Court Opinion

ID: 9351168
Source: CourtListenerOpinion
Date Created: 2022-12-29 17:00:29.375193+00
Date Added: 2024-06-11T16:58:17.776930
License: Public Domain

United States Court of Appeals
                            For the Eighth Circuit
                        ___________________________

                                No. 21-3443
                        ___________________________

                            United States of America

                                     Plaintiff - Appellant

                                        v.

              Anthony E. Myers, also known as Anthony E. Meyers

                                    Defendant - Appellee
                                 ____________

                     Appeal from United States District Court
                for the Western District of Missouri - Kansas City
                                 ____________

                           Submitted: June 17, 2022
                           Filed: December 29, 2022
                                 ____________

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

KELLY, Circuit Judge.

      1
        The Honorable Katherine M. Menendez, United States District Judge for the
District of Minnesota, sitting by designation.
       The government appeals the district court’s 2 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

        2
      The Honorable Beth Phillips, Chief Judge, United States District Court for
the Western District of Missouri.
        3
       18 U.S.C. § 924 was later amended; currently, § 924(a)(8) applies to
convictions under § 922(g).

      Myers was also convicted of possession of a controlled substance in violation
of 21 U.S.C. § 844(a) and sentenced to 12 months’ imprisonment on that count, to
run concurrently with the sentence imposed for illegal possession of a firearm.
The government does not appeal this aspect of his sentence.
        4
            Missouri repealed § 195.211 and recodified it in chapter 579, effective as of
2017.
                                             -2-
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

      5
       For ACCA purposes, the relevant federal definition is that “in effect at the
time of the federal offense.” United States v. Perez, 46 F.4th 691, 699 (8th Cir.
2022).
                                      -3-
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 conviction 6 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

      6
      Section 195.211 was divisible by controlled substance. See United States v.
Young, 6 F.4th 804, 810 (8th Cir. 2021).
      7
         See Perez, 46 F.4th at 700 (“[T]he categorical approach requires comparison
of the state drug schedule at the time of the prior state offense to the federal schedule
at the time of the federal offense.”).
                                           -4-
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).

      8
        The government attempts to distinguish Greene and James by pointing out
that those cases involved a debate over two optical isomers. True, but nothing in
those decisions suggests that the analysis would be different for another type of
isomer, here positional isomers. The Missouri courts interpreted the text of the
Missouri drug schedule as covering all isomers of cocaine, without regard to the type
of isomer. James, 796 S.W.2d at 399 (rejecting requirement that the state prove the
composition of cocaine samples to obtain a conviction); Greene, 785 S.W.2d at 578
(“[A]ll isomers of cocaine are prescribed.”).

                                         -5-
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.

      9
       Notably, Owen addressed Minnesota law, which at the time of Owen’s
convictions, as here, required the Minnesota drug schedule to similarly control
substances like its federal counterpart. See Minn. Stat. § 152.02, subd. 12 (1973)
(amended 2017).

                                         -6-
                                         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 an Executive Branch entity, the
Department of Health and Senior Services (DHSS), to add or remove substances
from any schedule, or transfer substances between schedules, under procedures and
substantive standards prescribed in the statute. See Mo. Rev. Stat. '' 195.015,
195.017. If DHSS receives notice that “any substance is designated, rescheduled, or
deleted as a controlled substance under federal law,” the Department “shall similarly
control the substance” unless, after providing public notice and an opportunity to be
heard, it “objects to inclusion, rescheduling or deletion.” ' 195.015.4.11 The

      10
        Because we affirm the sentence imposed on the basis that there is no
categorical match between the Missouri cocaine offense and the federal cocaine
offense, we need not address Myers’s argument regarding the government’s burden
of proof for establishing the existence of an ACCA predicate offense. Nor do we
reach Myers’s arguments that the government’s use of expert witnesses to prove a
predicate offense violated his Fifth and Sixth Amendment rights.
      11
         When a controlled substance is “designated, rescheduled, or deleted” under
federal law, and DHSS does not object, it “shall similarly control the substance under
this chapter” and submit emergency rules to the Secretary of State, “clearly stat[ing]
if the rules shall be in effect pursuant” to ' 195.015.4. By contrast, if DHSS seeks
to go beyond the federal schedules, it must do so through notice and comment
rulemaking and consider statutory listing factors. Mo. Rev. Stat. ' 195.015.

