Court Opinion

ID: 6113005
Source: CourtListenerOpinion
Date Created: 2022-01-26 22:01:31.848205+00
Date Added: 2024-06-11T08:59:49.267000
License: Public Domain

USCA11 Case: 19-13908     Date Filed: 01/26/2022       Page: 1 of 16

                                                        [PUBLISH]
                            In the
         United States Court of Appeals
                 For the Eleventh Circuit

                  ____________________

                         No. 19-13908
                  ____________________

SOLOMON CHAMU,
                                                         Petitioner,
versus
U.S. ATTORNEY GENERAL,
                                                       Respondent.

                  ____________________

            Petition for Review of a Decision of the
                 Board of Immigration Appeals
                   Agency No. A206-236-525
                   ____________________

Before BRANCH, GRANT, and BRASHER, Circuit Judges.
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2                       Opinion of the Court               19-13908

GRANT, Circuit Judge:
       Mexican national Solomon Chamu entered the United
States without inspection and subsequently committed several
crimes. When the government eventually placed him in removal
proceedings, he applied for cancellation of removal—a form of
discretionary relief that allows otherwise removable persons a
chance to stay in the country. But that limited relief is unavailable
to anyone convicted of an offense “relating to a controlled
substance” as defined by federal law. 8 U.S.C. §§ 1229b(b)(1)(C),
1182(a)(2)(A)(i)(II), 1227(a)(2)(B)(i). And one of the offenses that
Chamu had committed was cocaine possession under Florida law.
        Chamu argues that his conviction does not bar cancellation
because Florida’s cocaine possession statute covers more conduct
than its federal counterpart and is therefore not “related to” a
federally controlled substance. He offers two reasons this is true:
first, the state’s definition of cocaine extends to substances not
prohibited under federal law, and second, Florida’s possession law
does not require knowledge that the substance is illegal. We
disagree. Because Chamu has not met his burden of showing that
Florida’s cocaine statute covers more substances than the federal
statute, his conviction prevents cancellation of removal.
                                 I.
       Chamu was born in Mexico and entered the United States
without inspection in 1990. Thirteen years later, he was arrested
for and pleaded guilty to cocaine possession under Florida Statute
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19-13908                Opinion of the Court                         3

§ 893.13(6)(a). And fourteen years after that, he was ordered to
appear in a removal proceeding. See 8 U.S.C. § 1182(a)(6)(A)(i).
Chamu conceded that removal was proper. But he also applied for
cancellation of his removal, alleging that his mother and children
would suffer exceptional hardship if it were carried out.
       Cancellation is a form of discretionary relief allowing certain
immigrants who are otherwise removable, but who also have an
exceptional reason to remain in the United States, to do so. See 8
U.S.C. § 1229b(b). Good behavior is an essential prerequisite to
this relief. One limitation is for drug crimes; cancellation is
unavailable for those who have been convicted of a state offense
“relating to a controlled substance (as defined in section 802 of title
21)” of the United States Code. 8 U.S.C. §§ 1229b(b)(1)(C),
1182(a)(2)(A)(i)(II), 1227(a)(2)(B)(i). Section 802, in turn, defines
“controlled substance” as any substance included in one of five
federal controlled substance schedules. 21 U.S.C. § 802(6). A
conviction of an offense “relating to” one of those controlled
substances makes an alien ineligible for cancellation of removal.
See 8 U.S.C. §§ 1229b(b)(1)(C).
       Recognizing that his Florida cocaine possession conviction
would pose a problem for his cancellation request, Chamu
attempted to have it vacated in state court while his application was
pending before an immigration judge. After that strategy
predictably failed, Chamu shifted his approach, arguing that the
Florida statute was too broad to bar his cancellation request
because Florida considers some substances to be cocaine that the
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4                      Opinion of the Court                19-13908

