United States v. Reyes-Arzate

91 F.4th 616

• Court: Court of Appeals for the Second Circuit
• Decided: January 30, 2024
• Docket: 22-320
• Status: Published

Opinion

22-320-cr United States v. Reyes-Arzate

In the United States Court of Appeals for the Second Circuit ___________________________

August Term, 2023

No. 22-320

UNITED STATES OF AMERICA,

Appellee,

v.

IVAN REYES-ARZATE,

Defendant-Appellant.

___________________________

On Defense Counsel’s Anders Motion to Be Relieved and the Government’s Motion to Dismiss

(Submitted August 25, 2023; Decided January 30, 2024)

Before: LEE, NATHAN, and MERRIAM, Circuit Judges.

Counsel for defendant-appellant Ivan Reyes-Arzate moves to be relieved pursuant to Anders v. California, 386 U.S. 738 (1967), and the government moves to dismiss based on the waiver of appeal in Reyes-Arzate’s plea agreement. However, defendant-appellant’s counsel fails to address all of the components of Reyes-Arzate’s sentence and therefore falls short of the requirements articulated by this Court in United States v. Gomez-Perez, 215 F.3d 315 (2d Cir. 2000). Specifically, counsel does not discuss the non-imprisonment elements of defendant-appellant’s sentence—including forfeiture, the special assessment, and the term and conditions of supervised release—all of which are not unambiguously covered by defendant-appellant’s appeal waiver. Thus, we DEFER decision on the pending motions and ORDER counsel to file a supplemental brief. ___________________________

Susan Corkery, Philip Pilmar, Assistant United States Attorneys, for Breon Peace, United States Attorney for the Eastern District of New York, for Appellee.

Robin C. Smith, Law Office of Robin C. Smith, Esq., P.C., for Defendant-Appellant. ___________________________

EUNICE C. LEE, Circuit Judge:

Defendant-appellant Ivan Reyes-Arzate appeals from his conviction and

sentence after pleading guilty to a drug offense before the United States District

Court for the Eastern District of New York (Cogan, J.). He was sentenced on

February 9, 2022, to 120 months’ imprisonment and four years of supervised

release, as well as a special assessment and forfeiture. Before Reyes-Arzate filed

his appellate brief, the government moved to dismiss the appeal, arguing that

Reyes-Arzate had waived his appellate rights in his plea agreement. This Court

directed defense counsel to submit a Gomez-Perez response, requiring that counsel

file either a brief opposing the dismissal, or, if all issues for appeal would be

2 frivolous, an Anders brief detailing why the appeal waiver was knowing and

voluntary and why no non-frivolous appellate issues exist, and seeking to

withdraw as counsel, in accordance with Anders v. California, 386 U.S. 738 (1967).

See United States v. Gomez-Perez, 215 F.3d 315, 319–20 (2d Cir. 2000). In response,

defense counsel filed an Anders brief, explaining that Reyes-Arzate knowingly and

voluntarily entered into his plea agreement, which included a valid waiver of the

right to appeal any sentence of 293 months or less. Accordingly, counsel

concluded that there was no non-frivolous argument for appealing Reyes-Arzate’s

sentence because his term of imprisonment was less than the duration of months

stipulated in his appeal waiver.

However, like many Anders briefs this Court receives, counsel’s brief

addressed only the validity of Reyes-Arzate’s appeal waiver and did not discuss—

or even mention—the scope of the waiver and whether it encompassed the non-

imprisonment components of the sentence, such as the term and conditions of his

supervised release. Although we have not previously specified in a precedential

opinion the extent of counsel’s responsibility in an Anders brief to discuss the scope

of a waiver—or the waiver’s potential impact on the elements of a sentence that it

does not explicitly cover—we have otherwise made clear that counsel should

3 address these non-covered components of a sentence. 1 We now take this

opportunity to remind the defense bar—which we appreciate and recognize

performs a difficult job—that, when filing Anders briefs, they should address all

aspects of a defendant’s conviction and sentence that are not unambiguously

waived.

