United States v. Robert House ( 2022 )

FOR PUBLICATION
UNITED STATES COURT OF APPEALS
FOR THE NINTH CIRCUIT
UNITED STATES OF AMERICA, No. 20-30169
Plaintiff-Appellee,
D.C. No.
v. 1:19-cr-00096-SPW-1
ROBERT ANTHONY HOUSE,
Defendant-Appellant. OPINION
Appeal from the United States District Court
for the District of Montana
Susan P. Watters, District Judge, Presiding
Submitted November 10, 2021 *
Portland, Oregon
Filed April 15, 2022
Before: Susan P. Graber and Morgan Christen, Circuit
Judges, and George H. Wu, ** District Judge.
*
The panel unanimously concluded this case was suitable for
decision without oral argument. See Fed. R. App. P. 34(a)(2).
**
The Honorable George H. Wu, United States District Judge for
the Central District of California, sitting by designation.
2 UNITED STATES V. HOUSE
Per Curiam Opinion;
Concurrence by Judge Graber;
Concurrence by Judge Christen;
Concurrence by Judge Wu
SUMMARY ***
Criminal Law
The panel affirmed in part, reversed in part, and
remanded for resentencing in a case in which Robert
Anthony House pleaded guilty to being a prohibited person
in possession of a firearm in violation of 18 U.S.C.
§ 922(g)(1) and (g)(3).
At sentencing, the district court ruled that two of House’s
prior felony convictions—a 2007 conviction under Montana
Code Annotated § 45-9-103 for criminal possession of
dangerous drugs with intent to distribute (“2007 marijuana
conviction”) and a 2013 conviction under Montana Code
Annotated §§ 45-2-302 and 45-9-101 for accountability as
to criminal distribution of dangerous drugs (“2013 cocaine
conviction”)—qualified as “controlled substance offenses”
under USSG § 4B1.2(b). The district court, in turn, applied
the enhancement in USSG § 2K2.1(a)(2).
The panel accepted the government’s concession that
United States v. Bautista, 989 F.3d 698 (9th Cir. 2021), is
controlling as to the sentencing enhancement based on the
2007 marijuana conviction, and that this court should
***
This summary constitutes no part of the opinion of the court. It
has been prepared by court staff for the convenience of the reader.
UNITED STATES V. HOUSE 3
remand for resentencing without treating the marijuana
conviction as a qualifying offense.
As to whether the 2013 cocaine conviction is a
qualifying prior controlled substance offense, House raised
two arguments.
House first argued that “the plain language of the
§ 4B1.2 guideline and commentary definition of a controlled
substance offense does not include offers to engage in
prohibited conduct,” while Montana's accountability statutes
do, rendering the latter categorically overbroad. Because it
was bound by United States v. Crum, 934 F.3d 963 (9th Cir.
2019) (per curiam), the panel held that although Montana’s
accountability statutes include offers to engage in prohibited
conduct, they are not rendered categorically overbroad with
respect to §§ 4B1.2(b) and 2K2.1(a).
House argued, second, that Montana's drug statute is
categorically overbroad because its definition of cocaine
includes substances that are either not set forth in the federal
definition and/or are specifically excluded. Because House
raises new arguments on appeal, the panel reviewed the
district court’s sentencing calculation for plain error as to
those contentions. The panel observed (1) that when the
district court reached its decision that a cocaine conviction
under Montana Code Annotated §§ 45-9-101 and 50-32-
224(1)(d) could constitute a controlled substance offense
under § 4B1.2(b), there was no (and there still is no) binding
precedent to the contrary; and (2) that certain of the grounds
for the district court’s rulings were not rejected in binding
precedent until after its sentencing decision. The panel
concluded, accordingly, that the district court did not commit
plain error with respect to the cocaine overbreadth issue.
4 UNITED STATES V. HOUSE
Concurring, Judge Graber wrote separately to explain
her views concerning overbroad state statutes. She noted
that the general rule is that a state law cannot be considered
broader than a federal law if the state law’s breadth is
imagined or theoretical. In her view, this court has
distinguished between overbreadth that is “evident” from the
statute’s text, when a defendant may rely on the statutory
language to establish the statute as overly inclusive, and
overbreadth that is not “evident” from the text, when the
party arguing for overbreadth must find a relevant case
establishing a realistic probability of overbroad application.
Concurring, Judge Christen wrote separately because the
complicated categorical approach has proven inordinately
time consuming, and this court’s prior consideration of
Montana’s cocaine statute may result in confusion regarding
the methodology set forth in Taylor v. United States,
495 U.S. 575 (1990). She wrote that, in her view, the
categorical approach employed in United States v. Holliday,
853 F. App’x 53 (9th Cir. 2021), skipped an important step
by taking the holdings from United States v. Grisel, 488 F.3d
844 (9th Cir. 2007) (en banc), abrogated on other grounds
as recognized by United States v. Stitt, 139 S. Ct. 399 (2018),
and United States v. Bautista, 989 F.3d 698 (9th Cir. 2021),
out of context.
Concurring, District Judge Wu wrote separately to
specifically address the categorical/modified categorical
analysis as it relates to the cocaine overbreadth issue in the
context of Montana Code Annotated § 50-32-224(1)(d). He
would apply the reasonable probability factor articulated in
Gonzales v. Duennas-Alvarez, 549 U.S. 183 (2007), as
further considered in Moncrieffe v. Holder, 569 U.S. 184(2013), in initially determining whether the definition of
UNITED STATES V. HOUSE 5
cocaine in § 50-32-224(1)(d) is a categorical match with the
federal regulatory definition at 21 C.F.R. § 13-08.12(b)(4).
COUNSEL
Evangelo Arvanetes, Assistant Federal Defender; Anthony
R. Gallagher, Federal Defender; Federal Defenders of
Montana, Billings, Montana; for Defendant-Appellant.
Karla E. Painter, Assistant United States Attorney; Leif M.
Johnson, sActing United States Attorney; United States
Attorney’s Office, Billings, Montana; for Plaintiff-Appellee.
OPINION
PER CURIAM:
On January 23, 2020, Robert Anthony House pleaded
guilty to two counts of being a “prohibited person” in
possession of a firearm in violation of 18 U.S.C. § 922(g)(1)
and (g)(3). 1 At sentencing on August 5, 2020, the district
court ruled that two of his prior felony convictions—a 2007
conviction under Montana Code Annotated section 45-9-103
for criminal possession of dangerous drugs (i.e., marijuana 2)
1
Title 18 U.S.C. § 922(g)(1) prohibits a convicted felon from
possessing a firearm. Title 18 U.S.C. § 922(g)(3) bars such possession
by a person “who is an unlawful user of or addicted to any controlled
substance (as defined in section 102 of the Controlled Substances Act
(21 U.S.C. § 802)).”
2
The Montana criminal statutes use both spellings, i.e., “marijuana”
and “marihuana,” for that controlled substance. See, e.g., Montana Code
6 UNITED STATES V. HOUSE
with intent to distribute (“2007 marijuana conviction”) and
a 2013 conviction under Montana Code Annotated sections
45-2-302 and 45-9-101 for accountability as to criminal
distribution of dangerous drugs (i.e., cocaine) (“2013
cocaine conviction”)—qualified as “controlled substance
offenses” under United States Sentencing Commission
Guidelines Manual (“USSG”) § 4B1.2(b). Over House’s
objections, the court applied the sentencing enhancement in
USSG § 2K2.1(a)(2). House appeals. We affirm in part,
reverse in part, and remand for resentencing.
I. APPLICABLE LAW
For context, we provide a brief overview of the
convoluted law that has developed concerning the issues
raised in this appeal.
