Case Information
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Before F LAUM , S YKES , S T . E VE , Circuit Judges . S T E VE Circuit Judge . Zamudio organization dis tributed pounds cocaine through out Indianapolis, area. At top sat Jose Zamudio, who imported drugs suppliers Mex ico oversaw network distributors here. Reynold De La Torre, Christian Chapman, Je rey Rush, Adrian Ben ne tt four those local distributors. Maria Gonzalez Zamudio’s live girlfriend. Besides permi ing Zamudio 2009, store and tra ffi c drugs out of her home, Gonzalez helped laun der Zamudio’s money and wired hundreds thou sands dollars to Mexico and California.
Zamudio, Gonzalez, De La Torre, Chapman, Rush, and Benne tt all eventually pleaded guilty and were sentenced to lengthy prison terms. Each separately appealed di erent grounds, and we consolidated appeals. We ffi rm sen tences Gonzalez, De La Torre, and Benne vacate pleas Chapman and Rush and remand further proceedings.
I. Factual Procedural Background In early 2016, federal agents began investigating tra ffi cking activities Zamudio, along brother Juan Zamudio. (Because Juan Zamudio party appeal, we use “Zamudio” refer Jose Zamudio.) Agents received authorization intercept numerous telephone calls tween Zamudio associates. On November 2016, FBI executed approximately forty search warrants re sult its investigation into Zamudio organization. warrants led seizure over seventy rearms, approxi mately fteen pounds methamphetamine, smaller quanti ties cocaine, heroin, marijuana, cash. At least eight een individuals were indicted part conspiracy. A. Jose Zamudio
At top Zamudio organization brothers Jose Juan. brothers grew up very poor rural Mexico eventually made their way Indianapolis Zamudio worked multiple jobs while living in Indianapolis, mostly at restaurants dishwasher and cook. Sometime before FBI’s investigation began he went from working minimum wage jobs to leading drug tra ffi cking organiza tion and overseeing distribution hundreds thousands dollars methamphetamine.
As noted above, FBI intercepted numerous telephone conversations between Zamudio and drug distributors Mexico and United States. A search warrant was executed Zamudio’s home and seized 4.5 kilograms methamphetamine, ve fi rearms, over ten thousand dollars cash. Another kilograms methamphetamine seized from Juan’s home, Zamudio Juan used to store drugs.
Zamudio eventually pleaded four counts indictment included conspiracy distribute drugs, un lawful possession rearm, conspiracy launder money. He did so without bene t agreement. range Zamudio was life; received less. Zamudio’s total sentence was months’ imprisonment. B. Maria Gonzalez
Maria Gonzalez Jose Zamudio’s girlfriend. During least portion conspiracy Zamudio lived Gonza lez she allowed him store sell her home. Her most prominent role organization, though, laundering Zamudio’s money. Gonzalez utilized InterCambio Express, MoneyGram, Western Un ion wire proceeds Mexico Cali fornia. But she just launder money herself; Gonzalez recruited her son, girlfriend, and his girlfriend’s sister to help her by sending wires and making bank deposits.
Gonzalez pleaded to one count conspiracy to pos sess with intent to distribute to distribute controlled sub stances violation U.S.C. §§ counts conspiracy to launder monetary instruments vio lation §§ 1956(a)(1)(A)(i), (h) 1956(a)(1)(B)(i), (h). Before sentencing, sought to apply an ag gravating role enhancement pursuant to 3B1.1 Sen tencing for Gonzalez’s supervisory role ganization. Gonzalez objected to enhancement on ground she supervise enough participants qualify a supervisor. But, will become much clearer later, she misapprehended requirements for enhancement below objected incorrect basis. court overruled her objection applied
aggravating role enhancement, added three levels Gonzalez’s ense level total ense level forty three. With criminal history category I, Sentencing Guide lines imprisonment range was lifetime sentence. ultimately sentenced Gonzalez total months’ imprisonment. Gonzalez appeals application aggra vating role enhancement di erent ground she raised below.
C. Reynold De La Torre
Reynold De La Torre distributor Zamudio organization, receiving supply another co conspirator within organization. He charged count conspiracy possess with intent distribute distribute grams more violation of U.S.C. §§ 841(a)(1) and count of possession of a rearm furtherance of a tra ffi cking crime violation of 924(c)(1)(A). De La Torre pleaded both counts binding plea agreement pursuant Federal Rule Criminal Procedure 11(c)(1)(C). Under terms agreement, parties recommended total imprisonment tween months. The terms supervised release ne amount were not agreed upon by parties. plea agreement did, however, waive De La Torre’s right ap peal length conditions supervised release.
