United States v. Reynold De La Torre

In the

United States Court of Appeals

For the Seventh Circuit

____________________

Nos. 18‐2009, 18‐2218, 18‐2286, 18‐3303, and 19‐1299

UNITED STATES OF AMERICA,

Plaintiff‐Appellee,

v.

REYNOLD DE LA TORRE, et al.,

Defendants‐Appellants.

____________________

Appeals from the United States District Court for the

Southern District of Indiana, Indianapolis Division.

No. 1:16‐cr‐00251‐TWP‐MJD — Tanya Walton Pratt, Judge.

____________________

ARGUED SEPTEMBER 6, 2019 — DECIDED OCTOBER 10, 2019

____________________

Before FLAUM, SYKES, and ST. EVE, Circuit Judges.

ST. EVE, Circuit Judge. The Zamudio drug organization dis‐

tributed pounds of methamphetamine and cocaine through‐

out the Indianapolis, Indiana area. At the top sat Jose

Zamudio, who imported the drugs from his suppliers in Mex‐

ico and oversaw his network of distributors here. Reynold De

La Torre, Christian Chapman, Jeffrey Rush, and Adrian Ben‐

nett were four of those local distributors. Maria Gonzalez was

Zamudio’s live‐in girlfriend. Besides permitting Zamudio to

2 Nos. 18‐2009, et al.

store and traffic drugs out of her home, Gonzalez helped laun‐

der Zamudio’s drug money and wired hundreds of thou‐

sands of dollars to Mexico and California.

Zamudio, Gonzalez, De La Torre, Chapman, Rush, and

Bennett all eventually pleaded guilty and were sentenced to

lengthy prison terms. Each separately appealed on different

grounds, and we consolidated the appeals.1 We affirm the sen‐

tences of Gonzalez, De La Torre, and Bennett. We vacate the

guilty pleas of Chapman and Rush and remand for further

proceedings.

I. Factual and Procedural Background

In early 2016, federal agents began investigating the drug

trafficking activities of Zamudio, along with his brother Juan

Zamudio. (Because Juan Zamudio is not a party to this appeal,

we use “Zamudio” to refer to Jose Zamudio.) Agents received

court authorization to intercept numerous telephone calls be‐

tween Zamudio and his associates. On November 17, 2016,

the FBI executed approximately forty search warrants as a re‐

sult of its investigation into the Zamudio organization. The

warrants led to the seizure of over seventy firearms, approxi‐

mately fifteen pounds of methamphetamine, smaller quanti‐

ties of cocaine, heroin, and marijuana, and cash. At least eight‐

een individuals were indicted as part of the conspiracy.

A. Jose Zamudio

At the top of the Zamudio organization were brothers Jose

and Juan. The brothers grew up very poor in rural Mexico and

eventually made their way to Indianapolis in 2008. Zamudio

1

Counsel for Zamudio filed an Anders brief and we address

Zamudio’s appeal, No. 18‐3361, in a separate order issued today.

Nos. 18‐2009, et al. 3

worked multiple jobs while living in Indianapolis, mostly at

restaurants as a dishwasher and a cook. Sometime before the

FBI’s investigation began in 2016, he went from working two

minimum‐wage jobs to leading a drug trafficking organiza‐

tion and overseeing the distribution of hundreds of thousands

of dollars of methamphetamine.

As noted above, the FBI intercepted numerous telephone

conversations between Zamudio and his drug distributors in

Mexico and the United States. A search warrant was executed

on Zamudio’s home and the government seized 4.5 kilograms

of methamphetamine, five firearms, and over ten thousand

dollars in cash. Another 11 kilograms of methamphetamine

were seized from Juan’s home, which Zamudio and Juan used

to store drugs.

Zamudio eventually pleaded guilty to four counts of the

indictment that included conspiracy to distribute drugs, un‐

lawful possession of a firearm, and conspiracy to launder

money. He did so without the benefit of an agreement. The

Guidelines range for Zamudio was life; he received less.

Zamudio’s total sentence was 380 months’ imprisonment.

B. Maria Gonzalez

Maria Gonzalez was Jose Zamudio’s girlfriend. During at

least a portion of the conspiracy Zamudio lived with Gonza‐

lez and she allowed him to store and sell methamphetamine

in her home. Her most prominent role in the organization,

though, was laundering Zamudio’s drug money. Gonzalez

utilized InterCambio Express, MoneyGram, and Western Un‐

ion to wire drug proceeds from Indiana to Mexico and Cali‐

fornia. But she did not just launder money herself; Gonzalez

4 Nos. 18‐2009, et al.

recruited her son, his girlfriend, and his girlfriend’s sister to

help her by sending wires and making bank deposits.

Gonzalez pleaded guilty to one count of conspiracy to pos‐

sess with intent to distribute and to distribute controlled sub‐

stances in violation of 21 U.S.C. §§ 841 and 846, and two

counts of conspiracy to launder monetary instruments in vio‐

lation of 18 U.S.C. §§ 1956(a)(1)(A)(i), (h) and 1956(a)(1)(B)(i),

(h). Before sentencing, the government sought to apply an ag‐

gravating role enhancement pursuant to § 3B1.1 of the Sen‐

tencing Guidelines for Gonzalez’s supervisory role in the or‐

ganization. Gonzalez objected to the enhancement on the

ground that she did not supervise enough participants to

qualify as a supervisor. But, as will become much clearer later,

she misapprehended the requirements for the enhancement

below and objected on an incorrect basis.

