United States v. Requena ( 2020 )

18-1906 (L)
United States v. Requena
UNITED STATES COURT OF APPEALS
FOR THE SECOND CIRCUIT
August Term 2019
(Argued: October 22, 2019 Decided: November 4, 2020)
Nos. 18-1906-cr, 18-1923-cr
––––––––––––––––––––––––––––––––––––
UNITED STATES OF AMERICA
Appellee
-v.-
BRIAN REQUENA, ANDREW RAYMOND, 1
Defendants-Appellants
––––––––––––––––––––––––––––––––––––
Before: LIVINGSTON, Chief Judge, KEARSE and WALKER, Circuit Judges.
A jury in the Northern District of New York convicted Brian Requena and
Andrew Raymond, who together ran a synthetic marijuana production and
distribution operation, on one count of conspiracy to possess with intent to
distribute and to distribute a controlled substance analogue. Because the synthetic
marijuana they sold did not contain any chemicals listed on the federal controlled
substance schedules, the jury convicted Requena and Raymond pursuant to the
1 The Clerk of Court is respectfully instructed to amend the caption as set forth
above.
1
Controlled Substance Analogue Enforcement Act, which provides that substances
with chemical and pharmacological properties “substantially similar” to those of
substances listed on schedule I or II are treated for the purposes of federal law as
controlled substances. Requena and Raymond challenge their convictions and the
sentences imposed by the district court (Mordue, J.), arguing that (1) the Analogue
Act’s “substantial similarity” requirement is unconstitutionally vague on its face;
(2) the trial evidence was insufficient to prove their knowledge that they were
dealing in a “controlled substance”; (3) the district court erroneously permitted the
government’s experts to opine that the six synthetic cannabinoids at issue had
features “substantially similar” to those of a scheduled substance; (4) the district
court erroneously permitted the jury to convict Defendants without unanimous
agreement on which of the six synthetic cannabinoids at issue qualified as a
controlled substance analogue; and (5) the district court erroneously sentenced
them based on the total quantity of controlled substance analogues involved in the
conspiracy without determining which of the substances involved actually
qualified as a controlled substance analogue. We conclude that each of their claims
is meritless. Accordingly, the judgment of the district court is AFFIRMED.
FOR APPELLEE: STEVEN D. CLYMER, Assistant United States
Attorney (Carla B. Freedman, Michael F.
Perry, Assistant United States Attorneys, on
the brief), for Grant C. Jaquith, United States
Attorney for the Northern District of New
York, Syracuse, NY, for the United States of
America.
FOR DEFENDANTS-APPELLANTS: JAMES E. FELMAN (Brandon K. Breslow, on
the brief), Kynes Markman & Felman, PA,
Tampa, FL, for Brian Requena and Andrew
Raymond.
DEBRA ANN LIVINGSTON, Chief Judge:
Defendants-Appellants Brian Requena and Andrew Raymond (together,
“Defendants”) appeal from June 22, 2018 judgments of conviction and sentence in
2
the United States District Court for the Northern District of New York (Mordue,
J.), entered after a jury convicted Defendants of conspiracy to possess with intent
to distribute and to distribute a controlled substance analogue in violation of 21
U.S.C. §§ 846, 841(a)(1), and 841(b)(1)(C); and of conspiracy to commit money
laundering pursuant to 18 U.S.C. § 1956(a)(1)(A)(i), (a)(2)(A), and (h). Defendants’
convictions arose from their management of a business directed at the production
and sale of synthetic marijuana, which Defendants and their employees
manufactured using at least six distinct synthetic cannabinoids.
At the time Defendants conspired to distribute them, these synthetic
cannabinoids were not listed on the federal controlled substance schedules.
Instead, the government charged that these substances were “controlled substance
analogues” under the Controlled Substance Analogue Enforcement Act of 1986
(“Analogue Act”). The Analogue Act identifies a controlled substance analogue as
a substance with chemical and pharmacological properties “substantially similar”
to those of a substance listed on schedule I or II, 21 U.S.C. § 802(32), and directs, in
part, that these substances—if “intended for human consumption”—“be treated[]
for the purposes of any Federal law as a controlled substance in schedule I,” id. §
3
813(a). 2 In turn, 21 U.S.C. § 841(a)(1) and (b)(1)(C) prohibit the distribution of
schedule I controlled substances and subject violators to up to twenty years
imprisonment.
Defendants’ appeal challenges, in several respects, the determination that
the Analogue Act subjects them to conviction and sentence for a violation of the
federal drug laws. Principally, they argue (1) that the Analogue Act’s “substantial
similarity” requirement is unconstitutionally vague on its face; (2) that the trial
evidence was insufficient to prove Defendants’ knowledge that they were dealing
in a “controlled substance”; (3) that the district court erroneously permitted the
government’s experts to opine that the six synthetic cannabinoids at issue had
features “substantially similar” to those of a scheduled substance; and (4) that the
district court erroneously permitted the jury to convict Defendants without
unanimous agreement on which of the six synthetic cannabinoids at issue
2 Specifically, 21 U.S.C. § 802(32) provides that, in relevant part, a “controlled
substance analogue” is a substance “(i) the chemical structure of which is substantially
similar to the chemical structure of a controlled substance in schedule I or II; [and] (ii)
which has a stimulant, depressant, or hallucinogenic effect on the central nervous system
that is substantially similar to or greater than [that] of a controlled substance in schedule
I or II . . . .” See, e.g., United States v. Demott, 906 F.3d 231, 236 n.2 (2d Cir. 2018) (assuming
without deciding that these requirements are conjunctive). Section 813(a), in turn,
provides that “[a] controlled substance analogue shall, to the extent intended for human
consumption, be treated, for the purposes of any federal law as a controlled substance.”
21 U.S.C. § 813(a).
4
qualified as a controlled substance analogue. Alternatively, they urge us to
remand for resentencing because the district court calculated their base offense
levels—based in part on the total quantity of controlled substances involved in the
conspiracy—without expressly determining which of the six synthetic
cannabinoids qualified as controlled substance analogues.
We reject each of Defendants’ arguments and AFFIRM the judgment of the
district court.
BACKGROUND
I. Factual Background 3
A.
Sometime in early 2013, Defendant-Appellant Andrew Raymond called
Roger Upchurch with a business proposition. In 2011 and 2012, Raymond had
worked for a company called Airtime Distribution selling, among other things, a
selection of synthetic marijuana that he marketed as “herbal incense.” He reached
out to Upchurch—who owned an Arizona-based synthetic marijuana
manufacturing and distribution company called Driftwood Enterprises—in an
3 The factual background presented here is derived primarily from testimony and
exhibits presented by the government at trial.
5
effort to “get back into the business.” Trial Tr. 348. As it turned out, Upchurch was
nearing retirement and very receptive to Raymond’s offer to join forces.
After a few weeks of discussions, Raymond and Upchurch formed a
company called Real Feel Products and moved all of Upchurch’s synthetic
marijuana production operations from Phoenix to a warehouse in Los Angeles,
where Raymond lived. Upchurch, who lived in Indianapolis and visited Real
Feel’s California warehouse only infrequently, soon ceded nearly all operational
control of the new venture to Raymond, along with an equal 50% stake in the
company. Real Feel proved quite lucrative for both Raymond and Upchurch,
netting each partner profits of up to $20,000 a week in 2013 and early 2014.
Between 90 and 95% of these profits came from the sale of synthetic marijuana.
As Upchurch’s involvement in Real Feel waned during the late summer and
early fall of 2013, Raymond hired Defendant-Appellant Brian Requena to be the
company’s general manager. In that role, Requena served as Raymond’s “right-
hand man,” Trial Tr. 967, supervising Real Feel’s sales team and aiding in the
company’s overall administration. Shortly after Upchurch left Real Feel entirely in
February 2014, Raymond made Requena an equal partner. From that point until
at least December of 2014, each man drew weekly profits of between $50,000 and
6
$100,000. As before, around 90% of these profits came from the sale of synthetic
marijuana.
