PUBLISHED

UNITED STATES COURT OF APPEALS FOR THE FOURTH CIRCUIT

No. 19-4381

UNITED STATES OF AMERICA,

Plaintiff – Appellee,

v.

CHRISTOPHER RAYQUAZ SINGLETARY,

Defendant – Appellant.

Appeal from the United States District Court for the Eastern District of North Carolina, at Raleigh. James C. Dever III, District Judge. (5:18-cr-00097-D-1)

Argued: November 2, 2020 Decided: January 12, 2021

Before DIAZ, THACKER, and HARRIS, Circuit Judges.

Vacated and remanded by published opinion. Judge Harris wrote the opinion, in which Judge Diaz and Judge Thacker joined.

ARGUED: Jennifer Claire Leisten, OFFICE OF THE FEDERAL PUBLIC DEFENDER, Raleigh, North Carolina, for Appellant. David A. Bragdon, OFFICE OF THE UNITED STATES ATTORNEY, Raleigh, North Carolina, for Appellee. ON BRIEF: G. Alan DuBois, Federal Public Defender, OFFICE OF THE FEDERAL PUBLIC DEFENDER, Raleigh, North Carolina, for Appellant. Robert J. Higdon, Jr., United States Attorney, Jennifer P. May-Parker, Assistant United States Attorney, Evan M. Rikhye, Assistant United States Attorney, OFFICE OF THE UNITED STATES ATTORNEY, Raleigh, North Carolina, for Appellee.

2 PAMELA HARRIS, Circuit Judge:

Christopher Rayquaz Singletary pleaded guilty to Hobbs Act robbery and to use of

a firearm in the course of a crime of violence, and was sentenced to 13 years’ imprisonment

and five years’ supervised release. On appeal, he raises several claims relating to the terms

of his supervised release.

We need resolve only one of those claims today. Two of the conditions of

supervised release that appear in Singletary’s written judgment were not pronounced orally

by the district court during his sentencing hearing. That means, under our recent decision

in United States v. Rogers,

(4th Cir. 2020), that Singletary never was

sentenced to those conditions. For that reason alone, as in Rogers, we must vacate

Singletary’s sentence and remand for resentencing.

I.

In January of 2019, Singletary pleaded guilty to one count of Hobbs Act robbery in

violation of

and one count of using a firearm during and in relation to a

crime of violence in violation of

(c). His plea agreement contained a

standard appeal waiver, in which he waived his right to appeal his sentence on all but the

narrowest of grounds. Specifically, Singletary agreed

[t]o waive knowingly and expressly all rights, conferred by

, to appeal the conviction and whatever sentence is imposed on any ground, including any issues that relate to the establishment of the advisory Guideline range, reserving only the right to appeal from a sentence in excess of the applicable advisory Guideline range that is established at sentencing, and further to waive all rights to contest the conviction or sentence in any post- conviction proceeding, including one pursuant to

,

3 excepting an appeal or motion based upon grounds of ineffective assistance of counsel or prosecutorial misconduct not known to the defendant at the time of the defendant’s guilty plea.

J.A. 87–88.

Singletary was sentenced on May 15, 2019, to a 13-year prison term and five years

of supervised release. At the May 15 sentencing hearing – the point at which Singletary

actually was sentenced, see United States v. Rogers,

(4th Cir. 2020) –

the district court orally attached a series of conditions to Singletary’s supervised release

term, some of which were made mandatory by statute and some of which were not. Among

the non-mandatory conditions were several special conditions for which the district court

provided no explanation. 1

The district court then issued its written judgment, which was entered on May 29,

2019. That judgment included the special conditions pronounced at sentencing, but again

provided no explanation for their imposition. It also included two new non-mandatory

conditions that had not been pronounced at sentencing, which we refer to here as the

“financial conditions”: first, that “[t]he defendant shall not incur new credit charges or

open additional lines of credit without approval of the probation office”; and second, that

1 As we explained in Rogers,

(d) identifies certain “mandatory” conditions of supervised release that must be imposed in every case and also “discretionary” conditions that may be imposed only if the court finds that they are reasonable, based on an individualized assessment of the defendant under the relevant § 3553(a) sentencing factors, and consistent with Sentencing Commission policy statements.