At combined sentencing hearing, court informed De La Torre intended impose con ditions supervised release recommended by probation officer presentence investigation report (PSR). De La Torre stated reviewed conditions “carefully,” have any objections, waived formal reading conditions into record. then im posed conditions supervised release.
De La Torre now challenges conditions su pervised release vague unconstitutional:
[1] You shall knowingly purchase, possess, distribute, administer, or otherwise use any psychoactive substances (e.g., synthetic mariju ana, bath salts, Spice, glue, etc.) impair person’s physical mental functioning, whether intended human consump tion.
[2] You shall 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 length period supervised release ( ve years), term imprisonment (180 months), or amount ne ($2,000).
D. Je rey Rush
While De La Torre received methamphetamine supply from another co conspirator within organization, Je rey Rush went straight to top received methampheta mine supply directly Zamudio. In addition to selling drugs himself, Rush also supplied Christian Chapman down distribution line.
Rush charged with one count conspiracy to possess intent distribute to distribute grams more methamphetamine (mixture) and/or grams more cocaine (mixture), in violation U.S.C. §§ 841(a)(1) government led an information, pursuant U.S.C. 851(a), notifying Rush intended rely upon two previous felony convictions seek enhanced sentence. Both convictions Indiana state convic tions, one for felony dealing controlled substance (the “2001 Indiana conviction”) second fel ony possession (the “2010 con viction”). two convictions subjected Rush mandatory life imprisonment without re lease. 841(b)(1)
Facing life prison, Rush opted plead ex change dropping 7 prior felony convictions. His mandatory minimum sentence was now twenty years’ imprisonment, though he agreed to a binding plea agreement under Federal Rule Criminal Pro cedure 11(c)(1)(C) with a sentence to months, was within Sentencing range. sentenced Rush to prison months.
On appeal, Rush argues neither his two prior felony convictions in fact qualifying predicate enses § therefore should able to withdraw his binding agreement because it knowingly intelligently entered into. E. Christian Chapman
Christian Chapman received supply Rush then redistributed to own cus tomers. Chapman also stands in similar procedural posture Rush.
Chapman indicted count conspiracy pos sess with intent distribute distribute controlled sub stances violation U.S.C. §§ 841(a)(1) two counts possession intent distribute methampheta mine violation U.S.C. 841(a)(1). also led information notifying Chapman tended rely three prior felony convictions for enhanced sentencing: conviction Indiana felony possession schedule II controlled substance (the “2000 con viction”) convictions Illinois un lawful possession controlled substances (together “1993 Illinois convictions”). These convictions, too, meant Chapman faced mandatory minimum life imprisonment. See 841(b)(1)
Like Rush, Chapman agreed to plead guilty exchange government alleging only one of his three prior felony convictions under §§ and Chapman entered into a Rule 11(c)(1)(C) binding plea agreement and pleaded guilty to one count of conspiracy to possess with intent to distribute and to distribute controlled substances. The gov ernment dismissed remaining counts of indict ment against Chapman and fi led amended § infor mation re fl ecting only conviction. The plea agreement agreed upon period incarceration of months. court accepted plea agreement and imposed twenty fi ve year sentence.
Chapman appeals his sentence, asserting none his state convictions quali ed predicate enses § thus guilty plea knowing voluntary.
F. Adrian Benne tt
Adrian Benne like Rush, received supply metham phetamine cocaine directly Zamudio to then distrib ute. Benne tt indicted three counts: one count con spiracy possess with intent to distribute to distribute controlled substances violation U.S.C. §§ 841(a)(1) 846; one count possession with intent distribute con trolled substance violation U.S.C. 841(a)(1); one count possessing rearm convicted felon violation 922(g)(1).
He initially entered into agreement, wherein pleaded count conspiracy possess tent distribute distribute controlled substances. led information notifying Benne tt its intent rely prior o ff ense. Between the time Benne tt ’s plea was entered his sentencing, the First Step Act became law. See Pub. L. No. 115–391, Stat. (Dec. 2018). Title IV, Section the First Step Act precluded the o ense from qualifying as predicate ense §§ Because Benne tt was then no longer subject the enhancement, his statutory im prisonment range was signi cantly reduced.
At the sentencing hearing, Benne tt moved withdraw his agreement based the dramatic change circum stances. The object district court allowed withdrawal. After some additional discussion, Benne tt decided proceed open plea. Without enhancement, conviction carried statutory range ten years life imprisonment (down from mandatory minimum sentence life imprisonment). The Sentencing Guidelines range months months.