B.
From its establishment in 2013 to the time of Defendants’ arrests in 2015,
Real Feel’s core operations remained relatively consistent. The company
obtained—first through Upchurch and then through Raymond—multi-kilogram
quantities of raw synthetic cannabinoids in powder form from chemical suppliers
based in China. A division of Real Feel’s approximately 25 employees dissolved
the raw chemicals in acetone and treated leafy plant matter with the resulting
solution. Once the leaves were dry, employees added flavoring and placed the
finished product—which they called “herbal incense” or “potpourri”—into small
bags for sale. Despite this nomenclature, and the fact that each bag bore the label
“not for human consumption,” Trial Tr. 765, Defendants admit that everyone
involved “knew the product was sold with the intention that the consumer would
ingest it for the purpose of getting high,” Appellants’ Br. 4.
Employees shipped the finished and bagged product to customers from
various UPS shipping locations surrounding Real Feel’s warehouse. Defendants
sold the bulk of Real Feel’s synthetic marijuana to wholesalers, including
7
Raymond’s former employer Airtime Distribution and another distribution
company called Eagle Eye Products. Sales to these wholesalers were significant:
Between April 2013 and February 2014, revenues just from Eagle Eye and another
distributor with overlapping ownership ran to nearly $2 million. Real Feel’s sales
team also sold synthetic marijuana directly to smoke shops throughout the United
States.
It was not always easy for Real Feel to obtain the raw synthetic cannabinoids
that formed the heart of its manufacturing enterprise. From time to time, a
shipment of raw chemical would be seized at customs. And periodically,
Defendants learned that the United States Drug Enforcement Administration
(“DEA”) had decided to list the active chemical in their synthetic marijuana on the
federal controlled substance schedules. When this happened, Defendants sold all
remaining product incorporating that chemical at a discount and arranged for Real
Feel’s suppliers to ship an alternative chemical intended to produce the same high.
As a result, over the course of Real Feel’s existence, Defendants’ synthetic
marijuana incorporated a number of different synthetic cannabinoids.
C.
Unbeknownst to Defendants, Real Feel was under investigation from nearly
8
the time of its establishment. In early 2013, the New York State Police discovered
synthetic marijuana during a search of a smoke shop in DeWitt, New York. The
DEA adopted the investigation and traced the contraband to Eagle Eye. Further
inquiry revealed that Eagle Eye, in turn, bought its synthetic marijuana from Real
Feel. A few months after the seizure in DeWitt, DEA agents linked both Eagle Eye
and Real Feel to synthetic marijuana found in another smoke shop in Auburn,
New York. Around the same time, DEA agents in Los Angeles recovered artificial
cannabinoid residue from trash bags that Defendants’ employees had discarded
in a dumpster outside Real Feel’s warehouse. The same agents also observed
Raymond and other Real Feel personnel delivering boxes to Eagle Eye’s offices in
California.
On February 12, 2014, federal agents executed search warrants on multiple
locations including Real Feel’s warehouses in Los Angeles. 4 Their searches
recovered, inter alia, several varieties of raw synthetic cannabinoids, a substantial
quantity of finished synthetic marijuana, and sales records. The records connected
Real Feel to numerous sales of synthetic marijuana to various smoke shops in the
By this point, Real Feel had expanded its operations to two warehouses with a
4
common parking lot.
9
Northern District of New York, where Defendants were ultimately tried.
Following the searches on February 12, 2014, Upchurch terminated his
involvement with Real Feel, began cooperating with the DEA’s investigation, and
ultimately pleaded guilty in the Southern District of Indiana to charges mirroring
those brought against Defendants in the Northern District of New York.
After the February seizures, Raymond suspended Real Feel’s operations,
but did not dissolve the company. Instead, about two months later, Defendants
revived Real Feel and resumed production of synthetic marijuana in a larger
warehouse in a different part of Los Angeles. Requena, who became Raymond’s
partner shortly after reopening, opened several new bank accounts and postal
boxes on Real Feel’s behalf, often identifying Real Feel as a clothing business. Real
Feel’s operations, however, remained sharply focused on synthetic marijuana and,
as noted above, continued to net its owners substantial profits.
On April 14, 2015—after further investigation that included the seizure of
more than 50 kilograms of synthetic cannabinoids shipped to Requena from Real
Feel’s suppliers in China—federal agents executed a warrant to search Real Feel’s
new warehouse. There, agents recovered dozens of bins of synthetic marijuana
and multiple kilograms of raw synthetic cannabinoids. In all, seizures of Real
10
Feel’s product from its warehouses and its customers’ shops connected
Defendants to at least six synthetic cannabinoid compounds. On the same day,
both Defendants were arrested and taken into federal custody.
II. Procedural History
On March 24, 2016, a federal grand jury in the Northern District of New
York returned the operative indictment, which charged both Raymond and
Requena with one count of conspiring to distribute and possess with intent to
distribute one or more controlled substance analogues in violation of 21 U.S.C.
§ 841(a)(1)—rendering them subject to sentencing under § 841(b)(1)(C)—and one
count of conspiracy to commit promotional and international money laundering
in violation of 18 U.S.C. § 1956(a)(1)(A)(i), (a)(2)(A), and (h). The indictment
specifically alleged that Defendants’ offense involved the following six substances,
each of which it alleged was a controlled substance analogue: XLR11, PB-22, 5F-
PB-22, AB-PINACA, 5F-AB-PINACA, and APP-CHMINACA.
A jury trial commenced in the United States District Court for the Northern
District of New York (Mordue, J.) on July 12, 2017 and concluded on July 26, 2017.
Numerous witnesses—including Upchurch, former Real Feel employees, former
Real Feel customers, and DEA agents involved in the investigation—testified
11
regarding Real Feel’s operations and Defendants’ roles in them. The government
also offered the expert testimony of DEA chemist Michael Van Linn and DEA
pharmacologist Jordan Trecki, who opined that the six chemicals alleged in the
indictment were substantially similar in chemical structure and pharmacological
effect to various substances listed on the federal controlled substance schedules.
The jury retired to deliberate on July 25, 2017. Prior to its deliberations, the
district court instructed the jury, inter alia, that in order to convict Defendants of
conspiracy to distribute or possess with intent to distribute a controlled substance,
it must “unanimously agree that the government has proven that at least one of
the substances identified in Count [One] of the indictment qualifies as a controlled
substance analogue” but that it “need not . . . unanimously agree on which of the
substance or substances qualify.” A. 291–92. Neither party objected to this or any
other part of the instructions.
On July 26, 2017, the jury returned guilty verdicts as to both defendants on
both counts charged in the indictment. On June 20, 2018, the district court
sentenced Raymond to consecutive terms of 180 months’ imprisonment on Count
One and 120 months’ imprisonment on Count Two, followed by a three-year term
of supervised release. On the same day, it sentenced Requena to consecutive terms
12
of 180 months’ imprisonment on Count One and 60 months’ imprisonment on
Count Two, followed by a three-year term of supervised release. Both sentences
were substantially below the range indicated by the United States Sentencing
Guidelines, which the district court calculated based in part on the total weight of
controlled substance analogues federal agents seized from Defendants’
warehouses. Two days later, the district court entered its judgments of conviction
and sentence as to both Raymond and Requena. Both Defendants timely appealed.
DISCUSSION
I. Defendants’ Vagueness Challenge
Defendants first argue that we must vacate their convictions because the
Analogue Act is unconstitutionally vague on its face. They claim that since no
objective standard governs a juror’s determination of whether a substance has a
chemical structure and pharmacological effects that are “substantially similar” to
those of a scheduled substance, the Act’s definition of a “controlled substance
analogue” invites impermissibly arbitrary enforcement and provides potential
defendants with no warning about what conduct is prohibited. Defendants argue
that the Analogue Act is inherently vague as applied against any potential
defendant—necessarily including themselves—but make no separate, more
13
specific argument that the Act is unconstitutionally vague as applied to the facts
of this case.