federal government does not. He also claimed that the Florida
statute was too broad because it covered more states of mind than
its federal counterpart—that is, the Florida possession statute alone
presumes that a defendant knows a possessed substance is illegal,
whereas federal law requires proof of knowledge.                  The
immigration judge rejected Chamu’s contentions and found him
ineligible for cancellation.
       With a declaration from a chemistry expert in hand, Chamu
repeated his overbreadth argument in front of the Board of
Immigration Appeals, placing particular weight on the textual
differences between the state and federal statutory definitions of
cocaine. He also repeated his mens rea argument.
       The Board dismissed Chamu’s appeal. It accepted for the
sake of argument that his expert’s declaration was accurate, and
thus that the Florida and federal definitions of cocaine weren’t a
perfect match. But it concluded that the mismatch made no
difference. To prevail, Chamu needed to show “a realistic
probability, not a theoretical possibility,” that the Florida statute
covered more than its federal counterpart. See Gonzales v.
Duenas-Alvarez, 549 U.S. 183, 193 (2007). And while Chamu might
have shown a theoretical difference in statutory scope, the Board
concluded that he had not shown a realistic probability that the
Florida statute would be enforced more broadly. The Board also
concluded that the federal statutes at issue contained no mens rea
requirement. Chamu petitions for review of the Board’s decision.
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19-13908               Opinion of the Court                       5

                                II.
       We review questions of law raised in a petition for review of
a Board of Immigration Appeals decision de novo. 8 U.S.C.
§ 1252(a)(2)(D); Choizilme v. U.S. Att’y Gen., 886 F.3d 1016, 1022
(11th Cir. 2018). But we review the Board’s findings of fact for
substantial evidence, meaning that we must affirm the Board’s
findings if they are “supported by reasonable, substantial, and
probative evidence on the record considered as a whole.”
Kazemzadeh v. U.S. Att’y Gen., 577 F.3d 1341, 1351 (11th Cir. 2009)
(quotation omitted). We consider only issues the Board actually
reached, and because the Board did not expressly adopt the
immigration judge’s decision or rely on its reasoning, we review
only the Board’s decision. See Gonzalez v. U.S. Att’y Gen., 820
F.3d 399, 403 (11th Cir. 2016).
                                III.
       Chamu is ineligible for cancellation if he has been convicted
of an offense relating to a controlled substance banned under
federal law. See 8 U.S.C. §§ 1229b(b)(1)(C), 1182(a)(2)(A)(i)(II),
1227(a)(2)(B)(i). He admits that in 2003 he was convicted of a
violation of Florida’s cocaine possession statute. See Fla. Stat.
§ 893.13(6)(a). The only path open to him, then, is to show that his
conviction was not for an offense “relating to a controlled
substance” as federally defined.
      We apply the categorical approach in comparing the Florida
and federal offenses. That means we do not consider the facts
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6                          Opinion of the Court                        19-13908

specific to Chamu’s conviction. See Kawashima v. Holder, 565
U.S. 478, 483 (2012). Instead, we look “to the statute defining the
crime of conviction” to decide whether convictions under the state
statute “necessarily entail” the conduct that triggers federal
immigration consequences. Id.; Shular v. United States, 140 S. Ct.
779, 784 (2020) (quotation omitted). If a conviction under the
Florida cocaine possession statute always relates to a federally
controlled substance—that is, if the substances proscribed by the
Florida law are all federally controlled substances—then the state
conviction triggers immigration consequences. Cf. Kawashima,
565 U.S. at 483–85.
       Chamu argues that Florida’s cocaine possession statute fails
this test in two ways. First, it defines cocaine too broadly; and
second, it presumes that the possessor knows that a possessed
substance is illegal. Both arguments fall short. 1

1 The government argues that our precedent requires us to reject Chamu’s
petition without reaching the merits because we previously stated in Guillen
v. U.S. Attorney General that “convictions for possession of cocaine relate to
a controlled substance as defined by federal law.” 910 F.3d 1174, 1179 (11th
Cir. 2018). But this argument misreads Guillen. There, we held that Florida
Statute § 893.13(6)(a)—the statute under which Chamu was convicted—was
divisible as to the identity of a controlled substance; in other words, we ex-
plained that “the identity of the substance possessed is an element of posses-
sion.” Id. at 1182. This case presents an entirely different question: whether
“cocaine” as defined by Florida law fits entirely within the federal definition of
cocaine. Our application of the categorical approach in resolving that question
here is consistent with Guillen and does not affect our holding in that case.
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19-13908                Opinion of the Court                         7