                                         -7-
Supreme Court of Missouri upheld this statute, rejecting a constitutional challenge,
in State v. Thompson, 627 S.W.2d 298, 303 (Mo. banc 1982):

            Control by the federal government is the factor which triggers
      mandatory consideration of a substance by the Division of Health under
      ' 195.015.4, RSMo 1978. Whether federal control should mandate
      consideration of a substance is a decision for the General Assembly.

       The court concludes that in 2003, when Anthony Myers committed the
predicate state cocaine offense at issue, “cocaine” as listed in 19 C.S.R. 30-
1.002(1)(B)1, the DHSS list of Schedule II substances, was categorically broader
than 21 U.S.C. ' 812(c), Schedule II(a)(4), based on the court=s dictionary-fed
conclusion that the plain meaning of “isomer” is unambiguous. Under Missouri law,
to which we must look for the answer to this issue, plain meaning normally controls,
but the Supreme Court of Missouri “look[s] elsewhere for interpretation . . . when
the meaning . . . would lead to an illogical result defeating the purpose of the
legislature.” Spradlin v. City of Fulton, 982 S.W.2d 255, 258 (Mo. banc 1998)
(quotation omitted). In my view, that is manifestly true in this case. Accordingly, I
respectfully dissent.

                                         I.

       I begin my analysis with a highly relevant decision by Congress in the
Dangerous Drug Diversion Control Act of 1984 that the court ignores -- Congress
modified Schedule II(a)(4) by adding an explicit reference to cocaine to the
definition of “coca leaves” -- “(including cocaine and ecgonine and their salts,
isomers, derivatives, and salts of isomers and derivatives).” And it added a new
definition of “isomer” -- “[a]s used in schedule II(a)(4), the term isomer means the
‘optical or geometric isomer.’” Pub. L. No. 98-473 '' 507(a), (c), 98 Stat. 2071
(1984), codified at 21 U.S.C. '' 812(c), Schedule II(a)(4), and 802(14). The intent
of this amendment was not, as the court intimates, to remove positional isomers from
Schedule II(a)(4). Rather, the intent was to eliminate a “cocaine isomer defense”
that had been frustrating controlled substance prosecutions for possession and
                                         -8-
distribution of “coca leaves.” This “purely theoretical” defense was based on the
fact that only one of eight commonly recognized isomers of cocaine -- L-cocaine --
is natural, i.e., derived from the coca leaf; the others, including L-cocaine=s optical
isomer -- D-cocaine -- are manufactured (if they exist at all).12 By expressly
including optical and geometric isomers of cocaine in Schedule II(a)(4) Congress
eliminated the cocaine isomer defense. See S. Rep. No. 98-225 at 263 (1984), as
reprinted in 4 1984 U.S.C.C.A.N. 3182, 3445. The Report explained, “[t]here are
no significant changes in the scope of substances subject to control.” Id. 13

      The publication of this change to federal Schedule II(a)(4) in 51 Federal
Register 15317-01 (1986) triggered DHSS=s duty under Mo. Rev. Stat. ' 195.015.4
to “similarly control the substance under [Ch. 195],” or object to its inclusion.
Accordingly, on May 1, 1987, the Department of Health, Bureau of Narcotics and
Dangerous Drugs, published an Order of Rulemaking in the Missouri Register
amending its Schedule II listing of coca leaves, 19 C.S.R. 30-1.002(1)(B)1.D.,
adopting the same language Congress used in ' 507(c) of the Dangerous Drug
Diversion Control Act of 1984:

      coca leaves (9040) and any salt, compound, derivative or preparation
      of coca leaves (including cocaine (9041) and ecgonine (9180) and
      their salts isomers, derivatives and salts of isomers and derivatives)