A “statute is unconstitutionally vague if it fails to define the unlawful
conduct with ‘sufficient definiteness that ordinary people can understand what
conduct is prohibited,’ or if its vagueness makes the law unacceptably vulnerable
to ‘arbitrary enforcement.’” United States v. Demott, 906 F.3d 231, 237 (2d Cir. 2018)
(quoting Kolender v. Lawson, 461 U.S. 352, 357–58 (1983)). Vagueness challenges
typically concern a statute “as applied” to the challenger, who professes that the
law in question “cannot constitutionally be applied to the challenger’s individual
circumstances.” Copeland v. Vance, 893 F.3d 101, 110 (2d Cir. 2018). But a party may
also challenge a statute as vague on its face, asserting that it is “so fatally indefinite
that it cannot constitutionally be applied to anyone.” Id. In the ordinary case, a
facial vagueness challenge carries a significant burden: “the challenger must
establish that no set of circumstances exists under which the Act would be valid.”
Id. (quoting United States v. Salerno, 481 U.S. 739, 745 (1987)).
The Supreme Court has recognized three circumstances in which a statute
that is not necessarily vague in all applications may nonetheless be void for
vagueness on its face. In the most established of these, a challenger may raise a
14
facial challenge if the statute implicates rights protected by the First Amendment,
even if the statute is not vague as applied to that challenger’s conduct. See, e.g.,
Parker v. Levy, 417 U.S. 733, 759 (1974) (“First Amendment . . . attacks have been
permitted ‘on overly broad statutes with no requirement that the person making
the attack demonstrate that his own conduct could not be regulated by a statute
drawn with the requisite narrow specificity.’” (quoting Dombrowski v. Pfister, 380
U.S. 479, 486 (1965))); cf. Kolender, 461 U.S. at 358–59 n.8 (“[W]e permit a facial
challenge if a law reaches ‘a substantial amount of constitutionally protected
conduct.’” (quoting Village of Hoffman Estates v. Flipside, Hoffman Estates, Inc., 455
U.S. 489, 494 (1982))). A plurality of the Supreme Court has also suggested that “a
criminal law lacking a mens rea requirement and burdening a constitutional right
‘is subject to facial attack’ ‘[w]hen vagueness permeates the text of such a law,’”
even if that law does not impinge on rights guaranteed by the First Amendment
specifically. N.Y. State Rifle & Pistol Ass’n v. Cuomo, 804 F.3d 242, 265 (2d Cir. 2015)
(alteration in original) (quoting City of Chicago v. Morales, 527 U.S. 41, 55 (1999)
(plurality opinion)). Finally, in a recent trilogy of cases beginning with Johnson v.
United States, 576 U.S. 591 (2015), the Supreme Court struck down three statutes
that required courts to evaluate whether the “idealized ordinary case” of a
15
criminal offense constitutes a “violent felony,” 576 U.S. 602–04, or a “crime of
violence,” Sessions v. Dimaya, 138 S. Ct. 1204 (2018); United States v. Davis, 139 S. Ct.
2319 (2019). Johnson held, and Dimaya reaffirmed, that such a statute may be void
for vagueness even though “some conduct . . . clearly falls within the provision’s
grasp.” Johnson, 576 U.S. at 602; Dimaya, 138 S. Ct. at 1214 n.3. Neither the Supreme
Court nor our Court has definitively resolved whether facial vagueness challenges
not based on the First Amendment may proceed against statutes that can
constitutionally be applied to the challenger’s own conduct. Copeland, 893 F.3d at
111; see also Farrell, 449 F.3d at 495 n.12.
Instead, we typically evaluate “[v]agueness challenges to statutes not
threatening First Amendment interests . . . in light of the facts of the case at hand,”
i.e., only “on an as-applied basis.” Maynard v. Cartwright, 486 U.S. 356, 361 (1988);
accord United States v. Holcombe, 883 F.3d 12, 17 (2d Cir. 2018) (“Where . . . First
Amendment rights are not implicated, we evaluate such a challenge . . . [without]
regard to the facial validity of the criminal statute or regulation at issue.” (emphasis
added)). And we have often declined to entertain facial challenges where the
challenger asserts no infringement of First Amendment or other fundamental
rights protected by the Constitution. See Dickerson v. Napolitano, 604 F.3d 732, 743–
16
45 (2d Cir. 2010). Despite this “baseline aversion to facial challenges,” we are
permitted to consider them in appropriate cases, 5 id. at 742, and we have done so
in the past to facilitate a challenge’s definitive rejection, see United States v. Rybicki,
354 F.3d 124, 131–32 & n.3, 144 (2d Cir. 2003) (en banc) (“While it is unclear . . .
whether it is appropriate to decide the question of the asserted facial
invalidity . . . , we think that a conclusion of facial invalidity would be inconsistent
with the foregoing analysis.”); see also Farrell, 449 F.3d at 495 n.11 (acknowledging
the Rybicki court’s decision to “assess[] the facial validity of the statute even though
no First Amendment rights were implicated.”). But even where we have addressed
the merits of a facial challenge outside the First Amendment context, we have
recognized the Supreme Court’s instruction to at least “examine the complainant’s
conduct before analyzing other hypothetical applications of the law.” Rybicki, 354
F.3d at 130 (quoting Village of Hoffman Estates v. Flipside, Hoffman Estates, Inc., 455
U.S. 489, 495 (1982)).
5 Certain of our decisions’ unequivocal language notwithstanding, see Holcombe,
883 F.3d at 17; United States v. Nadi, 996 F.2d 548, 550 (2d Cir. 1993), we have declined to
endorse wholesale the proposition that facial challenges are entirely foreclosed outside
the First Amendment context. See N.Y. State Rifle & Pistol Ass’n, 804 F.3d at 265; Dickerson,
604 F.3d at 733; United States v. Rybicki, 354 F.3d 124, 131–32 & n.3, 144 (2d Cir. 2003) (en
banc).
17
In this case, however, we need not examine either Defendants’ conduct or
“other hypothetical applications of the law,” id., in order to reject their facial
challenge—assuming arguendo that they are entitled to bring one at all. Despite
Defendants’ contention that the Analogue Act is vague as applied to all possible
prosecutions, precedent definitively establishes that they cannot “establish that no
set of circumstances exists under which the Act would be valid.” Salerno, 481 U.S.
at 745. We have on several occasions upheld the Analogue Act’s definition of a
“controlled substance analogue” against as-applied vagueness challenges. 6
Demott, 906 F.3d at 237–39; United States v. Ansaldi, 372 F.3d 118, 122–24 (2d Cir.
2004), abrogated on other grounds by McFadden v. United States, 576 U.S. 186 (2015);
United States v. Roberts, 363 F.3d 118, 122–27 (2d Cir. 2004); see also United States v.
Lawton, 759 F. App’x 66, 67 (2d Cir. 2019) (summary order). It is therefore
impossible for Defendants to demonstrate the Analogue Act’s invalidity as
applied to every conceivable defendant.
Defendants attempt to skirt these precedents by arguing that the Supreme
6 Other circuits to have considered this issue have likewise concluded that the
“substantially similar” language in the Analogue Act is not unconstitutionally vague. See,
e.g., United States v. Turcotte, 405 F.3d 515, 531–32 (7th Cir. 2005) (collecting cases),
abrogated on other grounds by United States v. Novak, 841 F.3d 721, 729 (7th Cir. 2016).
18
Court’s recent decisions in Johnson, Dimaya, and Davis—each of which invalidated
a criminal statute as facially vague notwithstanding the potential for conduct that
“clearly falls within the provision’s grasp,” Johnson, 576 U.S. at 602—are
intervening authority that not only permit us to entertain a facial challenge outside
of the First Amendment context, but actually require us to repudiate our prior cases
sustaining the Analogue Act against as-applied vagueness challenges. See Lotes Co.
v. Hon Hai Precision Indus. Co., 753 F.3d 395, 405 (2d Cir. 2014) (explaining that one
panel of our Court may not usually overrule another unless “an intervening
Supreme Court decision [has] cast[] doubt on our controlling precedent” (quoting
In re Zarnel, 619 F.3d 156, 168 (2d Cir. 2010)). They claim that Johnson and its
progeny establish a new framework for facial vagueness challenges under which
(1) every application of the Analogue Act is unconstitutional and (2) in any case,
the existence of some straightforward applications cannot save the statute from
invalidation. We conclude that none of those decisions suggests that we may (or
should) depart from our prior decisions upholding the Analogue Act.