The district court overruled her objection and applied the

aggravating role enhancement, which added three levels to

Gonzalez’s offense level for a total offense level of forty‐three.

With a criminal history category of I, the Sentencing Guide‐

lines imprisonment range was a lifetime sentence. The court

ultimately sentenced Gonzalez to a total term of 300 months’

imprisonment. Gonzalez appeals the application of the aggra‐

vating role enhancement on a different ground than she

raised below.

C. Reynold De La Torre

Reynold De La Torre was a distributor for the Zamudio

organization, receiving his methamphetamine supply from

another co‐conspirator within the organization. He was

charged with one count of conspiracy to possess with intent

to distribute and to distribute 500 grams or more of

Nos. 18‐2009, et al. 5

methamphetamine in violation of 21 U.S.C. §§ 841(a)(1) and

846, and one count of possession of a firearm in furtherance

of a drug trafficking crime in violation of 18 U.S.C.

§ 924(c)(1)(A). De La Torre pleaded guilty to both counts in a

binding plea agreement pursuant to Federal Rule of Criminal

Procedure 11(c)(1)(C). Under the terms of the agreement, the

parties recommended a total term of imprisonment of be‐

tween 180 and 195 months. The terms of supervised release

and a fine amount were not agreed upon by the parties. The

plea agreement did, however, waive De La Torre’s right to ap‐

peal the length and conditions of supervised release.

At a combined plea and sentencing hearing, the district

court informed De La Torre that it intended to impose the con‐

ditions of supervised release that were recommended by the

probation officer in the presentence investigation report

(PSR). De La Torre stated that he reviewed the conditions

“carefully,” did not have any objections, and waived a formal

reading of the conditions into the record. The court then im‐

posed the conditions of supervised release.

De La Torre now challenges two of the conditions of su‐

pervised release as vague and unconstitutional:

[1] You shall not knowingly purchase, possess,

distribute, administer, or otherwise use any

psychoactive substances (e.g., synthetic mariju‐

ana, bath salts, Spice, glue, etc.) that impair a

person’s physical or mental functioning,

whether or not intended for human consump‐

tion.

6 Nos. 18‐2009, et al.

[2] You shall not be a member of any gang or

associate with individuals who are gang mem‐

bers.

He does not, however, challenge any other portion of his sen‐

tence, including the length of the period of supervised release

(five years), the term of imprisonment (180 months), or the

amount of the fine ($2,000).

D. Jeffrey Rush

While De La Torre received his methamphetamine supply

from another co‐conspirator within the organization, Jeffrey

Rush went straight to the top and received his methampheta‐

mine supply directly from Zamudio. In addition to selling the

drugs himself, Rush also supplied Christian Chapman down

the distribution line.

Rush was charged with one count of conspiracy to possess

with intent to distribute and to distribute 500 grams or more

of methamphetamine (mixture) and/or 500 grams or more of

cocaine (mixture), in violation of 21 U.S.C. §§ 841(a)(1) and

846. The government filed an information, pursuant to

21 U.S.C. § 851(a), notifying Rush that it intended to rely upon

two previous felony drug convictions to seek an enhanced

sentence. Both convictions were Indiana state court convic‐

tions, one in 2001 for felony dealing in a controlled substance

(the “2001 Indiana conviction”) and the second in 2010 for fel‐

ony possession of methamphetamine (the “2010 Indiana con‐

viction”). The two prior felony drug convictions subjected

Rush to a mandatory term of life imprisonment without re‐

lease. 21 U.S.C. § 841(b)(1) (2018).

Facing life in prison, Rush opted to plead guilty in ex‐

change for the government dropping one of the two § 851

Nos. 18‐2009, et al. 7

prior felony convictions. His mandatory minimum sentence

was now twenty years’ imprisonment, though he agreed to a

binding plea agreement under Federal Rule of Criminal Pro‐

cedure 11(c)(1)(C) with a sentence of 312 to 324 months, which

was within the Sentencing Guidelines range. The district

court sentenced Rush to a prison term of 312 months.

On appeal, Rush argues that neither of his two prior felony

drug convictions were in fact qualifying predicate offenses

under § 851 and therefore he should be able to withdraw his

binding guilty plea agreement because it was not knowingly

and intelligently entered into.

E. Christian Chapman

Christian Chapman received his drug supply from Rush

and then redistributed the methamphetamine to his own cus‐

tomers. Chapman also stands in a similar procedural posture

to Rush.

Chapman was indicted on one count of conspiracy to pos‐

sess with intent to distribute and to distribute controlled sub‐

stances in violation of 21 U.S.C. §§ 841(a)(1) and 846, and two

counts of possession with intent to distribute methampheta‐

mine in violation of 21 U.S.C. § 841(a)(1). The government

also filed a § 851 information notifying Chapman that it in‐

tended to rely on three prior felony convictions for enhanced

sentencing: a 2000 conviction in Indiana for felony possession

of a schedule II controlled substance (the “2000 Indiana con‐

viction”) and two 1993 convictions in Illinois for felony un‐

lawful possession of controlled substances (together the “1993

Illinois convictions”). These prior convictions, too, meant that

Chapman faced a mandatory minimum of life imprisonment.

See 21 U.S.C. § 841(b)(1) (2018).

