Jonathan Aguirre-Zuniga v. Merrick B. Garland ( 2022 )

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 21-1201
JONATHAN AGUIRRE-ZUNIGA,
Petitioner,
v.
MERRICK B. GARLAND, Attorney General of the United States,
Respondent.
____________________
Petition for Review of an Order of
the Board of Immigration Appeals.
No. A089-508-923
____________________
ARGUED NOVEMBER 2, 2021 — DECIDED JUNE 16, 2022
____________________
Before SYKES, Chief Judge, FLAUM and JACKSON-AKIWUMI,
Circuit Judges.
JACKSON-AKIWUMI, Circuit Judge. Jonathan Aguirre-Zun-
iga became a lawful permanent resident of the United States
in 2007. Approximately ten years later, he pled guilty to de-
livery of methamphetamine in Indiana. The Department of
Homeland Security concluded that his conviction was an ag-
gravated felony subjecting him to deportation, and the
2 No. 21-1201
Immigration Judge (IJ) and the Board of Immigration Appeals
(BIA) agreed.
The question before the Court is whether the Indiana law
prohibiting the delivery of methamphetamine criminalizes
more conduct than the corresponding federal law given that
Indiana defines “methamphetamine” in a way federal law
does not. Aguirre-Zuniga’s freedom to remain in the United
States hangs in the balance. For when a state statute is broader
than its federal counterpart, a conviction under that statute
cannot trigger a noncitizen’s deportation. We hold that
Aguirre-Zuniga’s conviction is not an aggravated felony for
purposes of removal because the statute of his conviction is
facially overbroad. We therefore grant Aguirre-Zuniga’s peti-
tion, vacate the BIA’s decision, and remand for further pro-
ceedings.
I
Aguirre-Zuniga’s family immigrated from Mexico to the
United States when he was three years old. He resides in In-
diana, where he has lived since he was eight years old and
where he is now raising his own six-year-old daughter, an
American citizen. He became a lawful permanent resident fif-
teen years ago. His primary language is English, and he has
visited Mexico only three times since emigrating as a toddler.
In November 2018, Aguirre-Zuniga pled guilty to one
count of dealing methamphetamine under Indiana Code § 35-
48-4-1.1 (the “Indiana Statute”). 1 Approximately one year
1 The state court sentenced Aguirre-Zuniga to 12 years—four years in
prison, four years in a community corrections program, and four years of
probation. The prison term was suspended. The state court later issued an
arrest warrant for Aguirre-Zuniga after he “failed to report to probation
No. 21-1201 3
later, the Department of Homeland Security sought to remove
him to Mexico. The agency asserted that his conviction quali-
fied as an aggravated felony; therefore, he was subject to re-
moval under 8 U.S.C. § 1227(a)(2)(A)(iii). Aguirre-Zuniga
filed a motion to terminate the proceedings. He argued that
his conviction did not qualify as an aggravated felony because
the Indiana statute was overbroad: it criminalized optical, po-
sitional, and geometric isomers of methamphetamine, while
the corresponding federal offense criminalized only optical
isomers. 2
The IJ denied the motion to terminate, and Aguirre-Zun-
iga filed a motion for reconsideration. In denying the latter
motion, the IJ reasoned that although the Indiana Statute was
“facially overbroad,” Aguirre-Zuniga was nonetheless re-
movable because he had not demonstrated under the “realis-
tic probability” test that the state had ever prosecuted a case
based on positional isomers of methamphetamine.
The BIA affirmed the IJ’s decision. The BIA stated that the
categorical approach—used to determine whether a convic-
tion is an aggravated felony for immigration purposes—fo-
cuses on the minimum conduct required to satisfy the ele-
ments of the state statutory offense. But the BIA held that
Aguirre-Zuniga still had to show 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.”
According to the BIA, because Aguirre-Zuniga did not show
that “the State court actually applied the statute to an offense
due to being detained at an I.C.E. detention center” as part of the admin-
istrative proceedings at issue here.
