United States v. Myers

56 F.4th 595

UNITED STATES of America, Plaintiff - Appellant

v.Anthony E. MYERS, also known as Anthony E. Meyers, Defendant - Appellee

No. 21-3443

United States Court of Appeals, Eighth Circuit.

Submitted: June 17, 2022

Filed: December 29, 2022

J. Benton Hurst, Asst. U.S. Atty., Kansas City, MO, argued (Teresa A. Moore, U.S. Atty., on the brief), for plaintiff-appellant.

Daniel P. Goldberg, Asst. Fed. Public Defender, Kansas City, MO, argued (Laine Cardarella, Fed. Public Defender, on the brief), for defendant-appellee.

Before LOKEN and KELLY, Circuit Judges, and MENENDEZ, District Judge.¹

KELLY, Circuit Judge.

The government appeals the district court's² ruling that Anthony Myers does not qualify for a sentencing enhancement under the Armed Career Criminal Act (ACCA), 18 U.S.C. § 924(e), because his prior cocaine conviction under Missouri law is not a "serious drug offense." We affirm.

I.

A defendant convicted of unlawful possession of a firearm under 18 U.S.C. § 922(g) who has three prior convictions for violent felonies and/or serious drug offenses faces a mandatory minimum sentence of 15 years. See 18 U.S.C. § 924(e). In July 2020, Myers was convicted by a jury of one count of being a felon in possession of a firearm, in violation of §§ 922(g)(1) and 924(a)(2).³ According to the presentence report, Myers was subject to the ACCA's mandatory minimum sentence because he had two prior convictions for violent felonies and one prior conviction for a serious drug offense. Myers objected, arguing that his 2003 conviction for the sale of cocaine under Missouri Revised Statute § 195.211 (2000)⁴ does not qualify as a serious drug offense under the ACCA because that Missouri statute criminalized conduct that does not violate federal law.

The district court sustained Myers's objection. The court agreed that Myers's conviction under § 195.211 was not a "serious drug offense" under the ACCA because at the time of his conviction in 2003, "Missouri law defined ‘cocaine’ as encompassing its ‘isomers’ without limiting the definition of ‘isomers’ to optical and geometric isomers as the federal statute did," meaning that Missouri's definition of cocaine was categorically broader than the federal definition. The court sentenced Myers to 120 months of imprisonment, the then-applicable statutory maximum under 18 U.S.C. § 924(a)(2) without the ACCA enhancement. The government appeals.

II.

We review de novo whether a prior conviction qualifies as a serious drug offense under the ACCA. United States v. Oliver, 987 F.3d 794, 805 (8th Cir. 2021). A serious drug offense is defined in relevant part as "an offense under State law, involving manufacturing, distributing, or possessing with intent to manufacture or distribute, a controlled substance (as defined in section 102 of the Controlled Substances Act ( 21 U.S.C. § 802 )), for which a maximum term of imprisonment of ten years or more is prescribed by law." 18 U.S.C. § 924(e)(2)(A)(ii). As relevant here, a prior state drug conviction is a predicate offense for purposes of the ACCA only if the state offense involved a "controlled substance" as that term is defined under federal law.⁵ Courts determine whether a prior conviction qualifies as a serious drug offense by looking to the scope of the state law, not to the specific facts underlying the prior conviction. Oliver, 987 F.3d at 806. This "categorical approach" focuses solely on whether the elements of the crime of conviction match the corresponding federal drug offense. Id.

Under the categorical approach, the ultimate burden is on the government to prove that the prior conviction is a qualifying offense under the ACCA. United States v. Clark, 1 F.4th 632, 635 (8th Cir. 2021). Where "the state offense sweeps more broadly, or punishes more conduct than the federal definition, the conviction does not qualify as a predicate offense." United States v. Vanoy, 957 F.3d 865, 867 (8th Cir. 2020). To determine whether a state statute "sweeps more broadly," we examine its text and structure. United States v. Owen, 51 F.4th 292, 294 (8th Cir. 2022) (per curiam). In doing so, we apply Missouri principles of statutory construction, which requires giving words their "plain and ordinary meaning." State v. Johnson, 524 S.W.3d 505, 510 (Mo. banc 2017) ; Behlmann v. Century Sur. Co., 794 F.3d 960, 963 (8th Cir. 2015) ("Interpreting state statutes, this court applies that state's rules of statutory construction."); see In re Trenton Farms RE, LLC v. Mo. Dep't of Nat. Res., 504 S.W.3d 157, 164 (Mo. Ct. App. 2016) (explaining that administrative rules and regulations are to be interpreted using same principles of construction as statutes). "Only where the language is ambiguous" should the court "resort to other rules of statutory construction." Treasurer of Mo.-Custodian of Second Inj. Fund v. Witte, 414 S.W.3d 455, 460 (Mo. banc 2013).