USSG § 2K2.1(a)(2) assigns a base offense level of 24
to a defendant convicted under 18 U.S.C. § 922(g) if the
defendant has previously sustained at least two felony
convictions of either a “crime of violence” as defined in
USSG § 4B1.2(a) or a “controlled substance offense” as
defined in § 4B1.2(b). If the defendant has only one such
prior conviction, the base offense level is 20. See
§ 2K2.1(a)(4). If the defendant has none, the base level is
14. See § 2K2.1(a)(6). USSG § 2K2.1(a) does not define
what constitutes a “controlled substance offense,” but
Application Note 1 of the Commentary to § 2K2.1 states that
it “has the meaning given that term in § 4B1.2(b) and
Annotated section 50-32-101(18). Although both spellings are also
found in various federal criminal statutes, in 21 U.S.C. § 802(16), which
sets out a definition of the drug, it is spelled “marihuana.”
UNITED STATES V. HOUSE 7
Application Note 1 of the Commentary to § 4B1.2[.]”
§ 2K2.1 cmt. n.1. In turn, § 4B1.2(b) states:
The term “controlled substance offense”
means an offense under federal or state law,
punishable by imprisonment for a term
exceeding one year, that prohibits the
manufacture, import, export, distribution, or
dispensing of a controlled substance (or a
counterfeit substance) or the possession of a
controlled substance (or a counterfeit
substance) with intent to manufacture,
import, export, distribute, or dispense.
Application Note 1 of the Commentary to § 4B1.2 expands
the prohibited conduct by providing that “‘controlled
substance offense’ include[s] the offenses of aiding and
abetting, conspiring, and attempting to commit such
offenses.” 3
To determine whether a prior state conviction qualifies
as a controlled substance offense for purposes of the federal
Sentencing Guidelines, we apply a three-step analysis. See
3
Federal circuit courts are split as to whether Application Note 1’s
expansion of the types of prohibited conduct that can constitute a
controlled substance offense lacks legal force because it goes beyond the
text of USSG § 4B1.2(b) itself. See United States v. Crum, 934 F.3d 963,
966 (9th Cir. 2019) (per curiam) (collecting cases). In Crum, we held
that we were “compelled by our court’s prior decision in United States
v. Vea-Gonzales, 999 F.2d 1326 (9th Cir. 1993), overruled on other
grounds by Custis v. United States, 511 U.S. 485 (1994), to [conclude]
. . . that Application Note 1 of § 4B1.2 is ‘perfectly consistent’ with the
text of § 4B1.2(b) . . . . [and] that Application Note 1 properly interprets
the definition of the term ‘controlled substance offense’ to encompass
aiding and abetting, conspiracy, attempt, and other forms of the
underlying offense.” 934 F.3d at 966-67.
8 UNITED STATES V. HOUSE
United States v. Martinez-Lopez, 864 F.3d 1034, 1038 (9th
Cir. 2017) (en banc); United States v. Figueroa-Beltran,
892 F.3d 997, 1001 (9th Cir. 2018). “First, we ask whether
the state law is a categorical match with a federal drug
trafficking offense.” Martinez-Lopez, 864 F.3d at 1038
(citing Taylor v. United States, 495 U.S. 575, 599–600
(1990)). In this initial step,
we look only to the “statutory definitions” of
the corresponding offenses. [Taylor,
495 U.S.] at 600. If a state law “proscribes
the same amount of or less conduct than” that
qualifying as a federal drug trafficking
offense, then the two offenses are a
categorical match. United States v.
Hernandez, 769 F.3d 1059, 1062 (9th Cir.
2014) (per curiam). In that scenario, a
conviction under state law automatically
qualifies as a predicate drug trafficking
offense—ending our analysis.
Martinez-Lopez, 864 F.3d at 1038; see also Crum, 934 F.3d
at 964. The categorical-match analysis typically focuses on
one or both of the following subjects: (1) the criminal
conduct necessary for the state trafficking conviction (i.e.,
the actus reus requirements), see, e.g., United States v.
Rivera-Sanchez, 247 F.3d 905, 908–09 (9th Cir. 2001) (en
banc) (comparing California’s statute criminalizing the
transportation of marijuana, which included solicitation
offenses, with the federal Controlled Substances Act, which
at that time did not), superseded on other grounds as
recognized in Martinez-Lopez, 864 F.3d at 1038; or (2) the
types or varieties of the substance that fall within the
definition of the outlawed drug (i.e., the scope of the
designated controlled substances), see, e.g., United States v.
UNITED STATES V. HOUSE 9
Bautista, 989 F.3d 698, 704–05 (9th Cir. 2021) (comparing
an Arizona criminal statute that included hemp in its
definition of marijuana with the federal Controlled
Substances Act, which was amended in 2018 to exclude
hemp from the federal definition of marijuana).
If there is not a categorical match, we proceed to the
second step and consider whether the state statute is
“divisible”—i.e., whether it “sets out one or more elements
of the offense in the alternative.” Martinez-Lopez, 864 F.3d
at 1038 (quoting Descamps v. United States, 570 U.S. 254,
257 (2013)). “A single statute may list elements in the
alternative, and thereby define multiple crimes.” Mathis v.
United States, 136 S. Ct. 2243, 2249 (2016).
If there is not a categorical match but the state statute is
divisible, we proceed to the third step of the analysis and
apply the modified categorical approach, where we examine
judicially noticeable documents of conviction “to determine
which statutory phrase was the basis for the conviction.”
Descamps, 570 U.S. at 263 (quoting Johnson v. United
States, 559 U.S. 133, 144 (2010)). If the defendant pleaded
to (or was found guilty of) the elements that constitute a
federal drug trafficking crime, “the prior state conviction
may serve as a predicate offense under the sentencing
guidelines.” Martinez-Lopez, 864 F.3d at 1039.
The Supreme Court has identified an additional factor for
courts to consider in the categorical/modified categorical
analyses. In Gonzales v. Duenas-Alvarez, 549 U.S. 183(2007), the Court stated:
[I]n our view, to find that a state statute
creates a crime outside the generic definition
of a listed crime in a federal statute requires
more than the application of legal
10 UNITED STATES V. HOUSE
imagination to a state statute’s language. It
requires a realistic probability, not a
theoretical possibility, that the State would
apply its statute to conduct that falls outside
the generic definition of a crime. To show
that realistic probability, an offender, of
course, may show that the statute was so
applied in his own case. But he must at least
point to his own case or other cases in which
the state courts in fact did apply the statute in
the special (nongeneric) manner for which he
argues.
Id. at 193. We have applied the Duenas-Alvarez’s holding
on several occasions. See, e.g., United States v. Rodriguez-
Gamboa, 972 F.3d 1148, 1150 (9th Cir. 2020) (concluding
that California’s statute prohibiting possession for sale of
both the geometric and optical isomers of methamphetamine
was not categorically overbroad—even though the federal
statute outlaws only possession of methamphetamine’s
optical isomers—because there was “unrebutted expert
testimony . . . that there is no such thing as a geometric
isomer of methamphetamine”); United States v. Perez,
932 F.3d 782, 788–89 (9th Cir. 2019) (holding that a
California statute criminalizing intentional use of physical
force that results in serious bodily injury was a crime of
violence even though the defendant found two state appellate
decisions that “dream[ed] up unusual scenarios” in which a
non-violent act could conceivably inflict substantial bodily
injury (alterations in original) (internal quotation marks
omitted)), cert. denied, 140 S. Ct. 2723 (2020).
UNITED STATES V. HOUSE 11
II. BACKGROUND
The government recommended a base offense level of 24
under USSG § 2K2.1(a)(2) because House had two prior
felony convictions for controlled substance offenses under
§ 4B1.2(b). In his sentencing memorandum, House argued
that his 2007 marijuana conviction did not qualify as a
“controlled substance offense” within § 4B1.2(b) because
the Montana statute criminalized more conduct than its
federal analogue. Specifically, the federal definition of
marijuana was amended in 2018 to expressly exclude hemp,
whereas the Montana statute does not contain that exclusion.