2 Aguirre-Zuniga does not discuss geometric isomers in his petition.
4 No. 21-1201
involving a substance that is not federally controlled,” his
conviction counts as an aggravated felony. Aguirre-Zuniga
timely petitioned this Court for review of the BIA’s decision.
II
Aguirre-Zuniga’s petition raises a question of law—
whether the Indiana Statute is overbroad—therefore jurisdic-
tion is proper. 8 U.S.C. § 1252(a)(2)(D). We review this issue
de novo. Garcia-Martinez v. Barr, 921 F.3d 674, 681 (7th Cir.
2019). Because the BIA affirmed the IJ’s decision but provided
its own analysis, we review both decisions. Dominguez-Pulido
v. Lynch, 821 F.3d 837, 841 (7th Cir. 2016).
A. The Categorical Approach
Under the Immigration and Nationality Act (INA), the De-
partment of Homeland Security may remove noncitizens for
a variety of reasons, including if they commit an “aggravated
felony at any time after admission” to the United States. 8
U.S.C. § 1227(a)(2)(A)(iii).
When the government seeks to remove a noncitizen under
this statute, courts “employ a categorical approach by looking
to the statute … of conviction, rather than to the specific facts
underlying the crime.” Esquivel-Quintana v. Sessions, 137 S. Ct.
1562, 1568 (2017) (citation omitted). In this analysis, courts de-
termine the minimal conduct criminalized by the state statute
at the time of conviction by comparing the elements of the
state statute with that of the federal analog. Shular v. United
States, 140 S. Ct. 779, 783 (2020) (citation omitted); Mellouli v.
Lynch, 575 U.S. 798, 808 (2015) (determining minimum con-
duct at the time of petitioner’s conviction). When “the [state]
statute is categorically broader than the federal definition” on
its face, the conviction is not an aggravated felony. United
No. 21-1201 5
States v. Ruth, 966 F.3d 642, 647 (7th Cir. 2020), cert. denied 141
S. Ct. 1239 (2021); United States v. De La Torre, 940 F.3d 938,
951–52 (7th Cir. 2019).
The Supreme Court has divided the categorical approach
into two distinct methodologies, which we have previously
called the “generic-offense” method and the “conduct-based”
method. Ruth, 966 F.3d at 646 (citing Shular, 140 S. Ct. at 783).
The generic-offense method applies to statutes invoking com-
mon crimes, like burglary, and requires courts “to come up
with a ‘generic’ version of a crime—that is, the elements of
‘the offense as commonly understood.’” Id. The conduct-
based method, on the other hand, applies to statutes “that do
not reference a certain offense, but rather ‘some other crite-
rion’ as the measure for prior convictions.” Id. For example,
where a noncitizen is subject to removal for prior convictions
involving fraud or deceit, courts “look[] to whether the prior
offense’s elements ‘necessarily entail fraudulent or deceitful
conduct’ as the appropriate measure.” Id.
If the plain language of the state statute is ambiguous or
has indeterminate reach, courts then turn to the “realistic
probability” test, which acts as a “backstop.” Hylton v. Ses-
sions, 897 F.3d 57, 63 (2d Cir. 2018) (citation omitted); Salmoran
v. Attorney General, 909 F.3d 73, 81–82 (3d Cir. 2018). Under
this test, the petitioner “must at least point to [their] own case
or other cases in which the state courts in fact did apply the
statute in the special (nongeneric) manner for which [they] ar-
gue[].” Gonzales v. Duenas-Alvarez, 549 U.S. 183, 193 (2007).
In the agency proceedings below, the government as-
serted that even when a statute is facially overbroad under the
categorical approach, noncitizens must still satisfy the realis-
tic probability test. On appeal, the government wisely
6 No. 21-1201
concedes that courts first apply the categorical approach and
look to realistic probability only if the statute is ambiguous.
