                              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.