Compare 21 U.S.C. § 802(16), with Montana Code
Annotated section 50-32-101(18). House also asserted that
his 2013 cocaine conviction was not a controlled substance
offense for two reasons. First, he argued that the Montana
accountability statutes (i.e., Montana Code Annotated
sections 45-2-302, 45-9-101 4) included aiding, abetting, and
solicitation, which goes beyond the text of USSG
§ 4B1.2(b). Second, House appeared to make a scope-of-
the-controlled-substance argument, though his contention in
this regard is difficult to decipher.
At sentencing, as to the 2007 marijuana conviction, the
district court ruled: (1) 21 U.S.C. § 802(16) was amended in
4
At the time of House’s sentencing, Montana Code Annotated
section 45-2-302(3) provided in relevant part: “[a] person is legally
accountable for the conduct of another when: . . . either before or during
the commission of an offense with the purpose to promote or facilitate
the commission, the person solicits, aids, abets, agrees, or attempts to aid
the other person in the planning or commission of the offense.” Montana
Code Annotated section 45-9-101(1) stated: “a person commits the
offense of criminal distribution of dangerous drugs if the person sells,
barters, exchanges, gives away, or offers to sell, barter, exchange, or give
away any dangerous drug[.]”
12 UNITED STATES V. HOUSE
2018 to exclude hemp from the federal definition of
marijuana; (2) Montana Code Annotated section 50-32-
101(18) makes no such distinction; but (3) “because this
change did not take place until 2018, House was not subject
to greater criminal liability in 2007 when he was convicted
of his marijuana felony.” Additionally, the district court
held that Montana Code Annotated section 50-32-101 was a
“divisible statute” for purposes of applying the modified
categorical approach, citing Coronado v. Holder, 759 F.3d
977, 984 (9th Cir. 2014). The court concluded that, although
“a defendant, possessing solely hemp, could be convicted of
criminal possession of marijuana under Montana law but not
under federal law,” House had to “demonstrate more than a
theoretical possibility that he faced greater criminal liability”
to establish that his prior conviction was not a match, citing
Duenas-Alvarez, 549 U.S. at 193. The court further stated
that “House not only failed to provide any Montana cases
imposing criminal liability for possession of hemp, but the
judicially noticeable facts described in the underlying
documents . . . establish that House plead[ed] guilty to
possession of marijuana, a substance still included in the
[Controlled Substances Act (“CSA”)], not possession of
hemp.” The district court held that House’s 2007 marijuana
conviction was a predicate offense for purposes of the
sentencing enhancement under USSG § 2K2.1(a).
As to the 2013 cocaine conviction, the district court
rejected House’s first argument (i.e., that Montana’s
accountability statute swept in more conduct than its federal
counterpart) because that contention had been rebuffed in
cases considering other similar state statutes, citing Crum,
934 F.3d at 965–66. Turning to House’s second contention
(i.e., whether Montana’s “accountability criminal
distribution of dangerous drugs – cocaine – [was] a
controlled substance offense”), the district court held:
UNITED STATES V. HOUSE 13
(1) that reference should be made to federal regulatory
definitions in making the comparison, and (2) in United
States v. Holliday, No. CR 18-118-BLG-SPW, 2020 WL
814030 (D. Mont. Feb. 19, 2020) (“Holliday I”), it had
“recently determined the issue of whether Montana’s
definition of cocaine fits the federal definition and
determined that it is a categorical match.”
The district court applied the USSG § 2K2.1(a)(2)
enhancement, which set the base offense level at 24 and
resulted in a Guidelines advisory range of 70 to 87 months’
imprisonment. The Government recommended a 72-month
sentence; House requested 27 to 33 months; and the court,
after weighing the aggravating and mitigating
circumstances, varied downward and sentenced him to
48 months.
After House filed his opening brief, we stayed this appeal
pending the resolution of United States v. Bautista, No. 19-
10448 (9th Cir. Feb. 26, 2021), because that case raised two
issues that were germane here: (1) whether a marijuana
conviction under Arizona Revised Statutes section 13-
13405(A)(4) could constitute a controlled substance offense
as defined in USSG § 4B1.2(b) following the removal of
hemp in 2018 from the definition of marijuana in the CSA,
and (2) whether, in comparing the defendant’s prior state
conviction with the federal law, a court uses the CSA and
corresponding Guidelines in existence at the time of the
federal sentencing or, instead, the federal counterpart in
existence at the time of the defendant’s underlying state
conviction. Bautista held:
At federal sentencing, the district judge was
required to compare the elements of the state
crime as they existed when Bautista was
convicted of that offense to those of the crime
14 UNITED STATES V. HOUSE
as defined in federal law at the time of federal
sentencing—that is, after the Agriculture
Improvement Act removed hemp from the
federal drug schedule. Because the federal
CSA excludes hemp but Section 13-3405 of
the Arizona Revised Statutes did not, the
latter crime’s “greater breadth is evident from
its text.” See [United States v.] Vidal,
504 F.3d [1072,] 1082 [(9th Cir. 2007)].
Bautista’s conviction is facially overbroad
and not a categorical match for a “controlled
substance offense,” and the district court
erred in applying the recidivist sentencing
enhancement for a controlled substance.
Bautista, 989 F.3d at 705.
Shortly thereafter, we reversed and remanded the district
court’s decision in Holliday I. See United States v. Holliday,
853 F. App’x 53 (9th Cir. 2021) (“Holliday II”). Relying on
Bautista, Holliday II held that Montana’s definition of
cocaine is broader than the federal counterpart. Id. at 54–55.
III. DISCUSSION
We review de novo a district court’s interpretation of the
Sentencing Guidelines, and its application of the Guidelines
to the facts of the case generally for abuse of discretion. See
United States v. Ayala-Nicanor, 659 F.3d 744, 746 (9th Cir.
2011). “A district court abuses its discretion when it errs in
its Guidelines calculation, imposes a sentence based on
clearly erroneous facts, or imposes a substantively
unreasonable sentence.” United States v. Burgos-Ortega,
777 F.3d 1047, 1052 (9th Cir. 2015). Where a defendant
proffers on appeal a sentencing issue that was not raised
before the district court, we review for plain error. See
UNITED STATES V. HOUSE 15
United States v. Depue, 912 F.3d 1227, 1232 (9th Cir. 2019)
(en banc); Fed. R. Crim. P. 52(b).
A. The 2007 Marijuana Conviction
The Government admits that Montana’s definition of
marijuana is substantially similar to the Arizona definition
we considered in Bautista. The Government also “concedes
that Bautista is controlling as to House’s first argument
regarding his marijuana conviction,” and agrees with House
that “this Court should remand for resentencing” without
treating House’s marijuana conviction as a qualifying
offense. We accept the government’s concession, reverse
the district court’s application of the sentencing
enhancement based on House’s 2007 marijuana conviction,
and remand for resentencing. Cf. United States v. Halamek,
5 F.4th 1081, 1091 (9th Cir. 2021) (accepting Government’s
concession as to sentencing error and remanding for
resentencing).
B. The 2013 Cocaine Conviction
As to whether his 2013 cocaine conviction is a qualifying
prior controlled substance offense, House raises two
arguments: (1) “the plain language of the § 4B1.2 guideline
and commentary definition of a controlled substance offense
does not include offers to engage in prohibited conduct,”
while Montana’s accountability statutes do, rendering the
latter categorically overbroad (“accountability
overbreadth”); and (2) Montana’s drug statute is
categorically overbroad because its definition of cocaine
includes substances that are either not set forth in the federal
definition and/or are specifically excluded (“cocaine
overbreadth”).
16 UNITED STATES V. HOUSE
1) Accountablity Overbreadth
House points out that the conduct specifically delineated
in USSG § 4B1.2(b) covers only “the manufacture, import,
export, distribution, or dispensing of a controlled substance”
or the possession thereof with such intent; whereas the
Montana statutes (i.e., sections 45-2-302 and 45-9-101)
include a person who “sells, barters, exchanges, gives away,
or offers to sell, barter, exchange, or give away any
dangerous drug.” House argues that Application Note 1 of
the Commentary to § 4B1.2 improperly expands the
prohibited conduct to “include the offenses of aiding and
abetting, conspiring, and attempting to commit such
offenses.”