Our holdings in De La Torre and Ruth make this clear. We
applied the categorical approach and concluded that the state
statutes at issue were overbroad. Ruth, 966 F.3d at 647; De La
Torre, 940 F.3d at 951. The government raised “theoretical”
challenges to this view in both cases, which we rejected. See
Ruth, 966 F.3d at 648; De La Torre, 940 F.3d at 952. In De La
Torre, the government argued that the statute was not over-
broad because “geometric isomers of methamphetamine do
not exist in the real world, and thus the [federal and state]
statutes actually mirror each other.” 940 F.3d at 951. We ex-
plained that this argument was irrelevant “when the plain
language chosen by the Indiana legislature dictates that the
Indiana statute is categorically broader than the federal defi-
nition of felony drug offense.” Id. at 952. Likewise, the gov-
ernment suggested in Ruth that the state statute at issue was
coextensive with federal law because “positional isomers of
cocaine [do not] exist in the drug trade.” 966 F.3d at 648. We
noted that “[i]t is not the province of the judiciary to rewrite
Illinois’s statute to conform to a supposed practical under-
standing of the drug trade.” Id. We then held that when “the
state statute of conviction is plain and intentional, our job is
straightforward: we compare the state statute to the federal
recidivism statute at issue and ask only if the state law is the
same as or narrower than federal law.” Id.
To the extent there is any room for doubt in our case law,
we reaffirm our statement in Ruth: If the statute is overbroad
on its face under the categorical approach, the inquiry ends.
Id. After applying the categorical approach, if the court deter-
mines that the statute is ambiguous or has indeterminate
No. 21-1201 7
reach, only then will the court turn to the realistic probability
test. See Gonzalez v. Wilkinson, 990 F.3d 654, 660 (8th Cir. 2021)
(citation omitted) (realistic probability test applies to “‘con-
duct that falls outside the generic definition of a crime [and]
operates as a backstop when a statute has indeterminate
reach’”); Swaby v. Yates, 847 F.3d 62, 66 (1st Cir. 2017) (realistic
probability test is a “sensible caution against crediting specu-
lative assertions regarding the potentially sweeping scope of
ambiguous state law crimes”).
B. The Indiana Statute
Having clarified the proper analysis, we turn to the Indi-
ana Statute. The INA defines “aggravated felony” to include
“illicit trafficking in a controlled substance (as defined in sec-
tion 802 of Title 21).” 8 U.S.C. § 1101(a)(43)(B). This immigra-
tion statute reaches felony convictions under the federal Con-
trolled Substances Act or a state statute “only if it proscribes
conduct punishable as a felony under that federal law.”
Moncrieffe v. Holder, 569 U.S. 184, 188 (2013) (citation omitted).
We therefore apply the conduct-based method of the categor-
ical approach and look to see if the Indiana Statute covers sub-
stances not prohibited under federal law. See Ruth, 966 F.3d at
646–47 (citation omitted) (applying the conduct-based
method to 21 U.S.C. § 841(b)(1)(C)’s sentencing enhancement
and comparing the definitions of cocaine under Illinois and
federal law).
Under federal law, methamphetamine is a Schedule II or
III controlled substance that includes “its salts, isomers, and
salt of isomers.” 21 U.S.C. §§ 802(6), 812, Schedule II(c), Sched-
ule III(a)(3). Under federal law, “isomer” of methampheta-
mine only refers to “the optical isomer.” 21 U.S.C. § 802(14).
8 No. 21-1201
The Indiana Statute provides that someone commits a fel-
ony when they “knowingly or intentionally deliver[] … meth-
amphetamine, pure or adulterated.” Ind. Code § 34-48-4-
1.1(a)(1)(A). The government states—and Aguirre-Zuniga
does not contest—that delivery of a controlled substance in
Indiana is analogous to trafficking under federal law. Sched-
ule II of the Indiana Code criminalizes “[m]ethamphetamine,
including its salts, isomers, and salts of its isomers.” Ind. Code
§ 34-48-2-6(d)(2). The Indiana legislature did not define “iso-
mer” at the time of Aguirre-Zuniga’s conviction. The sole
question for this Court, therefore, is whether, at the time of
Aguirre-Zuniga’s conviction, the definition of “methamphet-
amine” was broader under the Indiana Statute than federal
law.
