15

‐ 1080 (L)

United States v. Burden

UNITED STATES COURT OF APPEALS

F OR THE S ECOND C IRCUIT

_______________

August Term, 2016

(Argued: January 19, 2017 Decided: June 19, 2017)

Docket Nos. 15

‐ 1080, 15

‐ 1183

_______________

U NITED S TATES OF A MERICA

,

Appellee,

‐‐ v. ‐‐

K ELVIN B URDEN

, aka Waffle, aka Uncle, aka Unc,

J ERMAINE B UCHANAN

, aka Ski,

Defendants

‐ Appellants

,

T ERRENCE B OYD

, T ODD S UMMERVILLE

, A NTHONY B URDEN

, aka Tony, aka Mackey,

W ILLIE P REZZIE

, aka Dog, aka Prez, A NTHONY B UCHANAN

, aka Jungle, T ERRENCE

T HOMPSON

, aka Creed, M ICHAEL S AWYER

, aka Michael Moss, T ERRA N IVENS

, aka

Stink, aka Stinkfinger, F RANK K NIGHT

, aka Groovy, aka Ace, D WIGHT M ASCHEK

, aka Shorty, J ERMAINE M ARTIN

, aka Psycho, A NDRE M C C LENDON

, aka Popsicle,

M ICHAEL G LENN

, aka Rockafella, R OBERT J ONES

, aka Swinger, D AVID M. B URDEN

,

aka DMX, aka X, D AVID L. B URDEN

, aka Quinten, aka Sid, J OSEPH D ANIELS

, aka

Digital, L AVON G ODFREY

, A LVIN W HITE

, aka Uncle Lee, A NDRE D AWSON

, aka Yup2 Yup, J EFFREY F REDERICKS

, aka JL, aka Dahmer, J AHOD N ASH

, aka Hottie Jig,

M ARK C ALDWELL

, aka Lt. Sparks, K EVIN H AMLETTE

, aka Fresh, P ATRICE S T

. S URIN

, aka Patrick, aka Watty Wat, E RNEST E UGENE W ELDON

, aka Gene, aka Mean Gene,

aka Mean One, T HOMAS H OLMAN

, aka Uno, A DAM S ANDERS

, aka AD, K ENDAL

M ULLINS

, aka K

‐ Nice, T HOMAS F AGAN

, J OSEPH D ARDEN

, J EFFREY L OCKHART

,

L AMONT B ROWN

, aka L, S T

. C LAIR B URDEN

, aka Gowser, aka GP, aka Boo Boo,

C EDRIC B URDEN

, aka Sid, A NTONIO W ILLIAMS

, aka Lo Lo, A NGEL C ABRERA

, aka

Cheeks, K EITH L YONS

, aka Papa Large, aka Pops, B ARNEY B URDEN

, aka Rock, aka

Buddy, aka Buddy Rock, D EMETRIUS S TORY

, L ESLIE W AYNE C ARLOS

, aka Cheetah,

Defendants

.

_______________

B e f o r e:

K ATZMANN

, Chief Judge

, K EARSE and L IVINGSTON

, Circuit Judges

.

_______________

Defendant

‐ appellant Kelvin Burden appeals from a judgment entered

against him on March 23, 2015, resentencing him to 365 months’ imprisonment

and a life term of supervised release. Defendant

‐ appellant Jermaine Buchanan

appeals from a judgment entered against him on the same day, also resentencing

him to 365 months’ imprisonment and a life term of supervised release. Prior to

the resentencing proceedings, the defendants had entered into stipulations with

the government, pursuant to which each defendant withdrew his pending

habeas petition in exchange for being resentenced within a binding range of 262–

365 months’ imprisonment. On appeal, both defendants argue that the district

court erred in (1) failing to advise them before accepting their stipulations that

they faced terms of supervised release and (2) imposing life terms of supervised

release without adequate explanation. The government contends that the

defendants waived their right to appeal in the resentencing stipulations. We hold

that the appeal waivers are enforceable, but do not encompass the defendants’3 appeals of their terms of supervised release. We do not resolve whether the

district court erred in failing to advise the defendants that they faced terms of

supervised release, because even assuming that it did, the error was not plain.

Plain error was committed, however, when the district court implicitly hinged

the defendants’ life terms of supervised release on the need for retribution—an

imperative that is relevant to fashioning a term of incarceration, but not a term of

supervised release.

Accordingly, we VACATE the defendants’ terms of supervised release,

REMAND for resentencing as to supervised release, and AFFIRM the judgments

in all other respects.

