UNITED STATES OF AMERICA, Plaintiff-Appellant, v. FRANCISCA RODRIGUEZ-GAMBOA, Defendant-Appellee.
No. 19-50014
United States Court of Appeals for the Ninth Circuit
Filed August 27, 2020
D.C. No. 2:18-cr-00379-ODW-1
FOR PUBLICATION
OPINION
Appeal from the United States District Court for the Central District of California Otis D. Wright II, District Judge, Presiding
Argued and Submitted July 8, 2020 Pasadena, California
Before: Kim McLane Wardlaw and Andrew D. Hurwitz, Circuit Judges, and Joseph F. Bataillon,* District Judge.
Opinion by Judge Hurwitz
SUMMARY**
Criminal Law
The panel reversed the district court‘s dismissal of an information charging illegal reentry in violation of
The defendant sought dismissal of the information on the ground that
The panel held that the district court‘s factual finding that geometric isomers of methamphetamine do not exist, which it reviewed for clear error, finds overwhelming support in the record; and rejected the argument that the California statute‘s facial inclusion of “geometrical” isomers of methamphetamine reflects a legislative determination that such isomers actually exist.
The panel addressed the legal issue 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. Finding Gonzales v. Duenas-Alvarez, 549 U.S. 183 (2007), most instructive, the panel wrote that, based on the evidentiary record, there is simply no “realistic probability“—nor even a theoretical one—of the defendant facing liability under California law for the possession of geometric isomers of methamphetamine. The panel explained that the purpose of the categorical approach is to ascertain whether the defendant was necessarily convicted in state court of conduct that would also violate the relevant federal law, and wrote that if there is no realistic probability that this is not the case, the goal of the inquiry is surely satisfied. The panel concluded that because geometric isomers of methamphetamine are impossible, there is no realistic probability that the defendant‘s California methamphetamine statute of conviction will be used to prosecute someone in connection with geometric isomers of methamphetamine.
COUNSEL
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;
OPINION
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 (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.
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 (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
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
Rodriguez later reentered the United States without inspection. In 2018, she was charged in a criminal complaint with illegal reentry in violation of
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
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
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.
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, 139 S. Ct. 1872, 1877 (2019) (quoting Taylor, 495 U.S. at 599, 602). 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 possession for sale of methamphetamine or its “optical and geometrical” isomers,
Rodriguez argues that this ends the analysis. Her argument finds some support in the language of our prior opinions, such as Grisel, in which we held that Oregon second-degree burglary was not a burglary offense under the Armed Career Criminal Act because “[t]he text of the statute expressly includes in its definition that which the Supreme Court expressly excluded from the generic, federal definition,” such as burglary of a booth, vehicle, and aircraft.
488 F.3d at 850. We 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” and a statute‘s overbreadth “is evident from its text.” Id. (quoting Duenas-Alvarez, 549 U.S. at 193).
But, the overbroad portion of the state statute at issue in Grisel did not criminalize conduct that could not possibly occur. Burglary of a booth, vehicle, or aircraft is possible, albeit perhaps unlikely. Our cases applying Grisel similarly have involved state laws forbidding conduct that was factually possible, even if unlikely to be the subject of a charge. See, e.g., Barrera-Lima v. Sessions, 901 F.3d 1108, 1120 & n.11 (9th Cir. 2018) (finding Washington‘s indecent exposure statute overbroad because it included acts such as “flashing a
Grisel thus simply stands for the proposition that “[a]s long as the application of the statute‘s express text in the nongeneric manner is not a logical impossibility, the relative likelihood of application to nongeneric conduct is immaterial.” Lopez-Aguilar v. Barr, 948 F.3d 1143, 1147 (9th Cir. 2020) (citing United States v. Valdivia-Flores, 876 F.3d 1201, 1208 (9th Cir. 2017)); see Robles-Urrea v. Holder, 678 F.3d 702, 707 (9th Cir. 2012) (“In order to hold that the statute of conviction is overbroad, we must determine that there is a realistic probability of its application to conduct that falls beyond the scope of the generic federal offense.” (cleaned up)). It does not aid us in applying the categorical approach when there is no possibility of application of the state statute to nongeneric conduct.
