United States v. Nathaniel Ruth

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 20-1034
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
NATHANIEL RUTH,
Defendant-Appellant.
____________________
Appeal from the United States District Court
for the Central District of Illinois.
No. 19-cr-20005 — Michael M. Mihm, Judge.
____________________
ARGUED JUNE 3, 2020 — DECIDED JULY 20, 2020
____________________
Before SYKES, Chief Judge, and BAUER and ST. EVE, Circuit
Judges.
ST. EVE, Circuit Judge. In what is becoming an all-too-famil-
iar subject, this appeal raises a question about whether a state
drug statute sweeps more broadly than its federal counterpart
because the former includes a particular isomer of a substance
that the latter does not. Nathaniel Ruth pleaded guilty to fed-
eral gun and drug charges and received an enhanced sentence
due to his prior Illinois conviction for possession with intent
2 No. 20-1034
to deliver cocaine. The Illinois statute defines cocaine to in-
clude its positional isomers, whereas the federal definition co-
vers only cocaine’s optical and geometric isomers. Ruth now
appeals and claims that the district court erred in sentencing
him because, using the categorical approach, the overbreadth
of the Illinois statute disqualifies his prior conviction as a
predicate felony drug offense. We agree and therefore vacate
Ruth’s sentence and remand for resentencing.
I. Background
We can be brief in our summary of the facts because this
appeal raises challenges only to the application of sentencing
enhancements, which present pure questions of law. In 2018,
the Champaign, Illinois police department’s Street Crime
Task Force used a confidential source to conduct multiple
controlled buys of drugs from Nathaniel Ruth. That investi-
gation came to a head on December 5, 2018, when officers sur-
veilling Ruth pulled him over while driving and arrested
Ruth for driving with a revoked license. During the arrest,
Ruth told the officers that there was a firearm in the vehicle.
Officers subsequently executed a search warrant at Ruth’s res-
idence and recovered 2.9 grams of crack cocaine, 5.6 grams of
powder cocaine, a counterfeit $100 bill, $2,250 in U.S. cur-
rency, and various drug paraphernalia.
A grand jury indicted Ruth on two counts: one count of
possession of a firearm by a felon in violation of 18 U.S.C.
§ 922(g)(1), and one count of possession of cocaine with intent
to distribute in violation of 21 U.S.C. § 841(a)(1), (b)(1)(C). The
government then filed an information pursuant to 21 U.S.C.
§ 851 notifying Ruth that it intended to rely on a prior convic-
tion as a predicate felony drug offense to enhance his sen-
tence. Namely, the government intended to use a 2006 Illinois
No. 20-1034 3
conviction for possession of a controlled substance with intent
to distribute, 720 ILCS 570/401(c)(2). The § 851 enhancement
increased the statutory maximum sentence from twenty years
in prison to thirty years. See 21 U.S.C. § 841(b)(1)(C). Ruth did
not object to the government’s § 851 notice.
After ironing out a defect in the indictment, Ruth eventu-
ally pleaded guilty to both counts without a plea agreement.
The probation office determined that Ruth was a career of-
fender because at the time of the instant offenses, he had at
least two prior felony convictions for controlled substance of-
fenses. See U.S.S.G. § 4B1.1. One of the prior convictions was
the 2006 Illinois cocaine conviction noted above and subject
of the § 851 enhancement, and the second was a 2010 Illinois
conviction for possession with intent to deliver cannabis.
Ruth’s resulting Guidelines range was 188 to 235 months’ im-
prisonment.
Ruth objected to his classification as a career offender. He
argued that his 2006 Illinois conviction was not a “controlled
substance offense” under U.S.S.G. §§ 4B1.1(a) and 4B1.2(b) be-
cause the Illinois statute he was convicted under, 720 ILCS
570/401(c)(2), is categorically broader than federal law and
thus could not serve as a predicate felony controlled sub-
stance offense. Specifically, the Illinois statute prohibits pos-
session of positional isomers of cocaine whereas the federal
Controlled Substances Act does not. He similarly argued that
the Illinois statute’s definition of cocaine “analog” was cate-
gorically broader than the federal definition of a controlled
substance “analogue.” Despite his objections to the career of-
fender designation, Ruth did not object to the § 851 sentencing
enhancement based on the same 2006 Illinois conviction.
4 No. 20-1034
The government responded, primarily, that a plain read-
ing of the career-offender guideline covered both federal and
state definitions of controlled substance offenses. That is be-
cause the Guidelines, for purposes of the career offender en-
hancement, define a “controlled substance offense” as “an of-
fense under federal or state law, punishable by imprisonment
for a term exceeding one year, that prohibits … the possession
of a controlled substance (or a counterfeit substance) with in-
tent to manufacture, import, export, distribute, or dispense.”
