1st 

Cir. 2018)). In other words, "[c]ontext is important." United 

States v. De-La-Cruz Castro, 299 F.3d 5, 11 (1st Cir. 2002).

Thompson argues that the appellate waiver in his plea 

agreement should not be enforced, because the district court's 

colloquy with him about the waiver was "confusing and failed to 

clearly advise the defendant of the rights he was giving up." He 

lists three reasons why this was so: (1) the district court did 

not read Thompson the waiver or otherwise direct his attention to 

the specific text of the waiver, even though Thompson did not have 

the plea agreement with him; (2) the court mistakenly informed 

Thompson that he could appeal the denial of a motion to suppress 

that he had filed and, after subsequently clarifying with the 
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prosecutor that Thompson could not appeal that denial, told 

Thompson that he had waived the right to appeal "in most 

circumstances" without explaining what that meant; and (3) the 

court's exchanges with Thompson about his ability to challenge 

upward enhancements to the Sentencing Guidelines range were 

"confusing."

Two exchanges between the court and Thompson are 

primarily at issue. The first took place after the court outlined 

various rights Thompson would be waiving by pleading guilty:

THE DEFENDANT: . . . Your Honor, like I was 

saying, I accept the binding plea under the 

provisions of 11(c)(1)(C) on the one count. 

Even in the plea agreement I preserved the 

right in order to not be subjected -- to 

challenge any aggravating factors or any 

sentencing enhancements. I still preserve the 

right. I just wanted to clarify that to be 

sure on record.

THE COURT: Yes, sir. That's in the plea 

agreement.

THE DEFENDANT: Okay.

THE COURT: That you have maintained all of 

your rights to challenge the --

THE DEFENDANT: Aggravating factors.

THE COURT: -- sentencing guidelines and any --

THE DEFENDANT: Yes, sir.

THE COURT: -- and any additives or offense

characteristics or anything like that.

THE DEFENDANT: Yes, sir.
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THE COURT: You retain that right for sure.

The second exchange took place later in the hearing as 

the court turned to specifically discussing the appeal waiver:

THE COURT: Okay. Great. Also as part of the 

plea agreement you agree to waive any right to 

appeal the sentence I impose except for the 

issue of the denial of the motion to suppress 

which you have preserved. You've agreed not 

to appeal the sentence that I impose if I 

accept the plea agreement and impose within 

those parameters. Do you understand that?

THE DEFENDANT: Can I get verification on that 

aspect, your Honor?

THE COURT: Sure.

THE DEFENDANT: Based on what I asserted 

earlier as far as my right to preserve the 

challenge of the aggravating factors or the 

sentence enhancements, those issues will still 

be preserved, though, right, if they ever 

become an issue?

THE COURT: They will be preserved for me. You 

can argue that before me.

THE DEFENDANT: Okay.

THE COURT: But once I impose the sentence 

that's between five years and eight years, 

then you have no right to appeal that issue to 

the Court of Appeals.

THE DEFENDANT: All right.

THE COURT: I'm just -- Mr. Shah or Mr. Dawson, 

I'm just looking for in here did, in fact --

did they preserve the decision on the motion 

to suppress for appellate review or no?

MR. SHAH: No, your Honor. Paragraph 12 is the 

standard appellate waiver.
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THE COURT: Okay. So you've waived any right to 

appeal anything about this case in most 

circumstances as long as I follow the plea 

agreement and sentence you between five and 

eight years. Do you understand that?

THE DEFENDANT: Yes, your Honor.

Considering the transcript as a whole and taking the

district court's statements in context, we cannot say that these 

exchanges require abrogation of the appeal waiver. Thompson 

acknowledges that we have declined to prescribe a specific format 

that the colloquy regarding the waiver must take -- thus, the 

district court was not required to read the appeal waiver to 

Thompson. See Teeter, 257 F.3d at 24 n.7; Staveley, 43 F.4th at 

15 ("When the goal is to achieve a clear understanding, brevity 

can be a plus rather than a minus."). Despite not having the plea 

agreement in front of him, Thompson demonstrated detailed 

knowledge of the terms of both the appeal waiver and the plea 

agreement overall in his exchanges with the court, including 

reciting details of the agreement from memory and asking precise 

clarification questions. In response to questioning by the court, 

Thompson confirmed that he had signed the plea agreement 

voluntarily after thoroughly reviewing it and discussing it with 

his attorney. Thompson also confirmed that he was satisfied with 

his counsel's representation. And, as shown in the colloquy above, 
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the court inquired specifically into the waiver of appeal rights, 

as required by Teeter. 257 F.3d at 24.