But as House recognized in both his sentencing
memorandum to the district court and in his opening brief
here, in Crum: (1) we “acknowledged that the commentary
to § 4B1.2 does not mention solicitation, even though it
expands the definition of ‘controlled substance offense’ to
include aiding and abetting, conspiring, and attempting to
commit such an offense,” and held that “the definition of
‘controlled substance offense’ in § 4B1.2 [nevertheless]
encompasses solicitation offenses,” 934 F.3d at 965; and
(2) we declined to reconsider our holding in Vea-Gonzales
that Application Note 1 of the Commentary to § 4B1.2 is
“perfectly consistent” with the text of § 4B1.2(b), Crum,
934 F.3d at 966. Because we are bound by Crum, we hold
that although Montana’s accountability statutes include
offers to engage in prohibited conduct, they are not rendered
categorically overbroad with respect to USSG §§ 4B1.2(b)
and 2K2.1(a).
UNITED STATES V. HOUSE 17
2) Cocaine Overbreadth
As to House’s cocaine overbreadth contention, he raises
new arguments on appeal that he did not present to the
district court. In his opening brief, House asserts that “[t]he
federal statutory definition of cocaine and the State of
Montana statutory definition of cocaine differ, and the State
of Montana’s definition is broader.” 5 But in his sentencing
memorandum to the district court, House made different and
more limited arguments.
Because House did not raise his current arguments at
sentencing, we review the district court’s sentencing
calculation for plain error as to those contentions. See
United States v. Wijegoonaratna, 922 F.3d 983, 991 (9th Cir.
2019). The first two elements under that analysis are: (1) “an
error that has not been intentionally relinquished or
abandoned,” and (2) the error is plain—“that is to say, clear
or obvious.” 6 Rosales-Mireles v. United States, 138 S. Ct.
5Montana Code Annotated section 50-32-224(1)(d) defines cocaine
as including derivatives of cocaine. The CSA’s definition of cocaine at
21 U.S.C. § 812(c) Schedule II(a)(4) excludes derivatives. The
applicable federal regulation, 21 C.F.R. § 1308.12(b)(4), includes
derivatives but excludes [123I]ioflupane, which is a cocaine derivative.
Thus, the Montana statutory definition of cocaine is broader than both
the CSA definition and the federal regulatory definition.
6
The third element of plain error review requires a showing that the
error affects substantial rights of the defendant, which ordinarily means
establishing “a reasonable probability that, but for the error, the outcome
of the proceeding would have been different.” Molina-Martinez v.
United States, 578 U.S. 189, 194 (2016) (internal quotation marks
omitted). “In most cases a defendant who has shown that the district
court mistakenly deemed applicable an incorrect, higher Guidelines
range has demonstrated a reasonable probability of a different outcome.”
Id. at 200.
18 UNITED STATES V. HOUSE
1897, 1904 (2018) (quoting Molina-Martinez, 578 U.S.
at 194). “An error cannot be plain where there is no
controlling authority on point and where the most closely
analogous precedent leads to conflicting results.”
Wijegoonaratna, 922 F.3d at 991 (quoting United States v.
De La Fuente, 353 F.3d 766, 769 (9th Cir. 2003)). The
question is whether the district court plainly erred when it
held that House’s 2013 cocaine conviction pursuant to
Montana Code Annotated sections 45-9-101 and 50-32-
224(1)(d) was a controlled substance offense as set forth in
USSG § 4B1.2(b). We conclude that it did not.
First, applying the categorical approach, the court must
determine whether the Montana statutory definition of
cocaine is a match with federal law. As we have explained,
under federal law, cocaine is defined by both statute and
regulation, and the Montana definition is broader than either
federal definition. 21 U.S.C. § 812(c) Schedule II(a)(4) does
not expressly include cocaine derivatives within its
definition (although it does expressly reference ecgonine
derivatives). See footnote 5, supra. 21 C.F.R.
§ 1308.12(b)(4) expressly includes cocaine (and ecgonine)
derivatives, but also expressly excludes [123I]ioflupane.
Montana Code Annotated section 50-32-224(1)(d) expressly
includes cocaine derivatives but does not expressly exclude
or mention [123I]ioflupane.
When the district court reached its decision that a
cocaine conviction under Montana Code Annotated sections
45-9-101 and 50-32-224(1)(d) could constitute a controlled
substance offense under § 4B1.2(b), there was no (and there
still is no) binding precedent to the contrary. 7 House was
7
Holliday II—which held that the Montana schedules as to cocaine
“are facially overbroad when compared with both the federal statutory
UNITED STATES V. HOUSE 19
sentenced on August 5, 2020. At that time, the only case to
have considered the issue was the unpublished decision in
United States v. Lasalle, 758 F. App’x 410 (9th Cir. 2019),
which held that it was not plain error for a court to look to
the federal regulatory definition of cocaine (which during the
relevant period was purportedly a categorical match with the
Montana statute) and concluded that the defendant’s prior
conviction under Montana Code Annotated sections 45-9-
101 and 50-32-224(1)(d) fell within § 4B1.2(b). See id. at
411–12.
Second, certain of the grounds for the district court’s
rulings were not rejected in binding precedent until after its
sentencing decision. For example, the district court had (as
had many other federal courts) compared the elements of the
state conviction with the federal law that existed at the time
of the state sentencing, rather than the federal statutes and
guidelines that existed at the time of the federal sentencing.
See, e.g., Martinez v. Attorney General, 906 F.3d 281, 287
(3d Cir. 2018) (holding that, although 21 C.F.R.
§ 1308.12(b)(4) currently expressly exempts [123I]ioflupane
from the list of schedule II substances, the court uses the list
at the time of the defendant’s prior state conviction, which
had not yet added that exclusion). Bautista overturned that
approach and held, “In imposing a sentence, the district court
must consider the sentencing guidelines range ‘that . . . [is]
in effect on the date the defendant is sentenced.’ 18 U.S.C.
§ 3553(a)(4)(A)(ii).” 989 F.3d at 703 (alterations in
original).
schedules and the federal regulatory schedules” and, thus, the cocaine
conviction therein was not a controlled substance offense—was issued
on March 3, 2021 and was unpublished. 853 F. App’x at 54 n.1.
20 UNITED STATES V. HOUSE
Accordingly, the district court did not commit plain error
with respect to the cocaine overbreadth issue when it held
that House’s 2013 cocaine conviction was a controlled
substance offense as set forth in USSG § 4B1.2(b).
IV. CONCLUSION
We reverse the district court’s sentencing enhancement
insofar as it rested on House’s 2007 marijuana conviction
and remand for resentencing. But the district court’s
determination that House’s 2013 cocaine conviction was a
qualifying prior controlled substance offense for purposes of
the § 4B1.2(b) sentencing enhancement was not plainly
erroneous.
AFFIRMED IN PART, REVERSED IN PART, AND
REMANDED FOR RESENTENCING.
GRABER, Circuit Judge, concurring:
I concur in the per curiam opinion but write separately to
explain my views concerning overbroad state statutes. In my
view, we have distinguished between overbreadth that is
“evident” from the statute’s text and overbreadth that is not
“evident” from the text.
The general rule is that a state law cannot be considered
broader than a federal law if the state law’s breadth is
imagined or theoretical; in other words, the overbreadth
must be real. See Gonzales v. Duenas-Alvarez, 549 U.S.
183, 193 (2007) (“[T]o find that a state statute creates a
crime outside the generic definition of a listed crime in a
federal statute requires more than the application of legal
imagination to a state statute’s language. It requires a
UNITED STATES V. HOUSE 21
realistic probability, not a theoretical possibility, that the
State would apply its statute to conduct that falls outside the
generic definition of a crime.” (emphasis added)).
