United States v. Makkar

• Decision Date: 23 November 2015
• Docket Number: 14–5148.,Nos. 14–5147,s. 14–5147
• Citation: 810 F.3d 1139
• Parties: UNITED STATES of America, Plaintiff–Appellee, v. Iqbal MAKKAR, a/k/a Jack Singh, a/k/a Iqbal Singh Makkar, Defendant–Appellant. United States of America, Plaintiff–Appellee, v. Gaurav Sehgal, a/k/a Ricky Sehgal, Defendant–Appellant.
• Court: U.S. Court of Appeals — Tenth Circuit

810 F.3d 1139

UNITED STATES of America, Plaintiff–Appellee,

v.Iqbal MAKKAR, a/k/a Jack Singh, a/k/a Iqbal Singh Makkar, Defendant–Appellant.

United States of America, Plaintiff–Appellee,

v.Gaurav Sehgal, a/k/a Ricky Sehgal, Defendant–Appellant.

Nos. 14–5147

14–5148.

United States Court of Appeals, Tenth Circuit.

Nov. 23, 2015.

Guy A. Fortney (Robert R. Nigh, Jr. and Corbin C. Brewster on the briefs), Brewster & De Angelis, Tulsa, OK, for Defendant–Appellant Iqbal Makkar.

Stanley D. Monroe (Kirsten L. Palfreyman with him on the briefs), Monroe & Keele, P.C., Tulsa, OK, for Defendant–Appellant Gaurav Sehgal.

Leena Alam, Assistant United States Attorney (Danny C. Williams, Sr., United States Attorney, with her on the briefs), Tulsa, OK, for Plaintiff–Appellee.

Before TYMKOVICH, Chief Judge, GORSUCH and McHUGH, Circuit Judges.

GORSUCH, Circuit Judge.

Iqbal Makkar and Gaurav Sehgal ran the "Gitter Done," a small town convenience store in northeastern Oklahoma. When questions surfaced about the incense they carried on their shelves, the men spoke with state law enforcement officers, offered to have the officers test the incense to determine its legality, and offered as well to stop selling the product until the results came in. But this cooperation with state authorities apparently won the men little admiration from federal investigators: soon enough they found themselves under indictment and convicted for violating the Controlled Substance Analogue Enforcement Act (Analogue Act), conspiracy, and money laundering. In this appeal Mr. Makkar and Mr. Sehgal contend that the government overreached at trial—in the jury instructions it sought and won, and again in its successful efforts to exclude evidence of their cooperation with law enforcement. After our own review of the record, we have to agree.

*

Take first Mr. Makkar's argument about the jury instructions. The Analogue Act is a curious animal. It's familiar learning that the Controlled Substances Act (CSA) proscribes the knowing possession and distribution of certain listed substances (marijuana, cocaine, heroin, and the like). What's less well known is that the Analogue Act picks up where the CSA leaves off, forbidding the possession and distribution of substances analogous to those listed in the CSA. In this way, the relationship between the two statutes is not unlike the relationship between the different sections of the Armed Career Criminal Act (ACCA). Much as here, one part of that statute lists certain specific violent felonies and imposes special punishments for their commission. Meanwhile, another part of that statute—what's called its residual clause—extends the statute's punishments to other, unspecified offenses that can claim similarity to listed ones.

The resemblance between the Analogue Act and the residual clause of the ACCA might raise some questions in your mind. After all, the Supreme Court in Johnson v. United States, ––– U.S. ––––, 135 S.Ct. 2551, 192 L.Ed.2d 569 (2015), recently declared the ACCA's residual clause too vague to permit its constitutional application. But so far at least the Court hasn't reached a similar judgment about the Analogue Act. In fact, the Court only recently gave the Analogue Act a narrow construction that may go some way to alleviating potential concerns about the vagueness of its terms. In McFadden v. United States, ––– U.S. ––––, 135 S.Ct. 2298, 192 L.Ed.2d 260 (2015), the Court accepted the government's concession that to establish a violation of the Analogue Act it must prove the drug in question bears two features: (1) it must be substantially similar in chemical structure to a schedule I or II CSA controlled substance, and (2) it must have, or be represented or intended to have, an effect on the central nervous system that is substantially similar to that of a schedule I or II CSA controlled substance. Id. at 2305 n. 2. When it comes to mens rea, the Court further explained, the government must show that the defendant knew the drug he possessed either (1) had both of these features, or (2) was controlled by the CSA or Analogue Act. Id. at 2305. The Court seemed to suggest that this narrow construction would help alleviate potential vagueness concerns, at least in the face of a facial challenge. Id. at 2307. But whether this construction will suffice to save the Analogue Act from the same fate as the ACCA's residual clause may still remain to be seen. It's an open question, after all, what exactly it means for chemicals to have a "substantially similar" chemical structure—or effect. And whether terms like those will admit of fair application and afford citizens fair notice, or whether we will find ourselves wading incrementally, in one as-applied challenge after another, deeper into an analytical swamp much as we did with the ACCA's residual clause litigation.