                                  A.
       We begin with the definition of cocaine. Chamu’s argument
rests on the difference in statutory language between Florida’s
definition of cocaine and the federal definition. The crux of the
matter is that the two statutes refer to different types of cocaine
isomers. Isomers, as we will address in more detail later, are
chemical compounds that share a formula but are differently
structured. Florida’s cocaine definition includes one subset of
isomers: “any of [cocaine’s] stereoisomers.”               Fla. Stat.
§ 893.03(2)(a)(4) (2003). The federal definition, at least on its face,
describes another: cocaine’s “optical and geometric isomers.” 21
U.S.C. § 812(c), Sched. II(a)(4) (2003).
        The Supreme Court has made clear that litigants who
contend that state statutes are broader than their federal analogues
must come prepared. They cannot simply apply “legal imagination
to a state statute’s language” and hope to prevail. Duenas-Alvarez,
549 U.S. at 193. A relevant difference exists only when there is “a
realistic probability, not a theoretical possibility,” that the State
would apply its statute to conduct that does not meet the federal
standard. Id. The simplest way for an offender to show that
realistic probability is to point to a case in which the state statute
was used to prosecute such conduct. See id.
      Chamu offers no sample prosecution here—but that is not
the only way forward, at least in this Circuit. We explained in
Ramos v. U.S. Attorney General that an offender need not produce
a sample prosecution “when the statutory language itself, rather
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8                       Opinion of the Court                  19-13908

than the application of legal imagination to that language, creates
the realistic probability that a state would apply the statute to
conduct beyond the generic definition.” 709 F.3d 1066, 1072 (11th
Cir. 2013) (quotations omitted). Ramos thus allows a litigant to use
facially overbroad statutory text to meet the burden of showing the
realistic probability that the state law covers more conduct than the
federal. But it does not lift the burden entirely; a litigant still must
show that any textual differences carry actual legal consequences.
When state and federal statutes “do not diverge to any significant
degree”—that is, when a state statute with “different terminology”
is nonetheless “no broader than the federal standard”—no realistic
probability of broader prosecution exists. Bourtzakis v. U.S. Att’y
Gen., 940 F.3d 616, 624–25 (11th Cir. 2019). Different words alone
are not enough.
       Even so, Chamu rests his argument entirely on the facial
inconsistencies between the federal and state cocaine statutes,
attempting to persuade us that the obvious differences between the
two are enough to carry his burden. The federal statute indeed
omits a subcategory of cocaine isomers that the state statute does
not. But that omission is meaningless if the subcategory is a null
set—if so, the state statute covers exactly the same substances as
the federal.
       A closer look at the scientific terms found in the statutes
helps explain how that is possible. To start, isomers are chemical
compounds with “the same formula but a different arrangement of
atoms in the molecule and different properties.” New Oxford
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19-13908                  Opinion of the Court                               9

American Dictionary 921 (3d ed. 2010). In other words, they are
chemicals made from the same number and type of elements
combined in different ways. Stereoisomers are one set of isomers,
those that differ “only in the spatial arrangement of their atoms”—
all the atoms are linked in the same order, but each chemical’s 3D
shape is slightly different. Id. at 1709. Stereoisomers can be further
divided into three categories: optical isomers, geometric isomers,
and nongeometric diastereomers. 2
       Florida’s statutory definition of cocaine includes cocaine’s
stereoisomers, while the federal definition includes only two
subsets of cocaine’s stereoisomers—that is, optical isomers and
geometric isomers (which are themselves a subset of
diastereomers). Compare Fla. Stat. § 893.03(2)(a)(4) (2003), with 21
U.S.C. § 812(c), Sched. II(a)(4) (2003). So, Chamu argues, some
stereoisomers—nongeometric diastereomers—could conceivably
be covered by Florida’s definition but not the federal definition.

2 Stereoisomers, for what it is worth, are usually divided into two categories:
optical isomers (also called enantiomers) and diastereomers. See John
McMurry, Organic Chemistry 297, 302, 310 (7th ed. 2008). The diastereomer
category can be subdivided further. Some diastereomers are also geometric
isomers. See id. at 302, 310; L.G. Wade, Jr., Organic Chemistry 57–58 (4th ed.
1999). We use the catchall term “nongeometric diastereomers” to describe all
other isomers that fit into the diastereomer category.
The terms “optical isomer” and “geometric isomer” are no longer as common
as they once were, though they are still easily understood by chemists. See
Wade, Organic Chemistry, at 221 (defining both terms in more modern lan-
guage). We retain the statutory language here for the sake of clarity.
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10                    Opinion of the Court               19-13908

The shaded portion of the diagram below illustrates the subset of
stereoisomers in question.

