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 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

(g)(1),

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

more of methamphetamine under

(a)(1),

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

drug trafficking under

(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

- 2 - 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,

(1st Cir. 2001). To make

- 3 - this determination, we look to the "text of the plea agreement and

the content of the change-of-plea colloquy."

"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,

(1st Cir. 2016) (citing Teeter,

).

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

(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-of-

plea 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

- 4 - appellate rights" to ensure that the defendant "freely and

intelligently agreed to waive [his] right to appeal."

. 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."

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,

(1st

Cir. 2022) (quoting United States v. Morillo,

(1st

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

States v. De-La-Cruz Castro,

(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

- 5 - 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.

- 6 - 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.

- 7 - 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,

n.7; Staveley,

("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,

- 8 - the court inquired specifically into the waiver of appeal rights,

as required by Teeter.

.

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,

. 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,

; see also United States

v. Gil-Quezada,

(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,

. 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

- 9 - 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,

(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

- 10 - 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,

.

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,

, made a

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

of appeal," United States v. Padilla-Colón,

(1st

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

provisions, United States v. Pacheco,

(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

This issue was only raised in a supplemental brief tendered 1

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,

(2022), had already been

- 11 - 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,

. 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."

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,

(1st Cir. 2017) (quoting De-La-Cruz Castro,

). 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,

(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.

- 12 - United States v. Del Valle-Cruz,

(1st Cir. 2015),

or where "plea proceedings were tainted by ineffective assistance

of counsel," Ortiz-Vega,

(quoting Teeter,

n.9).

Here, Thompson argues that, under New York State Rifle

& Pistol Ass’n v. Bruen,

(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."

. 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."

A district court in West

Virginia subsequently applied this standard to

(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,

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

appeal that the reasoning in Price similarly applies to

- 13 - § 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

(k) is constitutional. See

United States v. Holton, No. 3:21-CR-0482,

, 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,

(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.

- 14 -