_______________

R OBERT M. S PECTOR (Marc H. Silverman, on the brief ), Assistant

United States Attorneys, for Deirdre M. Daly, United States

Attorney for the District of Connecticut, New Haven, CT.

H ARRY S ANDICK

, Patterson Belknap Webb & Tyler LLP, New York,

NY, for Kelvin Burden

.

M ARSHA R. T AUBENHAUS

, Law Offices of Marsha R. Taubenhaus,

New York, NY, for Jermaine Buchanan

.

_______________

P ER C URIAM :

In 2003, a jury convicted defendants

‐ appellants Kelvin Burden and

Jermaine Buchanan of, among other things, racketeering, violent crimes in aid of

racketeering, and conspiracy to distribute and possess with intent to distribute

more than 50 grams of cocaine base and five kilograms or more of cocaine. Both4 men were sentenced to life imprisonment. After exhausting their direct appeals,

both defendants brought habeas petitions to vacate their convictions pursuant to

28 U.S.C. § 2255. In October 2014, each defendant entered into a “Stipulation for

Resentencing” with the government, in which the defendants agreed that they

would withdraw their habeas petitions in exchange for being resentenced based

on a binding range of 262–365 months’ imprisonment. The district court (Hall, J. )

resentenced both Burden and Buchanan to 365 months’ imprisonment and to life

terms of supervised release.

On appeal, both defendants argue that the district court erred in (1) failing

to advise them before accepting their stipulations that they faced terms of

supervised release and (2) imposing life terms of supervised release without

adequate explanation. The government asserts that the defendants waived their

right to appeal in the resentencing stipulations. We hold that the appeal waivers

are enforceable, but we construe them narrowly so as not to encompass the

defendants’ appeals of their terms of supervised release. On the merits, we

decline to resolve whether the district court erred in failing to advise the

defendants that they faced terms of supervised release, because even assuming5 that it did, the error was not plain. Plain error was committed, however, when

the district court implicitly hinged the defendants’ life terms of supervised

release on the need for retribution—an imperative that is relevant to fashioning a

term of incarceration, but not to fashioning a term of supervised release.

Accordingly, we VACATE the defendants’ terms of supervised release,

REMAND for resentencing as to supervised release, and AFFIRM the judgments

in all other respects.

B ACKGROUND

From 1997 to 2001, Kelvin Burden and Jermaine Buchanan (among others)

participated in a cocaine trafficking conspiracy, operated out of Norwalk,

Connecticut. Burden supervised the conspiracy and Buchanan was heavily

involved. In 2003, a jury convicted both men of, among other things,

racketeering, in violation of 18 U.S.C. § 1962(c); violent crimes in aid of

racketeering (“VCAR”), including conspiracy to murder, attempted murder, and,

in the case of Burden, murder, all in violation of 18 U.S.C. § 1959(a); and

conspiracy to distribute and possess with intent to distribute more than 50 grams6 of cocaine base and five kilograms or more of cocaine, in violation of 21 U.S.C.

§§ 846 and 841(b)(1)(A).

Burden faced a mandatory minimum sentence of life imprisonment on the

VCAR murder count (Count Eight) and, in light of his prior felony drug

convictions, on the drug conspiracy count (Count Twelve). Accordingly, in

November 2003, the district court sentenced Burden principally to life

imprisonment. Buchanan did not face a statutory mandatory minimum of life

imprisonment, but the then

‐ mandatory Guidelines called for a term of life

imprisonment. In April 2004, the district court sentenced Buchanan principally to

life imprisonment.

About a decade later, after exhausting their direct appeals, both men

brought habeas petitions to vacate their convictions on the basis of undisclosed

Brady evidence—namely, contemporaneous benefits to a key cooperator—and

the partial recantation of the same cooperator. The government opposed the

motions. In October 2014, without conceding their positions, the defendants

entered into separate resentencing stipulations with the government to resolve

their pending habeas petitions.7 Pursuant to Burden’s stipulation, Burden agreed to amend his § 2255

petition to withdraw his request for a new trial and to replace it with a request to

vacate his VCAR murder conviction on Count Eight of the operative indictment.

The government, in turn, agreed that the district court should grant such relief

and that the district court should vacate the judgment and conduct a full

resentencing as to the remaining counts of conviction. The stipulation also

provided that the government would rely on only one of Burden’s prior drug

offenses at resentencing, with the result that Count Twelve (the drug conspiracy)

would carry a mandatory minimum sentence of 20 years rather than life. 1 The

parties further stipulated to a binding Guidelines range of 262–365 months’

incarceration. 2 The stipulation provided that, “if the Court accepts the agreement,

[the Court] will be bound to impose an incarceration term within the range of

262–365 months.” Burden App. 461. If, on the other hand, the district court did

1 Ultimately, the government did not rely on any of Burden’s prior drug offenses at

resentencing, and Burden’s mandatory minimum sentence at resentencing was thus 10

years.

