Scope of the Fifth Amendment Privilege in Post-Conviction Sentencing: Abuse of Discretion Standard in United States v. Oliver

Introduction

United States v. Winston Sylvester Oliver, II, 23-4544 (4th Cir. Apr. 8, 2025) confronts two interrelated issues that bear on federal criminal procedure: (1) the circumstances under which a third‐party witness—here, a co-defendant whose own sentencing appeal is pending—may invoke the Fifth Amendment privilege against self-incrimination during another defendant’s resentencing hearing; and (2) the procedural and substantive reasonableness of the upward‐variance sentence imposed after multiple resentencings. The Fourth Circuit, sitting en banc, affirmed both the district court’s handling of the privilege question—reviewed for abuse of discretion—and the ultimate 480-month sentence.

Parties:

Plaintiff–Appellee: United States of America
Defendant–Appellant: Winston Sylvester Oliver, II
Co-Defendant (third-party witness): Warren Brown

Court below: U.S. District Court for the Eastern District of Virginia (Judge Henry E. Hudson). Appellate panel: Judges Agee (opinion), Wilkinson, and Floyd.

Summary of the Judgment

In 2011, Oliver and Brown were convicted of Hobbs Act conspiracy and attempt (18 U.S.C. § 1951) and related § 924(c) firearm offenses. Following intervening law, two § 924(c) convictions were vacated and Oliver was resentenced. On the second resentencing, Brown—whose own resentencing appeal remained pending—was called by Oliver to authenticate letters recanting aspects of trial testimony. The district court, without abuse of discretion, allowed Brown to invoke his Fifth Amendment privilege when questions risked enhancing his own sentence on remand. Separately, the court applied enhancements for leadership/organizer role (§ 3B1.1), obstruction of justice (§ 3C1.1), and firearm discharge (§ 2B3.1), and imposed sentences on the remaining counts to run consecutively for a total of 480 months. On appeal, the Fourth Circuit—applying an abuse-of-discretion standard to the privilege issue and a deferential “reasonableness” review to sentencing—affirmed in all respects.

Analysis

1. Precedents Cited

Mitchell v. United States, 526 U.S. 314 (1999): Established that “where there can be no further incrimination, there is no basis for the assertion of the privilege.”
United States v. Branch, 537 F.3d 328 (4th Cir. 2008): Held that exclusion of a witness’s testimony under the Fifth Amendment is an evidentiary ruling reviewed for abuse of discretion.
United States v. Lara, 850 F.3d 686 (4th Cir. 2017): Confirmed de novo review when the defendant himself claims compulsion, but distinguished here because Brown was a witness.
United States v. Gaskins, 916 F.2d 941 (4th Cir. 1990): Requires a “proper and particularized inquiry” into a witness’s invocation of the privilege.
United States v. Slade, 631 F.3d 185 (4th Cir. 2011) & United States v. Steffen, 741 F.3d 411 (4th Cir. 2013): Address application of the § 3B1.1 leadership enhancement.
United States v. Dunnigan, 507 U.S. 87 (1993): Defines willful perjury threshold for § 3C1.1 obstruction enhancement.
Gall v. United States, 552 U.S. 38 (2007): Established the two‐step sentencing‐reasonableness framework.

2. Legal Reasoning

Privilege Allowance & Standard of Review
The Fourth Circuit held that when a third‐party witness invokes the Fifth Amendment during another defendant’s sentencing, the district court’s determination rests on an abuse-of-discretion standard (Branch), not de novo (Lara). It must:

Conduct a particularized inquiry into whether the witness faces “potential adverse consequences” from further testimony (Mitchell, Gaskins).
Balance the defendant’s compulsory‐process right against the witness’s self-incrimination privilege, giving priority to the privilege (Abbas, Lighty).

