United States v. Rodriguez-Gamboa

972 F.3d 1148

UNITED STATES of America, Plaintiff-Appellant,

v.Francisca RODRIGUEZ-GAMBOA, Defendant-Appellee.

No. 19-50014

United States Court of Appeals, Ninth Circuit.

Argued and Submitted July 8, 2020 Pasadena, California

Filed August 27, 2020

L. Ashley Aull (argued), Chief, Criminal Appeals Section; 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; Office of the Federal Public Defender, Los Angeles, California; for Defendant-Appellee.

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

HURWITZ, Circuit Judge:

This appeal requires us to delve once again into the mysteries of the "categorical approach" to determine whether a conviction under state law qualifies as a generic federal offense. See Taylor v. United States , 495 U.S. 575, 602, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990). The two statutes at issue today both prohibit the possession of methamphetamine for sale. California law prohibits the possession for sale of both the geometric and optical isomers of methamphetamine. Cal. Health & Safety Code §§ 11033, 11055(d)(2), 11378.¹ The relevant federal law, however, outlaws, possession only of methamphetamine's optical isomers. 21 U.S.C. §§ 802(14), 812(c), Schedule II(c), Schedule III(a)(3). Because the state law's "greater breadth is evident from its text," our traditional jurisprudence would suggest that it is not a categorical match to the federal law. United States v. Grisel , 488 F.3d 844, 850 (9th Cir. 2007) (en banc), abrogated on other grounds by United States v. Stitt , ––– U.S. ––––, 139 S. Ct. 399, 202 L.Ed.2d 364 (2018).

But we face an unusual situation today. At our request, the district court conducted an evidentiary hearing and, after hearing unrebutted expert testimony, concluded that there is no such thing as a geometric isomer of methamphetamine. The Supreme Court has pointedly instructed that the categorical approach should not be applied in a legal vacuum and that a finding of overbreadth "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." Gonzales v. Duenas-Alvarez , 549 U.S. 183, 193, 127 S.Ct. 815, 166 L.Ed.2d 683 (2007). Because there is no such possibility here, we opt for scientific reality over abstract legal doctrine and reverse the district court's dismissal of the information charging Rodriguez with illegal reentry under 8 U.S.C. § 1326.

I.

We described the facts and procedural history of this case in a prior opinion, United States v. Rodriguez-Gamboa , 946 F.3d 548 (9th Cir. 2019), and therefore recount them more briefly here. In 2017, Francisca Rodriguez-Gamboa, a native and citizen of Mexico, was removed because of an "aggravated felony" conviction—possession for sale of methamphetamine in violation of California Health & Safety Code § 11378.

Rodriguez later reentered the United States without inspection. In 2018, she was charged in a criminal complaint with illegal reentry in violation of 8 U.S.C. § 1326. Although she initially waived indictment and pleaded guilty, Rodriguez moved to withdraw her plea and dismiss the information after we issued our opinion in Lorenzo v. Sessions , holding that possession of methamphetamine for sale under California Health & Safety Code § 11378 "does not qualify as a controlled substance offense under 8 U.S.C. § 1227(a)(2)(B)(i)." 902 F.3d 930, 933 (9th Cir. 2018). Lorenzo found the California statute categorically overbroad because the definition of certain controlled substances, including methamphetamine, under California law includes both optical and geometric isomers, Cal. Health & Safety Code §§ 11033, 11055(d)(2), while the comparator federal statute, the Controlled Substances Act ("CSA"), 21 U.S.C. §§ 802(14), 812(c), Schedule II(c), Schedule III(a)(3), covers only the optical isomer. 902 F.3d at 935–36.

In opposition to Rodriguez's motion, the government argued that the California statute's apparent overbreadth was illusory because geometric isomers of methamphetamine do not exist. The government submitted two expert declarations in support of that position. The district court noted that geometric isomers of methamphetamine may not exist but held that it was bound by Lorenzo . The court therefore allowed Rodriguez to withdraw her plea and entered an order dismissing the information.

After the district court entered its order, the opinion in Lorenzo was withdrawn, Lorenzo v. Whitaker , 913 F.3d 930 (9th Cir. 2019) (order), and replaced with a non-precedential memorandum disposition, Lorenzo v. Whitaker , 752 F. App'x 482 (9th Cir. 2019). The memorandum disposition reached the same result as the opinion, but pretermitted the government's argument that "the facial overbreadth in California law is of no significance because geometric isomers of methamphetamine do not in fact exist" because it was raised 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.