2 The parties calculated Burden’s Guidelines range as life, but stipulated to a downward

variance.8 not accept the stipulation, the stipulation would be void and the parties would

continue litigating the § 2255 petition.

Buchanan’s stipulation with the government operated similarly, with the

parties agreeing that Buchanan would amend his § 2255 petition to withdraw his

request for a new trial in favor of a request to vacate the jury’s finding as to Act

of Racketeering 4 (murder) of Count One of the operative indictment. As with

Burden’s stipulation, Buchanan and the government stipulated that the district

court, if it were to accept the stipulation, would conduct a full resentencing based

on a binding Guidelines range of 262–365 months’ incarceration. 3

Finally, both stipulations contained identical appeal waivers:

[I]f the Court adopts this stipulation and imposes an incarceration

term within the agreed

‐ upon guideline range of 262–365 months’

incarceration, the petitioner waives and gives up his right to appeal

and/or collaterally attack any alleged error in connection with the re

‐ sentencing itself and waives and gives up any right to raise any

claim on direct appeal or collateral attack related to his remaining,

underlying convictions or anything that occurred in this case prior

to the re

‐ sentencing itself

. . . .

Burden App. 459; Buchanan App. 194–95.

3 The parties calculated Buchanan’s Guidelines range as 360 months to life, but

stipulated to a downward variance.9 Neither stipulation mentioned supervised release.

On October 24, 2014, the district court presided over a joint hearing

modeled on a Rule 11 plea hearing, in which it carefully canvassed the

defendants to ensure that they understood the stipulations and the rights that

they were waiving by entering into them. The district court did not advise the

defendants that they faced terms of supervised release. Based on their counts of

conviction, Burden faced a mandatory minimum term of 10 years’ supervised

release 4 and Buchanan faced a mandatory minimum term of 5 years’ supervised

release. Upon completing its respective canvass of each defendant, the district

court found that Burden and Buchanan had entered into their stipulations

knowingly and voluntarily. It deferred decision, however, on whether it would

accept the stipulations and proceed to resentence the defendants within the

stipulated sentencing ranges.

On March 13, 2015, the district court held a joint proceeding to determine

whether it could accept the resentencing stipulations. After hearing from the

4 Because the government opted at resentencing to withdraw the prior felony

information altogether, Burden ultimately faced a mandatory minimum term of 5 years’

supervised release. See 21 U.S.C. § 841(b)(1)(A).10 parties, the district court determined that it would enter the stipulations in both

cases and granted each defendant’s amended § 2255 petition. The district court

then sentenced Burden to 365 months’ imprisonment (the top of the stipulated

Guidelines range), emphasizing the seriousness of his offense. After announcing

the term of incarceration, the court imposed a life term of supervised release on

Burden, which was well above the Guidelines range of 5 years’ supervised

release. See U.S.S.G. § 5D1.2 cmt. n.6 (2014) (explaining that where “the relevant

statute requires a minimum term of supervised release of five years and a

maximum term of life, the term of supervised release provided by the guidelines

is five years”).

The court then turned to resentencing Buchanan and imposed a matching

sentence of 365 months’ imprisonment to be followed by the same above

‐

Guidelines life term of supervised release. The court explained that its sentence

was “really driven in large part by the seriousness of what Mr. Buchanan did,”

tempered by his mitigating personal characteristics and circumstances. Burden

App. 718. Neither Burden nor Buchanan objected to the district court’s imposition

of their supervised release terms.11 These appeals followed. 5

D ISCUSSION

I.

We begin with the enforceability of the defendants’ appeal waivers. We

have long held that “[w]aivers of the right to appeal a sentence are

presumptively enforceable.” United States v. Arevalo

, 628 F.3d 93, 98 (2d Cir.

