In this case, the defendant plead guilty. After expressing misgivings about the plea, making claims that he didn’t understand it, and expressing dissatisfaction with his attorney, the District Court granted the defendant’s motion to withdraw his plea and counsel’s motion to withdraw.
With new counsel, the District Court then reversed its ruling on both of these motions (although the new attorney stayed on the case and the first attorney never appeared again). The District Court then sentenced the defendant.
The Seventh Circuit held that this reversal by the District Court led to a plea that was not knowing or voluntary. The appellate court also allowed the defendant to appeal despite the existence of an appellate waiver in the plea agreement.
The case is United States v. Ricky Olson.