Neal v. United States

• Court: U.S. Court of Appeals — Seventh Circuit
• Writing for the Court: Kolar, Circuit Judge.
• Citation: Neal v. United States, 155 F.4th 678 (7th Cir. 2025)
• Docket Number: 23-1722
• Decision Date: 05 September 2025
• Parties: Tyree M. NEAL, Jr., Petitioner-Appellant, v. UNITED STATES of America, Respondent-Appellee.

155 F.4th 678

Tyree M. NEAL, Jr., Petitioner-Appellant, v. UNITED STATES of America, Respondent-Appellee.

No. 23-1722

United States Court of Appeals, Seventh Circuit

Argued October 22, 2024

Decided September 5, 2025

Appeal from the United States District Court for the Southern District of Illinois. No. 3:19-cv-01360 — J. Phil Gilbert, Judge.

Mary H. Schnoor, Attorney, McDermott Will & Schulte, Washington, DC, Robert Allen Long, Jr., Attorney, Covington & Burling LLP, Washington, DC, for Petitioner-Appellant.

Peter Reed, Attorney, Office of the United States Attorney, Fairview Heights, IL, for Respondent-Appellee.

Before Brennan, Jackson-Akiwumi, and Kolar, Circuit Judges.

Kolar, Circuit Judge.

Tyree M. Neal, Jr. pleaded guilty to conspiracy to distribute cocaine in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(C), and 846. At his sentencing, the district court found that Neal's prior Illinois cocaine conviction supported a recidivism enhancement under 21 U.S.C. § 841(b)(1)(C) that raised his maximum sentence from 20 years to 30 years' imprisonment. The district court then sentenced Neal to the 30-year maximum. Neal appealed and argued that he should have been allowed to withdraw his guilty plea because it was involuntary and lacked a factual basis; his appeal did not challenge the enhancement. We ruled against the arguments Neal raised on direct appeal. United States v. Neal, 907 F.3d 511 (7th Cir. 2018).

Two years after Neal's appeal, in United States v. Ruth, 966 F.3d 642 (7th Cir. 2020), we applied the "categorical approach" and held that 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 U.S.C. § 841(b)(1)(C). Accordingly, if Neal were sentenced today, his maximum sentence would be 20 years.

In the proceedings below, Neal sought Section 2255 relief for ineffective assistance of counsel, arguing that his appellate, sentencing, and plea counsel were all constitutionally deficient in failing to raise the argument that succeeded in Ruth. The district court denied his petition. We affirm.

I. Background

A. Neal's Conviction, Sentencing, and Appeal

In 2014, after Neal was indicted on one count of conspiracy to distribute cocaine in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(C), and 846, he evaded arrest and led officers on a 17-mile car chase at sustained speeds exceeding 100 miles per hour. Neal eventually abandoned his vehicle and carjacked a mother who was in a van with her three children. Neal forced her to drive to another vehicle that was waiting for him. With the help of that getaway car, Neal escaped from police pursuit. He was finally arrested in February 2015.

Following Neal's arrest, the government filed a Section 851 notice seeking a recidivism enhancement under 21 U.S.C. § 841(b)(1)(C) because Neal had a 2007 conviction for unlawful delivery of cocaine under 720 ILCS 570/401(c)(2). If the district court agreed that Neal had a "prior conviction for a felony drug offense," it would increase Neal's statutory maximum term of imprisonment from 20 years to 30 years. 21 U.S.C. § 841(b)(1)(C).

In August 2016, Neal pleaded guilty. During plea negotiations, he was represented by four successive attorneys, three of which withdrew due to disagreements with Neal. The final attorney was Heather Winslow, who recommended a guilty plea.

At the sentencing stage, Neal fired Winslow because they disagreed about how to address a potential career-offender classification. The district court appointed J. Christian Goeke in February 2017. Neal attempted to hire private counsel, but Goeke ultimately represented him through the end of sentencing.

As relevant to his sentencing, Neal had an extended criminal history that included convictions for 15 other offenses, including aggravated battery. And in March 2016, a jailhouse informant told authorities that Neal had said he paid someone to kill a witness. The Probation Office's Presentence Investigation Report (prepared using the 2015 United States Sentencing Guidelines) concluded that Neal was subject to an offense level of 35, criminal history category VI, and a 292-365 month sentencing range.¹ It found that Neal had accepted responsibility, but that enhancements applied for the drug amount, the use of violence, obstruction of justice, and reckless endangerment.

With the help of an investigator to interview witnesses, Goeke contested the use of violence, obstruction of justice, reckless endangerment, and career offender enhancements. However, Goeke did not object to the Section 841 recidivism enhancement, nor did he discuss such an objection with Neal.