U.S.S.G. § 4B1.2(b) (emphasis added). The government also
disputed Ruth’s arguments as to the Illinois statute’s divisi-
bility and categorical breadth.
The district court agreed with the government “that the
wording of the guideline is such that I don’t think the analysis
that defense counsel has made is the one that truly applies”
and overruled Ruth’s objection to the career offender en-
hancement. The court then sentenced Ruth to 108 months’ im-
prisonment on each of Count One and Count Two, to be
served concurrently. Ruth timely appealed.
II. Discussion
Ruth challenges his sentence on two related grounds—
both concerning his 2006 Illinois conviction for possession
with intent to deliver cocaine. First, Ruth argues that the dis-
trict court erred in applying the 21 U.S.C. § 851 sentencing en-
hancement because his 2006 Illinois conviction does not qual-
ify as a prior “felony drug offense.” And second, Ruth con-
tends that the 2006 Illinois conviction is not a “controlled sub-
stance offense” under the Sentencing Guidelines and thus the
court erroneously sentenced him as a career offender. As to
both, his argument is principally the same: the Illinois statute
is categorically broader than federal law. Though Ruth is
No. 20-1034 5
ultimately correct that the Illinois statute is broader and thus
he is entitled to be resentenced without the § 851 enhance-
ment, he is wrong that this conclusion applies equally to his
Guidelines challenge to the career offender enhancement.
A. Predicate Felony Drug Offense
Before sentencing, the government filed an information
pursuant to 21 U.S.C. § 851 notifying Ruth of its intent to rely
on his prior 2006 Illinois cocaine conviction as a qualifying
predicate “felony drug offense” to enhance his sentence. Ruth
did not object to the § 851 enhancement in the district court
and thus forfeited the argument. Our review is for plain error
only. Fed R. Crim. P. 52(b).
1. The categorical approach
Section 841(b)(1)(C), the applicable penalty provision for
Ruth’s instant federal cocaine conviction, provides that if a
defendant has a “prior conviction for a felony drug offense,”
the statutory maximum term of imprisonment increases from
twenty years’ imprisonment to thirty years’ imprisonment.
21 U.S.C. § 841(b)(1)(C). As used in the Controlled Substances
Act, 21 U.S.C. § 801 et seq., the term “felony drug offense”
means:
an offense that is punishable by imprisonment for
more than one year under any law of the United States
or of a State or foreign country that prohibits or re-
stricts conduct relating to narcotic drugs, marihuana,
anabolic steroids, or depressant or stimulant sub-
stances.
21 U.S.C. § 802(44); cf. Burgess v. United States, 553 U.S. 124,
126 (2008) (“The term ‘felony drug offense’ contained in
§ 841(b)(1)(A)[] … is defined exclusively by § 802(44) ….”).
6 No. 20-1034
Each of the four categories of covered drugs is also separately
defined in § 802. See 21 U.S.C. § 802(17) (defining “narcotic
drugs”); id. § 802(16) (defining “marihuana”); id. § 802(41)(A)
(defining “anabolic steroid”); id. § 802(9) (defining “depres-
sant or stimulant substance”). Relevant to this appeal, cocaine
is a narcotic drug defined in § 802(17)(D), and is listed in the
schedules of federally controlled substances at schedule
II(a)(4), id. § 812.
To determine whether Ruth’s prior Illinois conviction is a
“felony drug offense” within the meaning of federal law, we
apply the Taylor categorical approach. United States v. Elder,
900 F.3d 491, 497–501 (7th Cir. 2018) (citing Taylor v. United
States, 495 U.S. 575 (1990)). Under the categorical approach,
courts look solely to whether the elements of the crime of con-
viction match the elements of the federal recidivism statute.
Id. at 501. “If, and only if, the elements of the state law mirror
or are narrower than the federal statute can the prior convic-
tion qualify as a predicate felony drug offense.” United States
v. De La Torre, 940 F.3d 938, 948 (7th Cir. 2019).
The Supreme Court recently clarified its categorical-ap-
proach jurisprudence in Shular v. United States, 140 S. Ct. 779
(2020). There are “two categorical methodologies,” depend-
ing on the statute at issue. Id. at 783. In the first categorical
methodology, some statutes require “the court to come up
with a ‘generic’ version of a crime—that is, the elements of
‘the offense as commonly understood.’” Id. (quoting Mathis v.
United States, 136 S. Ct. 2243, 2247 (2016)). We will refer to this
first method as the generic-offense method. The archetypal
example is Taylor itself, which confronted the Armed Career
Criminal Act’s “unadorned reference to ‘burglary’” and re-
quired the Court to “identif[y] the elements of ‘generic
No. 20-1034 7
burglary’ based on the ‘sense in which the term is now used
in the criminal codes of most States.’” Id. (quoting Taylor,
495 U.S. at 598–99). The Court then matched the elements of
the offense of conviction against those of the generic crime. Id.