We next turn to the court's mistaken statement that 

Thompson could appeal the denial of his motion to suppress and 

subsequent clarification that he could not appeal "in most 

circumstances." We cannot say that this was a "direct 

contradiction of the tenor of the waiver" when taken in the context 

of the colloquy. De-La-Cruz Castro, 299 F.3d at 12. The court 

quickly clarified its mistake about the motion to suppress issue, 

and Thompson does not contend that he remained confused about 

whether he could appeal the denial of that motion. Rather, he 

focuses on the court's clarification that he had "waived any right 

to appeal anything about this case in most circumstances" if the 

court sentenced him between five and eight years. Advising a 

defendant who has signed an agreement containing an appeal waiver 

that he may appeal "in some circumstances" is not per se reversible 

error. De-La-Cruz Castro, 299 F.3d at 12; see also United States

v. Gil-Quezada, 445 F.3d 33, 37 (1st Cir. 2006). As we have 

previously observed, "[t]hat statement is correct in the sense 

that we may entertain an appeal in order to correct a 'miscarriage 

of justice' even in the face of a knowing and voluntary waiver of 

appeal." De-La-Cruz Castro, 299 F.3d at 12. Thompson argues that 

even if it did not constitute per se error, the confusing nature 

of the colloquy in his case left uncertainty as to whether he could 
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challenge aggravating factors or sentencing enhancements on 

appeal. But reviewing the exchange as a whole, it is evident that

the district court explicitly told Thompson that he could challenge 

those issues only before the district court. The court said, "They 

will be preserved for me. You can argue that before me. . . . But 

once I impose the sentence that's between five years and eight 

years, then you have no right to appeal that issue to the Court of 

Appeals." Thompson replied, "All right." The court's subsequent 

clarification that Thompson had not preserved the motion to 

suppress issue for appeal and that he had waived the right to 

appeal "in most circumstances" does not contradict this earlier 

explanation of Thompson's rights.

Furthermore, "[a]lthough the relevant knowledge under 

Teeter is what [the defendant] knew about the appellate waiver at 

the time the plea was accepted, we look to the whole record to 

determine what he understood about the waiver when he entered the 

plea." United States v. Villodas-Rosario, 901 F.3d 10, 18 (1st 

Cir. 2018). At the sentencing hearing, the district court again 

explained to Thompson that he had agreed to waive the right to 

appeal given that the court imposed a sentence of eight years --

the maximum sentence provided for in the plea agreement. The court 

summed up: "This, in fact, is a below-guideline-range sentence; 

and, therefore, you've waived your right to appeal the sentence 

that I've imposed." When the court asked Thompson's attorney 
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shortly after if there was anything else, counsel took no issue 

with the court's description of the appeal waiver, and Thompson 

expressed no concerns about the meaning of it. This lack of 

objection further supports the conclusion that Thompson understood 

the terms of the waiver when entering his plea. See, e.g.,

Villodas-Rosario, 901 F.3d at 18.

In sum, this was not a case in which the court provided 

broad assurances to the defendant that "directly contradicted the 

tenor of the waiver provision," Teeter, 257 F.3d at 27, made a 

statement that "was so misleading that it nullified [the] waiver 

of appeal," United States v. Padilla-Colón, 578 F.3d 23, 28 (1st 

Cir. 2009), or failed to correct a misstatement of the waiver 

provisions, United States v. Pacheco, 921 F.3d 1, 3 (1st Cir. 

2019). We therefore conclude that the second prong of Teeter was 

met.

B.

Turning to the third prong of Teeter, Thompson argues

that it would amount to a miscarriage of justice to enforce the 

appeal waiver regarding the serial number enhancement under 

§ 2K2.1(b)(4)(B) because that enhancement violates the Second 

Amendment.1 He does not argue that it would work a miscarriage of 

1 This issue was only raised in a supplemental brief tendered 

by Thompson (which we hereby accept for filing) and was not raised 

in Thompson's opening brief, even though New York State Rifle & 

Pistol Ass’n v. Bruen, 142 S. Ct. 2111 (2022), had already been 
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justice to enforce the appeal waiver with respect to 

§ 2K2.1(b)(6)(B), concerning the use of a firearm in connection 

with another felony offense, so we find that that argument is 

waived under the appeal waiver provision.