8 Nos. 18‐2009, et al.

Like Rush, Chapman agreed to plead guilty in exchange

for the government alleging only one of his three prior felony

drug convictions under §§ 841 and 851. Chapman entered

into a Rule 11(c)(1)(C) binding plea agreement and pleaded

guilty to the one count of conspiracy to possess with intent to

distribute and to distribute controlled substances. The gov‐

ernment dismissed the remaining two counts of the indict‐

ment against Chapman and filed an amended § 851 infor‐

mation reflecting only the 2000 Indiana conviction. The plea

agreement agreed upon a period of incarceration of 300

months. The district court accepted the plea agreement and

imposed the twenty‐five‐year sentence.

Chapman appeals his sentence, asserting that none of his

prior state court convictions qualified as predicate felony

drug offenses under § 851, and thus his guilty plea was not

knowing and voluntary.

F. Adrian Bennett

Adrian Bennett, like Rush, received his supply of metham‐

phetamine and cocaine directly from Zamudio to then distrib‐

ute. Bennett was indicted on three counts: one count of con‐

spiracy to possess with intent to distribute and to distribute

controlled substances in violation of 21 U.S.C. §§ 841(a)(1) and

846; one count of possession with intent to distribute a con‐

trolled substance in violation of 21 U.S.C. § 841(a)(1); and one

count of possessing a firearm as a convicted felon in violation

of 18 U.S.C. § 922(g)(1).

He initially entered into a plea agreement, wherein he

pleaded guilty to one count of conspiracy to possess with in‐

tent to distribute and to distribute controlled substances. The

government filed a § 851 information notifying Bennett of its

Nos. 18‐2009, et al. 9

intent to rely on one prior felony drug offense. Between the

time Bennett’s guilty plea was entered and his sentencing, the

First Step Act of 2018 became law. See Pub. L. No. 115–391, 132

Stat. 5194 (Dec. 21, 2018). Title IV, Section 401 of the First Step

Act precluded the prior drug offense from qualifying as a

predicate offense under §§ 841 and 851. Because Bennett was

then no longer subject to the enhancement, his statutory im‐

prisonment range was significantly reduced.

At the sentencing hearing, Bennett moved to withdraw his

plea agreement based on the dramatic change in circum‐

stances. The government did not object and the district court

allowed the withdrawal. After some additional discussion,

Bennett decided to proceed with an open plea. Without the

§ 851 enhancement, the conviction carried a statutory range

of ten years to life imprisonment (down from a mandatory

minimum sentence of life imprisonment). The Sentencing

Guidelines range was a term of 262 months to 327 months.

After the district court heard argument from defense

counsel and the government, and a statement of allocution

from Bennett, it imposed a below‐Guidelines sentence of 225

months’ imprisonment. The sentence was “based upon the

defendant’s remorse, his family ties, [and] his addictions,”

and “addresse[d] the defendant’s personal history, his char‐

acteristics, as well as the serious nature of the offense, by pro‐

moting respect for the law, providing deterrence, and protect‐

ing the public.” The court further explained its consideration

of the § 3553(a) factors in arriving at the below‐Guidelines

sentence.

Bennett appealed his sentence as unreasonable.

10 Nos. 18‐2009, et al.

II. Discussion

We address each defendant in turn, and Chapman and

Rush together to the extent their arguments overlap.

A. Gonzalez’s aggravating role enhancement

Gonzalez objected in the court below to the application of

the aggravating role adjustment to her offense level, but she

did so on a different basis than she presents now on appeal.

Section 3B1.1 of the Sentencing Guidelines provides that the

sentencing judge shall increase the defendant’s offense level

based on whether the defendant played an “aggravating role”

in committing the offense. An aggravating role is an “organ‐

izer, leader, manager, or supervisor of one or more other par‐

ticipants.” U.S.S.G. § 3B1.1 n.2. Relevant here, “[i]f the defend‐

ant was a manager or supervisor (but not an organizer or

leader) and the criminal activity involved five or more partic‐

ipants or was otherwise extensive,” the offense level is in‐

creased by three. U.S.S.G. § 3B1.1(b). Before the district court,

Gonzalez argued that she did not manage or supervise five or

more participants—only three: her son, her son’s girlfriend,

and the girlfriend’s sister. Gonzalez, however, conflated the

requirement for the size of the criminal activity overall—“five

or more participants or otherwise extensive”—with the re‐

quirement for the number of participants in the criminal en‐

terprise that the defendant had to manage or supervise—“one

or more other participants.” Compare § 3B1.1(b), with § 3B1.1

n.2.2 Gonzalez now argues that none of the three alleged su‐

pervisees qualify as a “participant” under the Guidelines.

2

Despite Gonzalez’s initial confusion, she no longer disputes that the

Zamudio drug trafficking enterprise involved five or more participants.

Nos. 18‐2009, et al. 11

Gonzalez advances this basis for her sentencing objection

for the first time on appeal, and thus forfeited the argument.

It is a completely different argument than the one she pre‐

sented to the district court, and she denied the judge the op‐

portunity to address the argument. Consequently, our review

of the district court’s application of the Guidelines is for plain

error only. See United States v. Harris, 791 F.3d 772, 779 (7th

Cir. 2015); United States v. Hawkins, 480 F.3d 476, 478 (7th Cir.

