United States v. Christopher Singletary ( 2021 )

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.
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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, 961 F.3d 291 (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 18 U.S.C. § 1951 and one count of using a firearm during and in relation to a
crime of violence in violation of 18 U.S.C. § 924(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 18 U.S.C. § 3742,
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 28 U.S.C. § 2255,
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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, 961 F.3d 291, 300 (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, 18 U.S.C. § 3583(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. 961 F.3d at 297. 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. Id. (internal quotation marks omitted); see U.S.S.G. § 5D1.3(c)–(e).
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“[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, 386 U.S. 738 (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, 914 F.3d 893, 897 n.3 (4th Cir. 2019) (internal
quotation marks omitted).
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supervised release, and why those conditions were appropriate in his individual case. See,
e.g., United States v. McMiller, 954 F.3d 670, 676 (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, 784 F.
App’x 141, 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
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United States v. Nash, 438 F.3d 1302, 1306 (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.
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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.
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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. 961 F.3d at 295.
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, 817 F.
App’x 234, 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 961 F.3d at 296 (“[A]ll non-mandatory conditions of supervised release must be
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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 id. at 299, 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.
961 F.3d at 300.
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 id. at 300–01; see also United States v. Sings, 816 F. App’x
850, 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
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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.’” 961 F.3d at 300
(quoting United States v. Diggles, 957 F.3d 551, 560 (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, 908 F.3d 61, 65 (4th Cir. 2018).
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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, 961 F.3d
at 300. 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
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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, 853 F.3d 706, 722
(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, 953 F.3d
236, 243 (4th Cir. 2020).
III.
For the reasons stated, we vacate Singletary’s sentence and remand for proceedings
consistent with this opinion.
VACATED AND REMANDED
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