       Chamu’s argument makes sense so far: stereoisomers
include at least one chemical subset that is not listed in federal
law—nongeometric diastereomers. The problem is that the
argument goes no further. Even if some chemical compounds
have nongeometric diastereomers, nothing in the record suggests
that cocaine has any, let alone that they exist in the quantities
required for an offender to be prosecuted for possessing them. If
cocaine does not have a nongeometric diastereomer, then the two
statutes cover exactly the same ground.
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19-13908              Opinion of the Court                      11

       We “would not find overbroad a state statute criminalizing
the possession of dangerous animals, defined to include dragons, if
the relevant federal comparator outlawed possession of the same
animals but did not include dragons”—unless, of course, the
offender provided evidence that dragons actually exist. See United
States v. Rodriguez-Gamboa, 972 F.3d 1148, 1155 (9th Cir. 2020).
Chamu shoulders the burden here, and he offers no proof to
support his allegation that an existing cocaine stereoisomer falls
outside the federal definition. We decline to hold that Florida’s
statute is broader than its federal counterpart based only on the
possibility that it might be so.
       Chamu insists that his expert’s declaration provides the
necessary proof that some types of cocaine criminalized in Florida
are allowed under federal law. He repeatedly points to the
declaration’s conclusion that “[s]ince there are diastereomers that
are not geometric isomers, the Florida definition of cocaine, which
encompasses all stereoisomers of cocaine, is broader than the
federal definition, which encompasses optical isomers and
geometric isomers (a subtype of diastereomer).” But that
statement does nothing more than describe the chart we included
a few paragraphs back. The declaration establishes only that, as a
matter of chemistry, some substances have stereoisomers that are
neither optical isomers nor geometric isomers.
       The statutes here, however, specifically describe isomers of
cocaine. And the declaration conspicuously fails to assert the
existence of a cocaine stereoisomer that falls outside the federal
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12                         Opinion of the Court                        19-13908

definition. As the Board explained, Chamu’s expert “conclusively
states that Florida’s definition of cocaine is broader,” but “gives no
examples of an actual isomer that is a diastereomer but not a
geometric isomer of cocaine.”
        Chamu attempts to fill the declaration’s gap in his appellate
arguments. He has suggested to this Court at various times that
particular substances are covered by the Florida statute and not by
federal law. Even assuming these new assertions have any
scientific basis (which, candidly, we seriously doubt), what matters
to this Court right now is that they have no basis in the record. We
may only reverse the Board on a factual finding if we find that “the
record not only supports reversal, but compels it.” Kazemzadeh,
577 F.3d at 1351 (quotation omitted). Here, the record is devoid of
evidence supporting Chamu’s theory.3
       Chamu urges us to consider other cases across the federal
system, arguing that his theory has been “raised with success
elsewhere.” But that path is also a dead end. The cases cited by
Chamu involve different state statutory definitions and different
burdens of proof. See United States v. Ruth, 966 F.3d 642, 647–48
(7th Cir. 2020) (placing the burden of proof on the government in
the sentencing context); United States v. Fernandez-Taveras, 511

3 We do not mean to suggest that identifying a specific chemical compound
covered by state (and not federal) law is sufficient to show a realistic probabil-
ity of prosecution. More is likely required. But at least identifying such a sub-
stance is a necessary first step.
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19-13908               Opinion of the Court                       13

F. Supp. 3d 367, 373–74 (E.D.N.Y. 2021) (involving a broader state
statutory definition). They are not in tension with our own
decision.
        In fact, we are not the only Circuit to hold that differing
statutory language does not automatically create a reasonable
probability under Duenas-Alvarez. The Fifth Circuit refused to
hold that a Texas cocaine definition was broader than the federal
definition when the defendant could not offer a sample
prosecution. Alexis v. Barr, 960 F.3d 722, 726, 729 (5th Cir. 2020),
cert. denied, 141 S. Ct. 845 (2020). And the Ninth Circuit held that
a California law covering methamphetamine’s geometric isomers
(where the federal law did not) was not overbroad. Rodriguez-
Gamboa, 972 F.3d at 1149–50, 1155. The court relied on
unrebutted testimony in the district court establishing that
“geometric isomers of methamphetamine do not chemically exist.”
Id. at 1155. Of course, no such testimony was offered here—but
neither was any proof that the disputed cocaine isomers do exist.
And that dearth of evidence is fatal for Chamu, who bears the
burden of proof.
        Because of the state of the record, we cannot hold that
Florida’s definition of cocaine is completely consistent with the
federal definition. But we do hold that Chamu has failed to prove
that it covers more substances. See Alexis, 960 F.3d at 729. Positing
the hypothetical existence of a form of cocaine that has slipped
through the cracks of federal legislation is no more than “legal
imagination” conjuring up a “theoretical possibility”—a practice
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14                     Opinion of the Court                19-13908