2007). To prevail under plain error, Gonzalez must show that

“(1) an error occurred, (2) the error was plain, (3) it affected

the defendant’s substantial rights, and (4) it seriously affected

the fairness, integrity, or public reputation of the proceed‐

ings.” United States v. Pierson, 925 F.3d 913, 919 (7th Cir. 2019).

For a defendant to receive an offense‐level enhancement

for being a supervisor of one or more participants, the partic‐

ipant must be “criminally responsible for the commission of

the offense, but need not have been convicted.” U.S.S.G.

§ 3B1.1 n.1. The participant need not have been charged ei‐

ther, as long as “the participant could have been charged.”

United States v. Pabey, 664 F.3d 1084, 1097 (7th Cir. 2011). A

participant is criminally responsible under § 3B1.1 if he or she

knowingly assisted the criminal enterprise. Id. Mere

knowledge of the conspiracy, however, is not enough.

The record sufficiently supports a finding that at mini‐

mum Gonzalez’s son, whom she trusted, knowingly assisted

his mother in laundering money. In her post‐Miranda state‐

ments, Gonzalez told agents that initially her son refused to

wire transfer money for her. After she asked him again, he

agreed, but told her he would only do it the one time. A total

of four wire transfers were made in his name. Gonzalez also

recruited her son’s girlfriend, who made nine wire transfers

12 Nos. 18‐2009, et al.

and six separate bank deposits at Gonzalez’s direction. See

United States v. Watts, 535 F.3d 650, 660 (7th Cir. 2008) (aggra‐

vating role enhancement applied to a defendant who re‐

cruited his wife to participate in bank fraud conspiracy based

on findings that the wife opened a bank account using false

information and attempted to deposit check from co‐con‐

spirator). Importantly, Gonzalez never contested any of these

factual allegations.

Those facts were also set forth in the PSR. Gonzalez ob‐

jected to the application of certain enhancements and related

underlying facts (such as the fact that she possessed a gun),

but did not object to the facts concerning the roles of her son,

his girlfriend, and his girlfriend’s sister in the money launder‐

ing scheme. To the contrary, at sentencing, Gonzalez argued

that she supervised only these three people, not five people—

that is more than the “one or more” participants the Guide‐

lines require for the aggravating role enhancement. In over‐

ruling Gonzalez’s objection, the district court expressly stated

that “[Gonzalez] was the manager and supervisor of three.”

There was no error in the district court’s application of the

aggravating role enhancement, and certainly not one that was

plain. We affirm Gonzalez’s sentence.

B. De La Torre’s conditions of supervised release

We have recently clarified our law regarding forfeiture

versus waiver of challenges to conditions of supervised re‐

lease made for the first time on appeal. See United States v. Flo‐

res, 929 F.3d 443, 450 (7th Cir. 2019); United States v. Hunt,

930 F.3d 921, 924 (7th Cir. 2019) (discussing our decision in

Flores). The Flores decision came out after briefing was

Nos. 18‐2009, et al. 13

submitted in this appeal,3 but the law is now clear in this cir‐

cuit. We will find challenges to supervised release conditions

waived when

the defendant has notice of the proposed condi‐

tions, a meaningful opportunity to object, and

she asserts (through counsel or directly) that she

does not object to the proposed conditions,

waives reading of those conditions and their

justifications, challenges certain conditions but

not the one(s) challenged on appeal, or other‐

wise evidences an intentional or strategic deci‐

sion not to object.

Flores, 929 F.3d at 450.

De La Torre waived his challenge. He was on notice of the

now‐challenged conditions since the disclosure of the initial

PSR, which proposed both conditions verbatim. He did not

file any objections. Any doubt that De La Torre did not have

sufficient advance notice of the challenged conditions was

erased at sentencing. Counsel told the sentencing judge that

De La Torre “carefully” reviewed the proposed conditions

and had no objections, and then waived a formal reading. De

La Torre had ample opportunity to raise objections to any

conditions that he knew could be imposed and passed on that

chance. We are satisfied from the record that De La Torre

3 In light of our circuit’s recent decisions, De La Torre’s appellate

counsel moved to waive oral argument and cede his time to the remaining

co‐defendants. We permitted counsel to appear by telephone and none‐

theless gave counsel the opportunity to make and respond to any argu‐

ments on behalf of De La Torre.

14 Nos. 18‐2009, et al.

intentionally waived his appellate challenge to the conditions

of supervised release.

C. Chapman’s and Rush’s predicate felony drug offenses

Chapman and Rush challenge the validity of their guilty

pleas based on perceived errors in the applicable mandatory

minimum sentences. For both defendants, the government

filed an information pursuant to 21 U.S.C. § 851(a) alleging

that prior state law convictions were each a “felony drug of‐

fense” under 21 U.S.C. § 841. As a result of the § 851 enhance‐

ments, Chapman and Rush each faced mandatory minimums

of life in prison. Both opted to reach a plea agreement in ex‐

change for the government amending the § 851 information

to allege only one prior felony drug conviction, which low‐

ered the mandatory minimum sentence. Because, they argue,

their plea agreements were based on errors regarding the

mandatory minimum sentences they would have otherwise

faced, the guilty pleas were not entered into knowingly and

intelligently and should be vacated. There is no contention

that either Chapman or Rush objected to the predicate of‐

fenses or requested that the district court vacate their pleas,

and thus our review is for plain error. We ultimately agree

that there was an error and it affected their substantial rights,

and thus vacate both Chapman’s and Rush’s plea agreements

and remand for further proceedings.