It is important for counsel to address these components because the non-

imprisonment provisions of a sentence, especially onerous conditions of

supervised release, can be severely restrictive and, in many cases, lead to

reincarceration if violated. 2 Additionally, meritorious appeals of supervised

1 This Court publishes detailed instructions regarding Anders briefs and requires that counsel analyze whether an appeal waiver unambiguously covers all components of a sentence and address any non-frivolous bases for challenging non-covered components. See How to File an Anders Brief, United States Court of Appeals for the Second Circuit (Oct. 24, 2011), https://www.ca2.uscourts.gov/clerk/case_filing/appealing_a_case/ Anders_brief/how_to_file_an_anders_brief.html. Moreover, several panels of this Court have recently reminded defense counsel to brief components of the sentence not covered by the waiver. See, e.g., Order, United States v. Clark, No. 21-1279 (2d Cir. July 5, 2023), ECF No. 104; Order, United States v. Rodriguez (Mullings), No. 21-1928 (2d Cir. July 24, 2023), ECF No. 75; Order, United States v. Stuart, No. 21-2835 (2d Cir. July 5, 2023), ECF No. 62. 2 In 2010, the U.S. Sentencing Commission found that approximately one-third of federal

offenders do not successfully complete their terms of supervised release and are sent back to prison, on average, for an additional eleven months. U.S. Sent’g Comm’n, Federal Offenders Sentenced to Supervised Release 4 (2010). Moreover, “roughly sixty percent of revocations are for non-criminal conduct. . . . such as failing to report to the probation officer, failing to submit monthly reports, and failing to attend drug or mental health treatment.” Fiona Doherty, Indeterminate Sentencing Returns: The Invention of Supervised Release, 88 N.Y.U. L. Rev. 958, 1016 (2013) (internal citation omitted).

4 release conditions are not uncommon because many appeal waivers routinely

used in this Circuit do not cover all components of a sentence. 3 For these reasons,

the Court’s instructions for filing Anders briefs expressly require counsel to

address “the scope of the defendant’s waiver . . . [including] any non-

imprisonment components of the sentence . . . and whether any ambiguity in the

language of the waiver affects the validity and scope of the waiver.” How to File

an Anders Brief, supra note 1. Furthermore, the instructions specify that “counsel’s

brief must discuss whether there is any non[-]frivolous basis for challenging [the

non-covered] components of the sentence.” Id.

The Anders brief in this case, like countless others we see each term, did not

address the scope of Reyes-Arzate’s appeal waiver or the portions of his sentence

3 Recently, panels of this Court have remanded in several cases in which Anders briefs were filed. See, e.g., Order, United States v. Edwards (Bryant), No. 21-1825 (2d Cir. Aug. 4, 2023), ECF No. 77 (denying Anders motion and vacating and remanding for the district court to strike a search condition not orally announced at sentencing); Order, United States v. Gordon (Joseph), No. 21-2907 (2d Cir. June 16, 2023), ECF No. 83 (denying Anders motion and vacating and remanding for the district court to strike or reimpose a mental health treatment condition not orally announced at sentencing); Order, United States v. Leyva, No. 22-202 (2d Cir. Aug. 4, 2023), ECF No. 69 (denying Anders motion and vacating and remanding for the district court to clarify ambiguities in the conditions of supervised release and restitution payment schedule); cf. Order, United States v. Caves, No. 23-6176 (2d Cir. Dec. 5, 2023), ECF No. 33 (granting limited remand for the district court to supplement the record regarding the imposition of special conditions of supervised release, which were outside the scope of the appeal waiver and not addressed in the initial Anders brief).

5 arguably not covered by the waiver, including the term and conditions of

supervised release. Thus, we DEFER decision on the motions and ORDER

assigned counsel to file a supplemental brief.

BACKGROUND

Reyes-Arzate pleaded guilty to conspiracy to distribute cocaine

internationally, in violation of 21 U.S.C. §§ 963, 960(b)(2)(B)(ii), and 959(d), and

entered into a plea agreement in which he agreed, among other things, to waive

his right to “file an appeal or otherwise challenge, by petition pursuant to

28 U.S.C. § 2255 or any other provision, the conviction or sentence in the event that

[the district court] imposes a term of imprisonment of 293 months or below.”

App’x 16. The language of the appeal waiver was silent on other components of

the potential sentence, including the term and conditions of supervised release,

restitution, forfeiture, and any special assessment. Ultimately, the district court

sentenced Reyes-Arzate to 120 months’ imprisonment and four years’ supervised

release with the “standard” conditions, as well as one special condition. 4 App’x

72–73. Further, the district court imposed a $100 special assessment and $290,000

4 The district court imposed the following special condition on Reyes-Arzate: “that he does not enter the country illegally again” “if he is removed or deported, as we expect he will be.” App’x 66.

6 in forfeiture.

Reyes-Arzate timely appealed, and the Court appointed the current

appellate defense counsel under the Criminal Justice Act, 18 U.S.C. § 3006A.