We analyzed an Indiana statute like the one at issue here
in De La Torre. The defendant there was convicted of dealing
methamphetamine under § 35-48-4-2. After looking to the
definition of methamphetamine in Schedule II, we held that
the statute was overbroad “[b]ecause the federal definition of
methamphetamine includes only its optical isomers whereas
the Indiana definition includes something more than just op-
tical isomers of methamphetamine.” 940 F.3d at 951.
Aguirre-Zuniga argues that De La Torre directly applies to
his case, but that is not so easily done. First, the statute in De
La Torre (§ 35-48-4-2) is not the one at issue here (§ 35-48-4-
1.1). It is not a foregone conclusion that De La Torre controls.
But second and more importantly, the Indiana legislature
amended its criminal code in 2006 to specifically carve out
methamphetamine crimes. Originally, methamphetamine-
dealing crimes fell under § 35-48-4-1, which criminalized the
delivery of “cocaine, or a narcotic drug, or methamphet-
No. 21-1201 9
amine, pure or adulterated, classified in schedule I or II.” Ind.
Code § 35-48-4-1 (2000). The Indiana legislature later excised
methamphetamine from this statute and criminalized it under
a new statute—the present Indiana Statute. See Ind. Legis.
Serv. P.L. 151-2006, §§ 22–23 (July 1, 2006).
Notably absent from the new statute is the phrase “classi-
fied in schedule I or II [of the Indiana Code],” which was pre-
sent in the De La Torre statute. See 940 F.3d at 950–51 (quoting
Ind. Code § 35-48-4-2(a) (2000)). Aguirre-Zuniga argues that
we should nonetheless refer to Schedule II again since that is
the only place in the Indiana Code that defines “methamphet-
amine.” Once we do so, Aguirre-Zuniga asks us to take note
that the Indiana Code’s use of the term “isomer” for metham-
phetamine in Schedule II included optical and positional iso-
mers at the time of his conviction, while the federal statute
covers only optical isomers.
Courts should read statutory provisions in the context of
surroundings provisions. Util. Ctr., Inc. v. City of Ft. Wayne,
868 N.E.2d 453, 457 (Ind. 2007); see Mellouli, 575 U.S. at 809
(citation omitted) (“Statutes should be interpreted ‘as a sym-
metrical and coherent regulatory scheme.’”). As noted above,
the only definition in the Indiana Code regarding metham-
phetamine appears in Schedule II, and at the time of Aguirre-
Zuniga’s conviction, there was no reference to Schedule II and
therefore no applicable definition of “isomer.”
The plain language of a statute is “the best evidence” of
the legislature’s intent. De La Torre, 940 F.3d at 951 (citations
omitted). An “isomer” is a substance that is “[c]omposed of
the same elements in the same proportions, and having the
same molecular weight, but forming different substances,
with different properties (owing to the different grouping or
10 No. 21-1201
arrangement of the constituent atoms).” See “Isomer” and
“Isomeric,” Oxford English Dictionary, Oxford Univ. Press (2d
ed. 1989), https://www.oed.com/oed2/00121969. Metham-
phetamine has optical and positional isomers, and metham-
phetamine itself exists in two isomeric forms, l-methamphet-
amine and d-methamphetamine, which themselves can be
combined into a potential third iteration known as a “racemic
mixture,” dl-methamphetamine. 3
With other drugs, the Indiana legislature criminalized
only certain types of isomers in Schedule I and other parts of
Schedule II. See, e.g., Ind. Code §§ 35-48-2-4(d)(31) (covering
Schedule I THC), 35-48-2-6(d)(1) (covering amphetamine).
