Failure to Anticipate Is Not Ineffective Assistance – Update for September 12, 2025

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

Should Have Seen That Coming

Tyree Neal pled guilty to conspiracy to distribute cocaine in violation of 21 USC §§ 841(a)(1), (b)(1)(C), and 846. At his sentencing, the district court found that Ty’s prior Illinois cocaine conviction supported a recidivism enhancement under § 841(b)(1)(C) that raised his maximum sentence from 20 years to 30 years. The district court hammered him with 30 years.

Two years after Tyree lost his appeal, the 7^th Circuit held in United States v. Ruth that under the “categorical approach,” because Illinois’s definition of cocaine is broader than the federal definition, an Illinois conviction for cocaine delivery could not support a recidivism enhancement under 21 USC § 841(b)(1)(C). This meant that if Ty were sentenced today, his maximum sentence would be 20 years.

Ty filed a 28 USC § 2255 habeas corpus motion arguing that his appellate, sentencing, and plea attorneys were all constitutionally deficient because they failed to anticipate the argument that ultimately won in Ruth. Ty claimed they should have seen it coming and raised it in his case.

The district court denied his § 2255 motion. Last week, the 7^th Circuit agreed.

The Circuit said the proper inquiry is “an objective assessment of counsel’s performance considering the options available to the defense.” Considering his appellate attorney, the 7^th agreed that “looking back, it is fair to say the Ruth argument was stronger than those appellate counsel made (if that is not already apparent from the outcome of Ruth compared to Neal’s direct appeal). But we cannot conclude the Ruth argument was “clearly stronger” at the time of Neal’s appeal.

“A significant obstacle to comparison is that the arguments aimed at different goals. As an appellate lawyer must, counsel curtailed the number of issues by focusing on Neal’s conviction. If her arguments prevailed, Neal would have had a second opportunity for trial and acquittal. A successful Ruth challenge would have left Neal with a 20-year sentence. Those different ends do not affect the likelihood of success for their different means, but they would influence an attorney’s professional judgment about the “strongest” issues for appeal. Although we can imagine situations where an argument against a defendant’s sentence is strong enough that it must be raised even if in the alternative, appellate attorneys are not always required to pick issues with a higher likelihood of success but a lower reward.”

“Holding that appellate counsel provided ineffective assistance would thus encourage a kitchen-sink approach to advocacy,” the Circuit said, “the implicit logic being that she should have made the Ruth argument in addition to the issues she raised, not instead. Would an attorney still think we would find the Ruth argument persuasive if she knew it shared a limited page-count with Neal’s plea arguments? “As for sentencing counsel, the 7^th said, he did what Ty asked him to, attackng the enhancements for use of violence, obstruction of justice, and reckless endangerment. After Neal provided “the names of a number of witnesses that he wanted counsel to interview,” counsel retained an investigator to interview those witnesses, subsequently spoke with several, and subpoenaed them to appear at Ty’s sentencing. Counsel also negotiated a plea deal that, if the court had followed it, would have given Ty the same 20-year sentence that a Ruth issue would have given him.

The Circuit said,

After Ruth, we can comment that sentencing counsel’s attempts to lower Neal’s offense level and convince the district court to exercise its discretion leniently were not the best possible approach to reducing Neal’s exposure. But it is difficult to establish ineffective assistance when counsel’s overall performance indicates active and capable advocacy.

Neal v. United States, Case No. 23-1722, 2025 USApp LEXIS 23018 (7th Cir. Sept 5, 2025)

United States v. Ruth, 966 F.3d 642 (7th Cir. 2020)

~ Thomas L. Root