How a Wrong Drug Minimum Shows § 2255 Prejudice

A prison term below the advisory range can still show prejudice under Strickland v. Washington when counsel never objected to a higher statutory drug penalty. On November 5, 2026, the Seventh Circuit applied that rule in Cherry v. United States, No. 21-2231 (Read the decision (PDF)). It vacated DeAndre Cherry's sentence and sent the case back for resentencing. It left the conviction in place and rejected two other ineffective-assistance claims.

What the court decided

A jury convicted Cherry of possessing 100 grams or more of heroin with intent to distribute. 21 U.S.C. § 841(a)(1). The court of appeals had affirmed that conviction on direct appeal. United States v. Cherry, 920 F.3d 1126 (7th Cir. 2019). This case was his later motion under 28 U.S.C. § 2255, No. 20 CV 4752, in the Northern District of Illinois.

Two parts of the presentence report matter. Counsel did not contest either one on legal grounds.

The report used the 2016 text of § 841(b)(1)(B). That text set a prison term of not less than 10 years, and supervised release of at least 8 years, for a person with "a prior conviction for a felony drug offense." Without that prior conviction, the same paragraph set a minimum of 5 years in prison and at least 4 years of supervised release. The government had filed an information under 21 U.S.C. § 851 naming a 2003 Illinois conviction for manufacturing or delivering cocaine.

The report also applied the career-offender guideline, U.S.S.G. § 4B1.1, from the 2015 Guidelines manual. With that enhancement, the advisory range was 30 years to life. The judge imposed 20 years in prison and, as the 2016 statutory text required, 8 years of supervised release.

After the direct appeal failed, Cherry filed a pro se § 2255 motion. The claims that reached this opinion were that trial counsel should have objected to both enhancements, and that trial and appellate counsel should have challenged an agent's testimony about a confidential informant. The district court denied relief. The court of appeals issued a certificate of appealability and later expanded it.

On the statutory enhancement, the government conceded that trial counsel's performance was deficient under Coleman v. United States, 79 F.4th 822 (7th Cir. 2023). The panel accepted the concession. It also said later cases read Coleman narrowly. Neal v. United States, 155 F.4th 678, 686–88 (7th Cir. 2025), rejected the claim that a lawyer who fails to consider a categorical challenge to a § 841 enhancement "necessarily" renders ineffective assistance. Elion v. United States, 155 F.4th 889, 905–06 (7th Cir. 2025), then stated the test: counsel is deficient only if the argument was so clearly foreshadowed that no reasonable attorney would fail to make it. Coleman, the panel said, "sits at the outer boundary" of that test. The government did not ask the panel to revisit the concession under Neal and Elion. The panel therefore assumed deficient performance. It did not hold that every missed categorical challenge is deficient performance.

Prejudice means a reasonable probability of a different result. Strickland, 466 U.S. 668, 694 (1984). For a sentencing error, that is a reasonable probability the judge would have imposed a lower sentence. Day v. United States, 962 F.3d 987, 992 (7th Cir. 2020).

The panel found that probability. It gave three reasons that work together.

The 2016 recidivist text raised the statutory range from 5 to 40 years up to 10 years to life, and it doubled the supervised-release floor from 4 years to 8. Statutory minimums and maximums "demarcate the range within which the judge may impose a sentence." United States v. Currie, 739 F.3d 960, 966 (7th Cir. 2014).

That statutory maximum also feeds the career-offender table. Under § 4B1.1(b) in the manual the report used, a maximum of life produced offense level 37 and a range of 360 months to life. A 40-year maximum would have produced offense level 34 and, on these facts, a range of 262 to 327 months. In Molina-Martinez v. United States, 578 U.S. 189, 200 (2016), the Supreme Court explained that the Guidelines are the starting point and the lodestar, and that a judge who starts from an incorrect, higher range has shown a reasonable probability of a different outcome in most cases. The Seventh Circuit treats an error that changes the Guidelines range as presumptively prejudicial absent unusual circumstances. Coleman, 79 F.4th at 832.

The 20-year prison term was 10 years below the 30-years-to-life range the judge used. Twenty years is 240 months, which is also below the 262-month bottom of the offense-level-34 range the panel described. The government argued that the term therefore had little to do with the ranges, and that the judge relied on the sentencing factors in 18 U.S.C. § 3553(a) and on Cherry's record. The panel disagreed. A judge's explanation rebuts the presumption only when the judge makes clear that the sentence rests on factors independent of the Guidelines, or that the same sentence would have been imposed anyway. Molina-Martinez, 578 U.S. at 200. This judge said that even leaving career-offender considerations aside, the criminal history was concerning. He did not say the 20-year term was appropriate irrespective of the § 841(b)(1)(B) enhancement.