2010). “[E]xceptions to the presumption of the enforceability of a waiver

. . .

occupy a very circumscribed area of our jurisprudence.” United States v. Gomez

‐

Perez

, 215 F.3d 315, 319 (2d Cir. 2000). In particular, we have in prior cases

articulated four grounds on which an appeal waiver may be deemed

unenforceable: (1) where the “waiver was not made knowingly, voluntarily, and

competently;” (2) where the sentence was “based on constitutionally

5 As the government notes, Buchanan’s appeal was untimely by several days. However,

in its brief, the government expressly forfeits any timeliness objection. See Gov’t Br. n.1

(citing United States v. Frias

, 521 F.3d 229, 231 (2d Cir. 2008) (“[T]he time limits of

[Federal Rule of Appellate Procedure] 4(b) are not jurisdictional and are therefore

capable of forfeiture by the government.”)). We see no reason not to consider

Buchanan’s arguments to the extent they are not foreclosed by his stipulation’s appeal

waiver.12 impermissible factors, such as ethnic, racial or other prohibited biases;” (3) where

the government breached the agreement containing the waiver; and (4) where

the district court “failed to enunciate any rationale for the defendant’s sentence.”

Id.

Buchanan argues that because his term of imprisonment and term of

supervised release exceed 365 months when combined, his stipulation was

breached and his appeal waiver is thus invalid. We find no merit in this

argument. Buchanan’s stipulation made clear that the binding sentencing range

of 262–365 months’ imprisonment encompassed only the term of incarceration.

See Buchanan App. 194–95 (“[I]f the Court adopts this stipulation and imposes an

incarceration term within the agreed

‐ upon guideline range of 262–365 months’

incarceration

. . . .” (emphasis added)); see also id. at 197 (“[I]f the Court accepts

the agreement, it will be bound to impose an incarceration term within the range

of 262–365 months.” (emphasis added)). Buchanan observes that, in canvassing

him on October 24, 2014, the district court described the parties’ agreement as

that Buchanan’s “sentence should be within the range of 262 to 365 months.” Id.

at 246

. But in making this and similar statements, the district court did not13 suggest that it was referring to anything other than the incarceration component

of Buchanan’s sentence, nor did it alter the terms of the stipulation.

To the extent Buchanan argues in the alternative that the district court

breached the stipulation by imposing any term of supervised release, this

argument also fails. Though the stipulations were silent regarding the potential

imposition of a term of supervised release—an omission we will return to in

construing the scope of the waivers—that silence is not tantamount to an implied

agreement that the sentence would not encompass such a term. Indeed, no such

agreement could legally have been reached, given that Buchanan faced a

mandatory minimum term of supervised release. Accordingly, the district court

did not run afoul of the stipulation when it sentenced Buchanan to a term of

incarceration within the agreed

‐ upon range, along with a term of supervised

release.

Buchanan next contends that the appeal waiver should not be enforced

because it is unilateral in nature and contravenes public policy. Although the

enforceability of unilateral appeal waivers in the plea context is well settled,

Buchanan urges us not to countenance them in the context of a stipulation14 resolving a § 2255 petition. We decline to adopt any such categorical rule. While

we scrutinize “unorthodox” appeal waivers closely, the waiver here was

accompanied—to the district court’s credit—by the procedural safeguards that

would be required in the familiar context of a guilty plea. United States v. Rosa

,

123 F.3d 94, 99 (2d Cir. 1997). Buchanan was represented by counsel and the

district court canvassed Buchanan repeatedly and specifically on his

understanding of the waiver. We thus see no reason, under the circumstances of

this case, to depart from our general rule that “[w]aivers of the right to appeal a

sentence are presumptively enforceable” and will be enforced so long as they are

knowing and voluntary. Arevalo

, 628 F.3d at 98. Moreover, to the extent

Buchanan is arguing that unilateral appeal waivers are fundamentally unfair, we

have explained that an appeal waiver can work to a defendant’s advantage

insofar as it constitutes a “bargaining chip” that “can be exchanged for

concessions from the [government].” United States v. Granik

, 386 F.3d 404, 412 (2d

Cir. 2004); cf. United States v. Mezzanatto

, 513 U.S. 196, 208 (1995) (“[I]f the

prosecutor is interested in ‘buying’ the reliability assurance that accompanies a

waiver agreement, then precluding waiver can only stifle the market for plea15 bargains. A defendant can ‘maximize’ what he has to ‘sell’ only if he is permitted

to offer what the prosecutor is most interested in buying.”).

Buchanan’s invocation of the public interest is particularly misplaced in

light of the relief he requests. Buchanan contends that it contravenes the public

interest to insulate significant violations and misconduct of the kind alleged in

his habeas petition from appellate review. But Buchanan is not seeking to press

the claims he raised in his habeas petition, either before us or below. Rather, he

asks that we vacate his sentence and remand for resentencing, meaning that the

violations he alleged in his habeas petition will remain insulated from review. In

any case, we have long permitted a defendant to waive his right to collaterally

attack his conviction and sentence. See Sanford v. United States

, 841 F.3d 578, 580

(2d Cir. 2016) (per curiam).