Myers's prior Missouri conviction⁶ involved cocaine, so we compare the definition of cocaine under Missouri law at the time of Myers's Missouri conviction with the definition of cocaine under federal law at the time of Myers's instant federal offense.⁷ In 2003, Missouri's definition of cocaine covered "coca leaves and any salt, compound, derivative or preparation of coca leaves including cocaine and ecgonine and their salts, isomers , derivatives and salts of isomers and derivatives and any salt, compound, derivative or preparation thereof which is chemically equivalent or identical with any of these substances." 19 C.S.R. 30-1.002(1)(B)1 (2000) (cleaned up and emphasis added). The Missouri schedule did not define isomer. Turning to the dictionary definition of isomer, the term encompasses "any one of a number of isomeric compounds." Isomer, Oxford English Dictionary, https://www.oed.com/view/Entry/100097?redirectedFrom=isomer#eid (last visited Dec. 1, 2022); see also Owen, 51 F.4th at 295 ("By specifically mentioning ‘the isomers of cocaine,’ the definition [of cocaine] sweeps in any substance with the same chemical composition as cocaine, even if it has a different structural form." (cleaned up) (quoting Dictionary of Science and Technology 1151 (1992)). Missouri's definition, then, swept in all isomers, including positional , optical, and geometric isomers.

The federal definition, however, criminalizes only optical and geometric isomers—but not positional isomers. 21 U.S.C. §§ 802(14), 812, sched. II(a)(4); 21 C.F.R. § 1308.02. Because Missouri's definition of cocaine included positional isomers while the federal definition does not, the Missouri definition is unambiguously broader than its federal counterpart. Moreover, Missouri courts have interpreted the Missouri drug schedule as making all isomers of cocaine illegal. See State v. Greene, 785 S.W.2d 574, 577–78 (Mo. Ct. App. 1990) (concluding that the Missouri drug schedule "renders [defendant]’s attempts to distinguish between isomers useless, as all isomers of cocaine are prescribed"); State v. James, 796 S.W.2d 398, 399 (Mo. Ct. App. 1990) (holding that the state's witness needed to testify only that the substance at issue was cocaine for it to fall within the language of the statute).⁸

The government contends that interpreting "isomers" in the cocaine schedule to include all isomers would render superfluous other provisions of the Missouri drug schedule that explicitly included "optical, position, and geometric" isomers as the proscribed isomers of a substance. See, e.g., 19 C.S.R. 30-1.002(1)(A)3 (2000). However, the substances whose isomers expressly included "optical, position, and geometric isomers" were found in Schedule I, which specified which forms of a given substance were prohibited drug-type by drug-type. But cocaine was a Schedule II drug. Unlike Schedule I, Schedule II included all forms of the listed substances. Compare, e.g., 19 C.S.R. 30-1.002(1)(A) (specifying that stimulants include only "optical isomers" while opiates include "their isomers" "whenever the existence of such isomers ... is possible"), with 19 C.S.R. 30-1.002(1)(B)1 (proscribing all forms of the listed substances whether of "vegetable origin or chemical synthesis" unless "specifically excepted" or "listed in another schedule"). Because Schedule II proscribed all forms, it was unnecessary for the state to expressly indicate that cocaine includes any one specific type of isomer. Indeed, no substances listed in Schedule II included the "optical, position, and geometric" description of isomer.

The government also raises arguments about the non-existence of positional isomers in the drug trade, such that Missouri would have no reason to criminalize them, and about Missouri's summary rulemaking process, which was designed to conform the Missouri schedules to the federal schedules. But absent ambiguity, we are "bound to give effect to the intent reflected in the statute's plain language and cannot resort to other means of interpretation." Karney v. Dep't of Lab. & Indus. Rels., 599 S.W.3d 157, 162 (Mo. banc 2020) ; see also Owen, 51 F.4th at 296. Because the text of the Missouri drug schedule plainly criminalized all isomers of cocaine, our inquiry ends there. Cf. Owen, 51 F.4th at 296 (concluding that Minnesota schedule proscribing "isomers of cocaine" was unambiguously broader than federal definition).⁹ Given the unambiguous breadth of Missouri's definition of cocaine, we agree with the district court that Myers's prior Missouri conviction for the sale of cocaine was not a predicate offense for purposes of the ACCA.

III.

For the foregoing reasons, we affirm the judgment of the district court.¹⁰

LOKEN, Circuit Judge, dissenting.

Like many States, Missouri adopted a version of the Uniform Narcotic Drug Act in Chapter 195 of its Revised Statutes. See 12 Vernon's Ann. Mo. Stat. § 195.005. Like its federal counterpart, 21 U.S.C. §§ 811(a), 812, the Missouri statute established five schedules of controlled substances; listed specific substances in each of the initial schedules; and authorized...