But we have applied that rule in two ways. “[W]hen the
state statute’s greater breadth is evident from its text, a
defendant may rely on the statutory language to establish the
statute as overly inclusive.” United States v. Vidal, 504 F.3d
1072, 1082 (9th Cir. 2007) (en banc) (internal citations and
quotation marks omitted) (emphasis added), abrogated on
other grounds as recognized in United States v. Bautista,
989 F.3d 698, 704 (9th Cir. 2021); see also United States v.
Grisel, 488 F.3d 844, 847 (9th Cir. 2007) (en banc) (“[When
a] state statute explicitly defines a crime more broadly than
the generic definition, no legal imagination[] is required to
hold that a realistic probability exists that the state will apply
its statute to conduct that falls outside the generic definition
of the crime. The state statute’s greater breadth is evident
from its text.” (internal citations and quotation marks
omitted) (emphasis added)), abrogated on other grounds by
United States v. Stitt, 139 S. Ct. 399 (2018).
When the state law’s overbreadth is not “evident from its
text,” the party arguing for overbreadth must find a relevant
case establishing a “realistic probability” of overbroad
application. See Vidal, 504 F.3d at 1082 (“In the absence of
any case in which the state courts in fact did apply the statute
in the special (nongeneric) manner, this argument failed for
lack of evidence that such an application of the state statute
was a realistic probability [and] not a theoretical
possibility.”(internal citations and quotation marks omitted)
(emphasis added)).
It is under that framework that we decided United States
v. Bautista, 989 F.3d 698 (9th Cir. 2021). In Bautista, we
held that the state law was overbroad. The state law
22 UNITED STATES V. HOUSE
criminalized both attempted transportation of hemp and
attempted transportation of marijuana; but the federal law
did not criminalize hemp at all. Thus, because the state law’s
greater breadth was evident from the text, the state law barred
more than the federal law. Id. at 705. For that reason,
Bautista rested on the correct proposition that the state law’s
“greater breadth is evident from its text.” Id. (quoting Vidal,
504 F.3d at 1082).
In sum, Duenas-Alvarez expressed the general rule: a
state law’s breadth in categorical-approach cases always
must be realistically probable and cannot be theoretical or
imagined. 549 U.S. at 193. We have construed facially
overbroad statutes as meeting that bar whenever the state
statute’s overbreadth is “evident from its text.” When a
federal statute contains an express exception but the parallel
state statute contains no such exception, the difference
between them is “evident” from the text. In that situation,
no evidentiary examples are required to demonstrate a
realistic probability of prosecution. Put another way, when
a state law prohibits “X” and a federal law prohibits “X
except Y is not included,” it is “evident” from the text that
the state statute is overbroad, so it is not necessary to find a
case demonstrating that the state prosecutes “Y.”
CHRISTEN, Circuit Judge, concurring:
I
The government concedes that House’s prior marijuana
conviction should not count as a “controlled substance
offense” in the calculation of House’s sentencing guidelines
range, and I agree that the district court did not plainly err in
determining that his prior cocaine-related offense did
UNITED STATES V. HOUSE 23
qualify. But, shortly after the district court ruled, our court
suggested in an unpublished decision that Montana’s
definition of cocaine is categorically overbroad. See United
States v. Holliday, 853 F. App’x 53 (9th Cir. 2021)
(“Holliday II”). In my view, Holliday II’s categorical
analysis skipped an important step by taking the holdings
from United States v. Grisel 1 and United States v. Bautista 2
out of context.
I write separately because the complicated categorical
approach has proven inordinately time consuming—for
district courts and for circuit courts—and our court’s prior
consideration of Montana’s cocaine statute may result in
confusion regarding the correct Taylor 3 methodology. The
Holliday II majority concluded that: (1) Montana’s
definition of cocaine is “facially overbroad” because it
includes a substance expressly excluded from the federal
counterpart; and (2) the “varieties of cocaine” included in
Montana’s drug schedules are “alternative means of
committing a single crime, not alternative elements of
separate crimes.” 853 F. App’x at 54–55. The Holliday II
majority stopped short of considering whether there is “a
realistic probability, not a theoretical possibility,” 4 that
Montana would apply its definition of cocaine to conduct
that falls outside the federal definition. See Holliday II,
853 F. App’x at 54–55. Rather than engaging in this inquiry,
Holliday II prematurely ended its analysis after concluding
1
488 F.3d 844 (9th Cir. 2007) (en banc), abrogated on other
grounds as recognized by United States v. Stitt, 139 S. Ct. 399 (2018).
2
989 F.3d 698 (9th Cir. 2021).
3
Taylor v. United States, 495 U.S. 575 (1990).
4
Gonzales v. Duenas-Alvarez, 549 U.S. 183, 193 (2007).
24 UNITED STATES V. HOUSE
that the “overbreadth” of Montana’s statute was “evident
from its text.” Id. (quoting Bautista, 989 F.3d at 705).
II
The first step in the Taylor categorical approach requires
us to compare the elements of the state statute with those in
the federal counterpart to determine whether the state statute
sweeps in more conduct or, as in House’s case, criminalizes
more controlled substances, than the federal definition. See
United States v. Martinez-Lopez, 864 F.3d 1034, 1038 (9th
Cir. 2017). Even when there is a mismatch between the state
and federal statutes, Duenas-Alvarez teaches that to find the
state statute categorically broader than its federal counterpart
“requires a realistic probability, not a theoretical possibility,
that the State would apply its statute to conduct that falls
outside the generic definition of a crime.” 549 U.S. at 193.
Soon after the Supreme Court decided Duenas-Alvarez,
our en banc court in Grisel considered whether Oregon’s
burglary statute was a categorical match to the generic
offense. The Supreme Court had defined the federal offense
to require unlawful entry into, or remaining in, “a building
or structure[] with intent to commit a crime.” Grisel,
488 F.3d at 848 (quoting Taylor, 495 U.S. at 599). Oregon’s
burglary statute starkly differed from the federal offense
because it defined “building” to include “any booth, vehicle,
boat, aircraft or other structure adapted for overnight
accommodation of persons or for carrying on business
therein.” Id. at 850 (quoting Or. Rev. Stat. § 164.205(1)).
Grisel went on to recognize that the Oregon legislature had
“consciously defined” burglary to be broader than the federal
definition “by extending the statute to non-buildings,” id.,and cited Oregon case law that pinpointed the legislature’s
express intent to sweep in more conduct, id. at 850 n.4.
Under those circumstances—and consistent with Duenas-
UNITED STATES V. HOUSE 25
Alvarez—we concluded “[t]he state statute’s greater breadth
is evident from its text,” and “no ‘legal imagination’ is
required to hold that a realistic probability exists that
[Oregon would] apply its statute to conduct that falls outside
the generic definition.” Id. at 850 (citation omitted) (quoting
Duenas-Alvarez, 549 U.S. at 193). Grisel does not stand for
the proposition that Taylor’s categorical inquiry ends simply
because a textual comparison of a state statute’s elements
shows the state statute sweeps more broadly than its federal
counterpart.
Since Grisel, we have recognized a subset of cases
addressing state statutes that only impliedly criminalize more
conduct than their federal counterparts. Rather than
including more conduct or controlled substances, these
statutes do not contain an exclusion that appears in the
corresponding federal law. See, e.g., United States v. Vega-
Ortiz, 822 F.3d 1031, 1035–36 (9th Cir. 2016); United States
v. Burgos-Ortega, 777 F.3d 1047, 1054–55 (9th Cir. 2015).
Cases involving statutes of this type are particularly relevant
to House’s appeal because, like Montana’s definition of
cocaine, they involve statutes that are silent about certain
substances expressly excluded from the federal definition of
a controlled substance. See, e.g., Vega-Ortiz, 822 F.3d
at 1036 (describing California’s definition of
methamphetamine as impliedly overbroad even though it
does “not expressly include conduct not covered by the
generic offense, but rather is silent as to the existence of a
parallel [L-meth] exception.’” (alteration in original)
(emphasis added) (quoting Burgos-Ortega, 777 F.3d
at 1055)).