The second categorical-approach method, though, concerns
statutes that do not reference a certain offense, but rather
“some other criterion” as the measure for prior convictions.
Id. The example given for this second methodology was
where an immigration statute assigned consequences for a
prior conviction for an offense that “involves fraud or deceit,”
and the Court simply looked to whether the prior offense’s
elements “necessarily entail fraudulent or deceitful conduct”
as the appropriate measure. Id. (quoting Kawashima v. Holder,
565 U.S. 478, 483–85 (2012)). We will call this second method
the conduct-based method.
In Shular, the Court held that the second categorical meth-
odology—the conduct-based method—applies to determin-
ing whether a state offense is a “serious drug offense” under
the Armed Career Criminal Act (ACCA), 18 U.S.C.
§ 924(e)(2)(A)(ii) (defining “serious drug offense” as “an of-
fense under State law, involving manufacturing, distributing,
or possessing with intent to manufacture or distribute, a con-
trolled substance”). The statute’s text and context convinced
the Court that it undoubtedly described conduct, not names of
generic offenses. Shular, 140 S. Ct. at 785. In contrast, ACCA’s
“violent felony” provision refers to a crime that “is burglary,
arson, or extortion,” which unambiguously names offenses.
Id. Therefore, a prior conviction qualifies as a predicate “seri-
ous drug offense” and triggers § 924(e)(2)(A)(ii)’s sentencing
enhancement when the predicate offense involved “the con-
duct of ‘manufacturing, distributing, or possessing with intent
8 No. 20-1034
to manufacture or distribute, a controlled substance.’” Id. at
787.
The conduct-based categorical approach applies here to
§ 841(b)(1)(C)’s sentencing enhancement. The term “felony
drug offense” describes predicate offenses “that prohibit[] or
restrict[] conduct relating to narcotic drugs, marihuana, ana-
bolic steroids, or depressant or stimulant substances.”
21 U.S.C. § 802(44) (emphasis added). This unquestionably re-
fers to conduct and not generic offenses. The task is simple,
then, and the court asks only whether the prior conviction’s
elements necessarily entail the conduct identified in § 802(44).
Indeed, even before Shular’s clarification, this court already
implicitly employed the conduct-based categorical methodol-
ogy for similar “felony drug offense” sentencing enhance-
ments. See, e.g., United States v. Garcia, 948 F.3d 789, 793 (7th
Cir. 2020); De La Torre, 940 F.3d at 949; Elder, 900 F.3d at 497.
Here the government filed an information pursuant to
21 U.S.C. § 851(a) identifying Ruth’s prior state court convic-
tion under 720 ILCS 570/401(c)(2). The Illinois statute makes
it unlawful to possess with intent to deliver “1 gram or more
but less than 15 grams of any substance containing cocaine, or
an analog thereof.” 720 ILCS 570/401(c)(2). Illinois’s schedule
of controlled substances defines cocaine as:
Coca leaves and any salt, compound, isomer, salt of an
isomer, derivative, or preparation of coca leaves in-
cluding cocaine or ecgonine, and any salt, compound,
isomer, derivative, or preparation thereof which is
chemically equivalent or identical with any of these
substances, but not including decocainized coca leaves
or extractions of coca leaves which do not contain co-
caine or ecgonine (for the purpose of this paragraph,
No. 20-1034 9
the term “isomer” includes optical, positional and ge-
ometric isomers)[.]
720 ILCS 570/206(b)(4). For our purposes, the critical language
is the final phrase—Illinois’s definition of cocaine includes
optical, positional, and geometric isomers. Under federal law,
cocaine is defined to include only its “optical and geometric
isomers.” 21 U.S.C. § 812, Schedule II(a)(4); see also id.
§ 802(14) (“As used in schedule II(a)(4), the term ‘isomer’
means any optical or geometric isomer.”); id. § 802(17)(D) (de-
fining “narcotic drug” to include “[c]ocaine, its salts, optical
and geometric isomers, and salts of isomers”). On its face,
then, the Illinois statute is categorically broader than the fed-
eral definition.
Despite the statutory mismatch, the government responds
that the Illinois statute nonetheless “substantially corre-
sponds” to the federal statute and thus is not overbroad. The
argument finds its roots in Quarles v. United States, where the
Supreme Court admonished that “the Taylor Court cautioned
courts against seizing on modest state-law deviations from
the generic definition of burglary,” and held that the relevant
question there was whether the state law “‘substantially cor-
responds’ to (or is narrower than) generic burglary.” 139 S. Ct.