First, we decided Demott after the Supreme Court had already published
Johnson and Dimaya. Indeed, our decision to reject the defendants’ as-applied
vagueness challenge to the Analogue Act’s “substantial similarity” requirement
19
relied in part on those cases’ explication of vagueness doctrine. See Demott, 906
F.3d at 237 (“[A]s the Supreme Court has recently explained, . . . ‘non-numeric,’
‘qualitative standard[s]’ abound in our law, and are not so inherently problematic
as to independently render a statute void for vagueness.” (quoting Dimaya, 138 S.
Ct. at 1215)). Demott also affirmed the continuing vitality of our prior case law
“uph[olding] the Analogue Act against vagueness challenges.” Id. In other words,
Johnson and Dimaya are not intervening authority at all.
Second, and more importantly, the “exceptional circumstances” that
justified Johnson’s extraordinary facial invalidation are not present here. See
Copeland, 893 F.3d at 111 n.2. Demott, which concerned only an as-applied
challenge to the Analogue Act’s “substantially similar” requirement, did not call
on us to expressly distinguish that statutory provision from those that Johnson and
its progeny invalidated as facially vague. That question is squarely before us now,
and we conclude that the concern that motivated the Supreme Court’s rulings in
Johnson, Dimaya, and Davis is inapplicable to the Analogue Act. Each of those
decisions invalidated a statute that required courts to apply the “categorical
approach”—that is, to estimate the degree of risk posed by the imagined
“idealized ordinary case” of a criminal offense, abstracted from the defendant’s
20
actual conduct. Johnson, 576 U.S. at 604. In each case, it was not the laws’
employment of qualitative standards, but rather those standards’ application to a
“judge-imagined abstraction,” that rendered them unconstitutionally vague.
Johnson, 576 U.S. at 598; see also Dimaya, 138 S. Ct. at 1215–16.
In Johnson, the Court explained that its holding does not call into “doubt the
constitutionality of laws that call for the application of a qualitative standard such
as ‘substantial risk’ to real-world conduct.” 576 U.S. at 604 (emphasis added). To the
contrary, it recognized that “the law is full of instances where a man’s fate depends
on his estimating rightly some matter of degree.” Id. (internal quotation marks and
alteration omitted). It is only when such a qualitative standard “conspire[s]” with
an ordinary-case requirement that the statute at issue “produces more
unpredictability and arbitrariness than the Due Process Clause tolerates.” Id.
The Analogue Act harbors no such conspiracy. We have recognized that
determining whether a substance is “substantially similar” to another “inevitably
involves a degree of uncertainty,” Demott, 906 F.3d at 237 (citing United States v.
Makkar, 810 F.3d 1139, 1143 (10th Cir. 2015) (Gorsuch, J.)). But the factfinder in an
Analogue Act prosecution applies its qualitative standard exclusively to a
defendant’s real-world conduct. Neither the Supreme Court nor our Court has
21
ever extended the reasoning in Johnson and its progeny to invalidate a statute that
does not require application of the categorical approach. Rather, this Court has
expressly cabined the Johnson reasoning to statutes that do. See Copeland, 893 F.3d
at 111 n.2 (suggesting that Johnson’s license to strike down a “criminal statute . . .
as facially vague even where it has some valid applications” extends only to the
“exceptional circumstances” present in that case and its progeny).
In an effort to bring this case within Johnson’s narrow ambit, Defendants
insist that the Analogue Act does “possess[] the same two features that warranted
the Supreme Court’s intervention” in that case. Appellants’ Br. at 30. This is so,
they argue, because the Analogue Act first imposes a qualitative “substantially
similar” standard, and second requires a defendant to know in advance a “jury-
imagined opinion of whether a substance is a controlled-substance analogue.” Id.
at 32. But this putative second problem—despite Defendants’ artful attempt to
mirror Johnson’s concern over a “judge-imagined abstraction”—is nothing more
than a restatement of the first, and certainly not equivalent to the application of
the categorical approach. That an Analogue Act defendant is subject to a jury’s
understanding of substantial similarity is simply one more (constitutionally
permissible) instance in which “a man’s fate depends on his estimating rightly
22
some matter of degree.” Johnson, 576 U.S. at 604 (internal quotation marks and
alteration omitted); see also Demott, 906 F.3d at 237 (emphasizing that “non-
numeric” and “qualitative” standards “are not so inherently problematic as to
independently render a statute void for vagueness”). The key to the Act’s
constitutionality under Johnson is that whoever applies its “substantial similarity”
standard—whether a potential defendant weighing the legality of his conduct ex
ante, or a juror doing so ex post—does so in connection with real-world conduct.
The Analogue Act imposes nothing resembling an “ordinary case” requirement; it
calls upon jurors to determine only whether the actual substance at issue is
substantially similar in both structure and effect to an actual scheduled substance.
In sum, Defendants’ contention that the Analogue Act “presents the same
problems as the application of the categorical approach,” Appellants’ Br. at 31, is
without merit. 7
7 The two circuits to have considered facial vagueness challenges to the Analogue
Act since Johnson have reached the same conclusion. United States v. Palmer, 917 F.3d 1035,
1038 (8th Cir. 2019) (rejecting a facial vagueness challenge based on Johnson in part
“[b]ecause we do not apply the categorical approach under the Analogue Act.”); United
States v. Larson, 747 F. App’x 927, 930 (4th Cir. 2018) (unpublished decision) (rejecting an
unpreserved facial challenge to the Analogue Act on plain error review but declining to
rule definitively on the Act’s constitutionality).
23
II. Defendants’ Sufficiency Challenge
Defendants next challenge the sufficiency of the government’s evidence to
prove their knowledge that they possessed or distributed a controlled substance
analogue. 8 We review challenges to the sufficiency of trial evidence de novo. United
States v. Lyle, 919 F.3d 716, 737 (2d Cir. 2019). In so doing, we view the evidence in
the light most favorable to the Government with all reasonable inferences resolved
in the Government’s favor. United States v. Anderson, 747 F.3d 51, 60 (2d Cir. 2014).
We must uphold the jury’s verdict “if any rational trier of fact could have found
the essential elements of the crime had been proved beyond a reasonable doubt.”
United States v. Valle, 807 F.3d 508, 515 (2d Cir. 2015) (emphasis added). We
therefore “assum[e] that the jury resolved all questions of witness credibility . . .
in favor of the prosecution,” United States v. Abu-Jihaad, 630 F.3d 102, 134 (2d Cir.
2010), and “defer to the jury’s determination of the weight of the evidence and the
credibility of the witnesses, and to the jury’s choice of the competing inferences
that can be drawn from the evidence,” United States v. Best, 219 F.3d 192, 200 (2d
Cir. 2000) (internal quotation marks omitted).
8 Defendants do not challenge the sufficiency of the evidence to prove that the
substances in question were controlled substance analogues, and their counsel conceded
at oral argument that such an argument would lack merit.
