Court Opinion

ID: 4468053
Source: CourtListenerOpinion
Date Created: 2019-12-27 18:00:33.794723+00
Date Added: 2024-06-11T14:35:18.664097
License: Public Domain

FOR PUBLICATION

   UNITED STATES COURT OF APPEALS
        FOR THE NINTH CIRCUIT

 UNITED STATES OF AMERICA,                         No. 19-50014
                Plaintiff-Appellant,
                                                     D.C. No.
                      v.                          2:18-cr-00379-
                                                     ODW-1
 FRANCISCA RODRIGUEZ-GAMBOA,
              Defendant-Appellee.                    OPINION

        Appeal from the United States District Court
           for the Central District of California
        Otis D. Wright II, District Judge, Presiding

           Argued and Submitted October 18, 2019
                    Pasadena, California

                    Filed December 27, 2019

 Before: Kim McLane Wardlaw and Andrew D. Hurwitz,
 Circuit Judges, and Joseph F. Bataillon, * District Judge.

                   Opinion by Judge Hurwitz

     *
       The Honorable Joseph F. Bataillon, United States District Judge
for the District of Nebraska, sitting by designation.
2          UNITED STATES V. RODRIGUEZ-GAMBOA

                          SUMMARY **

                           Immigration

    The panel affirmed the district court’s order permitting
the defendant to withdraw her guilty plea to illegal reentry
under 8 U.S.C. § 1326, vacated the district court’s dismissal
of the indictment, and remanded to the district court for the
limited purpose of resolving the factual issue of whether
geometric isomers of methamphetamine exist.

    The removal that served as the predicate for the
defendant’s § 1326 conviction was based on her prior
conviction for possession of methamphetamine for sale in
violation of California Health and Safety Code § 11378.
Shortly after the defendant pleaded guilty to the § 1326
information, this court held in Lorenzo v. Sessions, 902 F.3d
930 (9th Cir. 2018) (Lorenzo I), that the definition of
methamphetamine applicable to convictions under § 11378
is broader than the definition of methamphetamine under the
federal Controlled Substances Act. The district court
granted the defendant’s motion to withdraw her guilty plea
and to dismiss the information in light of Lorenzo I.

    The panel held that the district court did not abuse its
discretion in allowing the defendant to withdraw her guilty
plea following Lorenzo I because that decision effectively
invalidated her underlying removal.

    **
       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. RODRIGUEZ-GAMBOA                   3

    Following the defendant’s withdrawal of her guilty plea
and the dismissal of the information, this court withdrew the
opinion in Lorenzo I and replaced it with a non-precedential
memorandum disposition, Lorenzo v. Whitaker, 752
F. App’x 482 (9th Cir. 2019) (Lorenzo II). Lorenzo II
expressly stated that the government is not foreclosed from
raising in other cases the argument that any difference
between California and federal law about the definition of
methamphetamine is illusory.

    The government argues that because both California and
federal law prohibit possession for sale of methamphetamine
and “its” isomers, they are identical, because the California
statute is limited to those isomers of methamphetamine that
actually exist and geometric isomers of methamphetamine
do not. The panel declined the government’s invitation to
rewrite California law, whose statutory scheme strongly
suggests that the California legislature deliberately
distinguished between the various isomers of controlled
substances and expressly noted when its definitions were
conditioned on the existence of a particular isomer. But
because whether geometric isomers of methamphetamine
exist is a factual issue that has the potential to inform the
panel’s disposition of this appeal and future cases, and
because the district court has never made a finding as to that
factual issue, the panel remanded to the district court for the
limited purpose of resolving that evidentiary issue in the first
instance. The panel wrote that it will retain jurisdiction over
the appeal and address its merits after the district court
reports its factual findings.
4         UNITED STATES V. RODRIGUEZ-GAMBOA

                        COUNSEL

L. Ashley Aull (argued), Chief, Criminal Appeals Section;
Lawrence S. Middleton and Brandon D. Fox, Chief,
Criminal Division; Nicola T. Hanna, United States Attorney;
United States Attorney’s Office, Los Angeles, California;
for Plaintiff-Appellant.