The definition of methamphetamine in Schedule II, however,
does not have a similar limitation on the types of isomers. Be-
cause the Indiana legislature chose to limit the types of iso-
mers defining other drugs but did not do so with metham-
phetamine, we must read the schedules to define metham-
phetamine as including at least optical and positional iso-
mers. See De La Torre, 940 F.3d at 951 (citation omitted) (“It is
a general rule of statutory construction that ‘when the legisla-
ture uses certain language in one part of the statute and
3 Jane Carlisle Maxwell & Mary-Lynn Brecht, Methamphetamine: Here We
Go Again?, 36 Addictive Behaviors 1168, 1169 (2011); Douglas A. Morris,
Methamphetamine: Types, Forms, Effects, and the Federal Sentencing Guide-
lines, 32 The Champion 20, 21 (2009); Nat’l Ctr. for Biotechnology Info.,
“PubChem Compound Summary for CID 10836, Methamphetamine,”
PubChem, https://pubchem.ncbi.nlm.nih.gov/compound/Methampheta-
mine; see also United States v. Bogusz, 43 F.3d 82, 88–89 (3d Cir. 1994), super-
seded by regulation, U.S.S.G. § 2D1.1, amend. 518, as recognized in United
States v. DeJulius, 121 F.3d 891, 894 (3d Cir. 1997).
No. 21-1201 11
different language in another, the court assumes different
meanings were intended.’”).
Moreover, as of July 1, 2020, the Indiana Code now defines
“isomer” for methamphetamine as “an optical isomer.” Ind.
Code § 35-48-1-17.4(a). But at the time of Aguirre-Zuniga’s
conviction, that definition did not exist. By narrowing the def-
inition of “isomer” with this new provision, the Indiana leg-
islature recognized that the term was broader before 2020. Cf.
McCammon v. Ind. Dept. of Fin. Inst., 973 F.2d 1348, 1352 (7th
Cir. 1992) (citing K. v. G., 426 N.E.2d 129, 134 (Ind. Ct. App.
1981) and Van Orman v. State, 416 N.E.2d 1301, 1305 (Ind. Ct.
App. 1981)) (noting that Indiana recognizes the “rule of stat-
utory construction that the amendment of a statute, absent
clear intent to the contrary, raises the presumption that the
legislature intended to change the law.”).
The government, on the other hand, sees the Indiana leg-
islature’s omission of the language referencing the schedules
in 2006 as critical to its position. Without this language, the
government argues, the Indiana Statute is merely silent as to
what isomers, if any, it criminalizes. In the government’s
view, because the Indiana Statute does not include an explicit
reference to the schedules, the statute does not cover any iso-
mers, so the statute is not broader than federal law.
The government’s view, however, begs the question: How
does Indiana law define “methamphetamine”? The govern-
ment’s brief is mum on the issue. And, when asked at oral
argument, the government responded that “meth means
meth.” But that recursive logic does not comport with the
chemistry. Methamphetamine itself is comprised of two opti-
cal isomers. If the Indiana Statute does not cover any isomers,
it arguably would not reach methamphetamine itself. Such a
12 No. 21-1201
view would render the Indiana Statute impotent—a criminal
statute that criminalizes nothing. The government’s position
would have us drive the Indiana Statute into a no man’s land.
We decline to do so. The definition of methamphetamine
from Schedule II proscribes the scope of the Indiana Statute.
III
Because there are optical and positional isomers of meth-
amphetamine, and the Indiana legislature chose not to limit
the Indiana Statute to optical isomers at the time of Aguirre-
Zuniga’s conviction, “Indiana’s generic use of ‘isomer’ in re-
lation to methamphetamine must be broader than optical iso-
mers.” De La Torre, 940 F.3d at 951. Section 35-48-4-1.1 was fa-
cially overbroad at the time of Aguirre-Zuniga’s conviction;
thus, it does not qualify as an aggravated felony under the
INA. We therefore GRANT Aguirre-Zuniga’s petition, VACATE
the BIA’s decision, and REMAND the matter to the BIA for fur-
ther proceedings consistent with this opinion.