The government also conceded prejudice in one concrete way: the 8-year term of supervised release. The record did not show what the judge would have done with a 4-year floor. The panel treated the prison term and the supervised-release term as one sentencing package. United States v. Wilcher, 91 F.4th 864, 875 (7th Cir. 2024).

The panel stated the limit of that holding in plain terms. The judge may impose the same sentence again. The government may argue that the criminal history supports it. What Cherry showed is a reasonable probability of a lower sentence. That is the Strickland test. It is not a forecast of the next hearing.

The court tied the Illinois conviction to United States v. Ruth, 966 F.3d 642 (7th Cir. 2020). Ruth held that Illinois's definition of cocaine is categorically broader than the federal definition: state law includes isomers that the federal schedule does not. A cocaine conviction under section 401 of the Illinois Controlled Substances Act is therefore not a "felony drug offense" for a § 841(b)(1) enhancement. Ruth, 966 F.3d at 647, 650. Ruth was decided almost three years after Cherry was sentenced. The panel did not decide, as an original matter, that counsel had to predict Ruth. It accepted the government's concession that, under Coleman, failing to consider the categorical argument was deficient on these facts.

A footnote in the opinion flags today's statutory words. The current text of § 841(b)(1)(B) applies to a prior "serious drug felony" or "serious violent felony." The panel applied the 2016 phrase, "felony drug offense," because that was the text in the presentence report.

Why the other two claims failed

The career-offender claim failed for lack of prejudice, and Ruth was the reason. The same case that kept the Illinois cocaine conviction from counting as a federal "felony drug offense" held that the conviction still counts as a Guidelines "controlled substance offense." Section 4B1.2 does not copy the Controlled Substances Act's drug list for that phrase. Ruth, 966 F.3d at 651–52, 654. United States v. Hudson, 618 F.3d 700, 703 (7th Cir. 2010), was already decided at the time of sentencing and pointed the same way. An objection then was unlikely to remove the enhancement.

Cherry's 1993 sentences for attempted murder and armed robbery were imposed the same day, so they count as one prior conviction. U.S.S.G. §§ 4B1.2(c), 4A1.2(a)(2). He argued that neither the 2003 cocaine conviction nor a 2003 machine-gun conviction was a second qualifying prior. Once Ruth counted the cocaine conviction under the Guidelines, that argument did not show a reasonable probability of a different career-offender finding. A hope that the Supreme Court would later adopt another circuit's reading was not prejudice either. The Court denied review of that Guidelines question in Guerrant v. United States, 142 S. Ct. 640 (2022).

The claim about the agent's redirect testimony failed on prejudice as well. The panel assumed, without deciding, that counsel could have raised the Confrontation Clause and Federal Rule of Evidence 403. Cherry still had to show a reasonable probability of an acquittal if that testimony had been excluded. The judge told the jury to use the informant's statements only to explain what the agents did. The panel presumed the jury followed that instruction. United States v. Garcia, 81 F.4th 691, 698 (7th Cir. 2023). Other evidence included the drugs recovered from the vehicle and Cherry's own post-arrest account. The panel affirmed the judgment in part, reversed it in part, and vacated the sentence.

What it means for a § 2255 motion

• Separate the statute from the guideline. In the Seventh Circuit, Ruth says a state cocaine conviction can fail as a "felony drug offense" under the § 841 text the court applied and still count as a Guidelines controlled-substance offense. Another circuit may answer that question differently.

• Read the range the judge actually used. Here the 2016 statutory text changed both the minimums and the career-offender offense level, because § 4B1.1 looks at the statutory maximum. A sentence below the advisory range did not end the prejudice question. The judge did not say he would have imposed the same term without the enhancement. Sentencing examples on this site collect other lawyer-error cases at that stage.

• Count supervised release in the same package. The conceded error on the 8-year supervised-release floor kept the prison term in the remand. The panel did not split the two.

• Do not treat Coleman as an automatic rule. This panel assumed deficient performance because the government conceded it. Neal and Elion describe a narrower test. Whether counsel had to raise a categorical argument depends on the law at sentencing and on the choices then open.

• Check which statutory words apply. This opinion used "felony drug offense" from the 2016 text. A case sentenced under the current "serious drug felony" or "serious violent felony" wording asks a different predicate question. 21 U.S.C. § 841(b).

Pull the presentence report, the § 851 information, and the sentencing transcript. Note whether the judge said the sentence would have been the same under a different range. Request a consultation and tell us what happened.