David Menninger (argued), Deputy Federal Public
Defender; Hilary Potashner, Federal Public Defender; Office
of the Federal Public Defender, Los Angeles, California; for
Defendant-Appellee.

                         OPINION

HURWITZ, Circuit Judge:

    We are asked to decide whether the definition of
methamphetamine under California law is broader than the
definition under corresponding federal law. The issue is
pivotal in this case because appellee Francisca Rodriguez-
Gamboa did not commit illegal reentry under 8 U.S.C.
§ 1326 if the California law is categorically broader than the
federal one.

    The case arrives in an unusual procedural posture. The
parties agree that the relevant federal statute defines
methamphetamine as including only its optical isomer, while
California law defines methamphetamine as including its
geometric and optical isomers. But the government
contends that this apparent difference is illusory because
there is no such thing as a geometric isomer of
methamphetamine. And, the government presented expert
declarations in support of its position below.
          UNITED STATES V. RODRIGUEZ-GAMBOA                  5

    The district court, however, did not resolve whether a
geometric isomer of methamphetamine exists. While this
case was pending in the district court, we decided Lorenzo v.
Sessions (“Lorenzo I”), holding that the definition of
methamphetamine under California Health and Safety Code
§ 11378 was categorically broader than the definition of
methamphetamine under the Controlled Substances Act,
21 U.S.C. § 812, because the former included geometric
isomers and the latter did not. 902 F.3d 930, 932–38 (9th
Cir. 2018). The district court, naturally feeling itself bound
by Lorenzo I, allowed Rodriguez to withdraw her guilty plea
to a violation of 8 U.S.C. § 1326 and dismissed the
information. After the government filed a notice of appeal,
however, we withdrew our opinion in Lorenzo I, Lorenzo v.
Whitaker, 913 F.3d 930 (9th Cir. 2019), and replaced it with
a non-precedential memorandum disposition, Lorenzo v.
Whitaker (“Lorenzo II”), 752 F. App’x 482 (9th Cir. 2019).

    Lorenzo II reached the same result as Lorenzo I, but
expressly declined to address the factual argument raised
here, because the government had raised it for the first time
in a petition for panel rehearing. Id. at 485. The panel,
however, “d[id] not foreclose the government from
presenting its new argument or new evidence in another
case.” Id.

     This is that case. But, because the district court did not
confront the factual accuracy of the government’s argument,
we remand to the district court to address that issue in the
first instance.

               FACTUAL BACKGROUND

   In 2011, Rodriguez, a citizen of Mexico and an
undocumented resident of the United States, was convicted
of several offenses, including possession for sale of
6        UNITED STATES V. RODRIGUEZ-GAMBOA

methamphetamine in violation of California Health and
Safety Code § 11378, and sentenced to six years’
imprisonment. She later was served with a Notice of Intent
to Issue a Final Administrative Removal Order (“NOI”).
The NOI alleged that Rodriguez was removable because she
had been “convicted of an aggravated felony,” namely,
“Possession for Sale of a Controlled Substance, to wit:
Methamphetamine, in violation of Section 11378 of the
Health and Safety Code of California.”

    Rodriguez admitted the allegations in the NOI and
waived any right to remain in the United States while
applying for judicial review. After serving her state
sentence, she was removed to Mexico. She later reentered
the United States without inspection.

           PROCEDURAL BACKGROUND

   In 2018, Rodriguez was charged in a criminal complaint
with illegal reentry in violation of 8 U.S.C. § 1326. She
waived indictment and pleaded guilty to the information.

    Shortly thereafter, Lorenzo I held that possession of
methamphetamine for sale under California Health and
Safety Code § 11378 “does not qualify as a controlled
substance offense under 8 U.S.C. § 1227(a)(2)(B)(i).”
902 F.3d at 933. Lorenzo I found that “the definition of
‘methamphetamine’ applicable to convictions under
California Health & Safety Code §§ 11378 and 11379(a) is
broader than the definition of methamphetamine under the
federal Controlled Substances Act, 21 U.S.C. § 812.” Id.
at 932. The opinion reasoned that because the definition of
methamphetamine under California law includes both
optical and geometric isomers, Cal. Health & Safety Code
§§ 11033, 11055(d)(2), it is broader than the federal
definition under the Controlled Substances Act, 21 U.S.C.
         UNITED STATES V. RODRIGUEZ-GAMBOA                 7

§§ 802(14), 812, which covers only the optical isomer. Id.
at 935–36.

