Stewart v. United States

Decision Date05 August 2021
Docket NumberCase No. 4:19-cv-00392-SMR,Crim. No. 3:17-cr-00024-SMR-SBJ-1
Parties Derrick Anthony STEWART, Movant, v. UNITED STATES of America, Respondent.
CourtU.S. District Court — Southern District of Iowa

Andrew J. Dunn, Brown & Bergmann, L.L.P., Des Moines, IA, for Movant.

Clifford R. Cronk, III, United States Attorney's Office, Davenport, IA, for Respondent.



Derrick Anthony Stewart pleaded guilty to conspiring to distribute heroin and possessing a firearm in furtherance of a drug trafficking crime and his drug sentence was statutorily enhanced to a twenty-year mandatory minimum based on a prior conviction under the Illinois residual drug possession statute. J., United States v. Stewart , 3:17-cr-00024-SMR-SBJ-1 (S.D. Iowa Mar. 19, 2018) ("Crim. Case"). Stewart brings this motion to collaterally attack his sentence pursuant to 28 U.S.C. § 2255, arguing his state conviction does not qualify as a predicate "felony drug offense" under the Controlled Substances Act ("CSA") and that counsel was ineffective for failing to challenge the Government's enhancement information.


On April 19, 2017, Stewart was indicted on four federal charges:

• Conspiracy to Manufacture, Distribute, and Possess with Intent to Distribute 1,000 Grams and More of a Mixture and Substance Containing Detectable Amounts of Heroin under 21 U.S.C. §§ 841(a)(1), (b)(1)(A), 846, and 851 (Count 1);
• Possession with Intent to Distribute Heroin, in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(C) (Count 2);
• Possession of a Firearm in Furtherance of Drug Trafficking, in violation of 18 U.S.C. § 924(c) (Count 3); and
• Felon in Possession of a Firearm, in violation of 18 U.S.C. §§ 922(g)(1) and 924(a)(2) (Count 4).

Indictment, Crim. Case, ECF No. 31 (sealed). Prior to trial, the Government filed an information pursuant to 21 U.S.C. § 851 notifying Stewart that it intended to seek an increased penalty on the drug conspiracy charge due to his criminal history involving at least one "felony drug offense." Info., Crim Case, ECF No. 56. The statutory language in effect at the time of Stewart's conviction defined a "felony drug offense" under the CSA as "an offense that is punishable by imprisonment for more than one year under any law of the United States or of a State or foreign country that prohibits or restricts conduct relating to narcotic drugs, marihuana, anabolic steroids, or depressant or stimulant substances." 21 U.S.C. § 802(44) (2018) ; see Burgess v. United States , 553 U.S. 124, 126, 128 S.Ct. 1572, 170 L.Ed.2d 478, (2008) ("The term ‘felony drug offense’ contained in § 841(b)(1) [ ] ... is defined exclusively by § 802(44) ...."). Each category of prohibited substance was further defined by statute. 21 U.S.C. § 802(17) (defining "narcotic drug"); id. § 802(16) (defining "marihuana"); id. § 802(41)(A) (defining "anabolic steroid"); id. § 802(9) (defining "depressant or stimulant substance").

The Government's § 851 information identified a conviction in 2000 under Illinois's residual drug statute, 720 ILCS 570/402(c) (2000), which rendered it "unlawful for any person knowingly to possess a controlled or counterfeit substance." See also Info., Crim. Case, ECF No. 56. While other parts of the statute delineate specific penalties for violations involving different amounts of particular substances, subsection (c), the portion of the statute at issue here, is a residual clause providing that a person in possession of "an amount of a controlled or counterfeit substance not set forth in [the statute] is guilty of a Class 4 felony." 720 ILCS 570/402(c) (2000). A "controlled substance" under Illinois law includes any "drug, substance, or immediate precursor" listed in the Schedules of the Illinois Controlled Substances Act. 720 ILCS 570/102(f) (2000) ; see id. § 204 (Schedule I); id. § 206 (Schedule II); id. § 208 (Schedule III); id. § 210 (Schedule IV); id. § 212 (Schedule V). Class 4 felonies are subject to a sentence between one and three years’ imprisonment. 730 ILCS 5/5-4.5-45(a).

Stewart entered a conditional plea of guilty to Counts 1 and 3 under Rule 11(a)(2) of the Federal Rules of Criminal Procedure on November 13, 2017, without the benefit of a written plea agreement.1 At sentencing, the Court found a total offense level of 31 and criminal history category of V, producing an initial guideline range of 168 to 210 months’ imprisonment on Count 1 and a mandatory consecutive term of 60 months’ imprisonment on Count 3. Sent'g Tr. at 13, Crim. Case, ECF No. 129; see Min. Entry, Crim. Case, ECF No. 119 (sentencing). However, federal law in effect at the time subjected a defendant to a statutory minimum of twenty years’ imprisonment for a violation of § 841(a) if committed after one prior conviction for a "felony drug offense"; a violation after two or more prior such convictions resulted in a mandatory term of life imprisonment. 21 U.S.C. § 841(b)(1)(A) (2018).2 Because of the Government's single § 851 enhancement information, Stewart's guidelines range was increased to 240 months’ imprisonment on Count 1. See id. ; Sent'g Tr. at 13. The Court sentenced him to the statutory minimum—240 months’ imprisonment on Count 1, followed by a consecutive sentence of 60 months’ imprisonment on Count 3. J., Crim. Case, ECF No. 120. Counsel for Stewart did not object to the Government's § 851 information.