1872, 1880 (2019) (quoting Taylor, 495 U.S. at 602). But Quarles,
like Taylor itself, involved the generic-offense method of the
categorical approach that, when the statute at issue “refers
generally to an offense without specifying its elements,” re-
quires a court as a preliminary step to “define the offense so
that it can compare elements, not labels.” Shular, 140 S. Ct. at
783. This process of the court coming up with a generic ver-
sion of a crime must allow for some margin of inconsequential
discrepancy. Post-Shular, however, it is clear that looking to
10 No. 20-1034
whether the elements “substantially correspond” falls within
a different categorical approach methodology and does not
apply equally under the conduct-based method at play here.
There are no minor deviations in offense elements to assess,
only enumerated conduct.
Flowing from its reliance on the “substantial correspond-
ence” between the Illinois and federal statutes, the govern-
ment next argues that there is no basis to conclude that posi-
tional isomers of cocaine exist in the drug trade. In support of
its assertion, during sentencing in the district court, the gov-
ernment submitted an affidavit of a retired DEA research
chemist, John Casale. According to Agent Casale, during his
tenure at the DEA he analyzed over 50,000 cocaine samples
from law enforcement evidentiary seizures and did not iden-
tify any positional isomers of cocaine in any of those samples.
This may be so, but Agent Casale does not actually aver that
positional isomers of cocaine do not exist. And that is an im-
portant distinction. It is not the province of the judiciary to
rewrite Illinois’s statute to conform to a supposed practical
understanding of the drug trade. This is particularly true here
where the Illinois legislature purposefully included posi-
tional isomers of cocaine in its statute. Effective January 1,
1984, the legislature added the word “isomer” to the defini-
tion of cocaine. People v. Godek, 487 N.E.2d 810, 812 n.3 (Ill.
1986). Shortly thereafter, the legislature again amended the
statute to expressly identify optical, positional, and geometric
isomers, as it appears today. See Act of Sept. 8, 1985, § 1, 1985
Ill. Laws 2288, 2292–93. Though the government would have
us believe that Illinois’s inclusion of positional isomers of co-
caine is “nothing but spilled ink,” it was far from a potential
drafting oversight. Illinois went from generically prohibiting
“isomers” to expressly identifying the precise types of cocaine
No. 20-1034 11
isomers it sought to proscribe. We must give effect to the law
as written.
We encountered nearly identical facts and arguments in
De La Torre, save for the drug at issue being methampheta-
mine and its isomers, and we reach the same outcome.
940 F.3d at 950–52. Like there, the government offers theoret-
ical challenges to positional isomers of cocaine but cannot
avoid the inescapable conclusion that the plain language of
the state statute categorically covers a larger swath of conduct
than its federal counterpart. To be certain, in De La Torre we
noted that we took no position on the scientific merits of the
government’s isomer-related arguments, nor do we here. Id.
at 952 n.5. Although we left the door ajar for future science-
based arguments, it was not an open-ended invitation to ar-
gue that every isomeric mismatch is mere surplusage. There
may be an occasion where a state statute covers unquestiona-
bly nonexistent conduct, but we do not need to predetermine
how that analysis will look. It is enough for us to say that
where, as here, the state statute of conviction is plain and in-
tentional, our job is straightforward: we compare the state
statute to the federal recidivism statute at issue and ask only
if the state law is the same as or narrower than federal law.
2. Divisibility of 720 ILCS 570/401(c)(2)
Ruth is not quite out of the woods yet. Even if his state
statute of conviction is overbroad, the government urges that
it is divisible. A statute is divisible if it “sets out one or more
elements of the offense in the alternative.” Descamps v. United
States, 570 U.S. 254, 257 (2013). If so, we can apply what has
been dubbed the modified categorical approach and “consult
a limited class of documents” to determine which alternative
element of the statute formed the basis of Ruth’s 2006 Illinois
12 No. 20-1034
conviction. Id.; Elder, 900 F.3d at 502. The documents that a
sentencing court may consult include the charging document,
jury instructions, a written plea agreement, the transcript of a
plea colloquy, or some comparable judicial record. Shepard v.
United States, 544 U.S. 13, 20 (2005).
We start with the structure of the statute. Section 401, in
general, makes it “unlawful for any person knowingly to
manufacture or deliver, or possess with intent to manufacture
or deliver, a controlled substance … , a counterfeit substance,
or a controlled substance analog.” 720 ILCS 570/401. Subsec-
tions (a) through (i), and numerous subparts, then proceed to
set forth various controlled substances and respective quanti-
ties that each constitute separate violations of the Illinois Con-
trolled Substances Act resulting in different penalties. Subsec-
tion (c), in part, provides as follows:
(c) Any person who violates this Section with regard to
the following amounts of controlled or counterfeit sub-
stances or controlled substance analogs, notwithstand-
ing any of the provisions of subsections (a), (b), (d), (e),
(f), (g) or (h) to the contrary, is guilty of a Class 1 felony.