After a two-day sentencing hearing on September 18 and 19, 2017, the district court found that the recidivism enhancement applied, as well as the other challenged enhancements. It sentenced Neal to the statutory maximum, 30 years.

Neal appealed on September 25, 2017 and Assistant Federal Public Defender Johanna Christiansen was appointed to represent him. Christiansen argued that the district court erred in not allowing Neal to withdraw his guilty plea. Neal, 907 F.3d at 514-16. She asserted that Neal did not understand the conspiracy charge, making the plea involuntary, and that the plea was not supported by a sufficient factual basis. Id. On October 22, 2018, about three weeks after oral argument, our court rejected these contentions and affirmed Neal's conviction. Id. at 516-17. Christiansen did not argue against the Section 841 recidivism enhancement, nor did she tell Neal that any such argument existed.

B. The Categorical Approach to Recidivism Enhancements

To determine if a Section 841 recidivism enhancement applies, we use the "categorical approach" that looks solely to the elements of a defendant's offense and not to the specific facts underlying the conviction. Ruth, 966 F.3d at 646; see Taylor v. United States, 495 U.S. 575, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990). "If, and only if, the elements of the state law mirror or are narrower than the federal statute can the prior conviction qualify as a predicate felony drug offense." Ruth, 966 F.3d at 646 (quoting United States v. De La Torre, 940 F.3d 938, 948 (7th Cir. 2019)).

Our use of the categorical approach in assessing challenges to recidivism enhancements under Section 841 originated in 2018, contemporaneous with Neal's direct appeal. We first encountered "the question of whether the . . . categorical approach applies to the term 'felony drug offense' for the purpose of" Section 841 in Brock-Miller v. United States, where in April 2018, we reserved an answer "for another day." 887 F.3d 298, 307 (7th Cir. 2018). That day came four months later in August 2018, when we adopted the categorical approach for Section 841 enhancements in United States v. Elder, 900 F.3d 491 (7th Cir. 2018). Because the defendant in Elder was previously convicted under an Arizona statute that swept more broadly than federal law by including additional substances (propylhexedrine and scopolamine) in its definition of "dangerous drugs," that conviction could not serve as a predicate offense for the Section 841 enhancement. Id. at 501.

We decided our next categorical approach case in 2019, after Neal's appeal concluded. In United States v. De La Torre, we observed that both Indiana and federal law regulated methamphetamine and its isomers—an isomer shares the same number and type of atoms but with a distinct arrangement in space, which can give rise to different effects when used. 940 F.3d at 951. There are three relevant types of isomer: optical, positional, and geometric. Id. Consequently, despite a "seeming match" at first glance, "because the federal definition of methamphetamine includes only its optical isomers whereas the Indiana definition includes something more than just optical isomers of methamphetamine, the mismatch renders the Indiana statute overbroad" for purposes of supplying a predicate offense under Section 841. Id. We further stated that "our decision [was] not solely dependent on the definition of methamphetamine" because Indiana law also included two other substances (parahexyl and Telazol) not covered under federal law. Id. at 952.

That brings us to United States v. Ruth, a key case for this appeal.² In that 2020 decision, we remarked that the Illinois statutory definition of cocaine included "positional isomers" of cocaine, whereas the federal definition includes only "optical isomers" and "geometric isomers." Ruth, 966 F.3d at 647. "On its face, then, the Illinois statute is categorically broader than the federal definition." Id. We were uninterested in the government's contention that positional isomers of cocaine did not actually exist in the drug trade because "it is not the province of the judiciary to rewrite Illinois's statute to conform to a supposed practical understanding of the drug trade." Id. at 648. That led to the "inescapable conclusion that the plain language of the state statute categorically covers a larger swath of conduct than its federal counterpart." Id. Thus, the defendant's Illinois conviction under 720 ILCS 570/401(c)(2) was not a predicate "felony drug offense" that triggered Section 841(b)(1)(C)'s sentencing enhancement. Id. at 650.

C. Neal's Petition

This proceeding began when Neal filed a timely 28 U.S.C. § 2255 motion to vacate, set aside, or correct his sentence. Neal asserted that his appellate (Christiansen), sentencing (Goeke), and plea (Winslow) counsel each provided ineffective assistance in violation of the Sixth Amendment. According to Neal, all three attorneys were ineffective because they failed to argue that Neal's Illinois cocaine conviction did not qualify as a predicate "felony drug offense" supporting a recidivism enhancement under Section 841(b)(1), which we hereafter call the Ruth argument.

The district court denied Neal's claims of ineffective assistance from Goeke and Winslow and ordered an evidentiary...