Finally, the defendants contend that the district court erred in failing to

advise them of their exposure to terms of supervised release prior to accepting

their stipulations. Since neither defendant raised the claimed error below, our

review is for plain error. See United States v. Tulsiram

, 815 F.3d 114, 119 (2d Cir.

2016) (per curiam); Fed. R. Crim. P. 52(b). We analyze the argument at this16 juncture because, if the defendants were correct that the district court erred in

this manner, the error would arguably vitiate the defendants’ appeal waivers by

undermining their knowing and voluntary nature.

Rule 11 of the Federal Rules of Criminal Procedure requires district courts

to inform a defendant entering a guilty plea of, among other things, “any

maximum possible penalty, including imprisonment, fine, and term of

supervised release,” as well as “any mandatory minimum penalty.” Fed. R.

Crim. P. 11(b)(1)(H)

– (I). We need not resolve whether the district court was

subject to a similar obligation here—on a theory that a Rule 11

‐ like colloquy is

necessary to ensure that a resentencing stipulation resolving a habeas petition is

entered into knowingly and voluntarily—because, even assuming that it was, the

error would not be plain. 6

6 To the extent Buchanan contends that the district court’s alleged error in this regard

should be reviewed under a less rigorous standard because he could not have been

expected to know at the time that he faced a supervised release term, we disagree. In

the analogous Rule 11 context, a defendant who argues for the first time on appeal that

the district court did not comply with Rule 11 must show plain error in order to obtain

relief. See United States v. Dominguez Benitez

, 542 U.S. 74, 76 (2004).17 “Plain error review requires a defendant to demonstrate that (1) there was

error, (2) the error was plain, (3) the error prejudicially affected his substantial

rights, and (4) the error seriously affected the fairness, integrity or public

reputation of judicial proceedings.” United States v. Cook

, 722 F.3d 477, 481 (2d

Cir. 2013) (internal quotation mark omitted). Generally, the “substantial rights”

prong requires a defendant to demonstrate that the claimed error “‘affected the

outcome of the district court proceedings.’” Puckett v. United States

, 556 U.S. 129,

135 (2009) (quoting United States v. Olano

, 507 U.S. 725, 734 (1993)); cf. United

States v. Dominguez Benitez

, 542 U.S. 74, 83 (2004) (“[A] defendant who seeks

reversal of his conviction after a guilty plea, on the ground that the district court

committed plain error under Rule 11, must show a reasonable probability that,

but for the error, he would not have entered the plea.”). Neither defendant

makes that showing here. Buchanan does not claim he would not have entered

into the stipulation had he known he faced a term of supervised release. And

Burden effectively concedes he cannot make the required showing, instead

arguing that we should remand for fact

‐ finding on the question of what Burden

would have done had he been advised by the district court of his exposure to a18 term of supervised release at resentencing. We decline Burden’s invitation to

soften the strictures of plain error review. 7

Accordingly, the appeal waivers are enforceable.

II.

That the appeal waivers are enforceable does not resolve their scope. The

defendants waived their right to appeal “any alleged error in connection with the

re

‐ sentencing itself.” Burden App. 459; Buchanan App. 194–95. Despite the

apparent breadth of this language, the defendants argue that the waivers must be

construed narrowly so as not to extend to their challenges to their terms of

supervised release. We agree.

Because appeal waivers in the criminal context appear in “unique

contracts,” we “temper the application of ordinary contract principles with

7 Burden relies on United States v. Showerman

, 68 F.3d 1524 (2d Cir. 1995), in which we

reviewed a Rule 11 challenge for harmless error, rather than plain error, despite the

absence of a contemporaneous objection. See id. at 1527–28. Determining that the district

court’s failure to advise the defendant of its authority to impose a restitution order was

not harmless, we devised a flexible remedy that permitted the defendant to withdraw

his guilty plea if the district court did not refrain from imposing restitution on remand.

Id. at 1528–29. Showerman predated Dominguez Benitez

, however, and its relevance to the

appropriate remedy here is thus limited at best.19 special due process concerns for fairness and the adequacy of procedural

safeguards.” Granik

, 386 F.3d at 413 (internal quotation marks omitted). One way

we strike the balance is by applying appeal waivers “narrowly and constru[ing]

[them] strictly against the Government.” United States v. Pearson

, 570 F.3d 480,

485 (2d Cir. 2009) (per curiam) (internal quotation mark omitted).