The fine for violation of this subsection (c) shall not be
more than $250,000:
(1) 1 gram or more but less than 15 grams of any
substance containing heroin, or an analog thereof;
(1.5) 1 gram or more but less than 15 grams of any
substance containing fentanyl, or an analog thereof;
(2) 1 gram or more but less than 15 grams of any
substance containing cocaine, or an analog thereof;
No. 20-1034 13
(3) 10 grams or more but less than 15 grams of any
substance containing morphine, or an analog
thereof;
…
(11) 50 grams or more but less than 200 grams of any
substance containing a substance classified in Sched-
ules I or II, or an analog thereof, which is not otherwise
included in this subsection.
720 ILCS 570/401(c).
We pause here, though, to take a step back and clarify the
relevant divisibility question. The government argues
vaguely that the “relevant subsection” of the Illinois Con-
trolled Substances Act is divisible. Though far from apparent,
we think the government suggests merely that subsection (c)
is divisible from the rest of section 401 overall. The text makes
clear that 720 ILCS 570/401 is generally divisible. The provision
has almost a dozen subsections and dozens more subparts,
each regulating different drugs in different quantities. The
government would have us stop there at this topline divisibil-
ity and immediately examine Ruth’s Shepard-approved docu-
ments to determine the specific conduct—or here, sub-
stance—underlying Ruth’s state court conviction. General
statute divisibility, however, is not enough. The modified cat-
egorical approach is just that: a modification of the categorical
approach that simply acts as a “tool for implementing the cat-
egorical approach.” Descamps, 570 U.S. at 262. “It retains the
categorical approach’s central feature: a focus on the ele-
ments, rather than the facts, of a crime.” Id. at 263. To put it
more succinctly, the modified categorical approach helps a
14 No. 20-1034
court find out which crime the defendant was convicted of
when the statute lists several alternative crimes. Id. at 263–64.
No one disputes that Ruth was convicted under subsec-
tion (c)(2). So it does not matter for our purposes that the
higher level subsections (a), (b), (c), and so on are divisible
from each other—we can place Ruth’s conviction in the more
particular subdivision without recourse to any extra-statutory
Shepard documents. The only question that matters, then, is
whether subsection (c)(2) is itself divisible. As we alluded to
above, the government does not appear to argue that subsec-
tion (c)(2) is divisible, nor could it; the statutory provision is
clearly indivisible. Section 401(c)(2) lists only one crime: pos-
session with intent to distribute cocaine. Though the Illinois
statute may define cocaine overbroadly, there is no uncer-
tainty as to what statutory offense formed the basis of Ruth’s
crime of conviction and our inquiry ends there. Ruth’s 2006
Illinois conviction under 720 ILCS 570/401(c)(2) is not a pred-
icate “felony drug offense” that triggers 21 U.S.C.
§ 841(b)(1)(C)’s sentencing enhancement.
3. Plain error
Because Ruth’s 2006 Illinois conviction under 720 ILCS
570/401(c)(2) is not a predicate “felony drug offense” under
his applicable federal penalty statute, 21 U.S.C. § 841(b)(1)(C),
the district court erred in sentencing Ruth with the statutory
enhancement. To satisfy plain error review, however, the er-
ror must have been plain and must have affected Ruth’s sub-
stantial rights before we will exercise our discretion to correct
it. See United States v. Olano, 507 U.S. 725, 732 (1993). And even
then, we will exercise that discretion only if the error “seri-
ously affect[s] the fairness, integrity or public reputation of
No. 20-1034 15
judicial proceedings.” Id. at 736 (quoting United States v. At-
kinson, 297 U.S. 157, 160 (1936)).
An error is plain if it is “clear or obvious, rather than sub-
ject to reasonable dispute.” Puckett v. United States, 556 U.S.
129, 135 (2009). That is to say that “while the error must be
straightforward, it can be so in hindsight.” United States v. Ca-
puto, 978 F.2d 972, 975 (7th Cir. 1992). The error must be plain,
“but it needn’t be blatant.” Id. After all, “plain-error review is
not a grading system for trial judges.” Henderson v. United
States, 568 U.S. 266, 278 (2013). Though the parties missed the
argument, they did not miss the core issue. Ruth objected to
the career offender enhancement under the Guidelines based
on his 2006 Illinois conviction for the same categorical-over-
breadth reasons he now makes in relation to the § 851 sentenc-
ing enhancement. That the precise issue and arguments were
raised shows that the error was clear. That no one recognized
the additional application of the objection to his prior convic-
tion does not render the error so imperceptible as to except it
from review.