1. Predicate felony drug offenses

Section 841(b)(1)(A), the applicable penalty provision for

Chapman’s and Rush’s federal convictions, provided at that

time for a ten‐year mandatory minimum sentence that in‐

creased to a mandatory minimum term of imprisonment of

twenty years if the defendant was convicted “after a prior

Nos. 18‐2009, et al. 15

conviction for a felony drug offense.” 21 U.S.C. § 841(b)(1)(A)

(2018). The term “felony drug offense” is defined in 21 U.S.C.

§ 802(44) to mean:

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.

See Burgess v. United States, 553 U.S. 124, 126 (2008) (“The term

‘felony drug offense’ contained in § 841(b)(1)(A)[] … is de‐

fined exclusively by § 802(44) ….”). Each of the four catego‐

ries of covered drugs is also 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”).

The government filed an information identifying the prior

convictions pursuant to 21 U.S.C. § 851(a).

We must, then, determine whether Chapman’s or Rush’s

prior convictions under state law meet the federal definition

of “felony drug offense.” To do so, we apply the categorical

approach, which requires us to compare the elements of the

state statute of conviction to the elements of the federal recid‐

ivism statute. United States v. Elder, 900 F.3d 491, 501 (7th Cir.

2018). 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. Id. Importantly, un‐

der the categorical approach, it is only the elements that mat‐

ter, not the defendant’s underlying conduct.

16 Nos. 18‐2009, et al.

2. Chapman’s Illinois convictions

We begin with Chapman’s two 1993 Illinois convictions

because, although the Illinois convictions were not relied

upon as prior felony drug offenses under §§ 841(b)(1)(A) and

851 for purposes of his binding plea agreement, all parties

now agree that these convictions do not qualify as predicate

offenses and the error requires vacating the plea agreement.

Chapman has two convictions for felony unlawful posses‐

sion of controlled substances in violation of 720 ILCS

570/402(c) (1993). Subsection (c) is a broad residual provision

that applies to the possession of “a controlled or counterfeit

substance not set forth in subsection (a) or (d).” Id. The Illinois

statute defines “controlled substance” as “a drug, substance,

or immediate precursor in the Schedules of Article II of this

Act.” 720 ILCS 570/102(f). The Schedules, in turn, are found at

720 ILCS 570/204 (Schedule I), id. § 206 (Schedule II), id. § 208

(Schedule III), id. § 210 (Schedule IV), and id. § 212 (Sched‐

ule V).

The government first filed a § 851 information identifying

three prior convictions—these two 1993 Illinois convictions

and the 2000 Indiana conviction—that increased Chapman’s

statutory minimum sentence to life in prison. The government

agreed to withdraw the § 851 information as to the two Illinois

convictions, reducing Chapman’s mandatory minimum sen‐

tence to twenty years in prison, if Chapman pleaded guilty.

Chapman reluctantly accepted and pleaded guilty.

Two of our recent decisions bear directly on the outcome

of Chapman’s appeal. Shortly after Chapman pleaded guilty

and was sentenced, we held in Elder that an Arizona statute

that included propylhexedrine was mismatched with the

Nos. 18‐2009, et al. 17

federal definition of felony drug offense under § 802(44),

which does not cover propylhexedrine. Elder, 900 F.3d at 501.

Because in 1993 the Illinois schedules listed propylhexedrine

as a Schedule V controlled substance, see 720 ILCS 570/212(d)

(1993), it follows that Illinois’s § 402(c) is also categorically

broader than the federal definition of a felony drug offense.

The government did not contest this point, but instead argued

that the Illinois statute was divisible and thus we could look

to the elements of Chapman’s actual convictions.

After the briefing was submitted in this appeal, we de‐

cided Najera‐Rodriguez v. Barr, 926 F.3d 343 (7th Cir. 2019),

which held that 720 ILCS 570/402(c) is not divisible. In light of

this holding, the government conceded at oral argument that

Chapman’s Illinois convictions do not qualify as prior felony

drug offenses for purposes of the § 851 enhancement. Accord‐

ingly, the government agreed that this error affected Chap‐

man’s substantial rights and that his plea agreement must be

set aside.

3. Chapman’s guilty plea

We accept the government’s concession that Chapman’s

plea agreement should be vacated, and offer a brief explana‐

tion.

Chapman, the government, and the sentencing judge all

erroneously believed that Chapman’s multiple prior convic‐

tions subjected him to a mandatory life sentence. The record

is abundantly clear that Chapman only agreed to the plea

agreement because he believed life in prison was his only al‐

ternative. That was not true.

Without those two prior Illinois convictions, and assum‐

ing for the moment that his 2000 Indiana conviction was a

18 Nos. 18‐2009, et al.

qualifying predicate felony drug offense, Chapman’s manda‐

tory minimum immediately dropped from life to twenty

years’ imprisonment. See 21 U.S.C. § 841(b) (2018). Yet Chap‐

man agreed to a binding term of imprisonment of twenty‐five

years—a far greater prison sentence than he could have been

sentenced to without any plea agreement at all. And this is all

notwithstanding the presence of his 2000 Indiana conviction,

the absence of which would cut his mandatory minimum

term of incarceration in half, down to ten years. See 21 U.S.C.

§ 841(b) (2018).