Indeed, as the government acknowledges, “[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.” Gov’t

Br. 42. We have repeatedly applied this principle in narrowly construing appeal

waivers comparable in breadth to the one at issue here. For example, in United

States v. Oladimeji

, 463 F.3d 152 (2d Cir. 2006), we held that an appeal waiver

providing that the defendant would “not file an appeal or otherwise challenge

the conviction or sentence” if the court imposed a prison term within a particular

range did not bar the defendant’s appeal of the restitution order imposed as part

of his sentence—even though the court imposed a term of imprisonment within

the contemplated range. Id. at 156. We reasoned that “although a broad and

literal reading of the agreement would bar appeal from any aspect of the20 sentence, the agreement could also be reasonably construed to bar challenges to

the conviction and to the duration of confinement, but not to cover

determinations of restitution.” Id. at 157. Because, in context, the term “sentence”

could be read to refer to a period of incarceration alone, the term was ambiguous

and the ambiguity was resolved against the government. Id. Such an

interpretation accorded with “[t]he apparent logic of the agreement,” which

“was that the defendant would give up any challenges to the lawfulness of his

conviction and the determination of his prison sentence if his period of

imprisonment was below a specified maximum.” Id. at 156.

Similarly, in United States v. Cunningham

, 292 F.3d 115 (2d Cir. 2002), the

defendant agreed that he would not “file an appeal or otherwise challenge his

conviction or sentence in the event that the Court impose[d] the sentence

specified in paragraph 7(c) [of the plea agreement].” Id. at 116. Paragraph 7(c) of

the plea agreement specified that the government would recommend a term of

imprisonment of time served, but neither paragraph 7(c) nor the remainder of the

plea agreement spoke to supervised release. Id. The district court sentenced the

defendant to time served but also imposed a two

‐ year term of supervised release.21 Id. The defendant appealed, challenging the length of his supervised release

term. Id. at 117. Again, although the waiver read literally would bar the appeal,

we reasoned that because the defendant “was not sentenced solely to the

sentence specified in [paragraph] 7(c)—time served,” but rather “to time served

and two years’ supervised release,” we could not “say [that the defendant]

waived his right to appeal the length of his term of supervised release.” Id.

Likewise, here, the defendants were not sentenced solely to the

contemplated terms of incarceration, but also to life terms of supervised release.

The government does not present a basis for distinguishing Cunningham from this

case. And, as in Oladimeji

, the defendants’ appeal waivers can be construed

narrowly to cover only challenges to terms of incarceration, consistent with the

“apparent logic” of the defendants’ stipulations. Oladimeji

, 463 F.3d at 156. Just as

we narrowly construed the term “sentence” in Oladimeji to refer only to a period of

incarceration, we may narrowly construe the term “re

‐ sentencing” in the instant

appeal waivers in the same fashion. Given that the stipulations do not so much as

mention supervised release, such a construction follows directly from our

precedent. See also Pearson

, 570 F.3d at 485–86 (holding that defendant who waived22 right to appeal “any sentence incorporating [an order to pay restitution ‘in full’]”

did not waive right to appeal errors in calculating “full” restitution); United States

v. Stearns

, 479 F.3d 175, 177–78 (2d Cir. 2007) (per curiam) (holding that defendant

who waived “right to appeal

. . . any sentence imposed by the Court” at or below

the mandatory minimum did not waive right to appeal decision to run sentence

only partially concurrently with undischarged state sentence). 8

The government resists the application of these precedents, pointing to the

breadth of the appeal waivers at issue and noting that we have previously

invited the government “to negotiate for a broader waiver” if it wished to

preclude appeal of particular components of a sentence. Cunningham

, 292 F.3d at

117. But while Burden’s and Buchanan’s appeal waivers are broad as a literal

matter, so were those in the cases just discussed. The principle animating our

case law in this area is not that waivers must be “broader” to achieve broad

application, but that they must be sufficiently specific so as to properly safeguard

8 Though the government argues that the district court here advised the defendants as

to the breadth of the appeal waivers, the district court did not mention supervised

release until it imposed sentence. Thus, even assuming that those colloquies could

properly inform our construction of the waivers, the same analysis as was undertaken

in Oladimeji and Cunningham applies.23 defendants’ rights. Demanding such specificity helps to ensure that a defendant

understands precisely what it is that he is waiving and the consequences of his

waiver. Drafted as they are, we construe the waivers at issue narrowly to

encompass only appeals of the defendants’ terms of incarceration.