. The Sentencing Commission, for its part, has further subdivided “discretionary” conditions into “standard” conditions recommended for all terms of supervised release and “special” or “additional” conditions appropriate only in certain cases.

(internal quotation marks omitted); see U.S.S.G. § 5D1.3(c)–(e).

4 “[t]he defendant shall provide the probation office with access to any requested financial

information.” J.A. 82.

Singletary timely appealed from the judgment.

II.

A.

We begin by setting out the parties’ positions in what has turned out to be a

somewhat complicated appeal. The appeal began with an Anders brief filed by Singletary’s

counsel. 2 After reviewing the brief, the court ordered supplemental briefing on whether

the district court failed to adequately explain the special conditions of supervised release it

had imposed. And while that briefing was underway, the government also filed a separate

motion to dismiss the appeal based on the appeal waiver in Singletary’s plea agreement,

and Singletary opposed that motion. Rather than discussing each of these several briefs

individually, we summarize the parties’ overall merits positions here, returning to the

question of the appeal waiver below.

Across the briefing, Singletary raises three separate merits claims. First, he argues

that the district court erred when it failed to explain its imposition of special conditions of

2 Under Anders v. California,

(1967), “a lawyer who concludes that an appeal on behalf of his criminal defendant client would be wholly frivolous should advise the appellate court as such and request permission to withdraw from representation, but not before filing a brief referring to anything in the record that might arguably support the appeal.” United States v. Jones,

, 897 n.3 (4th Cir. 2019) (internal quotation marks omitted).

5 supervised release, and why those conditions were appropriate in his individual case. See,

e.g., United States v. McMiller,

(4th Cir. 2020) (holding that a district

court must explain its decision to attach special conditions to a term of supervised release).

Second, Singletary argues that because the district court did not orally pronounce the

financial conditions, in particular, at his sentencing hearing, those conditions are not a part

of his sentence at all under Rogers. See 961 F.3d at 295–99 (holding that district court

must orally pronounce all non-mandatory conditions of supervised release at sentencing

hearing). And finally, he argues that one of those financial conditions – barring him from

incurring new credit charges without probation-officer approval – impermissibly delegates

the court’s sentencing authority to a probation officer. See United States v. Shiraz,

, 143–44 (4th Cir. 2019) (per curiam) (setting out standard under which courts

may delegate to probation officers “ministerial acts or support services” related to

punishment but not the decision as to the “nature and extent” of the punishment (internal

quotation marks omitted)).

The government, as noted above, has moved to dismiss this appeal, arguing that all

of Singletary’s claims fall within the scope of the appeal waiver in his plea agreement. But

on the merits, it concedes Singletary’s first two claims: It agrees that the district court erred

by failing to explain the special conditions it imposed on Singletary’s supervised release,

and again under Rogers by including in its written judgment two conditions – the financial

conditions – that were not pronounced at the sentencing hearing. It disagrees, however,

with Singletary’s third claim, arguing that the challenged financial condition permissibly

delegates to the probation officer only the “ministerial” approval of particular charges. See

6 United States v. Nash,

(11th Cir. 2006) (upholding similar condition).

So if we decline to dismiss this case based on the appeal waiver, the government suggests,

then we should affirm the validity of the financial condition but remand for the district

court to address the Rogers error.

B.

In Rogers, we established that because a defendant has a right to be present when

he is sentenced, a district court must orally pronounce all non-mandatory conditions of

supervised release at the sentencing hearing. 961 F.3d at 296–99. Discretionary conditions

that appear for the first time in a subsequent written judgment, we held, are nullities; the

defendant has not been sentenced to those conditions, and a remand for resentencing is

required. Id. at 295, 300–01.

That clear rule is enough to dispose of this case. We agree with Singletary that his

Rogers claim – that he in fact never was sentenced to the financial conditions in his

judgment – is not barred by his appeal waiver, which applies only to challenges to a

sentence actually imposed on a defendant. And as the government concedes, there has

been a Rogers error in this case. By itself, that error requires that we vacate Singletary’s

sentence and remand for the district court to conduct the sentencing anew. Given that

disposition, we need not and should not proceed further to reach Singletary’s additional

arguments about his prior sentencing or the validity of a financial condition to which he

never was sentenced.