In our prior opinion in this case, we held that the district court did not abuse its discretion in permitting Rodriguez to withdraw her guilty plea. Rodriguez-Gamboa , 946 F.3d at 551. However, we vacated the dismissal of the information, noting that the opinion on which the district court had relied had been replaced by a memorandum disposition that left the government free to raise an argument in a future case that geometric isomers of methamphetamine do not exist. Id. at 552. We remanded to the district court for the limited purpose of addressing that issue. Id. at 552–53.

On remand, the district court held an evidentiary hearing at which the government presented testimony and declarations from three experts in organic chemistry: Dr. Travis Williams, professor of chemistry at the University of Southern California, Dr. Brian Stoltz, professor of chemistry at the California Institute of Technology, and Dr. Daniel Willenbring, a drug science specialist with the Drug Enforcement Administration. All stated that there are no geometric isomers of methamphetamine. Rodriguez presented no rebuttal experts. Accepting the experts’ testimony, the district court concluded that, because methamphetamine "lacks [certain] structural features," "geometric isomers" of methamphetamine "are impossible." We then reassumed jurisdiction over this appeal.

II.

The district court's factual finding that geometric isomers of methamphetamine do not exist, which we review for clear error, see United States v. Hinkson , 585 F.3d 1247, 1259–60 (9th Cir. 2009) (en banc), finds overwhelming support in the record. It is grounded in unrebutted expert testimony that because of the chemical structure of the methamphetamine molecule, methamphetamine cannot "possibly have geometric isomers."

Rodriguez's attempt to poke holes in the district court's factual finding fails. She argues that the district court should have interpreted the term "geometrical" isomer in California Health & Safety Code § 11033 as synonymous with a diastereomeric isomer, pointing to the parenthetical that follows the term "geometrical" in the California statute—"geometrical (diastereomeric) isomers." Rodriguez then cites the testimony of one expert that deuterium-labelled methamphetamine can have diastereomers. But, the unrebutted expert testimony was that although geometric isomers are a subtype of diastereomers, not all diastereomers are geometric. And, consistent with that testimony, the district court held that deuterium-labeled methamphetamine does not contain geometric isomers.²

We also reject the argument that the California statute's facial inclusion of "geometrical" isomers of methamphetamine reflects a legislative determination that such isomers actually exist. Section 11378 prohibits possession for sale of a number of controlled substances and their "isomers." Cal. Health & Safety Code §§ 11055(d)(2)–(4), (e), 11378. The term "isomer" is in turn defined in California Health & Safety Code § 11033 as "includ[ing] optical and geometrical (diastereomeric) isomers." That catch-all definition applies to all controlled substances with isomers, "except as otherwise defined," id. , and is thus plainly designed not as a legislative finding that methamphetamine has a geometrical isomer, but rather to ensure that all isomers of the banned substances are covered.

III.

Having resolved all other issues relevant to this appeal in our prior opinion, Rodriguez-Gamboa , 946 F.3d at 551–53, we now must confront the legal import of the district court's factual finding. The ultimate legal issue is whether the factual impossibility of a state statute being applied more broadly than a federal comparator means there is a categorical match between the two, even if the state statute is textually overbroad.

"Under the categorical approach, we compare the elements of the crime to the generic" federal offense. Hernandez-Gonzalez v. Holder , 778 F.3d 793, 801 (9th Cir. 2015) (cleaned up). A conviction under a state statute is a categorical match only "if the state statute—regardless of its ‘exact definition or label’—‘substantially corresponds’ to or is narrower than" the generic federal offense. Quarles v. United States , ––– U.S. ––––, 139 S. Ct. 1872, 1877, 204 L.Ed.2d 200 (2019) (quoting Taylor , 495 U.S. at 599, 602, 110 S.Ct. 2143 ). If the state statute regulates more conduct than the federal offense, it is overbroad, and a defendant convicted under the state statute is not removable for having committed an aggravated felony. See Rendon v. Holder , 764 F.3d 1077, 1083 (9th Cir. 2014).

As we recognized in our prior opinion, Rodriguez-Gamboa , 946 F.3d at 551–52, California law prohibits the...