      12
        See Best v. State, 556 A.2d 701, 711-19 (Md. Spec. App. 1989), discussing
decisions of eight of our sister circuits dealing with this issue, almost uniformly
rejecting the cocaine isomer defense. Our court apparently never faced the issue.
      13
        The court relies on two Missouri Court of Appeals decisions that dealt with
defendants who attempted to use the cocaine isomer defense to overturn their
cocaine convictions under state law. See State v. James, 796 S.W.2d 398 (Mo. App.
1990); State v. Greene, 785 S.W.2d 574 (Mo. App. 1990). In rejecting that defense,
the Court stated that DHSS’s 1987 change to 19 CSR 30-1.010 “renders appellant’s
attempts to distinguish between isomers useless, as all isomers of cocaine are
prescribed.” Id. at 577-78, followed in James, 796 S.W.2d at 400. On the issue we
are considering, the “all isomers” comment does not apply or is irrelevant dictum.

                                         -9-
      and any salt, compound, derivative or preparation thereof which is
      chemically equivalent or identical with any of these substances . . . .

The “Purpose” section of the Order of Rulemaking explained:

      This rule is being amended to revise the schedules to conform with
      the federal schedules. . . . The Department of Health did not object to
      the removal and additions to the Controlled Substances Schedules in
      Missouri; therefore, these substances will be similarly controlled in
      Missouri.

12. Mo. Reg. 623-24 (May 1, 1987) (emphases added).

       The court bases its conclusion that the Missouri statute is categorically
broader than 21 U.S.C. ' 812(c), Schedule II(a)(4), on the fact that the Missouri rule
uses the term cocaine “isomers” without defining it, whereas that term is defined in
the federal statute as limited to optical and geometric isomers of cocaine. But the
essential fact is that DHSS in the Missouri rule adopted the bare term “isomers” as
it was stated in the operative provision of federal Schedule II(a)(4) as amended by
Congress in ' 507(c) of the 1984 Act. So the intent of Congress was clear -- to add
cocaine to the listing, not remove one isomer of cocaine. And Missouri legislative
intent was equally clear -- to “similarly control” cocaine in Missouri. It is therefore
obvious, at least to me, that the Missouri rule must be interpreted as including (or
incorporating by implied reference) the federal definition of cocaine isomers
contained in a separate federal provision, ' 507(a) of the 1984 Act. The court’s
contrary interpretation, derived from dictionaries and ad hoc intuition, “lead[s] to an
illogical result defeating the purpose of the legislature,” contrary to Missouri law.
Under Missouri law (as elsewhere), “the true intention of the framers must be
followed and where necessary the strict letter of the act must yield to the manifest
intent of the Legislature.” BCI Corp. v. Charlebois Constr. Co., 673 S.W.2d 774,
780 (Mo. banc 1984). The court’s dictionary-based application of the categorical
approach violates the obvious intent of two legislatures, Congress and the Missouri
Legislature, as well as the Supreme Court of Missouri=s rules of statutory

                                         -10-
construction. I consider this a simultaneous violation of two constitutional
principles, separation of powers and federalism. I further note that our brief per
curiam opinion in United States v. Owen, 51 F.4th 292 (8th Cir. 2022), reviewed
neither the evolution of 21 U.S.C. ' 812, Sched. II (a)(4), nor the relationship
between the Minnesota and federal schedules.

       In two 1986 amendments, Congress substituted “cocaine, its salts, optical and
geometric isomers, and salts of isomers . . .” for the listing in ' 507(c) of the 1984
Act, “(including cocaine and ecgonine and their salts, isomers, derivatives, and salts
of isomers and derivatives).” See Anti-Drug Abuse Act, Pub. L. 99-570, ' 1867,
100 Stat. 3207 (Oct. 1986); Criminal Law and Procedure Technical Amendment
Act, Pub. L. 99-646, ' 84, 100 Stat. 3592 (Nov. 1986). This amendment
incorporated the special definition of controlled cocaine isomers in ' 802(14) into
the operative provision, ' 812(c), Schedule II(a)(4), leaving ' 802(14) unchanged.
There was no change in substance. In introducing this and other amendments in S.
1236 in 1985, Senator Thurmond described the bill as “a package of technical and
minor changes to the Comprehensive Crime Control Act of 1984.” 131 Cong. Rec.
S00000-12 *26 (1985). The specific amendment to ' 507(c) of the 1984 Act was
described as “preferable since there may be isomers of hallucinogens [listed in
Schedule I] and cocaine [listed in Schedule II] that are as yet unknown or
undetected.” Id. at *72.14

