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Slip opinion No. 23-3198

USA v Terry Ferguson, 23-3198

U.S. Court of Appeals, Seventh Circuit Criminal Federal Sentencing

Filed
Friday, August 7, 2026
Docket
23-3198
Status
Published opinion

Holdings

  • Seventh Circuit holds no actual attorney conflict existed years after a stale, unconfirmed investigation into defense counsel's conduct
  • Court reaffirms that § 2255 conflict-of-interest claims require proof of adverse effect on performance, not mere speculation about alternative strategies
  • Useful for federal criminal defense attorneys handling § 2255 ineffective assistance claims and appellate waiver enforcement issues

Summary

Terry Ferguson pleaded guilty to drug conspiracy and felon-in-possession charges under a written plea agreement containing an appellate waiver. Before and after his plea, he unsuccessfully moved to dismiss the indictment for vindictive or selective prosecution. He later filed a § 2255 motion arguing his attorney, Beau Brindley, labored under an actual conflict of interest—stemming from a years-earlier solicitation of cooperation related to a possible investigation into Brindley himself—which compromised Ferguson's representation. The district court denied both the dismissal motions and the § 2255 motion, and Ferguson brought consolidated appeals.

The Seventh Circuit affirmed denial of the § 2255 motion, holding that no actual conflict existed in 2023 when Ferguson pleaded guilty and was sentenced, because there was no evidence of an ongoing investigation into Brindley five years after the original 2018 solicitation, and Brindley himself did not believe a genuine investigation was occurring. Even assuming a conflict existed, the court held Ferguson failed to show it adversely affected Brindley's performance, rejecting as speculative his theories that a conflict-free attorney might have pursued cooperation or that Brindley should have raised the conflict earlier. Separately, the court dismissed Ferguson's appeal of the denial of his dismissal motions, finding the plea agreement's appellate waiver knowing, voluntary, and clearly applicable, and noting Ferguson forfeited any challenge to the waiver's enforceability by failing to address it in his briefs.

The decision offers practical guidance on the demanding standard for conflict-based ineffective assistance claims under § 2255 and reinforces strict enforcement of appellate waivers absent a developed challenge to their validity.

In short

No actual conflict of interest existed between Ferguson and his attorney at the time of the guilty plea and sentencing, given the lack of evidence of any ongoing investigation into counsel.

Even assuming a conflict existed, a § 2255 petitioner must show the conflict had an adverse effect on counsel's performance; speculative theories about alternative strategies are insufficient.

The government can waive an appellate waiver defense by failing to raise it until oral argument, under the party-presentation principle.

A knowing and voluntary appellate waiver in a plea agreement bars appeal of pretrial rulings (e.g., denial of motions to dismiss for vindictive/selective prosecution) that do not challenge the guilty plea or sentence itself, and failure to contest the waiver's enforceability in briefing forfeits that argument.

This summary was drafted by AI and verified against the slip opinion. It may contain errors and is not legal advice — always read the original before relying on it.