26 UNITED STATES V. HOUSE
Where a state statute is only impliedly overbroad, our
case law 5 requires that defendants identify “any case where
a defendant was in fact prosecuted or convicted” for the
impliedly included substance or conduct that the federal
definition expressly excludes. Burgos-Ortega, 777 F.3d
at 1054–55. This step determines whether the “theoretical
possibility[] that the State would apply its statute to conduct
that falls outside the generic definition” is a realistic one, as
the Supreme Court required in Duenas-Alvarez. 549 U.S. at
193.
Two of our cases are illustrative. Burgos-Ortega
involved a Washington state statute that criminalized, among
other things, distribution of a controlled substance. See
777 F.3d at 1052. Washington’s statute did not except
“administering” from the definition of “distribution,” but the
federal counterpart did. Id. We rejected Burgos-Ortega’s
argument that the state statute was “overbroad on its face”
merely because the state statute did not “expressly include
conduct not covered by the generic [federal] offense, but
rather [was] silent as to the existence of a parallel
administering exception.” Id. at 1055. Burgos-Ortega could
not point “to any case where a defendant was in fact
prosecuted or convicted for administering a drug under [the
state] statute,” and we upheld the district court’s sentencing
enhancement. Id.
A year later, we considered California’s definition of
methamphetamine in Vega-Ortiz. We first observed that
California’s definition was silent as to “L-meth,” a substance
the federal definition expressly excluded. See Vega-Ortiz,
822 F.3d at 1035–36. Citing Burgos-Ortega and Duenas-
Alvarez, we held that “to succeed on his claim[,] Vega-Ortiz
5
Holliday II was not published. See 853 F. App’x at 53.
UNITED STATES V. HOUSE 27
would need to show a ‘realistic probability’ that he would be
prosecuted under [the state statute] for possession of the
[federally] excluded product containing L-meth.” Id.
at 1036.
Like House’s case, United States v. Holliday, 853 F.
App’x 53 (9th Cir. 2021) (“Holliday II”), concerned
Montana’s definition of cocaine. Holliday II explained that
Montana’s statute impliedly includes “ioflupane” because it
makes no mention of that substance and ioflupane is
expressly excluded from the federal definition. Id. at 54. At
step one, Holliday II recognized the textual mismatch
between the state and federal definitions. Id. So far, so
good. But after the judicially noticeable documents showed
only that Holliday’s prior conviction was for selling
“cocaine,” the majority tripped up by concluding it was
“evident from [the] text” of the Montana statute that the state
definition of cocaine is “facially overbroad,” and ending its
analysis. 6 Id. at 54–55 (quoting Bautista, 989 F.3d at 705). 7
6
Judge Watford’s dissent in Holliday II recognized the disconnect
between the Holliday II majority’s conclusion and our precedent. His
dissent reasoned that Montana’s cocaine statute is the same type that was
at issue in Vega-Ortiz and Burgos-Ortega and that Montana’s definition
is overbroad “only if [a defendant shows] there is a realistic probability
of prosecution under Montana law for distribution of Ioflupane.” 853 F.
App’x at 56.
7
The Holliday II majority may have relied on a sentence from
Lopez-Aguilar v. Barr, 948 F.3d 1143 (9th Cir. 2020), which, if read
literally, suggests “the relative likelihood” that a state would apply its
statute to “nongeneric conduct is immaterial,” Holliday II, 853 F. App’x
at 55. That reading would be plainly inconsistent with Duenas-Alvarez.
Lopez-Aguilar and the case it cited, United States v. Valdivia-Flores,
876 F.3d 1201 (9th Cir. 2017), involved statutes that were akin to the one
at issue in Grisel, where “no ‘legal imagination’ [was] required” to
28 UNITED STATES V. HOUSE
To be sure, there are statutes like the burglary statute at
issue in Grisel where courts will have occasion to decide a
state law is so starkly overbroad that “no legal imagination
is required to hold that a realistic probability exists” the state
would apply its definition to a substance (or conduct) falling
outside of the generic definition. 488 F.3d at 850 (citations
omitted). But Grisel only required our court to recognize
that Oregon would apply its burglary statute to the unlawful
entry into vehicles, boats, or aircraft where the legislature
had expressly defined “building” to include vehicles, boats,
and aircraft. See 488 F.3d at 850. Given that circumstance,
it was indeed evident from the text of the statute that Oregon
would actually prosecute, as burglary, the unlawful entry
into vehicles, boats, or aircraft. Controlled substances
statutes are much less intuitive. Indeed, absent a degree in
pharmacology, it is doubtful there will be many judges in a
position to accurately predict from the text of a controlled
substances statute that a state would prosecute a particular
controlled substance. Cf. United States v. Rodriguez-
Gamboa, 972 F.3d 1148, 1151–53 (9th Cir. 2020)
(concluding California’s definition of methamphetamine
was not categorically overbroad, even though it included
“geometric isomers” and the federal definition did not,
because “unrebutted expert testimony” demonstrated
“geometric isomers of methamphetamine do not exist,” so
there was “no possibility of application of the state statute to
nongeneric conduct” (internal quotation marks omitted)).
recognize a “realistic probability” that the state would apply its statute in
the nongeneric manner, id. at 1208 (quoting Grisel, 488 F.3d at 850)
(distinguishing the federal “mens rea requirement of specific intent” and
Washington’s requirement of “mere[] knowledge”); Lopez-Aguilar,
948 F.3d at 1146–47 (recognizing Oregon’s definition of third-degree
robbery allowed consensual takings by deception whereas the federal
definition was limited to nonconsensual takings).
UNITED STATES V. HOUSE 29
This is why, even when a state statute sweeps in more
conduct or controlled substances, the complete Taylor
analysis includes the reality check the Supreme Court
introduced in Duenas-Alvarez to determine whether there is
a realistic probability a state would prosecute the possession
or distribution of a particular controlled substance. This step
can be particularly illuminating in cases involving impliedly
overbroad statutes. Expert testimony might establish that a
realistic probability does not exist; or, where a substance has
been removed from the federal schedule, the rationale relied
on by the federal government may be informative.
One member of our panel would decide that the
mismatch between Montana’s definition of cocaine and the
federal definition is “evident from the text” and end the
analysis there. In my view, there are two problems with this
approach. First, the nature of the categorical inquiry is such
that any mismatch between the state and federal elements
will always be evident from the text because the categorical
approach requires that we identify the elements of the
offense from the text of the state statute and compare them
to those in the federal counterpart. Second, Supreme Court
precedent requires that we consider whether there is a
realistic probability the state would actually prosecute the
overly broad portion of the statute. See Duenas-Alvarez,
549 U.S. at 193. My colleague treats this as one step, but in
my view it is necessarily two because the textual comparison
tells us only whether a state statute is overbroad; it tells us
nothing about whether the state would realistically prosecute
the substance (or conduct) included in the state statute.
A comparison of the elements of Montana’s statute with
those in the federal definition of cocaine shows that
Montana’s statute is impliedly broader because it does not
exclude ioflupane. Step two requires consideration of
30 UNITED STATES V. HOUSE
whether Montana would actually prosecute the distribution
of ioflupane, a substance the Food and Drug Administration
excepted from the federal definition because it is the active
ingredient in a product that “itself presents no practical
possibility of abuse, misuse, diversion or clandestine
production.” 8
III
I agree that the plain error standard applies to our review
of the district court’s analysis of House’s 2013 cocaine
conviction, and the parties agreed that the district court’s
application of a sentencing enhancement based on House’s
2007 marijuana conviction should be reversed. I therefore
concur in the court’s per curiam opinion.