24
In prosecutions involving controlled substance analogues, the government
may satisfy 21 U.S.C. § 841(a)(1)’s knowledge requirement in either of two ways:
First, it can present evidence that the defendant “knew that the substance with
which he was dealing is some controlled substance—that is, one actually listed on
the federal drug schedules or treated as such by operation of the Analogue Act—
regardless of whether he knew the particular identity of the substance.” McFadden,
576 U.S. at 194. Second, it can present evidence that the defendant knew that the
substance has a chemical structure and pharmacological effects substantially
similar to or greater than, those of a controlled substance in schedule I or II. 9 Id. at
9 McFadden explains these alternative methods of proving knowledge in several
places. In one such articulation of the second route, McFadden states that knowledge “can
be established by evidence that the defendant knew the specific analogue he was dealing
with, even if he did not know its legal status as an analogue.” 576 U.S. at 194. In isolation,
this language could be read to suggest that a defendant who knows the identity of the
analogue substance, but none of the features that make it an analogue, has the requisite
knowledge for conviction. Indeed, a nonprecedential summary order of this Court,
reviewing jury instructions for plain error, could without context be understood to
endorse such a reading. See United States v. Smutek, 730 F. App’x 18, 22 (2d Cir. 2018) (“The
district court correctly instructed the jury that the government was required to prove
beyond a reasonable doubt that Smutek knew: (1) that Potion 9 contained a controlled
substance analogue, even if he did not know the identity of the substance, or (2) that
Potion 9 contained 1,4 butanediol, even if he did not know that 1,4 butanediol was a
controlled substance analogue.”). But as the subsequent sentences of McFadden—as well
as other passages of the decision—make clear, the government must either prove that the
defendant knew that the substance at issue was controlled or that it had the chemical and
pharmacological features that make it an analogue. 576 U.S. at 194–95 (“The Analogue
Act defines a controlled substance analogue by its features . . . . A defendant who
possesses a substance with knowledge of those features knows all of the facts that make
25
189, 193–95. “Although the Government must prove that a defendant knew that
the substance in question was ‘a controlled substance’ under federal law, the
Government need not introduce direct evidence of such knowledge. As with
prosecutions involving substances actually listed on the drug schedules, the
Government may offer circumstantial evidence of that knowledge.” Id. at 195 n.3.
“Circumstantial evidence could include, for example, a defendant’s concealment
of his activities, evasive behavior with respect to law enforcement, knowledge that
a particular substance produces a ‘high’ similar to that produced by controlled
substances, and knowledge that a particular substance is subject to seizure at
customs.” Id. at 192 n.1.
The government presented ample direct and circumstantial evidence to
prove that Defendants knowingly possessed and distributed controlled substance
analogues. First, as Defendants admit on appeal, “[e]veryone material to the
his conduct illegal . . . .”); id. at 196 (“Knowledge [that a substance is controlled] can be
established . . . either by knowledge that a substance is listed or treated as listed by
operation of the Analogue Act or by knowledge of the physical characteristics that give
rise to that treatment. (internal citation omitted)); id. at 189 (“The knowledge requirement
is also met if the defendant knew the specific features of the substance that make it a
controlled substance analogue.” (internal quotation marks omitted)); cf. also id. at 198
(Roberts, C.J., concurring in part) (“[A] defendant needs to know more than the identity
of the substance; he needs to know that the substance is controlled.” (emphasis in
original)).
26
transaction . . . knew [Defendants’] product was sold with the intent that the
consumer would ingest it for the purpose of getting high.” Appellants’ Br. at 4.
Numerous witnesses testified that Defendants sought chemicals to produce a
“buzz” or “high” similar to or stronger than the one induced by smoking
marijuana, and that Defendants and their employees at times smoked their
product themselves to test its potency. 10 But despite their admitted knowledge
that their product was intended to be smoked, Defendants distributed it in
packages labeled “not for human consumption,” tracking the precise language of
the Analogue Act. See 21 U.S.C. § 813.
This purposeful misdirection was far from the only evidence that
Defendants knew their product was both similar to other controlled substances
and controlled in its own right. One former employee testified that each time the
active chemical in one of Defendants’ products was added to the federal drug
schedules, Defendants would replace it with another that they expected to
produce a similar high. The government also presented evidence that Defendants
labeled their products with designs evoking the use of controlled substances,
10 Employees testified that Real Feel at times produced products incorporating a
greater quantity of raw chemical to mimic the effects of a greater quantity of THC, the
primary psychoactive chemical in marijuana.
27
including, in Requena’s own words, “a Mule/Donkey that is smoked out” and a
“[r]eference to AMC’s Breaking Bad”—a television show about the manufacture
and distribution of methamphetamine. G.A. 294. Employee testimony suggested
that this was no innocent coincidence—one worker recalled that Raymond openly
informed Real Feel employees that “what we make . . . [is] more than
questionable.” Trial Tr. at 1070.
Evidence of the extreme precautions Defendants took to conceal the nature
of their operations further suggests that Defendants knew their product
incorporated controlled substance analogues. The government presented evidence
that not only did Defendants label their product using the language of the
Analogue Act, they also maintained a list of “words not to say!” including
“smoke” and “analog,” G.A. 245, and they instructed their salespeople not to use
language suggesting that customers should smoke or otherwise consume their
products.
Witnesses also testified that although Defendants initially had their
chemical supplier ship the raw synthetic cannabinoids directly to the warehouse
where it was incorporated into product for sale, they eventually had these
chemicals shipped to post office boxes or employees’ homes—and in one case to
28
an employee’s sister’s place of business—instead. 11 See United States v. O’Brien,
926 F.3d 57, 80–81 (2d Cir. 2019) (describing a defendant’s instructions to ship
drugs to multiple associates’ addresses and post office boxes as probative of his
knowledge that the drugs are controlled). Moreover, documents collected at
Defendants’ warehouse suggest that invoices accompanying at least some of the
raw chemical shipments misidentified the shipments’ contents and price. See id. at
81 (“The intercepted packages . . . bore labels that misrepresented their contents as
various uncontrolled substances, when in fact they contained [the controlled
substances] that O’Brien had ordered.”). And once Real Feel had incorporated the
raw chemicals into finished product, Raymond insisted that employees ship it to
customers from multiple UPS Stores surrounding Real Feel’s base of operations
because “he didn’t want UPS coming directly to” the warehouse. Trial Tr. 1063.
Other evidence suggested that Defendants attempted to conceal their
product entirely from public view. Photographic evidence and testimony
indicated that at an annual trade show for smoke shops, Defendants intentionally
did not display any of their principal product, exhibiting glassware instead.
11Evidence showed that Requena obfuscated the purpose of Defendants’ business
while completing the paperwork to open those post office boxes, a tactic he also
employed when opening Real Feel’s bank accounts.
29
Former employees also testified that Raymond filmed a reality-television-style
video to promote himself and Real Feel, but instructed workers to conceal raw
synthetic cannabinoids and finished products from view—and instead to display
glassware at the workstations where they typically incorporated raw synthetic
cannabinoids into product for sale.
Moreover, the government presented ample evidence that law enforcement
activity put Defendants on notice that they were dealing in controlled substances.
Defendants’ accountant testified that though Defendants knew customs
frequently seized chemicals en route from their supplier in China, they made no
effort to recover them and, in at least one case, filed a response voluntarily
abandoning a shipment. See McFadden, 576 U.S. at 192 n.1. When the DEA raided
Defendants’ warehouses in February 2014, agents seized all raw chemical and
finished product on the premises and left a copy of the search warrant, which
authorized the seizure of items related to a conspiracy to manufacture and
distribute a controlled substance analogue as defined in 21 U.S.C. §§ 802(32) and
813. Employees testified that though Defendants continued to operate the business
following the raid, they never attempted to recover the (very valuable) seized
material.
30
Finally, the government also presented direct evidence that Defendants
knew the specific structure and pharmacological effects of the chemicals in the
products they sold. Former Real Feel employees testified that Defendants, with the
assistance of their employees, researched state and federal drug laws—including
provisions on controlled substance analogues. Among research materials
recovered from Defendants’ electronic files was a DEA publication detailing the
chemical structure and pharmacological effects of two of the synthetic
cannabinoids at issue in this case, noting that each “may be treated as a ‘controlled
substance analogue’” pursuant to 21 U.S.C. § 813. G.A. 258.
In light of the foregoing, we easily conclude that the jury had sufficient
evidence to infer that Defendants knew they were dealing in a controlled
substance.