Accordingly, we hold that Buchanan, who alone complains of alleged

errors in connection with the incarceration component of his sentence, waived

his various challenges to the procedural and substantive reasonableness of his

term of incarceration. The defendants did not, however, waive their challenges to

the procedural reasonableness of their life terms of supervised release.

III.

Both defendants challenge the procedural reasonableness of their life terms

of supervised release, arguing that the district court did not adequately explain the

reasons for its significant variance from the Guidelines range of 5 years’

supervised release. “A district court commits procedural error where it

. . . fails

adequately to explain its chosen sentence

. . . .” United States v. Cavera

, 550 F.3d

180, 190 (2d Cir. 2008) (en banc). “Procedural reasonableness is reviewed for

abuse of discretion.” United States v. Desnoyers

, 708 F.3d 378, 385 (2d Cir. 2013).24 Where a defendant does not contemporaneously object to a district court’s failure

to provide an adequate explanation for its chosen sentence, “plain error analysis in

full rigor” applies. United States v. Villafuerte

, 502 F.3d 204, 211 (2d Cir. 2007). 9

The defendants’ challenge arises from the fact that the district court did

not separately address their above

‐ Guidelines life terms of supervised release,

instead providing one explanation for the entirety of each defendant’s sentence.

We need not resolve the extent to which the district court was required to

separately explain the above

‐ Guidelines supervised release terms because even

assuming that the district court was under no such general obligation, we do not

think its sentencing explanations could support either defendant’s life term of

supervised release.

Section 3553(a) provides the framework for sentencing decisions, requiring

the district court in imposing a sentence to consider, inter alia

, “the need for the

sentence imposed

. . . to reflect the seriousness of the offense, to promote respect

9 Buchanan suggests that we should relax the strictures of plain error review because he

lacked sufficient notice that the district court might impose a life term of supervised

release. However, the first page of the defendants’ respective Presentence Reports

disclosed that they faced up to life terms of supervised release. As a result, plain error

review applies to these challenges.25 for the law, and to provide just punishment for the offense.” 18 U.S.C.

§ 3553(a)(2)(A). Section 3583(c), which guides the district court in imposing a

term of supervised release, is different. That section requires the district court to

consider almost all of the § 3553(a) factors, but specifically does not require the

district court to consider the factors listed in § 3553(a)(2)(A), all of which go to

the seriousness of the defendant’s offense.

Congress’s omission of this set of factors accords with the purposes of

supervised release. “Supervised release

. . . is not a punishment in lieu of

incarceration.” United States v. Granderson

, 511 U.S. 39, 50 (1994). To the contrary,

“Congress intended supervised release to assist individuals in their transition to

community life.” United States v. Johnson, 529 U.S. 53, 59 (2000). Accordingly,

“[s]upervised release fulfills rehabilitative ends, distinct from those served by

incarceration.” Id. As such, “a court may not take account of retribution (the first

purpose listed in § 3553(a)(2)) when imposing a term of supervised release.”

Tapia v. United States

, 564 U.S. 319, 326 (2011) (citing 18 U.S.C. § 3583(c)).

Here, the district court advised Buchanan that its sentence was “really

driven in large part by the seriousness of what Mr. Buchanan did.” Burden App.26 718. And it advised Burden that although it believed he was a “changed person,”

his sentence was “at the top of the [stipulated] range

. . . because of really the

seriousness of what [he] did, and

. . . although years have passed, it doesn’t

change what [he was] doing.” Id. at 708. To be sure, in order to impose a term of

supervised release that takes account of “the nature and circumstances of the

offense,” 18 U.S.C. § 3553(a)(1), that “afford[s] adequate deterrence,”

§ 3553(a)(2)(B), and that “protect[s] the public from further crimes of the

defendant,” § 3553(a)(2)(C)—each of which is relevant to the supervised release

analysis, see § 3583(c)—it would be neither possible nor desirable to disregard the

seriousness of a defendant’s offense. A district court properly weighs the

seriousness of the offense as relevant to the application of these mandatory

considerations when imposing a term of supervised release. But when a

supervised release term is inflected with retributive interests—as appears may

have been the case here—the district court commits procedural error and the

supervised release term cannot stand.

United States v. Williams

, 443 F.3d 35 (2d Cir. 2006), is not to the contrary.

In Williams

, the defendant argued that the district court had impermissibly27 considered the seriousness of his offense in revoking his supervised release term

and sentencing him to a term of imprisonment pursuant to 18 U.S.C. § 3583(e).