"[I]f denying a right of appeal would work a miscarriage 

of justice, the appellate court, in its sound discretion, may 

refuse to honor the waiver." Teeter, 257 F.3d at 25. We have 

recognized that this category "is infinitely variable" and "is 

more a concept than a constant," but we have nevertheless 

articulated some factors to consider: "the clarity of the error, 

its gravity, its character (e.g., whether it concerns a fact issue, 

a sentencing guideline, or a statutory maximum), the impact of the 

error on the defendant, the impact of correcting the error on the 

government, and the extent to which the defendant acquiesced in 

the result." Id. at 25-26 & n.9. This "exception has been applied 

'sparingly and without undue generosity' and is therefore reserved 

for egregious circumstances." United States v. Ortiz-Vega, 860

F.3d 20, 28 (1st Cir. 2017) (quoting De-La-Cruz Castro, 299 F.3d 

at 13). For example, we have found a miscarriage of justice "when 

an error of significant or constitutional dimension is clear," 

decided. Although issues not raised in a party’s opening brief 

are typically waived, United States v. Mayendía-Blanco, 905 F.3d 

26, 32 (1st Cir. 2018), we conclude that this issue was already 

waived via the plea agreement, so we need not decide whether it

has been doubly waived.
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United States v. Del Valle-Cruz, 785 F.3d 48, 56 (1st Cir. 2015), 

or where "plea proceedings were tainted by ineffective assistance 

of counsel," Ortiz-Vega, 860 F.3d at 28 (quoting Teeter, 257 F.3d 

at 25 n.9).

Here, Thompson argues that, under New York State Rifle 

& Pistol Ass’n v. Bruen, 142 S. Ct. 2111 (2022), the serial number 

enhancement that was applied to his sentence is unconstitutional 

and that it would therefore work a miscarriage of justice to 

enforce the appeal waiver. Thompson's guideline sentencing range 

was increased by four levels pursuant to § 2K2.1(b)(4)(B), based 

on his possession of one or more firearms with an altered or 

obliterated serial number. In Bruen, the Supreme Court held that 

"when the Second Amendment's plain text covers an individual's 

conduct, the Constitution presumptively protects that conduct." 

142 S. Ct. at 2126. For a firearm regulation covering such conduct

to survive constitutional review, "the government must demonstrate 

that the regulation is consistent with this Nation's historical 

tradition of firearm regulation." Id. A district court in West 

Virginia subsequently applied this standard to 18 U.S.C. § 922(k), 

holding that statutory provision unconstitutional insofar as it 

criminalizes possession of a firearm with an altered or obliterated 

serial number. United States v. Price, No. 2:22-cr-97, 2022 WL 

6968457, at *2-6 (S.D. W.V. Oct. 12, 2022). Thompson argues on 

appeal that the reasoning in Price similarly applies to 
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§ 2K2.1(b)(4)(B), because the sentencing guideline provides for an 

enhanced sentence based on similar conduct.

Setting aside the ultimate merits of the question, 

Thompson's argument that enforcing the appeal waiver as to this 

issue would constitute a miscarriage of justice fails largely on 

the first factor discussed in Teeter: clarity. It is far from 

clear that § 2K2.1(b)(4)(B) is unconstitutional. We are unaware 

of any court having directly decided the constitutionality of that 

sentencing enhancement, and Thompson identifies only one district 

court case, Price, in which a similar criminal statute was 

invalidated. Another district court recently disagreed with 

Price, holding that 18 U.S.C. § 922(k) is constitutional. See

United States v. Holton, No. 3:21-CR-0482, 2022 WL 16701935, at 

*3-5 (N.D. Tex. Nov. 3, 2022). Thus, with some basis, Thompson

himself acknowledges that "[t]his is a rapidly developing issue of 

law." See, e.g., United States v. Rahimi, 59 F.4th 163 (5th Cir. 

2023) (federal statute prohibiting possession of firearm by 

someone subject to domestic violence restraining order is 

unconstitutional under Bruen). Clarity, therefore, does not yet 

exist. Given this lack of clarity, the district court's decision 

to impose the sentencing enhancement is not the type of "egregious" 

error requiring that we set aside the otherwise valid appeal 

waiver.

Based on the foregoing, we dismiss Thompson's appeal.