Still, in this case we face a much more prosaic problem. The government sought and secured an ambitious mens rea instruction that just will not square with the text of the statute or McFadden. At trial, the government didn't attempt to show that Mr. Makkar or Mr. Sehgal knew the incense they sold was unlawful under the CSA or Analogue Act—the second method of proving mens rea McFadden prescribed. Instead, the government attempted to show mens rea only in the first manner McFadden discussed—by showing that the defendants knew that the incense they sold had (1) a substantially similar chemical structure to JWH–18 (a synthetic cannabinoid with marijuana-like effects listed as a CSA controlled substance) and (2) a substantially similar effect to that of marijuana (another CSA listed substance). So far, at least for current purposes we may assume, so good.¹ The difficulty is that, after choosing to proceed this way, the government sought to shrug off the first of the mens rea requirements it had just agreed to shoulder. In fact, as far as we can tell, at trial the government introduced no evidence suggesting that the defendants knew anything about the chemical structure of the incense they sold. And as a way around this shortcoming the government sought—and the district court agreed to issue—an instruction permitting the jury to infer that the defendants knew the incense they sold had a substantially similar chemical structure to JWH–18 from the fact they knew the incense had a substantially similar effect to marijuana. Coming at the point another way, the government asked for and won the right to collapse its two separate elemental mens rea burdens into one. Under the inferential instruction it secured, the government was able to argue to the jury that it should find the first mens rea element satisfied beyond a reasonable doubt merely (and without more) because it found the second satisfied beyond a reasonable doubt.

This surely made trial easier for the government, but just as surely it means we must undo the judgment now. Before a district court may issue an instruction permitting the jury to infer the presence of even a single essential element from a set of facts the inference must—at the least—be shown capable of leading a rational trier of fact to the conclusion that the element in question is proven to the level demanded by the applicable standard of proof. United States v. Berry, 717 F.3d 823, 829 (10th Cir.2013). Neither may a district court ever issue instructions that effectively relieve the government of proving each essential element specified by Congress. See United States v. Gaudin, 515 U.S. 506, 511, 115 S.Ct. 2310, 132 L.Ed.2d 444 (1995). Both of these principles were violated here. The government's instructional inference invited the jury to infer the presence of one essential element from another, effectively collapsing two independent statutory inquiries into one. And it did so only by resort to a logical fallacy, a hasty generalization or associational error—an unwarranted assumption that because certain things share one characteristic they must share others. As a matter of common experience and logic, the fact that one drug produces a similar effect to a second drug just doesn't give rise to a rational inference—let alone rationally suggest beyond a reasonable doubt—that the first drug shares a similar chemical structure with the second drug. And it most certainly does not give rise to a qualifying inference that the first drug shares a similar chemical structure with a third drug—as the government was, in fact, allowed to argue to the jury in this case.

The government now admits all this, expressly acknowledging on appeal that different drugs can bear similar effects while lacking similar chemical structures. As Mr. Makkar notes by way of example, Tylenol

and Aspirin may do much the same job on your aches and pains but most scientists do not place them in the same chemical group. See Harold E. Doweiko, Concepts of Chemical Dependency 208–09 (9th ed.2015). Cocaine and methamphetamine are also sometimes said to have similar effects, but their chemical structures are rarely said to be substantially similar even by the government. See Drug Enforcement Administration, Drugs of Abuse 51 (2015); 2 Encyclopedia of Applied Developmental Science 1062 (Celia B. Fisher & Richard M. Lerner eds., 2005). Even closer to home, the DEA has issued published guidance acknowledging that, while JWH–18 and marijuana have similar effects, the former "is not related in chemical structure to [THC] or other cannabinoids contained in the cannabis plant." Drug Enforcement Administration, JWH–018 1–Pentyl–3–(1–naphthoyl)indole (2013). And closer to home still, the government's own chemistry experts advised the government and court in another case decided before Mr. Makkar's trial that the very inferential instruction it sought here "is not scientifically sound." United States v. Lane, No. CR–12–01419–PHX–DGC, 2013 WL 3716601, at *1 (D.Ariz. July 13, 2013).

But while conceding now that the jury instruction it sought and won in this case was wrong, the government also insists...