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YOU GOTTA SAY WHAT YOU MEAN TO BEAT § 2255 PREJUDICE ASSUMPTION
The appellate courts have given judges an easy out to avoid the need to resentence where a Guidelines or statutory sentencing error – or even a mistake by defense counsel – is concerned. All the judge has to do is say on the record that he or she would impose the same sentence when considering the 18 USC § 3553 statutory sentencgin factors even if the Guidelines calculations are wrong.
In other words, ‘I’m right even when I’m wrong.’
It’s such an easy dodge that I am always a bit surprised when the sentencing court doesn’t make this preventive statement. It’s sort of like putting a Band-Aid on before you cut yourself.
The 7th Circuit last week found that DeAndre Cherry’s defense attorney erred by not raising an error in finding the drug defendant eligible for a higher mandatory minimum sentence due to a prior drug case that should not have been counted as a controlled substance offense.
In most cases, a defendant who establishes that the district judge mistakenly started from an incorrect, higher Guidelines range has demonstrated a reasonable probability of a different outcome. And where the error has the judge starting from higher minimum and maximum statutory penalties, counsel’s failure to object is clearly prejudicial. Statutory minima and maxima have an obvious anchoring effect on the judge’s determination of a reasonable sentence because they demarcate the range within which the judge may impose a sentence.
But here, the government argued that DeAndre’s sentence was within his Guidelines range even with the decrease in his statutory minimum sentence, so there was no harm In the government’s view, 18 USC § 3553(a) sentencing factors — particularly DeAndre’s lengthy criminal record — drove the judge’s decision to impose 240-month sentence.
The 7th disagreed. “When the judge expressly states that he ‘would have imposed the same sentence” regardless of any potential error in the Guidelines calculation,” the Circuit wrote, “there is no reason to vacate the defendant’s sentence and remand for resentencing. Here, however, it’s not clear that the judge would have imposed the same 20-year sentence had he known the correct sentencing ranges. He certainly didn’t say as much. It’s true, as the government argues, that the judge emphasized Cherry’s criminal history… But [a] vague reference to Cherry’s criminal record does not confirm that the judge thought the 20-year sentence was appropriate ‘irrespective of’ the § 841(b)(1)(B) enhancement. On this record, the judge’s sentencing remarks are not enough to overcome the ordinary presumption of prejudice.”
Besides, the 7th said, “trial counsel’s failure to object to the… enhancement prejudiced Cherry in at least one way—namely, in the imposition of an 8-year term of supervised release. This concession is appropriate. The record gives us no clue as to what the judge might have done had he known that Cherry was subject to a 4-year minimum rather than an 8-year minimum term of supervised release.”
Cherry v. United States, Case No. 21-2231, 2026 U.S.App. LEXIS 34037 (7th Cir. November 5, 2026)
~ Thomas L. Root