Chapman has met his burden of showing that the error re‐

garding the use of the 1993 Illinois convictions as prior felony

drug offenses was prejudicial. See United States v. Olano,

507 U.S. 725, 734 (1993). An error such as the one we have here

“establishes a reasonable probability that a defendant will

serve a prison sentence that is more than ‘necessary’ to fulfill

the purposes of incarceration.” Rosales‐Mireles v. United States,

138 S. Ct. 1897, 1907 (2018) (holding that a plain error in cal‐

culating the correct Guidelines range affected the defendant’s

substantial rights and warranted relief). Chapman’s sentenc‐

ing transcript reflects more than a reasonable probability of

additional jail time. In accepting the binding plea agreement,

the sentencing judge expressed concern over the length of the

sentence and stated that it was “difficult to find that this 300‐

month sentence of imprisonment is not greater than neces‐

sary.” Without correction of this error, Chapman may be un‐

necessarily deprived of his liberty and may spend more time

in jail than necessary, which we find “seriously affects the fair‐

ness, integrity or public reputation of judicial proceedings.”

Olano, 507 U.S. at 736 (brackets omitted).

Nos. 18‐2009, et al. 19

4. Rush’s 2001 Indiana conviction

The government’s initial § 851 informations identified

three Indiana convictions as prior felony drug offenses:

Rush’s 2001 Indiana conviction for dealing in a schedule I, II,

or III controlled substance; Rush’s 2010 Indiana conviction for

possession of methamphetamine; and Chapman’s 2000 Indi‐

ana conviction for possession of a controlled substance.4 We

start with Rush’s 2001 Indiana conviction because it is dispos‐

itive.

Rush was convicted in 2001 of dealing in a schedule I, II,

or III controlled substance in violation of Indiana Code § 35‐

48‐4‐2 (2000). That statute provides, in pertinent part, that:

A person who:

(1) knowingly or intentionally:

(A) manufactures;

(B) finances the manufacture of;

(C) delivers; or

4 Because we already vacated Chapman’s plea agreement based on

the disqualified 1993 Illinois convictions, we do not reach his 2000 Indiana

conviction that was relied upon for purposes of the plea. The analysis of

the 2000 Indiana conviction for possession of a controlled substance under

Indiana Code § 35‐48‐4‐7 would largely track the analysis of Rush’s 2001

Indiana conviction due to the significant similarities between the two stat‐

utes with respect to their coverage of controlled substances. As we will see

next, Rush’s 2001 Indiana conviction is not a qualifying predicate felony

drug offense. Without deciding the question, we think it is unlikely that

Chapman’s 2000 Indiana conviction qualifies as a predicate felony drug

offense, though we leave it to the parties and the court to appropriately

address on remand as necessary.

20 Nos. 18‐2009, et al.

(D) finances the delivery of;

a controlled substance, pure or adulterated,

classified in schedule I, II, or III, except mariju‐

ana, hash oil, or hashish; or

(2) possesses, with intent to:

(A) manufacture;

(B) finance the manufacture of;

(C) deliver; or

(D) finance the delivery of;

a controlled substance, pure or adulterated,

classified in schedule I, II, or III, except mariju‐

ana, hash oil, or hashish;

commits dealing in a schedule I, II, or III con‐

trolled substance ….

Ind. Code § 35‐48‐4‐2(a) (2000). The schedule I, II, and III con‐

trolled substances are found at Indiana Code §§ 35‐48‐2‐4, 35‐

48‐2‐6, and 35‐48‐2‐8, respectively.

To demonstrate the overbreadth of the Indiana statute,

Rush points to methamphetamine in schedule II. There,

schedule II lists “[m]ethamphetamine, including its salts, iso‐

mers, and salts of its isomers.” Ind. Code § 35‐48‐2‐6(d)(2).

The federal statute similarly controls “methamphetamine, in‐

cluding its salts, isomers, and salts of isomers.” See 21 U.S.C.

§ 812, Schedule II(c), Schedule III(a)(3). A seeming match. But

a closer look reveals otherwise.

The federal Controlled Substances Act also specifically de‐

fines the term “isomer” to mean “the optical isomer,” except

as used in schedule I(c) and schedule II(a)(4), where isomer

Nos. 18‐2009, et al. 21

means “any optical, positional, or geometric isomer.”

21 U.S.C. § 802(14). Methamphetamine is not listed in sched‐

ule I(c) or schedule II(a)(4) and thus, for purposes of federal

drug offenses, methamphetamine includes only its optical

isomers.

The Indiana Code, on the other hand, does not define the

term “isomer.” “In Indiana, the lodestar of statutory interpre‐

tation is legislative intent, and the plain language of the stat‐

ute is the ‘best evidence of ... [that] intent.’” Estate of Moreland

v. Dieter, 576 F.3d 691, 695 (7th Cir. 2009) (quoting Cubel v.

Cubel, 876 N.E.2d 1117, 1120 (Ind. 2007)); see also Johnson v.

State, 87 N.E.3d 471, 472 (Ind. 2017) (“Our first task when in‐

terpreting a statute is to give its words their plain meaning by

considering the text and structure of the statute.”). Ascertain‐

ing the “ordinary” meaning of isomer might be a fool’s er‐

rand, but it is not one we must undertake here. A statute

“should be examined as a whole, avoiding both excessive re‐

liance on strict literal meaning and selective reading of indi‐

vidual words.” Estate of Moreland, 576 F.3d at 695 (quoting

Cubel, 876 N.E.2d at 1120). The structure of Indiana’s Con‐

trolled Substances Act guides the conclusion in this case.

