UNITED STATES OF AMERICA v. CHRISTOPHER RAYQUAZ SINGLETARY
No. 21-4351
United States Court of Appeals, Fourth Circuit
August 1, 2023
UNITED STATES COURT OF APPEALS
FOR THE FOURTH CIRCUIT
No. 21-4351
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: December 8, 2022 Decided: August 1, 2023
Before HARRIS and RICHARDSON, Circuit Judges, and Patricia Tolliver GILES, United States District Judge for the Eastern District of Virginia, sitting by designation.
Affirmed by published opinion. Judge Harris wrote the opinion, in which Judge Richardson and Judge Giles 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. Michael F. Easley, Jr., United States Attorney, Joshua L. Rogers, Assistant United States Attorney, for OFFICE OF THE UNITED STATES ATTORNEY, Raleigh, North Carolina, for Appellee.
In 2019, Christopher Rayquaz Singletary received a 13-year sentence for Hobbs Act robbery and a related firearm offense. We then vacated Singletary’s sentence on procedural grounds and remanded for resentencing. United States v. Singletary, 984 F.3d 341 (4th Cir. 2021). At resentencing, the district court increased Singletary’s sentence by six months and ran that term consecutively to an intervening state sentence on unrelated charges. Singletary now argues that he was resentenced vindictively as punishment for successfully exercising his right to appeal. But the district court expressly based its increased sentence on objective information post-dating Singletary’s initial sentencing – namely, Singletary’s new state convictions and his lengthy disciplinary record while incarcerated. Because these developments suffice to rebut any presumption of vindictiveness, we affirm the district court’s judgment.
I.
A.
We first review the facts of Singletary’s initial sentence and appeal to the extent they bear on his claim of judicial vindictiveness at resentencing. On October 5, 2017, Singletary, then 21 years old, used a firearm to rob a restaurant in Raleigh, North Carolina. He was arrested soon after and pleaded guilty to Hobbs Act robbery,
As part of his plea agreement, Singletary waived his right to appeal “the conviction and whatever sentence is imposed on any ground,” save a few narrow exceptions not relevant here. J.A. 129. Nonetheless, Singletary appealed, arguing that the district court had included two discretionary conditions of supervised release in its judgment that it failed to pronounce at sentencing. See United States v. Rogers, 961 F.3d 291, 300 (4th Cir. 2020) (holding that the district court must orally pronounce all non-mandatory conditions of supervised release at sentencing). The government moved to dismiss Singletary’s appeal as within the scope of his appeal waiver.
A panel of this court held that Singletary’s pronouncement claim was not barred by his waiver. United States v. Singletary, 984 F.3d 341, 344 (4th Cir. 2021). Although Singletary had waived his right to appeal “whatever sentence is imposed,” the panel reasoned, the thrust of his pronouncement claim was “that he in fact never was sentenced to the [challenged] conditions in his judgment.” Id. Because this contention fell “outside the scope of his promise not to appeal the ‘sentence’ actually ‘imposed’ upon him,” the court proceeded to the merits of Singletary’s claim. Id. at 345. And on the merits, the panel agreed that the district court had failed to pronounce the challenged conditions.
B.
Singletary was resentenced on July 6, 2021. Before the hearing, the government filed a revised memorandum highlighting two developments post-dating Singletary’s initial sentencing. First, the government pointed to Singletary’s significant disciplinary record while incarcerated: Since his sentencing, Singletary had incurred at least 15 infractions, including “three instances of weapons possession, three instances of threatening to harm correctional officers, five instances of disobeying lawful orders, one instance of lock tampering, and one sexual act.” J.A. 108.
And second, the government noted that Singletary had since pleaded guilty to three North Carolina state charges arising from an unrelated armed robbery he committed in 2017.1 The state court sentenced Singletary to a total term of 126 to 173 months’ imprisonment – roughly 10.5 to 14.5 years – but it ran this term concurrently with Singletary’s since-vacated federal sentence. In the government’s view, this concurrent state sentence had “effectively subsume[d]” Singletary’s federal term and left him “unpunished for his federal offenses.” J.A. 170, 178. The government thus requested that the court run any new sentence consecutively to Singletary’s state term. See U.S.S.G.