Stewart filed this motion attacking his sentence under § 2255 on December 5, 2019. [ECF No. 1]. He raises two grounds for relief. First, he asserts his mandatory minimum sentence was unlawfully enhanced under § 841(b)(1)(A) based on a state conviction that is categorically broader than the federal definition of a "felony drug offense," contrary to the principles espoused in Mathis v. United States , ––– U.S. ––––, 136 S. Ct. 2243, 195 L.Ed.2d 604 (2016) (Ground 1). He also claims he was denied the effective assistance of counsel, in violation of his rights under the Sixth Amendment to the United States Constitution, when his attorney failed to investigate the prior conviction listed in the Government's § 851 notice and challenge the predicate offense at the time of sentencing or on appeal (Ground 2).


A federal inmate may file a motion to "vacate, set aside, or correct" his or her sentence under 28 U.S.C. § 2255 "upon the ground that the sentence was imposed in violation of the Constitution or laws of the United States, or that the court was without jurisdiction to impose such sentence, or that the sentence was in excess of the maximum authorized by law, or is otherwise subject to collateral attack." 28 U.S.C. § 2255(a). That statute gives federal prisoners a remedy identical in scope to federal habeas corpus. Sun Bear v. United States , 644 F.3d 700, 704 (8th Cir. 2011).

Not all claimed errors in conviction and sentencing provide a basis for relief, however. Id. Beyond jurisdictional and constitutional errors, the permissible scope of a § 2255 collateral attack on a final conviction or sentence is "severely limited." Id. Federal habeas relief seeks to correct "a fundamental defect which inherently results in a complete miscarriage of justice, ... an omission inconsistent with the rudimentary demands of fair procedure,[ ] ... [or] ‘exceptional circumstances where the need for the remedy afforded by the writ of habeas corpus is apparent.’ " Hill v. United States , 368 U.S. 424, 428, 82 S.Ct. 468, 7 L.Ed.2d 417 (1962) (citation omitted); see United States v. Apfel , 97 F.3d 1074, 1076 (8th Cir. 1996) ("Relief under 28 U.S.C. § 2255 is reserved for transgressions of constitutional rights and for a narrow range of injuries that could not have been raised on direct appeal and, if uncorrected, would result in a complete miscarriage of justice."). Generally, a movant "is entitled to an evidentiary hearing on a section 2255 motion unless the motion and the files and records of the case conclusively show that the prisoner is entitled to no relief." Voytik v. United States , 778 F.2d 1306, 1308 (8th Cir. 1985) (citing 28 U.S.C. § 2255 ); see also Franco v. United States , 762 F.3d 761, 763 (8th Cir. 2014) ("No hearing is required, however, where the claim is inadequate on its face or if the record affirmatively refutes the factual assertions upon which it is based." (citation omitted)).


At bottom, Stewart's claim for relief hinges on the assertion that his prior conviction under the Illinois residual drug possession statute does not qualify as a predicate "felony drug offense" for purposes of sentencing enhancements under the CSA because the state law is categorically broader than the federal statute. The Government contends the "categorical approach" does not apply to the CSA's definition of "felony drug offense" and, even if it does, looking at Stewart's conduct underlying his prior conviction satisfies the federal recidivism statute. "There is little authority on this question." United States v. Brown , 598 F.3d 1013, 1015 (8th Cir. 2010).

A. "Felony Drug Offense"

Stewart contends his 2000 conviction for possession of a "controlled substance" under 720 ILCS 570/402(c) is categorically broader than the federal definition of a "felony drug offense" and therefore cannot serve as a predicate statutorily enhancing his sentence. See Taylor v. United States , 495 U.S. 575, 602, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990). Under the Taylor "categorical approach" to federal recidivism statutes, courts generally ignore the particular facts of the prior offense and "focus solely on whether the elements of the crime of conviction sufficiently match the elements of the [federal statute]." Mathis , 136 S. Ct. at 2248.3 When a statute is "divisible"—that is, when the statute "sets out one or more elements of the offense in the alternative"—a modified approach allows courts to look beyond the face of the statute and consult additional documents to specify...

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    ...While not cited by either party, the Court finds Stewart v. United States, 552 F.Supp.3d 834 (S.D. Iowa 2021) particularly persuasive. In Stewart, the addressed a strikingly similar “felony drug offense” and ineffective assistance of counsel claim in a § 2255 motion. Id. The defendant in St......

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