When Indiana intended to limit the specific isomer for a

drug, it expressly did so. Indiana’s schedule II controls

“[a]mphetamine, its salts, optical isomers, and salts of its op‐

tical isomers.” Ind. Code § 35‐48‐2‐6(d)(1) (2000). Elsewhere,

schedule III lists certain stimulants and in the preamble notes

that each substance “includ[es] its salts, isomers (whether op‐

tical, position, or geometric), and salts of such isomers.” Ind.

Code § 35‐48‐2‐8(b) (2000). The Indiana legislature knew how

to limit a listed drug to include only its optical isomers. It is a

general rule of statutory construction that “when the

22 Nos. 18‐2009, et al.

legislature uses certain language in one part of the statute and

different language in another, the court assumes different

meanings were intended.” Sosa v. Alvarez‐Machain, 542 U.S.

692, 712 n.9 (2004). According to Rush, then, Indiana’s generic

use of “isomer” in relation to methamphetamine must be

broader than optical isomers. We agree. Because the federal

definition of methamphetamine includes only its optical iso‐

mers whereas the Indiana definition includes something more

than just optical isomers of methamphetamine, the mismatch

renders the Indiana statute overbroad.

The government does not contest that Indiana’s statute, on

its face, is broader than federal law, but contends that geomet‐

ric isomers of methamphetamine do not exist in the real

world, and thus the statutes actually mirror each other. The

government’s argument suffers a few fatal flaws at this junc‐

ture. First, the government asks us to take judicial notice of

two expert declarations from different cases in different

courts that discuss the isomer forms of methamphetamine.

These declarations were not before the district court and are

not the proper subject of judicial notice. The Federal Rules of

Evidence permit a court to take judicial notice of a fact that is

“not subject to reasonable dispute” because it is “generally

known” or “can be accurately and readily determined from

sources whose accuracy cannot reasonably be questioned.”

Fed. R. Evid. 201(b). The isomeric nature of methampheta‐

mine is not “generally known,” at least to us. Nor are the dec‐

larations incontrovertible—the declarants were not subjected

to Daubert challenges, cross‐examined, or tested with compet‐

ing expert testimony. None of the defendants had the ability

Nos. 18‐2009, et al. 23

to challenge these declarations in the district court.5 Second,

the declarations were crafted in other cases with an eye to‐

wards the issues at hand in those cases. It seems, for example,

that the declarations are primarily focused on proving that

geometric isomers of methamphetamine do not exist because

the state statute specifically included both optical and geo‐

metric isomers of methamphetamine. For our purposes, the

declarations do not tell us whether any other types of isomers

of methamphetamine could possibly exist. That issue is the

heart of the dispute here. In short, the content of the declara‐

tions is “arguably subject to reasonable dispute and therefore

not a proper subject of judicial notice.” Tobey v. Chibucos,

890 F.3d 634, 648 (7th Cir. 2018). Finally, notwithstanding the

declarations, we do not think that the government’s theoreti‐

cal challenges are pertinent here when the plain language

chosen by the Indiana legislature dictates that the Indiana

statute is categorically broader than the federal definition of

felony drug offense.

No matter, our decision is not solely dependent on the def‐

inition of methamphetamine and which of its isomers do or

do not exist. Indiana Code § 35‐48‐4‐2 reaches at least two

other substances that are not included in § 802(44). Specifi‐

cally, Indiana lists “[p]arahexyl” as a schedule I drug and a

“combination product containing tiletimine and zolazepam

(Telazol)” as a schedule III drug. Ind. Code §§ 35‐48‐2‐

4(d)(16), 35‐48‐2‐8(c)(12) (2000). Neither substance is covered

5 Granted, Rush and Chapman did not challenge their prior convic‐

tions below, which deprived the government of the opportunity to intro‐

duce this evidence in the district court. Our opinion takes no position on

the scientific merits, nor should it be read as limiting the government’s

ability to present such an argument in future proceedings.

24 Nos. 18‐2009, et al.

under the definitions in § 802(44). To put it succinctly, Rush

could have been convicted under § 35‐48‐4‐2 for dealing in a

controlled substance that would not be a felony drug offense

under § 802(44). The Indiana law is categorically broader.

Rush’s 2001 Indiana conviction for dealing in a schedule I,

II, or III controlled substance cannot serve as a predicate fel‐

ony drug offense under § 841(b)(1)(A) and § 802(44).

5. Rush’s guilty plea

Having found that Rush’s 2001 Indiana conviction does

not qualify as a predicate felony drug offense, this error

clearly affected Rush’s substantial rights. If Rush had known

that his 2001 Indiana conviction was not a qualifying felony

drug offense, it would have changed the calculus and he

likely would have proceeded differently. Without two prior

felony drug offenses, Rush did not face a potential mandatory

minimum life sentence and instead would have been sen‐

tenced in consideration of a Guidelines range of 262 to 327

months’ imprisonment.6 The binding plea agreement called

for a sentence in the middle of that range, 312 months, which

the court imposed. In doing so, the sentencing judge noted

that the 312‐month term of imprisonment “might be greater

than necessary” but that it was “the minimum the [c]ourt

[could] give the defendant” because of the plea agreement.

