Background
Antwon Tolefree pleaded guilty to conspiring to distribute less than 50 kilograms of marijuana, money laundering, and being a drug user in possession of a firearm. Largely because of his substantial assistance in prosecuting others, the district court sentenced him to five years of probation.
While Tolefree was serving probation, the probation office alleged that he violated its conditions, including by selling fentanyl. After finding that he committed the alleged violations, the district court revoked probation and sentenced him to 78 months in prison. Tolefree appealed, arguing that the prison sentence was substantively unreasonable, and the government moved to dismiss based on the appeal waiver in his plea agreement.
The Court’s Holding
The Eighth Circuit granted the government’s motion and dismissed the appeal. The court held that Tolefree’s waiver of his right to appeal “his sentence” encompassed the sentence imposed after revocation of probation. The agreement permitted an appeal from an illegal sentence but expressly excluded an unreasonable sentence from that exception, so Tolefree’s substantive-reasonableness challenge fell within the waiver.
The court explained that revoking probation under 18 U.S.C. § 3565(a)(2) requires the court to resentence the defendant for the underlying offenses. That resentencing is part of the sentence arising from the original conviction and remains subject to the negotiated appeal waiver. The court distinguished supervised-release revocation, which produces a separate sentence serving forward-looking purposes and does not constitute a resentencing for the original crimes.
Key Takeaways
- A broadly worded waiver of the right to appeal “his sentence” applies to a sentence imposed after probation is revoked, even if the agreement does not expressly mention probation revocation.
- Probation revocation results in resentencing for the underlying offenses under 18 U.S.C. § 3565(a), unlike supervised-release revocation.
- An exception permitting challenges to an illegal sentence did not preserve Tolefree’s claim because the plea agreement expressly stated that an unreasonable sentence was not an illegal sentence.
Why It Matters
The decision confirms that, in the Eighth Circuit, an appellate waiver generally continues to bind a defendant when probation is revoked and the defendant is resentenced for the original offenses. Defendants cannot avoid such a waiver merely because the challenged punishment was imposed at a later probation-revocation proceeding.
The opinion also draws a consequential distinction between probation and supervised release: probation revocation triggers a do-over of the original sentencing, while supervised-release revocation produces a separate sentence directed at deterrence, incapacitation, and rehabilitation.