Here, Brown’s pending sentencing appeal carried possible enhancements if his testimony:

Reopened weapon‐discharge questions (§ 2B3.1)—seven‐level increase;
Led to a leadership enhancement (§ 3B1.1) or obstruction enhancement (§ 3C1.1) on remand;
Impacted the district court’s 18 U.S.C. § 3553(a) calculus on resentencing.

The court found these risks sufficient to let Brown invoke the privilege. Even though Oliver requested Brown be called, the district court thoughtfully offered a question-by-question approach before concluding a blanket invocation was appropriate. On such a record, the ruling was not an abuse of discretion.

Sentencing Enhancements & Reasonableness
Under Gall’s two-step framework, the Fourth Circuit reviewed procedure de novo and facts for clear error, then assessed the substantive reasonableness of the 480-month sentence. The court found no procedural error:

§ 3B1.1 Leader/Organizer: Oliver planned, recruited Brown, supplied the gun, and directed tactics—clear evidence of “management or supervision” over at least one co-conspirator (Steffen v. Slade distinction).
§ 3C1.1 Obstruction: Oliver procured and drafted false affidavits to suborn perjury; willful obstruction was established under Dunnigan’s standard and Andrews.
§ 2B3.1 Firearm Discharge: The robbery involved a shooting, and Brown’s custodial statement that Oliver provided the weapon supported the seven-level increase.
Consecutive Sentences: Consistent with Iannelli v. United States, conspiracy and completed‐offense counts may carry separate, consecutive sentences when each offense is proven and punished.

Substantively, the court gave “due deference” to the district court’s weighing of:

Defendant’s extensive criminal history (27 prior convictions; serious violence);
Aggravating facts (multiple gunshot wounds to an innocent customer; permanent injuries; psychological harm to employees);
Mitigation (good prison behavior; mental‐health diagnoses; difficult upbringing).

The modest upward variance (480 months vs. 292–365 Guidelines) was well within discretion to secure respect for the law, deterrence, and protection of the public.

3. Impact on Future Cases

This decision clarifies and cements the following principles:

When a third-party witness’s own sentence is under appeal or remand, district courts may permit a blanket invocation of the Fifth Amendment where questioning poses a “real risk” of adverse enhancement—subject to an abuse-of-discretion review.
Defendants must offer more than theoretical or speculative prejudice to insist on calling such witnesses; the district court’s careful inquiry and balancing will seldom be second-guessed.
Sentencing courts retain broad discretion to apply leadership, obstruction, and firearm enhancements and to order consecutive terms—Gall’s framework remains alive and robust in the Fourth Circuit.

Complex Concepts Simplified

Fifth Amendment Privilege: Protects any person—defendant or witness—from being forced to testify if their answers could lead to more charges or a greater sentence.
Abuse of Discretion: A deferential standard: an appellate court will overturn only if the lower court made a clear error of judgment or applied the wrong legal standard.
Leadership Enhancement (§ 3B1.1): Adds points when a defendant organized, supervised, or managed at least one accomplice in the crime.
Obstruction Enhancement (§ 3C1.1): Applies when a defendant willfully lies, influences or threatens another to lie, or otherwise impedes the judicial process.
Variance vs. Departure: A Guidelines departure modifies the Guidelines range based on legal provisions, while a variance arises from the sentencing court’s broader consideration of the Section 3553(a) factors.

Conclusion

United States v. Oliver reaffirms district courts’ wide latitude in balancing a witness’s Fifth Amendment rights against a criminal defendant’s compulsory-process interest in calling that witness to testify at sentencing. By upholding an abuse-of-discretion standard and emphasizing a fact-specific inquiry, the Fourth Circuit ensures predictable, disciplined analysis of such privilege questions. Moreover, the court’s thorough application of sentencing enhancements and its deference to the district court’s evaluation of Section 3553(a) factors confirm that substantial upward variances remain appropriate in cases of violent recidivism. Oliver’s 480-month sentence thus stands as a robust affirmation of judicial discretion in both evidentiary and sentencing domains.