WU, District Judge, concurring:
I. Introduction
I concur in the per curiam opinion but write separately to
specifically address the categorical/modified categorical
analysis as it relates to the cocaine overbreadth issue in the
context of the applicable Montana statute, i.e., Mont. Code
Ann. § 50-32-224(1)(d). The area is hopelessly confused,
and I suggest a modest solution. A brief overview of the law
8
Schedules of Controlled Substances: Removal of [123I]Ioflupane
from Schedule II of the Controlled Substances Act, 80 Fed. Reg. 31521-
01, 31523 (June 3, 2015). Ioflupane “is the active pharmaceutical
ingredient . . . in DaTscan,” which the FDA approved for use with
“patients with suspected Parkinsonian syndromes.” Id. at 31522–23.
According to the FDA,“DaTscan itself presents no practical possibility
of abuse, misuse, diversion or clandestine production.” Id.UNITED STATES V. HOUSE 31
as to that analysis in regards to the definitions of cocaine is
necessary and provided initially.
II. An Issue Stemming from the Varying Federal
Delineations of Cocaine
For purposes of the categorical/modified categorical
analysis, the Ninth Circuit has interpreted the term
“controlled substance” as used in USSG §§ 2K2.1(a) and
4B1.2(b) “to mean a substance listed in the Controlled
Substances Act (‘CSA’), 21 U.S.C. § 801 et seq.” United
States v. Bautista, 989 F.3d 698, 702 (9th Cir. 2021).
“[C]onstruing the phrase in the Guidelines to refer to the
definition of ‘controlled substance’ in the CSA—rather than
to the varying definitions of ‘controlled substance’ in the
different states—furthers uniform application of federal
sentencing law, thus serving the stated goals of both the
Guidelines and the categorical approach.” 1 Id. (citing to
United States v. Leal-Vega, 680 F.3d 1160, 1167 (9th Cir.
2012), and Taylor v. United States, 495 U.S. 575, 589
(1990)).
1
The goal of achieving a uniform application of federal sentencing
law in this area is initially vitiated by fact that there is a split amongst the
federal circuits as to whether the definition of “controlled substance” is
limited to federal law (i.e., the substances listed in the CSA) or whether
the definition is based on relevant state law. See Guerrant v. United
States, 142 S. Ct. 640 (2022) (Sotomayor, J., concurring in denial of
certiorari) (observing that the Second and Ninth Circuits “have turned to
federal law to define the term”; the First and Fifth Circuits “have not
directly resolved the question, but have indicated agreement with that
approach”; the Fourth, Seventh, Eighth and Tenth Circuits “define[]
what qualifies as a ‘controlled substance’ based on relevant state law”;
and the Sixth and Eleventh Circuits “have issued internally inconsistent
decisions on the question.”). Id. at 640 (citations omitted).
32 UNITED STATES V. HOUSE
In determining the federal demarcation of a particular
controlled substance, one initially examines the CSA—i.e.,
21 U.S.C. Chapter 13, Subchapter I. The CSA defines a
“controlled substance” as “a drug or other substance, or
immediate precursor, included in schedule I, II, III, IV, or V
of part B of this subchapter [i.e., 21 U.S.C. § 812].”
21 U.S.C. § 802(6). While various drugs are identified and
listed in the schedules, the actual definitions and/or
descriptions of the substances are delineated in a number of
different locations within the CSA and not just within the
schedules. See, e.g., 21 U.S.C. § 812(c), Schedule I(c)(10)
(listing “marihuana” as a Schedule I drug); 21 U.S.C.
§ 802(16) (containing a definition of “[t]he term
‘marihuana’”).
Additionally, 21 U.S.C. § 811(a) allows the United
States Attorney General, pursuant to the rulemaking
provisions of the Administrative Procedure Act (5 U.S.C.
§§ 551–59), to “add to such a schedule or transfer between
such schedules any drug or other substance” or “remove any
drug or other substance from the schedules . . . .” See also
21 U.S.C. § 812(c) (“Schedules I, II, III, IV, and V shall,
unless and until amended pursuant to section 811 of this title
[21 U.S.C. § 811], consist of the following drugs or other
substances, by whatever official name, common or usual
name, chemical name, or brand name designated . . . .”
(emphasis added, footnote omitted)). Therefore, in
determining whether a particular drug or its variants are
designated as federal controlled substances, one must also
review the relevant regulations promulgated by the Attorney
General. See 21 C.F.R. § 1308.02 (“Any term contained in
this part shall have the definition set forth in section 102 of
the Act (21 U.S.C. 802) or part 1300 of this chapter.”). The
Ninth Circuit has, on occasion, relied upon the federal
regulatory definitions of controlled substances when
UNITED STATES V. HOUSE 33
conducting a categorical analysis under Taylor. See, e.g.,
Coronado v. Holder, 759 F.3d 977, 988 Appendix 1 (9th Cir.
2014) (In engaging in the categorical analysis to determine
whether there was a match as to California law and the CSA,
the panel made comparisons between the state statutes and
the corresponding federal regulations in 21 C.F.R.
§§ 1308.11–1308.15.).
Turning to the various definitions of cocaine involved in
this case, it would appear that the Montana statutory
definition of cocaine is broader than both the CSA definition
(because the Montana statute includes derivatives of cocaine
whereas the CSA does not), and the federal regulatory
definition (because it does not specifically exclude
[123I]ioflupane 2—which is a cocaine derivative—whereas
21 C.F.R. § 1308.12(b)(4) does). 3 However, it would also
[ I]ioflupane is the active pharmaceutical ingredient in DaTscan,
2 123
“a single-dose, injectable diagnostic radiopharmaceutical,” which was
approved for use by the Food and Drug Administration in January 2011.
Schedules of Controlled Substances: Removal of [<123>I]Ioflupane
From Schedule II of the Controlled Substances Act, 80 Fed. Reg. 31521-
22 (June 3, 2015). “[123I]Ioflupane [was], by definition, a schedule II
controlled substance because it is derived from cocaine, a schedule II
substance, via ecgonine (a schedule II substance).” Id.3
Mont. Code Ann. § 50-32-224(1)(d) delineates the following
substances:
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 of them that is chemically
equivalent or identical with any of these substances,
except that these substances do not include
decocainized coca leaves or extraction of coca leaves,
34 UNITED STATES V. HOUSE
appear that the CSA and the federal regulatory definitions of
cocaine are likewise not a categorical match with each other.
21 U.S.C. § 812(c) Schedule II(a)(4) does not expressly
include cocaine derivatives within its definition (although it
does expressly reference ecgonine derivatives) nor does it
expressly exclude [123I]ioflupane. 21 C.F.R.
which extractions do not contain cocaine or ecgonine
....
The CSA at 21 U.S.C. § 812(c) Schedule II(a)(4) includes:
coca leaves, except coca leaves and extracts of coca
leaves from which cocaine, ecgonine, and derivatives
of ecgonine or their salts have been removed; cocaine,
its salts, optical and geometric isomers, and salts of
isomers; ecgonine, its derivatives, their salts, isomers,
and salts of isomers; or any compound, mixture, or
preparation which contains any quantity of any of the
substances referred to in this paragraph.
The applicable federal regulation, i.e., 21 C.F.R. § 1308.12(b)(4), states:
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), and
any salt, compound, derivative, or preparation thereof
which is chemically equivalent or identical with any of
these substances, except that the substances shall not
include:
(i) Decocainized coca leaves or extraction of
coca leaves, which extractions do not contain
cocaine or ecgonine; or
(ii) [123I]ioflupane.
UNITED STATES V. HOUSE 35
§ 1308.12(b)(4) expressly includes cocaine (and ecgonine)
derivatives, but also expressly excludes [123I]ioflupane.
The Ninth Circuit has not yet determined whether “the
definition of cocaine in the CSA, rather than the definition
in the corresponding regulation, should be the controlling
definition for the purposes of the Taylor analysis.” United
States v. Lasalle, 785 F. App’x 410, 412 (9th Cir. 2019); see
also United States v. Holliday, 853 F. App’x 53, 54 n.1 (9th
Cir. 2021) (noting the difference but not deciding whether
the “federal statutory schedules” or the “federal regulatory
schedules” are the “appropriate comparator” in regards to
“cocaine-related substances.”). There is also no precedent
as to what a court should do in the context of the categorical
analysis where the definition of a controlled substance in the
CSA differs from the definition in the corresponding federal
regulation.