At resentencing, the court expressed that it was “tremendously concerned” by these post-sentencing developments. J.A. 92. Citing Pepper v. United States, 562 U.S. 476 (2011), the court advised that it would conduct a de novo resentencing, “tak[ing] into account new information, including the new convictions and the multitude of extremely serious infractions.” J.A. 92. The court stated that it had “learned a lot about” Singletary since its initial sentencing, before recounting Singletary’s disciplinary record in detail. J.A. 107–08. It then turned to Singletary’s state convictions, observing that it “did not have the benefit” at its initial sentencing “of having that insight into who Christopher Singletary really is.” J.A. 109. And it concluded that this “conduct in the totality bespeaks a tremendous need for society to be protected from Christopher Singletary.” Id.
The court then imposed an aggregate federal term of 13.5 years’ imprisonment – a six-month increase from its initial 13-year sentence and the top of Singletary’s advisory Guidelines range. And it ordered that this sentence run consecutively to Singletary’s state term, “reject[ing] the argument that” a consecutive sentence “would be disrespectful to the [s]tate” court’s intent. J.A. 111; see id. (“I absolutely have the discretion to run this consecutively . . . and I will run it consecutively because society needs to be protected from Mr. Singletary for an extremely long time.”). Singletary then filed this timely appeal.
Singletary now argues that the district court increased his sentence vindictively as punishment for his initial appeal. In North Carolina v. Pearce, 395 U.S. 711, 725 (1969), overruled on other grounds by Alabama v. Smith, 490 U.S. 794 (1989), the Supreme Court recognized that “[d]ue process . . . requires that vindictiveness against a defendant for having successfully attacked his first conviction must play no part in the sentence he receives” on remand. Singletary contends that when the district court added six months to his federal sentence and ran that term consecutively to his 10.5- to 14.5-year state term, it “effectively increased his sentence on remand by at least eleven years.” And he claims that this “dramatic” increase gives rise to a presumption of vindictive motives, one the court’s stated rationales at resentencing fail to rebut. See Smith, 490 U.S. at 798–99.
We will address the merits of this argument in a moment. But we begin with a threshold dispute: Once again, the government contends that Singletary’s appeal must be dismissed based on the appeal waiver in his plea agreement.
A.
We review the scope of a defendant’s appeal waiver de novo. United States v. Blick, 408 F.3d 162, 168 (4th Cir. 2005). As discussed above, Singletary waived his right to
A panel of this court held that Singletary’s initial appeal – in which he argued that the district court’s judgment included certain supervised release conditions not pronounced at sentencing – fell “outside the scope of his promise not to appeal the ‘sentence’ actually ‘imposed’ upon him.” Singletary, 984 F.3d at 345. But here, where Singletary directly challenges the sentence he received, his claim appears to fall within the four corners of his waiver.
This observation does not end our inquiry, however. As we have emphasized, “a defendant who executes a general waiver of the right to appeal” does not “subject himself to being sentenced entirely at the whim of the district court.’” United States v. Attar, 38 F.3d 727, 732 (4th Cir. 1994) (quoting United States v. Marin, 961 F.2d 493, 496 (4th Cir. 1992)). Instead, we recognize a “narrow class of claims that we have allowed a defendant to raise on direct appeal despite a general waiver of appellate rights.” United States v. Lemaster, 403 F.3d 216, 220 n.2 (4th Cir. 2005); see United States v. Moran, 70 F.4th 797, 802 n.3 (4th Cir. 2023) (collecting cases).
Relevant here, we will “decline[] to enforce a valid appeal waiver . . . where the sentencing court violated a fundamental constitutional or statutory right that was firmly established at the time of sentencing,” United States v. Archie, 771 F.3d 217, 223 (4th Cir.