Although Rush received a within‐Guidelines sentence—

otherwise presumed reasonable on review—given the facts

and the sentencing judge’s statements in the record, Rush has

6 Even with only one prior felony conviction, such as the 2010 Indiana

conviction, Rush would have been subject to a mandatory minimum term

of imprisonment of ten years, or less than his Guidelines range. See

21 U.S.C. § 841(b) (2018).

Nos. 18‐2009, et al. 25

met his burden under the plain error standard. He has shown

a reasonable probability that, but for the error regarding the

2001 Indiana conviction, the outcome of the proceeding may

have been different and that he may have received less prison

time absent the error. See Molina‐Martinez v. United States,

136 S. Ct. 1338, 1343 (2016). “Any amount of actual jail time is

significant and has exceptionally severe consequences for the

incarcerated individual and for society which bears the direct

and indirect costs of incarceration.” Rosales‐Mireles, 138 S. Ct.

at 1907 (cleaned up). That error, affecting Rush’s fundamental

rights, left uncorrected would undermine the integrity and

fairness of judicial proceedings.7

Not every error relating to a plea agreement will demand

correction under plain error. But based on the facts of this

case, Rush has satisfied his burden. We, therefore, vacate

Rush’s plea agreement and remand to the district court for

further proceedings.

D. Reasonableness of Bennett’s below‐Guidelines sentence

Our final co‐defendant in this appeal, Adrian Bennett, ap‐

peals his below‐Guidelines sentence of 225 months’ imprison‐

ment as unreasonable. “We review a district court’s choice of

sentence in two steps. First, we assess de novo whether the

7 We do not need to address Rush’s 2010 Indiana conviction because

the inclusion of the 2001 Indiana conviction as a qualifying predicate of‐

fense is a plain error that requires remand. We note, however, that Rush

treated the definition of methamphetamine as identical between Indiana

Code §§ 35‐48‐4‐6.1 and 35‐48‐4‐2. We are not convinced that that assump‐

tion is correct, but the government did not raise the argument that differ‐

ent definitions of methamphetamine applied to the two sections, and thus

likely waived the argument on appeal. Regardless, we do not need to de‐

cide the issue.

26 Nos. 18‐2009, et al.

court followed proper procedures. If the decision below is

procedurally sound, then we ask whether the resulting sen‐

tence is substantively reasonable.” United States v. Mbaye,

827 F.3d 617, 622 (7th Cir. 2016) (quoting United States v.

Warner, 792 F.3d 847, 855 (7th Cir. 2015)). Whether the sen‐

tence imposed is inside or outside the Guidelines range, we

review the sentence for an abuse of discretion. Gall v. United

States, 552 U.S. 38, 51 (2007). “A below‐guidelines sentence,

like a within‐guidelines one, is presumed reasonable against

a defendant’s challenge that it is too high.” United States v.

Poetz, 582 F.3d 835, 837 (7th Cir. 2009). A defendant can only

rebut this presumption of reasonableness “by showing that

the sentence does not comport with the factors outlined in 18

U.S.C. § 3553(a).” United States v. Patel, 921 F.3d 663, 672 (7th

Cir. 2019) (quoting United States v. Solomon, 892 F.3d 273, 278

(7th Cir. 2018)).

Bennett does not identify any procedural errors. Nor could

he. The district judge’s sentencing was procedurally sound.

The judge correctly calculated his Guidelines range, consid‐

ered all of the § 3553(a) factors, and adequately explained the

reasons for the sentence. The district court then sentenced

Bennett to 225 months of incarceration, thirty‐seven months

below the low end of his Guidelines range of 262 to 327

months’ imprisonment. Our only task, then, is to review

whether the district court abused its discretion in sentencing

Bennett to 225 months in prison, below the Guidelines range.

It did not.

On appeal, Bennett simply attempts to reargue the

§ 3553(a) factors, and makes substantially the same argu‐

ments he did below. But the district court considered all of

Bennett’s arguments at sentencing and took them all into

Nos. 18‐2009, et al. 27

account in crafting an appropriate sentence. It is not our job

to reweigh the § 3553(a) factors. For example, Bennett argues

that his sentence creates an unwarranted sentencing dispar‐

ity. See 18 U.S.C. § 3553(a)(6). But other than giving the aver‐

age sentence for a drug trafficking offense in the Southern Dis‐

trict of Indiana and nationally across the United States, Ben‐

nett provides nothing more. As the district court stated at sen‐

tencing, Bennett distributed significant quantities of metham‐

phetamine and cocaine throughout Indianapolis and the sur‐

rounding communities. The harmful effects of his conduct

cannot go understated.

The district judge imposed a sentence that addressed Ben‐

nett’s personal history and characteristics, reflected the seri‐

ousness of the offense, and was sufficient, but not greater than

necessary. In sum, Bennett fails to identify a specific reason to

question the substantive reasonableness of his below‐Guide‐

lines sentence. A below‐Guidelines sentence will almost never

be unreasonable, United States v. Trudeau, 812 F.3d 578, 594

(7th Cir. 2016), and it was not here. Bennett’s sentence is af‐

firmed.

***

We AFFIRM the sentences of Gonzalez, De La Torre, and

Bennett, and we VACATE Chapman’s and Rush’s guilty pleas

and REMAND for further proceedings.