Shortly thereafter, but prior to Reyes-Arzate filing an appellate brief, the

government moved to dismiss the appeal because Reyes-Arzate’s 120-month

prison sentence was below the 293-month threshold stipulated in his plea

agreement’s appeal waiver. The Court then ordered defense counsel to file a

Gomez-Perez response. See Gomez-Perez, 215 F.3d at 319 (holding that in cases

where the government files a motion to dismiss a defendant’s appeal based on an

appeal waiver, defense counsel must either contest the validity of the waiver, or

file “a brief similar to that required by Anders”).

Pursuant to the Court’s order, counsel filed an Anders brief, asserting a lack

of non-frivolous issues on appeal. Reciting the details of the plea proceedings,

counsel represented that the plea complied with Federal Rule of Criminal

Procedure 11(b), and thus there was no basis to conclude it was not knowing and

voluntary. Counsel also concluded that the custodial sentence could not be

challenged because the appeal waiver was valid and Reyes-Arzate received an

imprisonment term below the waiver’s stipulated maximum of 293 months.

While noting that Reyes-Arzate was sentenced to a four-year term of supervised

7 release, counsel made no reference to its conditions or to any other sentencing

components, but nevertheless concluded that there were no non-frivolous issues

for this Court’s review.

DISCUSSION

I. The Anders Procedure

The well-established Anders procedure governs requests by defense counsel

to withdraw from an appeal if, after “conscientious examination” of the record,

she determines the appeal “to be wholly frivolous.” Anders, 386 U.S. at 744.

Counsel’s motion to be relieved must be “accompanied by a brief”—now widely

known as an Anders brief—“referring to anything in the record that might

arguably support the appeal.” Id. A defendant, “[f]urnished with his counsel’s

Anders brief, . . . may then ‘raise any points that he chooses’ in a pro se appellate

brief.” United States v. Fleming, 5 F.4th 189, 192 (2d Cir. 2021) (quoting Anders, 386

U.S. at 744). “These steps are necessary, but not sufficient by themselves, to

warrant withdrawal.” United States v. 777 Greene Ave., 609 F.3d 94, 99 (2d Cir.

2010). Rather, after counsel fulfills these obligations, “the court—not counsel—

then proceeds, after a full examination of all the proceedings, to decide whether

the case is wholly frivolous.” Anders, 386 U.S. at 744.

“We will not grant an Anders motion unless we are satisfied that ‘counsel

8 has diligently searched the record for any arguably meritorious issue in support

of his client’s appeal,’ and that counsel’s characterization of the appeal as

‘frivolous is, in fact, legally correct.’” 777 Greene Ave., 609 F.3d at 99 (quoting

United States v. Burnett, 989 F.2d 100, 104 (2d Cir. 1993)). We cannot proceed to

the final step—an independent judicial assessment of the criminal appeal’s

merits—“absent a properly prepared Anders brief.” United States v. Kosic, 944 F.3d

448, 451 (2d Cir. 2019) (quoting Burnett, 989 F.2d at 104).

II. Gomez-Perez and the Rise of Appeal Waivers

Appeal waivers require defendants to “for[ego] certain, but not all, possible

appellate claims” as part of a plea agreement. Garza v. Idaho, 139 S. Ct. 738, 742

(2019). Such waivers are generally enforceable if “entered into knowingly and

voluntarily,” United States v. Yemitan, 70 F.3d 746, 747 (2d Cir. 1995). Anders,

decided in 1967, pre-dated the rise of the use of appeal waivers in guilty pleas.

See Nancy J. King & Michael E. O’Neill, Appeal Waivers and the Future of Sentencing

Policy, 55 Duke L.J. 209, 219–25 (2005) (discussing the growth in popularity of

appeal waivers in the 1990s). While appellate counsel’s responsibility in

preparing an Anders brief is to identify any and all “issues that have at least

arguable merit supported by legal authority,” Burnett, 989 F.2d at 103, the

widespread adoption of appeal waivers has substantially narrowed the universe

9 of viable issues for appeal.

In 2000, in light of the “phenomenon” of defendants waiving their appellate

rights, the Court set forth specific requirements for Anders briefs in appeal-waiver

cases. Gomez-Perez, 215 F.3d at 318. In Gomez-Perez, we held that when the

government moves to dismiss an appeal based on an appeal waiver and defense

counsel does not have meritorious grounds to oppose the motion, she must file an

Anders brief addressing the following limited issues:

(1) [W]hether defendant’s plea and waiver of appellate rights were knowing, voluntary, and competent; or (2) whether it would be against the defendant’s interest to contest his plea; and (3) any issues implicating a defendant’s constitutional or statutory rights that either cannot be waived, or cannot be considered waived by the defendant in light of the particular circumstances.