We conclude that an allegation of judicial vindictiveness fits squarely within this narrow class of claims. A defendant’s fundamental due process right to appeal his sentence without fear of retribution by the sentencing court has been firmly established for half a century. See Pearce, 395 U.S. at 725; cf. United States v. Lundien, 769 F.2d 981, 987 (4th Cir. 1985) (“[I]t is beyond doubt that a sentence enhanced . . . because of the vindictiveness or other plainly improper motive of the trial court would be fundamentally unfair and would deny the defendant due process.”). And much as a defendant cannot “fairly be said to have waived his right to appeal” a sentence based on his race or other protected characteristic, Attar, 38 F.3d at 732, we think a defendant’s execution of a general appeal waiver is “implicitly conditioned on the assumption” that he will be sentenced free from the trial court’s vindictiveness, id. To conclude otherwise would permit defendants who waive their appeal rights to be “sentenced entirely at the whim of the district court,” Marin, 961 F.2d at 496 – precisely the result our precedent rejects. We hold, then, that Singletary’s
B.
With that settled, we turn to the merits. To refresh, Singletary argues that the district court failed to justify the “dramatic” increase in his sentence after remand, leading to an unrebutted presumption of vindictive motives under North Carolina v. Pearce, 395 U.S. at 725. We begin with the legal framework governing his claim.4
When a defendant’s sentence has been vacated on appeal and remanded for resentencing, the district court may impose “a new sentence, whether greater or less than
There are two ways a defendant may establish judicial vindictiveness. First, he may “affirmatively prove actual vindictiveness” through direct evidence of animus. Wasman v. United States, 468 U.S. 559, 568–69 (1984). But Singletary does not attempt to directly prove such vindictive motives here; as the Supreme Court has recognized, “[t]he existence of a retaliatory motivation would, of course, be extremely difficult to prove in any individual case.” Pearce, 395 U.S. at 725 n.20.5
As the Supreme Court later clarified in Alabama v. Smith, the “presumption of vindictiveness does not apply in every case where a convicted defendant receives a higher sentence on retrial.” Smith, 490 U.S. at 799 (cleaned up). In certain categories of cases, the Court observed, the procedural posture makes it improbable that any sentencing authority would have vindictive motives for an increased sentence. Id. For example, when a defendant is resentenced by a different court, Colten v. Kentucky, 407 U.S. 104 (1972),
But when, as here, a defendant is resentenced by the same judge, in the same posture, following a successful appeal, Smith leaves no doubt that a presumption of vindictiveness applies to any unexplained increase in his sentence. See id. at 802. And in Singletary’s view, the district court failed to adequately justify its increased sentence, requiring us to conclude that this sentence was presumptively vindictive. We address this argument next.
C.
1.
To decide Singletary’s Pearce claim, we must answer two questions. “[W]e first ask whether the new sentence is actually harsher than that imposed prior to successful appeal.” United States v. Kincaid, 964 F.2d 325, 328 (4th Cir. 1992) (internal quotation marks omitted). If it is, we next ask whether the district court justified its increase by “affirmatively identifying relevant conduct or events that occurred subsequent to the original sentencing proceedings.” Wasman, 468 U.S. at 572.
We need not resolve this dispute, because however we describe the extent of Singletary’s sentence increase, the district court amply rebutted any presumption of vindictiveness by affirmative reference to objective, post-sentencing events. At the outset of resentencing, the court expressed that it was “tremendously concerned” by the new information it had learned since its initial sentencing. J.A. 92. It advised that it would “take into account new information, including the new convictions and the multitude of extremely serious infractions.” Id. It described Singletary’s intervening disciplinary record at length, concluding that Singletary’s remorse at his initial allocution was a “false apology,” and that his conduct in prison “showed us who he is.” J.A. 97. The court then discussed Singletary’s new state convictions, which it said provided further “insight” into Singletary’s character, before concluding that this “conduct in the totality bespeaks a tremendous need for society to be protected from Christopher Singletary.” J.A. 109. Then, faced for the first time with these state convictions, the court chose a consecutive sentence “because society needs to be protected from Mr. Singletary for an extremely long time.” J.A. 111. There is little doubt, then, that the “trial judge here carefully explained his reasons for imposing the greater sentence.” Wasman, 468 U.S. at 569.