The error here affected Ruth’s substantial rights because
the enhancement increased his Guidelines range. Without the
§ 851 enhancement, Ruth’s Guidelines range would have
been 151 to 188 months. 1 The § 851 enhancement, which
raised the statutory maximum sentence and thus increased
his offense level, resulted in a higher Guidelines range of 188
to 235 months. Although the district court ultimately sen-
tenced Ruth to 108 months’ imprisonment, below either
Guidelines range, in the ordinary case the Guidelines range
will “anchor the court’s discretion in selecting an appropriate
1 This includes the career offender enhancement.
16 No. 20-1034
sentence.” Molina-Martinez v. United States, 136 S. Ct. 1338,
1349 (2016). “It follows, then, that in most cases the Guidelines
range will affect the sentence.” Id. “We have repeatedly held
that ‘[a] sentencing based on an incorrect Guidelines range
constitutes plain error and warrants a remand for resentenc-
ing, unless we have reason to believe that the error in no way
affected the district court’s selection of a particular sentence.’”
United States v. Martin, 692 F.3d 760, 766 (7th Cir. 2012) (quot-
ing United States v. Farmer, 543 F.3d 363, 375 (7th Cir. 2008)).
There is nothing in the sentencing transcript that would give
us any reason to believe that the increased Guidelines range
did not affect the district court’s chosen sentence. “When a
defendant is sentenced under an incorrect Guidelines range—
whether or not the defendant’s ultimate sentence falls within
the correct range—the error itself can, and most often will, be
sufficient to show a reasonable probability of a different out-
come absent the error.” Molina-Martinez, 136 S. Ct. at 1345. Be-
cause the plain Guidelines error here risks an unnecessary
deprivation of Ruth’s liberty, and given “the relative ease of
correcting the error,” Rosales-Mireles v. United States, 138 S. Ct.
1897, 1908 (2018), leaving this error uncorrected would under-
mine the “fairness, integrity or public reputation of judicial
proceedings.” Olano, 507 U.S. at 736. We therefore vacate
Ruth’s sentence and remand.
B. Career Offender Enhancement
Ruth also contends that his 2006 Illinois conviction is not
a “controlled substance offense” under the Guidelines and
thus argues he was erroneously sentenced as a career offender
as well. Ruth objected to the career offender enhancement at
sentencing and preserved this challenge. Whether a prior of-
fense is a predicate controlled substance offense under the
No. 20-1034 17
Guidelines is a question of law that we review de novo. United
States v. Tate, 822 F.3d 370, 375 (7th Cir. 2016).
A defendant is a career offender if, among other require-
ments, “the defendant has at least two prior felony convic-
tions of either a crime of violence or a controlled substance
offense.” U.S.S.G. § 4B1.1(a). As used in the career-offender
guideline, the term “controlled substance offense” is defined
as:
an offense under federal or state law, punishable by
imprisonment for a term exceeding one year, that pro-
hibits the manufacture, import, export, distribution, or
dispensing of a controlled substance (or a counterfeit
substance) or the possession of a controlled substance
(or a counterfeit substance) with intent to manufacture,
import, export, distribute, or dispense.
Id. § 4B1.2(b). The Guidelines do not further define “con-
trolled substance,” so Ruth’s argument in this instance is
premised on incorporating the federal Controlled Substances
Act’s definition of controlled substance (and its schedules of
enumerated substances) into the career-offender guideline.
See 21 U.S.C. § 802(6). Doing so would lead to the same result
we reached above—the Illinois statute covering positional
isomers of cocaine is broader than the federal definition of co-
caine and thus his 2006 conviction cannot serve as a predicate
controlled substance offense.
The fatal flaw in Ruth’s logic is that the career-offender
guideline, and its definition of controlled substance offense,
does not incorporate, cross-reference, or in any way refer to
the Controlled Substances Act. This is significant. The Sen-
tencing Commission clearly knows how to cross-reference
18 No. 20-1034
federal statutory definitions when it wants to. Indeed, in the
very same definitional section for the career-offender guide-
line, the Commission defined “crime of violence” to incorpo-
rate the definition of firearm from 26 U.S.C. § 5845(a) and “ex-
plosive material as defined in 18 U.S.C. § 841(c).” U.S.S.G.
§ 4B1.2(a)(2). Elsewhere, § 2D1.1 of the Guidelines expressly
provides that it applies to “‘counterfeit’ substances, which are
defined in 21 U.S.C. § 802,” and tells us that “‘analogue,’ for
purposes of this guideline, has the meaning given the term
‘controlled substance analogue’ in 21 U.S.C. § 802(32).”
U.S.S.G. § 2D1.1 cmt. nn.4 & 6. Yet, no such signal is anywhere
in the career-offender guideline’s definition for controlled
substance offense. What is perhaps even more telling, when
the Guidelines were first introduced, the Sentencing Commis-
sion defined the term “controlled substance offense” in the
career offender provision to mean “an offense identified in
21 U.S.C. §§ 841, 952(a), 955, 955a, 959; §§ 405B and 416 of the
Controlled Substance Act as amended in 1986, and similar of-
fenses.” U.S.S.G. § 4B1.2(2) (1987). Shortly thereafter, the
Commission amended the definition to what is substantially,
and substantively, its current form, without any cross-refer-
ences. See id. § 4B1.2(2) (1989). Ruth offers no compelling rea-
son for us to now import the federal definition of controlled
substance on our own.