       It is not clear why DHSS in May 1987 adopted the 1984 federal statutory
listing in ' 507(c), rather than the amended language now found in ' 812(c),
Schedule II(a)(4). Perhaps DHSS was not given notice of this later amendment, as

      14
        Regarding Congress’s decision to include positional isomers of
hallucinogens in Schedule I, but not positional isomers of cocaine in Schedule II,
H.R. Rep. 1030 explained, “clandestine manufacturers have attempted to circumvent
the law by manufacturing positional and geometric isomers of hallucinogens in
Schedule I and optical and geometric isomers of cocaine.” 4 1984 U.S.C.C.A.N. at
3445.

                                        -11-
Mo. Rev. Stat. ' 195.015.4 requires. Perhaps this was not deemed a substantive
change to the federal schedules requiring DHSS action. Or perhaps DHSS simply
overlooked a technical amendment to the federal Schedule II listing when DHSS
decided that the addition of cocaine to Schedule II(a)(4) should be “similarly
controlled” in Missouri. But whatever the reason, I conclude the Supreme Court of
Missouri would hold that, by adopting the earlier wording of the federal listing, to
which the ' 802(14) limiting definition applied, rather than the later provision that
inserted the ' 802(14) language in the operative federal provision, DHSS did not
add positional cocaine isomers when it revised the substances controlled in Missouri
Schedule II(a)(4) “to conform with the [newly modified] federal schedules” that
excluded positional isomers. Under the Missouri statute, when DHSS used the
expedited procedure to “similarly control” cocaine in 19 C.S.R. 30-1.002(1)(B)1,
the regulation would have been invalid if it added a cocaine isomer not controlled
under federal law. When “interpreting a regulation, courts should employ a
construction that will avoid invalidity when possible.” See State Dep’t of Lab &
Indus. Rels. v. Bd. of Pub. Utils. of Springfield, 910 S.W.2d 737, 741 (Mo. App.
1995). Thus, positional isomers of cocaine are not Schedule II controlled substances
under Missouri law.

                                         II.

       The above analysis answers the 18 U.S.C. ' 924(e) sentencing enhancement
issue raised in this appeal. But there is another reason I disagree with the court’s
conclusion. In United States v. Swopes, the en banc court held:

             In applying the categorical approach under the ACCA, we
      examine both the text of the statute and how the state courts have
      applied the statute. Before we conclude that a state statute sweeps more
      broadly than the federal definition of violent felony, there must be a
      “realistic probability, not a theoretical possibility,” that the statute
      encompasses conduct that does not involve use or threatened use of
      violent force.

                                        -12-
886 F.3d 668, 671 (8th Cir. 2018) (en banc) (citation omitted). Some recent
decisions such as Owen have suggested, contrary to Swopes, that the realistic
probability rule does not apply if a panel concludes that a state statute is
“unambiguous.” In my view, the proposition is obviously false. At the very least,
evidence establishing no realistic probability that a defendant would be prosecuted
and/or convicted of the allegedly overbroad offense is strong evidence that the
statute does not unambiguously include that offense.

       That is particularly true in this case. It is doubtful that positional isomers of
cocaine exist outside a laboratory. It is also quite clear that no positional cocaine
isomer offense has ever been prosecuted in Missouri. Indeed, the statute makes it
clear that no such offense could be prosecuted because cocaine positional isomers
have not been lawfully scheduled in accordance with ' 195.015.4. What Missouri
prosecutor would even attempt to bring such a charge, knowing it would be subject
to a clear invalidity defense? In these circumstances, the realistic probability rule
should apply and reinforce my conclusion that the Missouri statute is not overbroad.
I urge the en banc court to take up this issue.

     For these reasons, I would reverse the district court’s decision not to sentence
Anthony Myers under the Armed Career Criminal Act.
                     ______________________________

                                         -13-