1.

7 Arguments over the scope and enforceability of the appeal waiver in Singletary’s

plea agreement comprise much of the parties’ briefing on appeal. Singletary argues that

the government’s motion to dismiss on the basis of the waiver should be denied for two

reasons. First, according to Singletary, the motion is untimely, because it was filed more

than a year after he noted his appeal and several months after his counsel submitted the

Anders brief. And second, Singletary contends, the waiver in any event would not apply

to his Rogers claim. The government, for its part, argues that its motion to dismiss was

timely filed, emphasizing that although it did not invoke the plea waiver in its response to

the Anders brief, it did expressly reserve the right to invoke that waiver in the future. And

the government insists that Singletary’s Rogers claim is indeed encompassed by his waiver

of the right to appeal his sentence.

We need not decide the timeliness issue, because even assuming the government

timely invoked the appeal waiver, 3 Singletary’s Rogers claim falls outside its scope. What

Singletary waived in his plea agreement was the right to appeal “the conviction and

whatever sentence is imposed.” J.A. 87 (emphasis added). And the heart of a Rogers claim

3 Neither party addresses the local rule of this court under which the timeliness of the government’s invocation would be assessed. Adopted in October 2018 – relatively recently, but before the briefing on the government’s motion to dismiss – Local Rule 27(f)(2) provides that “[m]otions to dismiss based upon the ground that the appeal is not within the jurisdiction of the Court or on other procedural grounds should be filed within the time allowed for the filing of the response brief.” This court has yet to consider whether and how application of that rule might be affected by a purported reservation, by the government, of its right to invoke an appeal waiver at some later date.

8 is that discretionary conditions appearing for the first time in a written judgment in fact

have not been “imposed” on the defendant. We said as much in Rogers, explaining that

Rogers’s was the “unusual sentencing appeal” that did not challenge the substantive or

procedural reasonableness of his sentence, but instead made the “more elementary

contention” that certain conditions in his written judgment were “not part of his sentence”

at all.

.

This is not a claim, in other words, that the district court erred in the process by

which it sentenced Singletary to the financial conditions on his supervised release, or that

those conditions cannot reasonably be applied to Singletary – matters that would be

covered by the appeal waiver. Instead, if Singletary is right on the merits of his Rogers

claim, then he has never been sentenced to those conditions at all. Like the Seventh Circuit,

we think that brings Singletary’s Rogers claim outside the scope of his promise not to

appeal the “sentence” actually “imposed” upon him. See United States v. Tancil,

, 236 (7th Cir. 2020) (unpublished) (“[T]his [inconsistent-judgment] appeal does

not fall under the waiver. Tancil is not appealing the components of his sentence or the

manner in which his sentence was determined or imposed.”).

2.

That brings us to the merits of Singletary’s Rogers claim, which are plain and

uncontested by the government. To reiterate, under Rogers, in order to sentence a

defendant to a non-mandatory condition of supervised release, the sentencing court must

include that condition in its oral pronouncement of a defendant’s sentence in open court.

See

(“[A]ll non-mandatory conditions of supervised release must be

9 announced at a defendant’s sentencing hearing.”). It is undisputed that the district court

here did not expressly include the two financial conditions in its oral pronouncement at

Singletary’s sentencing hearing. And while a district court may incorporate by reference

a condition or set of conditions during a hearing, see

, that also did not happen

here: The court at sentencing referenced “standard” conditions, J.A. 73, but the “standard”

conditions set out by the Sentencing Guidelines do not include the financial conditions at

issue here. See U.S.S.G. § 5D1.3(c) (listing 13 “standard” conditions of supervised

release). Thus, as in Rogers, “[w]e are left without any objective indication that at the time

of sentencing – the time that counts, when the defendant is in the courtroom – the district

court actually imposed” the financial conditions on Singletary’s term of supervised release.

.