In addressing the scenario today before us, we find Duenas-Alvarez most instructive. In that case, the Supreme Court stated 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 State would apply its statute to conduct that falls outside the generic definition of a crime.” Duenas-Alvarez, 549 U.S. at 193. Here, based on the evidentiary record before us, there is simply no “realistic probability“—nor even a theoretical one—of Rodriguez facing criminal liability under California law for the possession of geometric isomers of methamphetamine.
To be sure, as Rodriguez notes, Duenas-Alvarez involved a state statute that facially was a categorical match to the federal generic crime, but which the petitioner argued had been applied in an overbroad manner. See id. at 190-91, 193. But we read the teaching of Duenas-Alvarez more broadly. The purpose of the categorical approach is to ascertain whether the defendant was necessarily convicted in state court of conduct that would also violate the relevant federal law. If there is no “realistic probability” that this is not the case, id. at 193, the goal of the inquiry is surely satisfied.
Indeed, the Court has implied as much in Moncrieffe v. Holder, 569 U.S. 184 (2013). There, the government
expressed concern that the Court‘s eventual holding would suggest that many state statutes prohibiting possession of firearms were categorically overbroad, because they did not except antiques, while the corresponding federal generic crime did. Id. at 205-06. The Court rejected this textual argument, reiterating that ”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.‘” Id. (quoting Duenas-Alvarez, 549 U.S. at 193). Indeed, it explained further that, “to defeat the categorical approach in this manner, a noncitizen would have to demonstrate the State actually prosecutes the relevant offense in cases involving antique firearms.” Id. at 206; see also Dominguez v. Barr, No. 18-72731, 2020 WL 4187377, at *9 (9th Cir. July 21, 2020) (concluding that the “inclusion” of an additional word “in Oregon‘s definition of manufacture does not criminalize any conduct beyond the reach of the Controlled Substances Act‘s definition” and therefore
Rodriguez also argues that because the categorical approach was designed in part to avoid fact-specific inquiries about how a given defendant committed a state crime, the evidentiary hearing we ordered in this case is
irrelevant.3 But the inquiry we asked the district court to conduct is quite different than looking into the facts of a crime. We did not ask the court to determine what type of isomers of methamphetamine Rodriguez‘s conviction actually involved, but rather whether it was physically possible for anyone to possess a geometric isomer of methamphetamine. The practical concerns with fact-specific evidentiary hearings about the defendant‘s state conviction that underly the categorical approach4 are not present when the inquiry is a purely scientific one about the statute of conviction.5
no choice but to follow it, even if convinced that such authority was wrongly decided.“). Of course, even for a state statute that is otherwise a categorical match, an offender may always show overbreadth by “point[ing] 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.
IV.
Contrary to Rodriguez‘s assertions, we do not today create a split with the Seventh Circuit. In United States v. De La Torre, that court addressed whether an Indiana statute outlawing methamphetamine and its “isomers” was broader than the generic federal definition, which, as we have noted, only extends to the optical isomer of methamphetamine. 940 F.3d 938, 951 (7th Cir. 2019) (citations omitted). In that case, the panel declined to consider declarations from government experts about whether geometric isomers of methamphetamine exist because they were presented for the first time on appeal and crafted for other cases. Id. at 952. Pointedly,
In United States v. Ruth, the Seventh Circuit recently addressed whether an Illinois statute outlawing cocaine and “its optical, positional, and geometric isomers” was broader than a federal law which only regulated its “optical and geometric isomers.” No. 20-1034, 2020 WL 4045885, at *4 (7th Cir. July 20, 2020) (citations omitted). Although the court found the state statute overbroad, it expressly noted that the government had not presented evidence that the apparent overbreadth consisted entirely of impossible conduct. Id. at *5. More significantly, the court explicitly “left the door ajar for future science based arguments” and
said that “[t]here may be an occasion where a state statute covers unquestionably nonexistent conduct, but we do not need to predetermine how that analysis will look.” Id.
In this case, the district court held an evidentiary hearing, heard the testimony of expert witnesses, and concluded that geometric isomers of methamphetamine do not chemically exist. Because we know as a scientific fact that dragons have never existed, 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. We see no reason to reach a different result here.
V.
We reverse the dismissal of the information and remand for further proceedings.
REVERSED AND REMANDED.