We addressed a similar question in United States v. Hudson,
whether, under the Sentencing Guidelines, crimes involving
phony versions of illegal drugs are properly characterized as
controlled substance offenses, and it guides us here. 618 F.3d
700, 701 (7th Cir. 2010). The defendant in that case was con-
victed of possession of a firearm by a felon under 18 U.S.C.
§ 922(g) and was subject to a sentencing enhancement under
U.S.S.G. § 2K2.1(a)(4)(A) if he had a prior felony conviction
No. 20-1034 19
for a controlled substance offense. Id. at 702. Section 2K2.1 of
the Guidelines does not define “controlled substance of-
fense,” but instead takes the “meaning given that term in
§ 4B1.2(b) and Application Note 1 of the Commentary to
§ 4B1.2.” U.S.S.G. § 2K2.1 cmt. n.1. Turning to § 4B1.2(b), we
found that the “definition lays out our guide-posts: con-
trolled-substance offenses include state-law offenses related
to controlled or counterfeit substances punishable by impris-
onment for a term exceeding one year.” Hudson, 618 F.3d at
703. But Hudson “was convicted of an Indiana offense related
to a substance masquerading as a controlled substance, not
under Indiana’s law addressing counterfeit substances.” Id.
So it was not clear whether his prior conviction was an offense
related to “counterfeit substances.” The guideline does not
define “counterfeit substance,” however, and we saw no rea-
son to restrict the definition “to a particular state’s concept of
what is meant by that term.” Id. Instead, we looked more
broadly to how the term is commonly understood and gave it
its natural meaning. Id.
Notwithstanding our conclusion in Hudson, Ruth instead
points to our decision in United States v. Smith, 921 F.3d 708
(7th Cir. 2019), and asserts that we have already agreed with
his reading of the Guidelines. In Smith, the defendant chal-
lenged whether “his conviction under Indiana’s ‘Dealing in
cocaine or narcotic drug’ statute, Ind. Code § 35-48-4-1, is …
a predicate controlled substance offense under § 4B1.2(b) of
the Guidelines.” Id. at 712. Though Smith applied the categor-
ical approach to determine whether the elements of his prior
conviction matched the generic version of the offense, we said
nothing about incorporating the federal Controlled Sub-
stances Act’s definition of “controlled substance” into the
Guidelines. Rather, we were primarily concerned with
20 No. 20-1034
whether the elements of the Indiana crime “match the Guide-
lines’ definition of a controlled substance: (1) possession (2) of
a controlled substance (3) with the intent to distribute that
substance.” Id. at 715–16. As to that, we found the elements
easily matched. But in Smith we did not have the occasion to
consider the question before us now.
We recognize that a circuit split exists on this issue, and
that the weight of authority favors Ruth. As far as we are
aware, the Second, Fifth, Eighth, and Ninth Circuits have all
concluded that “controlled substance” in U.S.S.G. § 4B1.2(b)
refers to the federal definition. Most recently, the Second Cir-
cuit applied the so-called Jerome presumption that as a general
rule “the application of a federal law does not depend on state
law unless Congress plainly indicates otherwise.” United
States v. Townsend, 897 F.3d 66, 71 (2d Cir. 2018) (citing Jerome
v. United States, 318 U.S. 101, 104 (1943)). The court also found
that Taylor and the Supreme Court’s subsequent categorical-
approach cases “reinforce the idea that imposing a federal sen-
tencing enhancement under the Guidelines requires some-
thing more than a conviction based on a state’s determination
that a given substance should be controlled.” Id. For those rea-
sons, the Second Circuit was “confident that federal law is the
interpretive anchor to resolve the ambiguity” over the defini-
tion of “controlled substance offense.” Id. “Any other out-
come would allow the Guidelines enhancement to turn on
whatever substance ‘is illegal under the particular law of the
State where the defendant was convicted,’ a clear departure
from Jerome and its progeny.” Id.
Our colleagues on the Fifth, Eighth, and Ninth Circuits all
considered a different provision of the Guidelines and a dif-
ferent term, but applied the same basic reasoning. The Ninth
No. 20-1034 21
Circuit held that the meaning of “drug trafficking offense”
under U.S.S.G. § 2L1.2 “should not ‘depend on the definition
adopted by the State of conviction’” because it would be in-
consistent with the principles underlying the Taylor categori-
cal approach. United States v. Leal-Vega, 680 F.3d 1160, 1166
(9th Cir. 2012); see also United States v. Gomez-Alvarez, 781 F.3d
787, 793 (5th Cir. 2015) (adopting reasoning of Leal-Vega for
same guideline provision); United States v. Sanchez-Garcia,
642 F.3d 658, 661 (8th Cir. 2011) (interpreting same guideline
provision and using the federal Controlled Substances Act
definition of “controlled substance”).