III. Defendants’ Challenge Regarding Expert Testimony
Defendants also argue that the district court should have excluded
testimony by the government’s two expert witnesses, Dr. Michael Van Linn and
Dr. Jordan Trecki, as to whether the synthetic cannabinoids at issue were
“substantially similar” in structure and pharmacological effect to controlled
substances. They argue that because there is no objective chemical or
31
pharmacological standard for substantial similarity, the district court should not
have admitted expert testimony on that question under the principles articulated
in Daubert v. Merrell Dow Pharmaceuticals, Inc., 509 U.S. 579, 592–94 (1993).
We review a district court’s decision to admit expert testimony for abuse of
discretion. United States v. Williams, 506 F.3d 151, 159–60 (2d Cir. 2007). Our review
is “highly deferential,” and we will sustain the district court’s decision unless it is
“manifestly erroneous.” Restivo v. Hessemann, 846 F.3d 547, 575 (2d Cir. 2017)
(quoting Lore v. City of Syracuse, 670 F.3d 127, 155 (2d Cir. 2012)). Pursuant to
Federal Rule of Evidence 702, a district court exercises a gatekeeping function to
ensure that a testifying expert’s “scientific, technical, or other specialized
knowledge will help the trier of fact to understand the evidence or to determine a
fact in issue,” that the testimony is “based on sufficient facts or data,” and that
such testimony is “the product of reliable principles and methods . . . reliably
applied . . . to the facts of the case.” Fed. R. Evid. 702. Defendants’ challenge focuses
on the last of these: they contend that Dr. Van Linn’s and Dr. Trecki’s opinions of
whether one substance is “substantially similar” to another are “not subject to
verification through any means,” and lack “any known error rate, possible means
of replicating or testing the correctness of the opinions, testing conditions, or
32
evidence of peer review,” and so should have been excluded. Appellants’ Br. 47.
In assessing the reliability of an expert’s methodology, the district court may
consider, among other factors, “(1) whether a theory or technique has been or can
be tested; (2) ‘whether the theory or technique has been subjected to peer review
and publication;’ (3) the technique’s ‘known or potential rate of error’ and ‘the
existence and maintenance of standards controlling the technique's operation;’
and (4) whether a particular technique or theory has gained general acceptance in
the relevant scientific community.” Williams, 506 F.3d at 160 (quoting Daubert, 509
U.S. at 593–94 (1993)). But these factors are by no means a “definitive checklist or
test.” Kumho Tire Co. v. Carmichael, 526 U.S. 137, 150 (1999). Rather, “the
gatekeeping inquiry must be tied to the facts of a particular case,” and we defer
“as much to the trial court’s decisions about how to determine reliability as to its
ultimate conclusion.” Id. at 150, 152 (internal quotation marks omitted); see also
United States v. Romano, 794 F.3d 317, 331 (2d Cir. 2015) (“Whether Daubert’s
specific factors are . . . reasonable measures of reliability in a particular case is a
matter that the law grants the trial judge broad latitude to determine.” (internal
quotation marks and alterations omitted)).
We conclude that the district court did not abuse its discretion in permitting
33
the government’s experts to opine that the synthetic cannabinoids at issue are
substantially similar in structure and pharmacological effect to scheduled
substances. Although substantial similarity is not itself a scientific standard, the
district court had ample basis to conclude that the experts’ opinions were
nonetheless “the product of reliable principles and methods . . . applied . . . to the
facts of the case.” Fed. R. Evid. 702(c) (emphasis added). In explaining his
conclusion that the substances at issue had a substantially similar chemical
structure to scheduled substances, Dr. Van Linn described how chemists depict
the makeup and structure of organic molecules using two-dimensional diagrams.
He proceeded to use such diagrams to compare the structures of each of the
synthetic cannabinoids at issue with their alleged scheduled analogues. Likewise,
Dr. Trecki explained various ways pharmacologists assess a substance’s effect on
the central nervous system—including visual examination, in vitro binding assays,
in vitro functional assays, animal trials, and case reports—and referred to these
methods to compare the hypothesized or observed pharmacological effects of each
of the synthetic cannabinoids at issue with those of allegedly similar scheduled
substances.
Admitting that the above methodologies are reliable, Defendants concede
34
that it was appropriate to permit the experts to describe their analytical methods,
as well as the specific ways in which the substances at issue are similar to and
different from scheduled substances. They challenge only the experts’ application
of these methods to draw a conclusion on the ultimate question of substantial
similarity. 12 But even this limited challenge must fail.
Defendants are correct that the actual determination of substantial similarity
is not a scientific one. 13 But as they rightly concede, the government’s experts’
“opinions . . . regarding the substantial similarity of [the] substances” in this case
12 Of course, expert testimony is not objectionable “merely because it ‘embraces
an ultimate issue’ to be decided by the factfinder.” Lore, 670 F.3d at 155 (quoting Fed. R.
Evid. 704(a)). Indeed, such testimony is sometimes critical in helping a jury understand
highly technical evidence. In analogue prosecutions, for instance, many jurors might find
the sort of chemical and pharmacological evidence necessary to prove that a substance is
a controlled substance analogue all but inscrutable, absent expert guidance of this sort.
13 We note parenthetically that a district court could well abuse its discretion by
permitting an expert to affirm that “substantial similarity” is a matter of objective
scientific fact rather than a subjective conclusion based on a conventional understanding
of the words “substantial” and “similar.” The experts in this case, however, did no such
thing. To the contrary, Dr. Van Linn testified that “substantially similar” is “not a
scientific term” and “not a scientific question,” acknowledging that he reached an
understanding of its meaning after looking up its constituent words in a standard
dictionary. Trial Tr. 1539. Likewise, Dr. Trecki testified that “substantial similarity” is
“just a plain English term” and “not scientific,” explaining that he, too, had used a
dictionary to determine its meaning. Tr. 1666–67. And in its instructions, the district court
admonished the jury not to “substitute [the experts’ opinions] for your own reason,
judgment, and common sense” because “[t]he determination of the facts in this case rests
solely with you.” A. 274.
35
are “based on . . . scientific facts or findings.” Appellants’ Br. 48 (emphasis added).
And the inferential step between the experts’ uncontroversial scientific
observations and the ultimate question of whether the substances have
“substantially similar” properties is not unduly “speculative[,] conjectural[,] or
based on assumptions that are so unrealistic and contradictory as to suggest bad
faith.” Zerega Ave. Realty Corp. v. Hornbeck Offshore Transp., LLC, 571 F.3d 206, 214
(2d Cir. 2009) (internal quotation marks and alteration omitted). Instead, these
experts’ opinions on substantial similarity are “the product of reliable principles
and methods . . . reliably applied to the facts of the case,” precisely as Rule 702
requires. Fed. R. Evid. 702; see also Restivo, 846 F.3d at 576 (explaining that under
Rule 702, scientists “may express professional opinions that fall short of definitive
proof” (internal quotation marks omitted)). Accordingly, we reject Defendants’
claim that the district court abused its discretion. 14
14 To our knowledge, every Court of Appeals to have considered a similar
question has reached the same conclusion. See, e.g., United States v. Carlson, 810 F.3d 544,
553 (8th Cir. 2016) (affirming the district court’s discretion to admit expert testimony on
substantial similarity “based on” evidence, specialized knowledge, literature review, and
discussions with other scientists); cf. United States v. Galecki, 932 F.3d 176, 183, 186 (4th
Cir. 2019) (declaring that an expert’s testimony that a putative analogue was not
“substantially similar” to a scheduled substance would have “violated no Federal Rules
of Evidence”).
36
IV. Defendants’ Challenge to the Jury Instructions
Defendants further contend that the district court erred in instructing the
jury that it must unanimously agree that at least one of the charged synthetic
cannabinoids qualifies as a controlled substance analogue, but that it need not
unanimously agree on precisely which substances so qualify. Since Defendants
did not object to the district court’s instructions before the jury retired to
deliberate, we review the jury instructions for plain error. See Fed. R. Crim. P.