    Relying on Lorenzo I, Rodriguez moved under 8 U.S.C.
§ 1326(d) to withdraw her guilty plea and dismiss the
information. In opposition, the government argued that any
apparent overbreadth of the California statute was illusory,
because geometric isomers of methamphetamine do not in
fact exist. The government submitted declarations from two
experts so opining. Although the district court gave
Rodriguez an opportunity to submit rebutting evidence, she
declined to do so, asserting that “no evidence is necessary,
because the Ninth Circuit already decided the issue in
Lorenzo, which remains binding precedent.”

    Agreeing, the district court granted Rodriguez’s motion
to withdraw her guilty plea and dismissed the information.
The court noted that geometric isomers of methamphetamine
may not exist, but concluded that it did not have to decide
the issue in light of Lorenzo I. The government timely
appealed.

   JURISDICTION AND STANDARD OF REVIEW

    We have jurisdiction of the government’s appeal under
18 U.S.C § 3731 and 28 U.S.C. § 1291. A “district court’s
ruling on a defendant’s collateral attack of a deportation
proceeding is reviewed de novo,” United States v. Gonzalez-
Valerio, 342 F.3d 1051, 1053 (9th Cir. 2003), as is dismissal
of an information, see United States v. Huping Zhou,
678 F.3d 1110, 1113 (9th Cir. 2012). A district court’s
ruling on a motion to withdraw a guilty plea is reviewed for
abuse of discretion. See United States v. Garcia, 909 F.2d
1346, 1348 (9th Cir. 1990).
8         UNITED STATES V. RODRIGUEZ-GAMBOA

                       DISCUSSION

    A. Withdrawal of Guilty Plea

    The district court may allow a guilty plea to be
withdrawn if “the defendant can show a fair and just reason
for requesting the withdrawal.”        Fed. R. Crim. P.
11(d)(2)(B). A fair and just reason includes “intervening
circumstances, or any other reason for withdrawing the plea
that did not exist when the defendant entered his plea.”
United States v. Ortega-Ascanio, 376 F.3d 879, 883 (9th Cir.
2004). A change in the law can justify withdrawal of a plea.
See id. at 887.

    The district court did not abuse its discretion in allowing
Rodriguez to withdraw her plea. After that plea was entered,
Lorenzo I held that the definition of methamphetamine under
§ 11378 was broader than the definition under the federal
Controlled Substances Act, and a violation of § 11378
therefore did not qualify as a controlled substance offense
under 8 U.S.C. § 1227(a)(2)(B)(i). 902 F.3d at 933, 939–40.
Because a drug offense can only be an aggravated felony
justifying removal if it involves a federally controlled
substance, see 8 U.S.C. § 1101(a)(43)(B), Lorenzo I
effectively invalidated Rodriguez’s underlying removal.

    B. Dismissal of Information

    In dismissing the information, the district court found
that Lorenzo I foreclosed the government’s argument that
any difference between California and federal law about the
definition of methamphetamine is illusory. But Lorenzo I
has since been withdrawn, and Lorenzo II expressly stated
that the government is not foreclosed from raising this
argument in other cases. 752 F. App’x at 485. The
           UNITED STATES V. RODRIGUEZ-GAMBOA                          9

argument, even assuming it was foreclosed under Lorenzo I,
is therefore properly before us.

    We start by considering whether the California statute is
on its face broader than the relevant federal law. See
Moncrieffe v. Holder, 569 U.S. 184, 190 (2013). California
prohibits possessing for sale any “controlled substance” that
is “specified in subdivision (d) . . . of Section 11055.” Cal.
Health & Safety Code § 11378. Section 1105(d), in turn,
defines as a controlled substance “[m]ethamphetamine, its
salts, isomers, and salts of its isomers.” Cal. Health & Safety
Code § 11055(d)(2).         And another California statute
provides that “except as otherwise defined, the term ‘isomer’
includes optical and geometrical (diastereometric) isomers.”
Cal. Health & Safety Code § 11033. Federal law similarly
prohibits possession for sale of “methamphetamine,
including its salts, isomers, and salts of isomers,” but states
that the “term ‘isomer’ means the optical isomer.” 21 U.S.C.
§§ 802(14), 812 Sched. II(c), Sched. III(a)(3).