See id. at 47. Like 18 U.S.C. § 3583(c), § 3583(e) omits § 3553(a)(2)(A) from the list

of § 3553(a) factors that courts are instructed to consider in modifying the

conditions of or revoking supervised release. In Williams

, we held that § 3583(e)

did not “forbid[] consideration of other pertinent factors” and could not

“reasonably be interpreted to exclude consideration of the seriousness of the

releasee’s violation, given the other factors that must be considered.” Williams

,

443 F.3d at 47–48. But the district court in Williams specifically focused not on the

seriousness of the offense per se

, but on the risk to the public that the seriousness

of the defendant’s offense suggested. See id. at 44 (“While this sentence reflects

the seriousness of the offense

. . . the court was most concerned with protecting

the public from further crimes of the defendant when it imposed the

. . .

sentence.” (emphasis omitted)). Here, by contrast, the district court repeatedly

emphasized that its sentence was driven by the seriousness of Buchanan’s crimes

and that, though Burden had changed in the intervening years, a long sentence

was necessary to reflect the seriousness of Burden’s crimes. Thus, in contrast to28 Williams

, the terms of supervised release in this case appear to have been driven

largely by the past seriousness of the defendants’ crimes, standing alone. Because

this retributive rationale cannot support the lifetime sentences of supervised

release imposed, remand is appropriate if this error was plain. 10

Respectfully, we believe that, as applied to the terms of supervised release,

it was. In light of the structure of § 3583(c), the district court’s error was clear,

thus meeting the first and second prongs of the plain error test; because the

defendants’ supervised release terms might have been substantially different but

for the error, the error affected their substantial rights; and, finally, for essentially

those same reasons, the error goes directly to “the fairness, integrity or public

reputation of judicial proceedings.” United States v. Cook

, 722 F.3d 477, 481 (2d

Cir. 2013).

Because district courts, understandably, often provide only one

explanation for the entirety of a sentence—and because the need for retribution is

10 Moreover, the purpose of revoking a supervised release term, as occurred in Williams

,

is fundamentally different from the purpose of imposing a supervised release term.

Whereas the latter is designed to rehabilitate and not to punish, the former is designed

primarily to “sanction

. . . the defendant’s breach of trust.” See U.S.S.G. Ch. 7, Pt. A,

intro. comment. 3(b) (2014).29 properly considered in imposing a term of incarceration but not a term of

supervised release—the procedural error we identify here is one that might be

inadvertently made. Even if a district court’s imposition of a supervised release

term was not ultimately motivated by considerations of retribution, it will often

be difficult for a reviewing court to make that judgment (as is the case here). In

light of this dynamic, to the extent a district court bases a term of incarceration

substantially upon the seriousness of the offense, it would be advisable for the

district court to separately state its reasons for the term of supervised release

imposed.

Because we vacate the terms of supervised release on this basis, we need

not address Buchanan’s argument that the district court erred in imposing

special conditions on him. Those conditions are vacated along with his

supervised release term.

C ONCLUSION

For the foregoing reasons, we VACATE the defendants’ terms of

supervised release, REMAND for resentencing as to supervised release, and

AFFIRM the judgments in all other respects.15

‐ 1080 (L)

United States v. Burden

K EARSE

, Circuit Judge

, concurring:

I concur in the majority opinion, although I find it difficult to interpret the

stipulations in which these federal habeas corpus petitioners agreed to forgo

review of their new sentences as not encompassing all facets of their new

sentences. Each petitioner agreed that:

[I]f the Court adopts this stipulation and imposes an incarceration

term within the agreed

‐ upon guideline range of 262–365 months’

incarceration, the petitioner waives and gives up his right to appeal

and/or collaterally attack any alleged error in connection with the

re

‐ sentencing itself and waives and gives up any right to raise any

claim on direct appeal or collateral attack related to his remaining,

underlying convictions or anything that occurred in this case prior

to the re

‐ sentencing itself

. . . .

(Emphases added.)

I regard this language—“any alleged error in connection with the re

‐

sentencing” and “anything that occurred in this case prior to the re

‐

sentencing”—as encompassing everything in connection with petitioners’

resentencings and everything in the case that preceded their resentencings.

However, because in some cases involving stipulations whose language was

slightly less broad, see, e.g.

, United States v. Cardona

, 612 F. App’x 622 (2d Cir.2 2015); United States v. Tourloukis

, 558 F. App’x 112, 113, 115 (2d Cir. 2014), we

have found no waiver as to unmentioned aspects of the sentence, I do not

dissent.