Singletary offers two arguments why these detailed, affirmative reasons for the court’s increased sentence still fail to rebut a presumption of vindictiveness. Neither is persuasive. First, he observes that the armed robbery underlying his state convictions took place in 2017, almost two years before his original sentencing. And he notes that the district court was made aware of those pending charges when it first sentenced him. Because these convictions were thus based on known conduct occurring before his initial sentencing, Singletary argues that they cannot support a sentence increase.
But as the Supreme Court has held, a sentence increase may be justified by reference to “conduct or events that occurred subsequent to the original sentencing proceedings,” including new, post-sentencing convictions. Wasman, 468 U.S. at 572 (emphasis added). In Wasman, the trial court initially declined to consider an unrelated, pending criminal charge against the defendant at sentencing. But when the defendant was convicted of that charge before resentencing, the court cited that conviction as justification for its increased sentence. Id. at 569. And the Supreme Court held that “[c]onsideration of a criminal conviction obtained in the interim between an original sentencing and a sentencing after retrial is manifestly legitimate.” Id. at 569–70. The Court emphasized that there is “no logical support for a distinction between [intervening] ‘events’ and ‘conduct’ of the defendant,” as long as the new information is probative of the sentencer’s “nonvindictive motive.” Id. at 571–72.
Here, as in Wasman, the district court stated that it “did not take into account . . . pending charges” at its initial sentencing. J.A. 106. It then faced the “reality” of
Second, Singletary argues that the post-sentencing events on which the court relied simply cannot support the extent of the increase in his sentence. He contends that, though he has admittedly “performed poorly thus far” in prison, his intervening conduct does not warrant an eleven-year increase in his total period of incarceration. But whatever the merits of this claim, it is beside the point here. This argument, rather than addressing the vindictiveness of the district court, goes to the overall reasonableness of Singletary’s sentence. Singletary seems to posit that in order to rebut Pearce’s presumption, the court’s stated reasons for its increase must be roughly proportional to the size of the increase. But even when reviewing a sentence for substantive reasonableness – a claim Singletary concedes is barred by his appeal waiver – we afford far more deference to the judgment of the district court. See United States v. Spencer, 848 F.3d 324, 327 (4th Cir. 2017) (describing the “deferential abuse-of-discretion standard” applicable to substantive reasonableness claims).
As the government forthrightly acknowledged at oral argument, it is possible – though unlikely – that a case could arise in which a district court’s stated reasons for an increased sentence are so facially implausible, pretextual, or disproportionate that they cannot rebut the presumption of vindictiveness. But that is not this case. Here, the district court extensively justified its higher sentence by reference to material, legitimately aggravating “conduct [and] events that occurred subsequent to the original sentencing.” Wasman, 468 U.S. at 572. Under Pearce and its progeny, no more is required.
* * *
As Singletary’s able counsel reminded us at oral argument, Singletary is unlikely to appreciate these fine distinctions: From his perspective, before his appeal, he faced 13 years in prison for both his state and federal offenses; after vindicating his claim on appeal,
And we do not minimize the impact of these developments on Singletary. But the district court provided a careful explanation of its decision to increase Singletary’s sentence and run it consecutively to a newly imposed sentence. And it grounded this decision in objective developments post-dating Singletary’s initial sentencing. That suffices to dispel any presumption of vindictiveness that otherwise would arise. Accordingly, Singletary’s increased sentence presents no constitutional issue, and we affirm.8
III.
For the reasons given above, the judgment of the district court is affirmed.
AFFIRMED