    The government, relying on California Health and Safety
Code § 11001 (“Unless the context otherwise requires, the
definitions in this chapter govern the construction of this
division.”), urges that based on its statutory “context,” the
California law is not broader than federal law. 1 The
government argues that because both California and federal
law prohibit possession for sale of methamphetamine and
“its” isomers, they are identical, because the California
statute is limited to those isomers of methamphetamine that
    1
       The government argues that Rodriguez did not satisfy the
requirements of 8 U.S.C. § 1326(d) by exhausting her administrative
remedies and demonstrating deprivation of the opportunity for judicial
review. But the government concedes that this argument is foreclosed
by United States v. Ochoa, 861 F.3d 1010 (9th Cir. 2017), and raises the
issue only to preserve it for further review.
10        UNITED STATES V. RODRIGUEZ-GAMBOA

actually exist and geometric isomers of methamphetamine
do not.

    We decline the government’s invitation to rewrite
California law. The argument requires us to look beyond the
statutory language to matters of organic chemistry. And, the
statutory scheme strongly suggests that the California
legislature deliberately distinguished between the various
isomers of controlled substances in its definitions and
expressly noted when its definitions were conditioned on the
existence of a particular isomer. See Cal. Health & Safety
Code § 11055(d)(1) (defining amphetamine to include only
“optical isomers”); § 11054(d) (defining the “optical,
position, and geometric isomers” of hallucinogens as
controlled substances); § 11054(d)(20) (defining certain
tetrahydrocannabinols as including their “optical isomers”);
§ 11057(e) (defining fenfluramine as including its “isomers
(whether optical, position, or geometric) . . . whenever the
existence of those . . . isomers . . . is possible”).

    Rodriguez argues that this textual distinction ends the
analysis. That argument finds support in our precedents. We
have previously stated that if “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.”
United States v. Grisel, 488 F.3d 844, 850 (9th Cir. 2007)
(internal citation omitted), abrogated on other grounds by
United States v. Stitt, 139 S. Ct. 399 (2018). In response, the
government cites the Supreme Court’s statement that “to
find that a state statute creates a crime outside the generic
definition of a listed crime in a federal statute” requires “a
realistic probability, not a theoretical possibility, that the
           UNITED STATES V. RODRIGUEZ-GAMBOA                       11

State would apply its statute to conduct that falls outside the
generic definition of a crime.” Gonzales v. Duenas-Alvarez,
549 U.S. 183, 193 (2007). If there is no geometric isomer of
methamphetamine, the government argues, there is also no
“realistic probability” of California applying its statutes to
conduct not forbidden by federal law.

    The government’s argument rests entirely on its factual
assertion that the geometric isomer of methamphetamine
does not exist. But, the district court never made such a
finding, and we cannot do so for the first time on appeal. 2
See Icicle Seafoods, Inc. v. Worthington, 475 U.S. 709, 714
(1986). Because resolution of the factual issue of whether
geometric isomers of methamphetamine exist has the
potential to inform our disposition of this appeal and future
cases, we remand to the district court for the limited purpose
of resolving that evidentiary issue in the first instance. The
panel will retain jurisdiction over the appeal and address its
merits after the district court reports its factual findings.

                         CONCLUSION

    We affirm the district court’s order permitting Rodriguez
to withdraw her guilty plea, vacate the dismissal of the
information, and remand for further proceedings consistent
with this opinion.

  AFFIRMED IN PART, VACATED IN PART, AND
REMANDED.

    2
      We reject the government’s argument that Rodriguez has forfeited
any factual arguments on this issue by not responding to the expert
declarations submitted by the government below. She, like the district
court, appropriately relied on the then-extant opinion in Lorenzo I.