In regards to cocaine, because the appropriate categorical
analysis under Taylor will differ depending upon whether
one compares the Montana statute with the CSA (where the
overbreadth rests on Mont. Code Ann. § 50-32-224(1)(d)’s
inclusion of cocaine derivatives in its definition) versus
comparing the Montana statute with 21 C.F.R.
§ 1308.12(b)(4) (where the overbreadth arises from the
latter’s express exclusion of [123I]ioflupane), it is essential to
select the appropriate comparator at the first step of the
analysis. Given that: (1) the schedules of controlled
substances in the CSA are to be updated annually, see
21 U.S.C. § 812(a); Coronado, 759 F.3d at 983; (2) the
“drugs and other substances” designated in the schedules
remain there “unless and until amended pursuant to section
811,” 21 U.S.C. § 812(c); and (3) 21 U.S.C. § 811(a)
authorizes the Attorney General to add, remove or transfer
substances between the schedules, I would hold that—where
36 UNITED STATES V. HOUSE
there is a difference in the delineation of a substance between
the CSA and a subsequent regulation promulgated by the
Attorney General—the latter controls for purposes of the
categorical analysis.
III. The Appropriate Procedure Where There Is
Overbreadth as Between the Federal Definition of a
Controlled Substance and the State Definition
In their concurrences, Judges Graber and Christen assert
that, where there is overbreadth between the federal and state
definitions of a controlled substance, the correct procedure
(regarding whether and when one should consider the
realistic probability factor from Gonzales v. Duenas-
Alvarez, 549 U.S. 183, 193 (2007)) is dependent upon
whether one characterizes the overbreadth as being
“explicit/evident” versus “implied/implicit.” I find that step
ambiguous and unnecessary in regards to the differing
articulations of cocaine in this case and would simply apply
the Duenas-Alvarez realistic probability factor regardless.
First, where the issue arises from the differing
delineations of a controlled substance in statutes and/or
regulations, one is not engaged in the comparison of “the
elements of the crime of conviction with the elements of the
‘generic’ version of the listed offense—i.e., the offense as
commonly understood.” Mathis v. United States, 136 S. Ct.
2243, 2247 (2016). Thus, the reasoning and holdings of
cases such as United States v. Grisel, 488 F.3d 844, 847 (9th
Cir. 2007) (en banc), abrogated on other grounds by United
States v. Stitt, 139 S. Ct. 399 (2018)—which employ the
notion of a state law’s overbreadth being evident or explicit
from its text in that process—are not applicable here.
Second, in the context of comparing Mont. Code Ann.
§ 50-32-224(1)(d) with 21 C.F.R. § 1308.12(b)(4), the
UNITED STATES V. HOUSE 37
resulting overbreadth arises solely because in 2015 the
Attorney General expressly excepted [123I]ioflupane from
the regulatory delineation of cocaine. It is unclear on what
basis one would characterize that particular overbreadth as
being “evident,” “explicit,” “implied,” or “implicit.”
Third, the Attorney General has an annual opportunity to
modify the definition of a particular drug in the CSA’s
schedules of controlled substances. The unintended
consequence of the exercise of this authority may be the
wholesale exclusion of prior convictions that were based
upon the affected drug for purposes of USSG § 4B1.2(b),
unless state legislatures immediately amend their definitions
of the substance to conform with the new federal regulatory
definition. The present case typifies the problem. There
previously was a categorical match as to cocaine between the
federal regulation and the Montana statute. However, in
2015, the Attorney General specifically excluded from that
substance’s description “[123I]ioflupane”—the active
pharmaceutical ingredient in a “single-dose, injectable
diagnostic radiopharmaceutical for use in hospital settings
with specialized gamma cameras” for treatment of patients
with Parkinson disease where the drug “presents no practical
possibility of abuse, misuse, diversion or clandestine
production.” 80 Fed. Reg. 31522-23. The Taylor
categorical analysis’s goal of uniform application of federal
sentencing law would not be furthered in any way by a
finding that prior state cocaine convictions are no longer
“controlled substance offenses” merely because of the
discrepancy created by 2015 amendment to the regulation.
Fourth, the Ninth Circuit has applied the Duenas-Alvarez
realistic probability criterion in a similar situation where
there was overbreadth between a state statutory definition of
a drug and its federal analogue. United States v. Rodriguez-
38 UNITED STATES V. HOUSE
Gamboa, 946 F.3d 548 (9th Cir. 2019) (“Rodriguez-Gamboa
I”), involved a state statute (i.e., Cal. Health & Safety Code
§ 11378) which prohibited possessing for sale any controlled
substance that was “specified” in § 11055(d), which
included “[m]ethamphetamine, its salts, isomers, and salts of
its isomers.” Cal. Health & Safety Code § 11033 provided
that “the term ‘isomer’ includes optical and geometrical
(diastereometric) isomers.” Id. at 551–52. The federal
statute also prohibited the possession for sale of
“methamphetamine, including its salts, isomers, and salts of
isomers,” but stated that the “term ‘isomer’ means the optical
isomer.” Id. (referencing 21 U.S.C. §§ 802(14),
812 Schedule II(c), Schedule III(a)(3)). Citing to the state
statutes’ inclusion of geometrical isomers of
methamphetamine which were not included in the federal
statute, the defendant-appellee argued that the “textual
distinction” ended the categorical analysis because the “state
statute’s greater breadth is evident from its text” and hence
“no ‘legal imagination’ is required to hold that a realistic
probability exists that the state will apply its statute to
conduct that falls outside the generic definition of the
crime.” Id. at 552 (quoting Grisel, 488 F.3d at 850). In
response, the Government asserted that “the geometric
isomer of methamphetamine does not exist” and, citing to
Duenas-Alvarez, argued that, despite the difference in the
statutes’ respective texts, it was still necessary to show “a
realistic probability, not a theoretical possibility, that the
State would apply its statute to [the alleged] conduct . . . .”
Id. The panel in Rodriguez-Gamboa I agreed; but, because
the district court had not resolved the factual issue of the
existence of geometric isomers of methamphetamine, the
matter was remanded for that limited purpose. Id. at 552–
53.
UNITED STATES V. HOUSE 39
Upon the return of case to the circuit, the panel made
reference to the Supreme Court’s indication in Moncrieffe v.
Holder, 569 U.S. 184 (2013), that Duenas-Alvarez’s
reasonable probability criterion should be applied even
where there is a readily apparent overbreadth between the
federal statute and its state counterpart. See United States v.
Rodriguez-Gamboa, 972 F.3d 1148, 1153–54 (9th Cir.
2019). As stated in Moncrieffe:
Finally, the Government suggests that our
holding will frustrate the enforcement of
other aggravated felony provisions, like
§1101(a)(43)(C), which refers to a federal
firearms statute that contains an exception for
“antique firearm[s],” 18 U.S.C. §921(a)(3).
The Government fears that a conviction
under any state firearms law that lacks such
an exception will be deemed to fail the
categorical inquiry. But Duenas-Alvarez
requires that there be “a realistic probability,
not a theoretical possibility, that the State
would apply its statute to conduct that falls
outside the generic definition of a crime.”
549 U.S., at 193. To defeat the categorical
comparison in this manner, a noncitizen
would have to demonstrate that the State
actually prosecutes the relevant offense in
cases involving antique firearms.
569 U.S. at 205–06.
In conclusion, I would apply the Duenas-Alvarez’s
reasonable probability factor (as further considered in
Moncrieffe) in initially determining whether the definition of
cocaine in Mont. Code Ann. § 50-32-224(1)(d) is a
40 UNITED STATES V. HOUSE
categorical match with its delineation in 21 C.F.R.
§ 1308.12(b)(4).