Guilty Pleas Are Solid and Eternal – Update for February 10, 2026

We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

DIAMONDS AREN’T FOREVER – BUT PLEA AGREEMENTS ARE

When I was a kid, I learned in grade school that diamonds are formed by immense pressure over immense time, and that humanity would never be able to make diamonds because we couldn’t begin to duplicate nature’s processes.

It turns out that Mrs. McGinnis – my 6^th grade teacher – was wrong. The diamond business is being upended because factories can now crank out the glistening lab-grown stones, making diamonds’ rarity commonplace and prices plummet.

So James Bond was wrong, too.  Diamonds are not forever.

Last week, however, two Circuits reminded us that plea deals and guilty pleas last longer and are more solid than any chunk of compressed carbon shining on your beloved’s finger.

Waivers Are Forever – Brandi Appleton pled guilty to drug distribution and a felon-in-possession charge. Her plea agreement included the usual waiver of her right to appeal the sentence. Although the Guidelines recommended 41 to 51 months given Brandi’s offense level and criminal history, the district court sentenced her to five years of probation due to her difficult childhood, drug addiction, and the fact that she would probably lose her parental rights if she was locked up. The court was impressed by Brandi having completed a residential drug treatment program and her employment history while on pretrial release.

But Brandi’s good fortune didn’t last. Six weeks into the probation, she was arrested for possession of personal use drugs. The court revoked her probation and gave her 44 months.

Brandi appealed the sentence, but last week, the 6^th Circuit threw out the appeal because of her plea agreement waiver.

Brandi argued that the waiver no longer counted because the imprisonment was imposed only after a probation-revocation hearing. The 6^th, however, ruled that “revocation sentences are part and parcel of the sentence underlying the original conviction, not a freestanding, unrelated sentence.” Brandi’s initial probation depended on compliance with the terms of supervision, so that her “subsequent term of imprisonment following the revocation of probation was a sentence for the same underlying offense addressed in [the] initial sentence. It follows that Appleton’s appeal waiver applies to the sentence imposed at her probation revocation hearing.”

Unlike diamonds, plea waivers are forever.

Answers Are Forever – Steve Boria took medications for sleeping problems and bipolar disorder the night before he pled guilty to a drug conspiracy and gun charge. During the plea hearing, the district court learned that Steve had taken these medications and asked several follow-up questions to confirm that he understood the proceedings and felt “clearheaded.” Steve decided to challenge his conviction and sentence on appeal despite an appeal waiver in his plea agreement, arguing that the district court violated F.R.Crim.P. 11 and his constitutional rights because it did not ask enough about the impact of his medications.

Last week, the 2^nd Circuit disagreed. The judge asked what he had taken, when he had taken it, and whether he understood what was going on in court. Steve said he did. The Court said Steve’s “conduct during the plea hearing raised no red flags,” so the district court fulfilled its Rule 11 obligation to “explore on the record defendant’s ability to understand the nature and consequences of his decision to plead guilty” by confirming that Steve understood the proceedings and felt clearheaded.

Steve’s clear answers to the Judge’s clear questions were binding.

Steve’s additional problem was that his lawyer did not object at the time that the Court had not asked enough, so Steve had to show “plain error,” that is, an obvious mistake that raised a reasonable probability that Steve would not have pled guilty but for the alleged error. This is a great example of the reason for F.R.Crim.P. 52(b) “plain error.” If Steve’s lawyer had objected at the time, the judge probably would have postponed the plea hearing, thus solving the medication problem.

United States v. Appleton, Case No. 25-5051, 2026 U.S.App. LEXIS 3687 (6th Cir., February 5, 2026)

United States v. Boria, Case No. 24-1871, 2026 U.S.App. LEXIS 3472 (2d Cir. February 4, 2026)

~ Thomas L. Root