On the other side of the ledger are the Sixth and Eleventh
Circuits—albeit in unpublished opinions only. The Sixth Cir-
cuit first addressed the issue in United States v. Smith, where
the defendant “argue[d] that because the list of controlled
substances criminalized under Illinois law [720 ILCS 570/401]
includes a substance that is not prohibited under federal law,
his prior convictions cannot serve as predicate controlled-
substance offenses.” 681 F. App’x 483, 488 (6th Cir. 2017). The
Sixth Circuit disagreed:
[B]ecause the Guidelines specifically include offenses
under state law in § 4B1.2, the fact that Illinois may
have criminalized the ‘manufacture, import, export,
distribution, or dispensing’ of some substances that are
not criminalized under federal law does not prevent
conduct prohibited under the Illinois statute from
qualifying, categorically, as a predicate offense.
Smith’s prior convictions under 720 Ill. Comp. Stat.
§ 570/401(d) thus are predicate offenses.
Id. at 489. Simply, “there is no requirement that the particular
controlled substance underlying a state conviction also be
22 No. 20-1034
controlled by the federal government.” Id. In a subsequent
opinion, the Sixth Circuit reiterated Smith’s holding and
added that “[i]n crafting the federal sentencing Guidelines
and substantive federal criminal laws, Congress was well
aware of the significant variations that existed in state crimi-
nal law.” United States v. Whitfield, 726 F. App’x 373, 376 (6th
Cir. 2018). But see United States v. Pittman, 736 F. App’x 551,
553 (6th Cir. 2018) (defining “controlled substance” in
U.S.S.G. § 4B1.2(b) by reference to the Controlled Substance
Act, 21 U.S.C. § 802(6), without citing Smith or otherwise
providing any analysis or reasoning). And just recently, the
Sixth Circuit recognized the circuit split on this question but
explicitly “decline[d] to adopt the reasoning embraced by our
sister circuits” in Townsend, Leal-Vega, and Sanchez-Garcia.
United States v. Sheffey, — F. App’x —, 2020 WL 3495944, at *6
(6th Cir. June 29, 2020). Instead, the court continued to em-
brace Smith’s reasoning and held that “the career offender en-
hancement … does not limit its definition of controlled sub-
stance offense to specific federal violations.” Id. We think that
the Sixth and Eleventh Circuits have the better take of the is-
sue.
But we are not joining a side today; we have already
staked out our position in Hudson. Granted, in Leal-Vega, the
Ninth Circuit distinguished the reasoning of our Hudson de-
cision as to the term “counterfeit substance” because “[t]he
word ‘counterfeit’ has a normal, everyday meaning that we
all understand,” whereas “[t]he same is not true of the word
‘controlled.’” Leal-Vega, 680 F.3d at 1166–67. “While the word
‘controlled’ may have a plain and ordinary meaning, whether
a substance is ‘controlled’ must, of necessity, be tethered to
some state, federal, or local law in a way that is not true of the
definition of ‘counterfeit.’” Id. at 1167. But none of the
No. 20-1034 23
reasoning in Hudson turned on the specific word “counterfeit”
having some sort of special independent, everyday meaning
that sets it apart from other words. Indeed, that seems to draw
an arbitrary line between how we interpret one term versus
another term in the very same definition. We see no textual
basis to engraft the federal Controlled Substances Act’s defi-
nition of “controlled substance” into the career-offender
guideline.
The career-offender guideline defines the term controlled
substance offense broadly, and the definition is most plainly
read to “include state-law offenses related to controlled or
counterfeit substances punishable by imprisonment for a
term exceeding one year.” Hudson, 618 F.3d at 703. A con-
trolled substance is generally understood to be “any of a cat-
egory of behavior-altering or addictive drugs, as heroin or co-
caine, whose possession and use are restricted by law.” Con-
trolled substance, The Random House Dictionary of the English
Language (2d ed. 1987). Given the natural meaning of a con-
trolled substance, Ruth’s 2006 cocaine conviction under Illi-
nois law is a controlled substance offense according to the ca-
reer-offender guideline.
III. Conclusion
Although the district court properly sentenced Ruth as a
career offender, his Guidelines range was further elevated
due to the increase in his statutory maximum sentence as a
result of the erroneous § 851 sentencing enhancement. Be-
cause the district court calculated an incorrect Guidelines
range, we VACATE Ruth’s sentence and REMAND to the district
court for resentencing.