Under Rogers, the remedy for this error is not, as Singletary suggests, simply to

strike the financial conditions from the written judgment. Rather, as we held in Rogers and

have reiterated since, it is to vacate the sentence and remand for the district court to

resentence Singletary. See

at 300–01; see also United States v. Sings,

, 851–52 (4th Cir. 2020) (per curiam) (applying Rogers and vacating sentence where

written judgment included non-mandatory conditions not pronounced at sentencing). We

likewise do so here. 4 And that leaves us with no occasion to reach Singletary’s other

4 To the extent the government suggests that vacatur should be limited to the supervised release portion of Singletary’s sentence, we disagree. Rogers drew no distinction between the defendant’s supervised release sentence and his custodial sentence; instead, it simply vacated his entire sentence and remanded for resentencing. See 961 F.3d at 300–01. Although the parties do not squarely present the issue here, this appears to be

10 arguments. Even assuming, in other words, that the appeal waiver was unenforceable

because it was not timely invoked, or that one or both of Singletary’s other claims fell

outside its scope – matters on which we express no view – there would be no reason for us

to determine here the adequacy of the explanation for special conditions of Singletary’s

now-vacated supervised-release sentence, or the validity of a financial condition never

imposed on Singletary.

3.

The government nevertheless urges us to decide now that the financial condition at

issue – requiring a probation officer to approve credit charges – is not an improper

delegation of sentencing authority. The premise for the government’s invitation appears

to be that our remand is a mere formality: We may assume that on remand, the district

court simply will “harmonize” its oral pronouncement with the written judgment, imposing

on Singletary the two financial conditions that it failed to announce at the first sentencing

hearing. Appellee’s Suppl. Br. 14. Because that premise misunderstands the fundamental

nature of a Rogers error, we address it briefly here.

As we explained in Rogers, the requirement that a district court orally pronounce all

non-mandatory conditions of supervised release is “not a meaningless formality,” but a

“critical ‘part of the defendant’s right to be present at sentencing.’”

(quoting United States v. Diggles,

(5th Cir. 2020) (en banc)). If a

the proper approach, given that “custodial and supervised release terms [are] components of one unified sentence.” United States v. Ketter,

(4th Cir. 2018).

11 condition is imposed in open court and in the defendant’s presence, then the defendant will

have the opportunity to object – an opportunity that is lost if a condition is imposed for the

first time in a subsequent written judgment. Id. at 298. And that opportunity is critical,

because it allows defendants to explain why particular discretionary conditions – which

may not be imposed unless “an individualized assessment indicates that they are justified

in light of the statutory factors” – are not sufficiently “tailored to their individual

circumstances.” Id. at 297, 300. The very point of Rogers, in other words, is that we may

not simply assume that whether a defendant is present for his sentencing will make no

difference to the sentencing court’s supervised-release decisions.

Indeed, this case bears out that rationale. The financial condition subject to

Singletary’s impermissible delegation challenge, requiring probation-officer approval for

all credit charges, is recommended by the Sentencing Guidelines only under specified

conditions: when an installment plan for the payment of restitution or a fine has been

imposed and the defendant is not in compliance with the payment schedule. See U.S.S.G.

§ 5D1.3(d)(2). But Singletary is not subject to any such installment plan. It is possible, of

course, that the district court on remand nevertheless will impose that condition, finding it

“tailored” to Singletary’s circumstances for some non-Guidelines reason. Rogers,

. But it is also possible that with Singletary in the courtroom and able to object, the

district court will determine that the condition is not appropriate in Singletary’s case.

In short, we must decline the government’s request to take up Singletary’s

impermissible delegation claim on this appeal. As of now, Singletary has not been

sentenced to the financial condition at issue, and there is no justification for assuming that

12 he will be on remand. Passing on the validity of that condition would come perilously

close to a forbidden advisory opinion. See United States v. Under Seal,

(4th Cir. 2017). It also would deprive the district court – were it inclined to impose the

condition on remand – of the first chance to decide the question, thereby overstepping our

role as “a court of review, not first view.” See Biggs v. N.C. Dep’t of Pub. Safety,

(4th Cir. 2020).

III.

For the reasons stated, we vacate Singletary’s sentence and remand for proceedings

consistent with this opinion.

VACATED AND REMANDED

13