30(d). Under this standard, we will disturb the district court’s decision only where
“(1) there is an error; (2) the error is clear or obvious, rather than subject to
reasonable dispute; (3) the error affected the appellant's substantial rights, which
in the ordinary case means it affected the outcome of the district court proceedings;
and (4) the error seriously affect[s] the fairness, integrity or public reputation of
judicial proceedings.” United States v. Marcus, 560 U.S. 258, 262 (2010). Because we
hold that the district court’s instruction was not erroneous, Defendants’ challenge
fails at the first step of this analysis.
The Sixth Amendment to the Constitution guarantees that a federal criminal
jury “cannot convict unless it unanimously finds that the Government has proved
each element” of the charged offense. Richardson v. United States, 526 U.S. 813, 817
37
(1999). But a disagreement about “which of several possible sets of underlying
brute facts make up a particular element”—in other words, “which of several
possible means the defendant used to commit an element of the crime”—does “not
matter as long as all 12 jurors unanimously conclude[] that the Government ha[s]
prove[d] the necessary related element . . . .” Id.
Elements, as opposed to “means” or “brute facts,” are “ordinarily listed in
the statute that defines the crime.” Id.; see also United States v. O’Brien, 560 U.S. 218,
225 (2010) (“[W]hether a given fact is an element of the crime . . . is a question for
Congress.”). Additional details not set out in the statute typically are not elements
even if they seem intuitively central to the commission of an offense. For example,
in Mathis v. United States, 136 S. Ct. 2243, 2249 (2016), the Supreme Court discussed
a hypothetical statute that “requires use of a ‘deadly weapon’ as an element of a
crime and further provides that the use of a ‘knife, gun, bat, or similar weapon’
would all qualify.” The Court explained that because only the use of a deadly
weapon is an element—and the illustrative list “merely specifies diverse means of
satisfying [that] element”—a “jury could convict even if some jurors concluded
that the defendant used a knife while others concluded he used a gun, so long as
38
all agreed that the defendant used a ‘deadly weapon.’” 15 Id. (internal quotation
marks and alterations omitted). That said, if “statutory alternatives carry different
[maximum or minimum] punishments, then . . . they must be elements.” Id. at
2256; Apprendi v. New Jersey, 530 U.S. 466, 490 (2000) (“Other than the fact of a prior
conviction, any fact that increases the penalty for a crime beyond the prescribed
statutory maximum must be submitted to a jury . . . .”); Alleyne v. United States, 570
U.S. 99, 113–14 (2013) (expanding the rule of Apprendi to facts that increase or
decrease the prescribed statutory minimum).
Applying these principles to the controlled substance context, we have
explained that the type and quantity of drugs involved in a violation of § 841(a)
must be submitted to the jury “as an element . . . only in cases where the
Government will seek a sentence above” the statutory maximum imposed by
§ 841(b)(1)(C)—the penalty provision that applies to violations involving schedule
I or II controlled substances of “indeterminate” or “unspecified” amount and
15 This principle applies equally to a statute that leaves the many potential means
of fulfilling its elements entirely to the jury’s imagination. See Descamps v. United States,
570 U.S. 254, 273 (2013) (“As long as the statute itself requires only an indeterminate
‘weapon,’ . . . [t]he jurors need not all agree on whether the defendant used a gun or a
knife or a tire iron . . . because the actual statute requires the jury to find only a
‘weapon.’”).
39
identity. 16 United States v. Thomas, 274 F.3d 655, 660 & nn.2–3 (2d Cir. 2001) (en
banc); see also id. at 664, 673 (explaining that drug quantity need not be treated as
an element where the sentence imposed is within the range authorized by
§ 841(b)(1)(C)). Otherwise, as long as the jury unanimously agrees that the offense
involved some schedule I or II controlled substance, the specific nature of that
substance has no bearing on the statutory penalty range and, as a result, “[t]he
constitutional rule [requiring jury unanimity] does not apply.” 17 Id. at 664; cf.
United States v. Reyes, 13 F.3d 638, 640 (2d Cir. 1994) (recognizing that “[t]he nature
of the controlled substance is . . . not an essential element of” a criminal statute
16 21 U.S.C. § 841(b)(1)(C) establishes maximum penalties for any violation of §
841(a) involving a schedule I or II controlled substance. Separately, § 841(b)(1)(A) and (B)
provide that violations involving certain specific types and quantities of schedule I or II
substances may carry penalties in excess of those authorized by § 841(b)(1)(C). Under
Apprendi and Alleyne, a district court may not sentence a defendant under these enhanced
penalty provisions unless the jury unanimously determines that the offense involved the
specific types and quantities of drugs that trigger them. See Thomas, 274 F.3d at 673.
17 Section 841(b)(1)(C)’s generic reference to “a controlled substance in schedule I
or II” supports the conclusion that a jury need not agree on a particular controlled
substance to convict. 21 U.S.C. § 841(b)(1)(C) (emphasis added). In assessing § 841’s
knowledge requirement, McFadden put special emphasis on the fact that § 841 prohibits
conduct involving “a controlled substance.” 576 U.S. at 191–92. Because the “indefinite
article[] ‘a’ means ‘[s]ome undetermined or unspecified particular,” the Court held that
§ 841(a)(1) “requires a defendant to know only that the substance he is dealing with is
some unspecified substance listed on the federal drug schedules.” Id. (citation omitted).
The same interpretive principle demands that we treat the language “a controlled
substance in schedule I or II” to refer “only” to “some unspecified substance listed on
[schedule I or II].”
40
prohibiting the importation of a “controlled substance”).
In practice, this means that a jury can convict a defendant for violating § 841
even if some jurors believe that the defendant distributed one drug (say, cocaine)
and others believe that he actually distributed another (say, heroin). 18
Analogizing to the Supreme Court’s “deadly weapon” example, we have held that
a New York statute prohibiting the sale of a “controlled substance” operates in
precisely the same way: Under that statute, “if some jurors believed that a
defendant had sold cocaine, and others believed that he had sold heroin, they
could still agree that he had sold ‘a controlled substance,’ and issue a guilty
verdict.” Harbin v. Sessions, 860 F.3d 58, 65 (2d Cir. 2017) (citing Mathis, 136 S. Ct.
at 2249).
But our past decisions have had occasion to distinguish means from
elements only in cases involving scheduled substances. This case demands that we
consider whether, in a § 841 prosecution involving a controlled substance analogue,
the fact that a particular substance is an analogue becomes an additional element
of the offense, or whether a substance’s analogue status is merely one of “various
18 Cocaine is a schedule II controlled substance. 21 U.S.C. § 812, sched. II(a)(4).
Heroin is a schedule I controlled substance. Id. § 812, sched. I(b)(10).
41
factual means of” qualifying as a “controlled substance.” Mathis, 136 S. Ct. at 2249.
Unsurprisingly, the government takes the latter view. In response, Defendants
contend that a putative analogue may not “be treated . . . as a controlled substance”
by operation of 21 U.S.C. § 813 unless a jury has first determined unanimously that
the same substance meets the statutory definition of “controlled substance
analogue” set out in § 802(32). In other words, Defendants argue that even if a jury
need not agree on precisely which analogues a defendant manufactured,
distributed, or possessed, it must still unanimously agree that each particular
substance forming the basis of the conviction does, in fact, qualify as an analogue.
We disagree. We conclude instead that in a prosecution for a violation of 21
U.S.C. § 841(a) subject to the statutory penalties in § 841(b)(1)(C), a substance’s
analogue status is nothing more than a means of fulfilling the element that the
defendant’s conduct involved a “controlled substance” in schedule I or II. Thus,
though a jury must unanimously find that the defendant manufactured,
distributed, or possessed with the intent to distribute some schedule I or II
controlled substance, it need not unanimously agree on any more specific
description of that substance. Just as distributing a scheduled substance is a
42
potential means of fulfilling that element, so too is distributing an analogue. 19 And
just as the specific identity of a scheduled substance is irrelevant to a conviction
pursuant to § 841(a) and (b)(1)(C), so too is the specific identity of an analogue.
