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-familiar 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 federal 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 include its positional isomers, whereas the federal definition covers 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 investigation came to a head on December 5, 2018, when officers surveilling 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 residence and recovered 2.9 grams of crack cocaine, 5.6 grams of 

powder cocaine, a counterfeit $100 bill, $2,250 in U.S. currency, 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 conviction as a predicate felony drug offense to enhance his sentence. 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 eventually pleaded guilty to both counts without a plea agreement. 

The probation office determined that Ruth was a career offender because at the time of the instant offenses, he had at 

least two prior felony convictions for controlled substance offenses. 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’ imprisonment. 

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) because 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 substance offense. Specifically, the Illinois statute prohibits possession 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 categorically broader than the federal definition of a controlled 

substance “analogue.” Despite his objections to the career offender 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 reading of the career-offender guideline covered both federal and 

state definitions of controlled substance offenses. That is because the Guidelines, for purposes of the career offender enhancement, define a “controlled substance offense” as “an offense 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 intent 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 divisibility 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 enhancement. The court then sentenced Ruth to 108 months’ imprisonment 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 district court erred in applying the 21 U.S.C. § 851 sentencing enhancement because his 2006 Illinois conviction does not qualify as a prior “felony drug offense.” And second, Ruth contends that the 2006 Illinois conviction is not a “controlled substance 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 enhancement, 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 restricts conduct relating to narcotic drugs, marihuana, 

anabolic steroids, or depressant or stimulant substances.

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 “depressant 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 conviction 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 conviction 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-approach jurisprudence in Shular v. United States, 140 S. Ct. 779 

(2020). There are “two categorical methodologies,” depending 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 required 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 methodology—the conduct-based method—applies to determining 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 offense under State law, involving manufacturing, distributing, 

or possessing with intent to manufacture or distribute, a controlled 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 “serious drug offense” and triggers § 924(e)(2)(A)(ii)’s sentencing 

enhancement when the predicate offense involved “the conduct 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, anabolic steroids, or depressant or stimulant substances.” 

21 U.S.C. § 802(44) (emphasis added). This unquestionably refers 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 methodology for similar “felony drug offense” sentencing enhancements. 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 conviction 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 including 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 cocaine or ecgonine (for the purpose of this paragraph, 
No. 20-1034 9

the term “isomer” includes optical, positional and geometric 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) (defining “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 federal definition. 

Despite the statutory mismatch, the government responds

that the Illinois statute nonetheless “substantially corresponds” 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 corresponds’ 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,” requires 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 version 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 correspondence” between the Illinois and federal statutes, the government next argues that there is no basis to conclude that positional isomers of cocaine exist in the drug trade. In support of 

its assertion, during sentencing in the district court, the government 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 identify 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 important 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 positional isomers of cocaine in its statute. Effective January 1, 

1984, the legislature added the word “isomer” to the definition 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 cocaine 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 methamphetamine and its isomers, and we reach the same outcome.

940 F.3d at 950–52. Like there, the government offers theoretical 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 sciencebased arguments, it was not an open-ended invitation to argue that every isomeric mismatch is mere surplusage. There 

may be an occasion where a state statute covers unquestionably 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 intentional, 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. Subsections (a) through (i), and numerous subparts, then proceed to 

set forth various controlled substances and respective quantities that each constitute separate violations of the Illinois Controlled Substances Act resulting in different penalties. Subsection (c), in part, provides as follows: 

(c) Any person who violates this Section with regard to 

the following amounts of controlled or counterfeit substances or controlled substance analogs, notwithstanding 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 Schedules 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 Controlled 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 divisibility and immediately examine Ruth’s Shepard-approved documents to determine the specific conduct—or here, substance—underlying Ruth’s state court conviction. General

statute divisibility, however, is not enough. The modified categorical approach is just that: a modification of the categorical 

approach that simply acts as a “tool for implementing the categorical approach.” Descamps, 570 U.S. at 262. “It retains the 

categorical approach’s central feature: a focus on the elements, 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 subsection (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 subsection (c)(2) is divisible, nor could it; the statutory provision is 

clearly indivisible. Section 401(c)(2) lists only one crime: possession with intent to distribute cocaine. Though the Illinois 

statute may define cocaine overbroadly, there is no uncertainty 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 predicate “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 error must have been plain and must have affected Ruth’s substantial 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 “seriously affect[s] the fairness, integrity or public reputation of 
No. 20-1034 15

judicial proceedings.” Id. at 736 (quoting United States v. Atkinson, 297 U.S. 157, 160 (1936)).

An error is plain if it is “clear or obvious, rather than subject 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. Caputo, 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-overbreadth reasons he now makes in relation to the § 851 sentencing 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 conviction 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 sentenced 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 resentencing, 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) (quoting 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 outcome absent the error.” Molina-Martinez, 136 S. Ct. at 1345. Because 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 undermine 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 offense 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 requirements, “the defendant has at least two prior felony convictions 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 prohibits 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 “controlled 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 cocaine 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 Sentencing 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 guideline, the Commission defined “crime of violence” to incorporate the definition of firearm from 26 U.S.C. § 5845(a) and “explosive 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 Commission 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 offenses.” 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-references. See id. § 4B1.2(2) (1989). Ruth offers no compelling reason 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 convicted 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 offense,” 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: controlled-substance offenses 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. 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 reason 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 challenged 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 categorical 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 Substances 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 Guidelines’ 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 Circuit 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 categoricalapproach cases “reinforce the idea that imposing a federal sentencing enhancement under the Guidelines requires something more than a conviction based on a state’s determination 

that a given substance should be controlled.” Id. For those reasons, the Second Circuit was “confident that federal law is the 

interpretive anchor to resolve the ambiguity” over the definition of “controlled substance offense.” Id. “Any other outcome 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 different 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 inconsistent with the principles underlying the Taylor categorical 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 Circuit 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 controlledsubstance 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 criminal 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 embrace Smith’s reasoning and held that “the career offender enhancement ... does not limit its definition of controlled substance offense to specific federal violations.” Id. We think that 

the Sixth and Eleventh Circuits have the better take of the issue.

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 decision 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 definition 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 controlled substance is generally understood to be “any of a category of behavior-altering or addictive drugs, as heroin or cocaine, whose possession and use are restricted by law.” Controlled substance, The Random House Dictionary of the English 

Language (2d ed. 1987). Given the natural meaning of a controlled substance, Ruth’s 2006 cocaine conviction under Illinois law is a controlled substance offense according to the career-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. Because the district court calculated an incorrect Guidelines 

range, we VACATE Ruth’s sentence and REMAND to the district 

court for resentencing.