forbidden by the Supreme Court. Duenas-Alvarez, 549 U.S. at 193.
Chamu gives us no reason to disturb the Board’s conclusion that
his theory is “highly improbable.”
                                B.
        Chamu also posits that Florida’s cocaine possession statute
is problematic in another way: he says it does not require the state
to prove that a defendant knew the possessed substance was illegal.
Chamu suggests that the federal immigration statutes at issue
“invoke generic offenses” that must be compared to Florida’s
statute, and he concludes that knowledge of a substance’s illicit
nature is an “essential element” of the generic federal crime of
cocaine possession. He argues that Florida’s statute lacks that
element and is “completely dissonant with the federal offense”—
so it cannot trigger immigration consequences. The argument falls
short on a fundamental level.
        To begin, Chamu misconceives how the categorical
approach applies here. As the Supreme Court explained in Shular,
that approach has two forms. 140 S. Ct. at 783. When a statute
invokes the generic version of a crime—say “burglary” or a “drug
trafficking crime”—then a court must discern “the elements of the
offense as commonly understood” and compare them to the ones
in the state statute of conviction. Id. (quotation omitted). The
mens rea, of course, can be one of those elements. See, e.g.,
Donawa v. U.S. Att’y Gen., 735 F.3d 1275, 1281–82 (11th Cir. 2013).
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19-13908                    Opinion of the Court                                 15

        But other statutes requiring the categorical approach “ask
the court to determine not whether the prior conviction was for a
certain offense, but whether the conviction meets some other
criterion.” Shular, 140 S. Ct. at 783. To apply the categorical
approach to these statutes, a court must assess whether convictions
under the state statute “necessarily entail” the criterion described
by the federal statute. Id. at 784 (quotation omitted).
       Here, that criterion is whether the state statute involves
conduct “relating to a controlled substance.” See 8 U.S.C.
§§ 1229b(b)(1)(C), 1182(a)(2)(A)(i)(II), 1227(a)(2)(B)(i). The phrase
“controlled substance” does not describe an offense, but a physical
thing. And the federal immigration statutes say that convictions
under a state statute relating to this physical thing, the controlled
substance, carry immigration consequences. See Mellouli v.
Lynch, 575 U.S. 798, 813 (2015). What the federal immigration
statutes do not reference is mens rea. We thus have nothing to
compare between the federal and statute statutes; Florida’s mens
rea requirements, whatever they may be, are irrelevant. 4

4 We do note that Chamu “overstates Florida’s disregard for mens rea.” See
Shular v. United States, 140 S. Ct. 779, 787 (2020). Florida law, it is true, pre-
sumes that the possessor of a controlled substance knows of the substance’s
illicit nature. Fla. Stat. § 893.101(3). But it also allows a defendant to assert an
affirmative defense that he lacked such knowledge. Id. § 893.101(2). The Su-
preme Court has indicated that Florida’s scheme is permissible. See Shular,
140 S. Ct. at 787. So even if the statute were to list a generic possession offense,
the gap, if it exists at all, is not what Chamu suggests.
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       For his part, Chamu asks us to apply the offense-based
categorical approach, and to add a mens rea requirement to the
federal immigration statutes in order to do so. We decline that
invitation, mindful that “courts obviously must follow Congress’
intent as to the required level of mental culpability for any
particular offense.” See United States v. Bailey, 444 U.S. 394, 406
(1980). We also decline to accept his novel interpretation of Shular,
which he contends shows that any statutory language other than
“involving” (the word used in the statute at issue in that case) must
require an illicit-nature mens rea whenever the categorical
approach is applied. That interpretation both misreads Shular and
applies an offense-based categorical comparison that is not relevant
here.
       We thus hold that no illicit-nature mens rea is necessary to
trigger removal consequences for offenses listed under 8 U.S.C.
§§ 1182(a)(2)(A)(i)(II) and 1227(a)(2)(B)(i).
                           *        *     *
         Chamu has failed to show that Florida’s definition of cocaine
covers more than its federal counterpart. And the lack of an explicit
illicit-nature mens rea element in the Florida statute does not
invalidate the immigration consequences of his conviction. We
therefore DENY Chamu’s petition.