In a significant ruling, the Seventh Circuit Court of Appeals has ordered a new sentencing for Deandre Cherry, who was previously convicted of heroin possession with intent to distribute. The court found that Cherry’s legal counsel had been ineffective during his trial and sentencing, particularly regarding enhancements that increased his prison term. This decision could have lasting implications for Cherry, who is currently serving a 20-year sentence.

The court's ruling, issued on November 5, 2026, comes after Cherry filed a post-conviction motion under 28 U.S.C. § 2255, claiming that his Sixth Amendment rights were violated due to ineffective assistance of counsel. The case highlights the importance of proper legal representation in criminal proceedings and the potential for a defendant's sentence to be significantly impacted by their attorney's actions.

Background

Deandre Cherry was arrested by federal agents from the Drug Enforcement Administration (DEA) following a sting operation. The operation was initiated after a confidential informant informed agents that Cherry was involved in drug trafficking. In 2019, a jury found Cherry guilty of possessing over 100 grams of heroin with the intent to distribute, leading to his sentencing in 2020.

Cherry's criminal history includes a 2003 conviction for manufacturing or delivering cocaine, which was used to enhance his sentence under 21 U.S.C. § 841(b)(1)(B). The district judge also applied a career-offender enhancement under the Sentencing Guidelines due to Cherry's extensive criminal background. This resulted in a 20-year prison sentence, which was 10 years above the statutory minimum.

After his conviction was affirmed on direct appeal, Cherry sought post-conviction relief, arguing that his trial counsel failed to challenge the sentencing enhancements that contributed to his lengthy sentence. The district court denied his motion, prompting Cherry to appeal to the Seventh Circuit.

The Ruling

The Seventh Circuit, led by Judge Sykes, ruled in favor of Cherry regarding the statutory sentencing enhancement under 21 U.S.C. § 841(b)(1)(B). The court agreed that Cherry's trial counsel should have objected to this enhancement, which increased both the advisory Guidelines range and the mandatory minimum terms of imprisonment and supervised release. The court stated, "Counsel’s failure to object to the § 841(b)(1)(B) statutory enhancement prejudiced Cherry because it increased both the advisory Guidelines range and the mandatory minimum terms of imprisonment and supervised release."

While the court acknowledged that the government conceded the ineffectiveness of Cherry's counsel regarding the statutory enhancement, it also noted that the remaining claims of ineffective assistance were without merit. The court affirmed that the admission of testimony from Special Agent David Brazao did not prejudice Cherry's defense.

Impact

This ruling has significant implications for Cherry, as it vacates his 20-year sentence and remands the case for resentencing. The court's decision underscores the critical role that effective legal representation plays in ensuring fair sentencing outcomes. It also highlights the importance of properly challenging sentencing enhancements that can drastically alter the length of a prison term.

The decision could set a precedent for similar cases where defendants claim ineffective assistance of counsel related to sentencing enhancements. It may encourage other defendants to seek post-conviction relief if they believe their legal representation failed to adequately challenge enhancements that could lead to longer sentences.

What's Next

Following this ruling, Cherry will be resentenced in the district court. The government may still argue for a substantial sentence based on his criminal history, but the absence of the § 841(b)(1)(B) enhancement could lead to a significantly reduced term. There are no indications that the case will be appealed further at this time, but Cherry's legal team may explore additional avenues for relief during the resentencing process.