Id. at 319 (citations omitted). Counsel should also “examine both the adequacy of

the defendant’s waiver and whether the defendant’s plea and sentence were in

accord with the applicable law.” Id.

III. Appeal Waivers Are Narrowly and Strictly Construed

While Gomez-Perez remains this Circuit’s standard in appeal-waiver cases,

we must clarify counsel’s requirement to address “any issues . . . that either cannot

be waived, or cannot be considered waived by the defendant in light of the

particular circumstances.” Id. First, plea agreements themselves are construed

10 according to contract law principles, “tempered with an awareness of due process

concerns for fairness and . . . adequacy” and construed “strictly against the

government,” which is both the “drafting party” and has an “overwhelmingly

superior bargaining position.” United States v. Gottesman, 122 F.3d 150, 152 (2d

Cir. 1997) (quotation marks omitted). It follows that “waivers of appellate rights

[in] plea agreements are to be applied narrowly and construed strictly against the

[g]overnment.” United States v. Hernandez, 242 F.3d 110, 113 (2d Cir. 2001)

(quotation marks omitted). Thus, no appeal waiver, even if valid, “serves as an

absolute bar to all appellate claims.” Garza, 139 S. Ct. at 744. Instead, a “valid

and enforceable appeal waiver . . . only precludes challenges that fall within its

scope.” Id. (quoting United States v. Hardman, 778 F.3d 896, 899 (11th Cir. 2014));

see also id. (explaining that “some waiver clauses leav[e] many types of claims

unwaived”).

Under this principle of narrow construction, we have held that a sentencing

appeal waiver “can be construed narrowly to cover only challenges to terms of

incarceration,” United States v. Burden, 860 F.3d 45, 54 (2d Cir. 2017) (per curiam),

and does not unambiguously bar challenges to restitution orders and terms of

supervised release, if the waiver does not so specify. See, e.g., id. at 54–55; United

States v. Oladimeji, 463 F.3d 152, 156–57 (2d Cir. 2006) (finding that defendant’s

11 appeal waiver, construed narrowly, did not bar challenges to “the portion of his

sentence commanding payment of restitution”). In other words, an appeal

waiver that expressly specifies certain aspects of sentencing and their triggering

thresholds (such as a term of imprisonment below a set number of months)—but

does not reference the other components (such as the term or conditions of

supervised release)—introduces ambiguity into the waiver’s scope and allows

appeals of the unenumerated components. See Burden, 860 F.3d at 54 (“[W]hen

an appeal waiver is silent regarding a specific aspect of a sentence, this Court

generally finds that the appeal waiver does not foreclose challenges to that aspect

of the sentence.”).

IV. Anders Briefs Must Address All Components of a Sentence Under Gomez-Perez

In light of the above, we hold that defense counsel’s responsibility to

address “any issues . . . that either cannot be waived, or cannot be considered

waived by the defendant in light of the particular circumstances,” Gomez-Perez,

215 F.3d at 319, includes examining the scope of an appeal waiver and determining

whether there are non-frivolous issues for appeal regarding sentencing

components arguably not covered by the waiver. Moreover, when defense

counsel determines that an appeal waiver covers only part of a sentence, counsel

12 must separately address the procedural and substantive reasonableness of the

non-covered components. By requiring counsel to discuss these issues in an

Anders brief, we hope to minimize the filing of Anders motions in cases that would

otherwise proceed to merits briefing, as well as minimize the need for

supplemental Anders briefing.

Here, Reyes-Arzate’s appeal waiver specifies that he “agrees not to file an

appeal or otherwise challenge . . . the conviction or sentence in the event that the

Court imposes a term of imprisonment of 293 months or below,” but it is silent

regarding all other aspects of his sentence. App’x 16–17. Yet, the Anders brief

does not address these other components that are not unambiguously barred from

an appeal, including the term and conditions of his supervised release, his

forfeiture order, and the special assessment. Thus, counsel’s brief does not meet

the requirements articulated by Anders and Gomez-Perez, and the Court requires

supplemental briefing.

CONCLUSION

Decision on the motions is hereby DEFERRED. Counsel must, within 30

days of the date of this opinion, file a supplemental brief that complies with Gomez-

Perez by addressing whether the non-imprisonment components of the sentence,

which are not unambiguously covered by the appeal waiver, present any non-

13 frivolous issues for appeal. Counsel’s supplemental brief may also address any

other issues she deems relevant. Alternatively, counsel may, of course, withdraw

the Anders brief and pursue a merits brief, as counsel deems appropriate. If

counsel files a supplemental Anders brief, the Anders motion and motion to dismiss

will be decided by a new panel in the ordinary course.