Our conclusion is rooted in the applicable statutory language and penalty
structure. See Harbin, 860 F.3d at 64–65. As explained above, the specific nature of
a scheduled substance is not an element of the offense set out in § 841(a). Nothing
in the Analogue Act’s language indicates that it adds a new element to that offense
when the alleged conduct involves a controlled substance analogue. To the
contrary, the instruction to “treat” an analogue as a schedule I controlled substance
“for the purposes of any Federal law” strongly suggests the Analogue Act merely
provides an alternative means of committing controlled substance offenses
already defined elsewhere. 21 U.S.C. § 813(a). As the Supreme Court pointedly
observed in McFadden, “[t]he Analogue Act does not alter [§ 841(a)(1)].” 576 U.S.
at 193–94.
Following § 813’s instruction to treat a controlled substance analogue as a
controlled substance, Congress could rewrite § 841—insofar as the offense
19 Indeed, though not relevant here, a jury could convict a defendant for violating
§ 841 even if some jurors believed the defendant distributed an analogue and others
believed he distributed a substance actually listed on schedule I or II.
43
involves an analogue—to make it unlawful to “knowingly or intentionally . . .
manufacture, distribute, or dispense, or possess with intent to manufacture,
distribute, or dispense,” 21 U.S.C. § 841(a), “a substance[,] . . . the chemical
structure of which is substantially similar to the chemical structure of a controlled
substance in schedule I or II [and] . . . which has [an] effect on the central nervous
system that is substantially similar to or greater than [that] of a controlled
substance in schedule I or II,” id. § 802(32)(A). As McFadden explained, phrases set
off with the “indefinite article ‘a’” refer to “some undetermined or unspecified
particular.” McFadden, 576 U.S. at 191–92 (brackets omitted). Accordingly, even
when combined with the Analogue Act, § 841 requires only that the jury find an
“undetermined or unspecified” substance with the characteristics set out in §
802(32)(A).
The applicable penalty provisions point to the same conclusion. Since all
analogues are treated as schedule I controlled substances, § 841(b)(1)(C) imposes
the same penalties no matter what analogue is involved in the offense. It follows
that an analogue’s specific identity, which has no bearing on a defendant’s
sentencing range, is a means rather than an additional element. Cf. Harbin, 860 F.3d
at 65 (“[That] [t]he law’s penalty provisions . . . prescribe the same narrow range
44
of penalties . . . no matter which controlled substance a defendant has sold . . .
[aligns] with our reading . . . that each controlled substance is a mere ‘means’ of
violating the statute, not a separate alternative element.”).
Resisting this logic, Defendants insist that an unscheduled substance “is
only an analogue at the time of the jury’s proclamation,” and that a jury must
therefore make this proclamation unanimously. Appellants’ Br. 54. But their
assumption that “a substance is not an analogue until a jury unanimously finds
that it is,” Reply Br. 24, begs the question. Not every fact that calls for a qualitative
determination based on conflicting evidence is an element. 20 After all, a
substance’s analogue status is no more dependent on a “jury’s proclamation” than
an implement’s “deadly weapon” status in the hypothetical posed in Mathis. See
Mathis, 136 S. Ct. at 2249. And in that case, the Supreme Court clearly envisioned
that a jury harboring disagreements about the particular deadly weapon involved
could convict without taking separate, unanimous votes on whether each
20 In their briefing and at oral argument, Defendants claimed that a footnote in our
decision in Ansaldi identified “substantial similarity” as an element of an offense
involving an analogue. See Ansaldi, 372 F.3d at 123 n.2. But the cited passage is a summary
of the defendants’ briefing in that case, not a declaration of the law. While an analogue-
based prosecution does require unanimous agreement that a defendant’s offense involved
a substance substantially similar to a scheduled substance, individual jurors need not
agree on precisely which substance bears the requisite similarity.
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individual juror’s chosen implement qualified as a deadly weapon. See id.; see also
Descamps v. United States, 570 U.S. 254, 273 (2013) (“[A] court blessed with sufficient
time and imagination could devise a laundry list of potential ‘weapons’
[including] (for starters) grenades, pipe bombs, spears, tire irons, BB guns,
nunchucks, and crossbows.”). Taking Defendant’s theory to its logical conclusion,
Mathis’s declaration that “a jury need not find . . . a particular item,” would extend
only to the knives, guns, and bats listed explicitly in the statute. 136 S. Ct. at 2249.
We strenuously doubt that the Supreme Court meant, but declined to make
express, that the specific weapon involved in the crime vaults from means to
element status as soon as a single juror concludes that a defendant used not a
“knife, gun, [or] bat,” but instead a “similar weapon.” Id. The same logic applies
to analogues. As such, we reject Defendants’ argument that a jury must
unanimously identify particular analogues before individual jurors may treat
those analogues as means of fulfilling “the necessary related element”—that is, the
involvement of a controlled substance. Richardson, 526 U.S. at 817.
For the foregoing reasons, the district court’s instruction regarding
unanimity was not error, plain or otherwise.
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V. Defendants’ Sentencing Challenge
Defendants next argue that the trial court committed procedural error by
failing to determine before sentencing which of the six synthetic cannabinoids at
issue qualified as a controlled substance analogue. They contend that in the
absence of such findings, the district court’s calculation of the total quantity of
illegal substances in Defendants’ possession could not have been proper. But these
arguments, too, are unavailing. Although a district court must rule on any material
dispute regarding the presentence report (“PSR”), Fed. R. Crim. P. 32(i)(3)(B), it
“satisfies its obligation to make the requisite specific factual findings when it
explicitly adopts the factual findings set forth in the [PSR] . . . at the sentencing
hearing or in the written judgment it files later.” United States v. Molina, 356 F.3d
269, 275–76 (2d Cir. 2004). “Facts in support of a sentencing calculation need only
be proven by a preponderance of the evidence, and the district court’s findings
will not be disturbed unless clearly erroneous.” United States v. Halloran, 821 F.3d
321, 341 (2d Cir. 2016).
Here, the district court explicitly adopted the PSR’s factual findings, which
identified the relevant substances as controlled substance analogues. The court
likewise identified all six of the charged substances in a post-trial order as “the
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controlled substance analogues defendants conspired to possess with the intent to
distribute and to distribute” in its decision following a pre-sentencing evidentiary
hearing. G.A. 315. The district court heard more than sufficient testimony at trial
to find that each of these substances was a controlled substance analogue by a
preponderance of the evidence. And because the resolution of disputed facts at
sentencing is a task for the district court alone, the fact that the jury made no
explicit findings as to which specific cannabinoids qualified as controlled
substance analogues is irrelevant. We therefore detect no error in the sentence
imposed by the district court.
VI. Defendants’ Conviction for Money Laundering
Finally, Defendants ask us to extend any relief granted based on the
foregoing to their convictions for money laundering, which are premised in part
on their drug violation. Since we have determined that Defendants are entitled to
no relief in connection with their conviction for conspiracy to distribute controlled
substance analogues, we need not revisit their convictions for money laundering.
CONCLUSION
In sum, we hold that:
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(1) The Analogue Act’s instruction to treat a substance with chemical and
pharmacological properties “substantially similar” to those of a scheduled
substance as a controlled substance in schedule I is not unconstitutionally
vague on its face, the Supreme Court’s decisions in Johnson, Dimaya, and
Davis notwithstanding.
(2) The government’s evidence was sufficient to prove beyond a reasonable
doubt that Defendants knew they distributed a controlled substance.
(3) The district court did not abuse its discretion when it allowed the
government’s experts to testify that the synthetic cannabinoids at issue had
chemical and pharmacological properties “substantially similar” to those of
controlled substances in schedule I.
(4) The district court correctly instructed the jury that it need not unanimously
agree on which of the six synthetic cannabinoids charged in the indictment
meet the statutory definition of a controlled substance analogue.
(5) The district court made all of the factual findings necessary to calculate
Defendants’ base offense level at sentencing.
(6) Because Defendants are entitled to no relief in connection with their drug
conviction, their money laundering conviction likewise stands.
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Accordingly, we AFFIRM the judgment of the district court.
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