After court heard argument from defense counsel government, statement allocution Benne imposed below Guidelines sentence months’ imprisonment. sentence “based upon defendant’s remorse, his family ties, [and] his addictions,” “addresse[d] defendant’s personal history, char acteristics, well as serious nature ense, by pro moting respect law, providing deterrence, protect ing public.” further explained its consideration 3553(a) factors arriving below sentence.
Benne tt appealed sentence unreasonable.
II. Discussion address each defendant turn, Chapman
Rush together the extent their arguments overlap. A. Gonzalez’s aggravating role enhancement
Gonzalez objected the below the application the aggravating role adjustment her o ff ense level, but she did so di ff erent basis she presents now on appeal. Section 3B1.1 the Sentencing provides that the sentencing judge shall increase the defendant’s o ense level based whether the defendant played an “aggravating role” commi ing the ense. An aggravating role an “organ izer, leader, manager, or supervisor or more other par ticipants.” U.S.S.G. § 3B1.1 n.2. Relevant here, “[i]f the defend ant manager or supervisor (but organizer or leader) criminal activity involved ve or more partic ipants or otherwise extensive,” ense level creased by three. U.S.S.G. 3B1.1(b). Before court, Gonzalez argued she manage or supervise ve or more participants—only three: her son, her son’s girlfriend, girlfriend’s sister. Gonzalez, however, con fl ated requirement size criminal activity overall—“ ve or more participants or otherwise extensive”—with re quirement number participants criminal en terprise defendant had manage or supervise—“one more other participants.” Compare 3B1.1(b), 3B1.1 n.2. Gonzalez now argues none three alleged su pervisees qualify “participant” Guidelines. 2009, . Gonzalez advances basis for her sentencing objection for the rst time appeal, thus forfeited the argument. It is completely di ff erent argument the one she pre sented district court, she denied the judge the op portunity address argument. Consequently, our review court’s application is for plain error only. See United States v. Harris , F.3d 772, (7th Cir. 2015); United States v. Hawkins , F.3d 476, (7th Cir. 2007). To prevail under plain error, Gonzalez must show “(1) an error occurred, (2) error plain, (3) it ff ected defendant’s substantial rights, (4) it seriously ected fairness, integrity, or public reputation proceed ings.” United States v. Pierson , F.3d (7th Cir. 2019).
For defendant receive ense level enhancement for being supervisor one more participants, partic ipant must “criminally responsible commission ense, but need have been convicted.” U.S.S.G. 3B1.1 n.1. participant need have been charged ei ther, long “the participant could have been charged.” United States Pabey F.3d (7th Cir. 2011). A participant criminally responsible 3B1.1 if he she knowingly assisted criminal enterprise. Id Mere knowledge conspiracy, however, enough. record su ffi ciently supports nding mini mum Gonzalez’s son, whom she trusted, knowingly assisted mother laundering money. In her post Miranda state ments, Gonzalez told agents initially her son refused wire transfer money her. After she asked him again, he agreed, but told her would only do time. A total four wire transfers made name. Gonzalez also recruited her son’s girlfriend, who made nine wire transfers 2009, six separate bank deposits at Gonzalez’s direction. See United States v. Wa tt s , F.3d 650, (7th Cir. 2008) (aggra ‐ vating role enhancement applied defendant who re cruited his wife participate bank fraud conspiracy based fi ndings that the wife opened bank account using false information empted deposit check co con spirator). Importantly, Gonzalez never contested any these factual allegations.
Those facts also set forth the PSR. Gonzalez ob jected application certain enhancements related underlying facts (such fact that she possessed gun), but object facts concerning roles her son, girlfriend, girlfriend’s sister money launder ing scheme. To contrary, sentencing, Gonzalez argued she supervised only these three people, fi ve people— more “one more” participants Guide lines require aggravating role enhancement. In over ruling Gonzalez’s objection, district expressly stated “[Gonzalez] was manager supervisor three.”
There was no error court’s application aggravating role enhancement, certainly plain. We ffi rm Gonzalez’s sentence.
B. De La Torre’s conditions supervised release have recently clari ed our law regarding forfeiture versus waiver challenges conditions supervised re lease made rst time appeal. See United States v. Flo res F.3d (7th Cir. 2019); United States Hunt , F.3d (7th Cir. 2019) (discussing our decision Flores ). Flores decision came out after brie ng submi ed appeal, but law now clear this cir cuit. We will fi nd challenges to supervised release conditions waived when defendant has notice proposed condi
tions, meaningful opportunity to object, and she asserts (through counsel or directly) that she does not object to proposed conditions, waives reading those conditions their justi cations, challenges certain conditions but not one(s) challenged on appeal, other wise evidences intentional strategic deci sion to object.
Flores F.3d at
De La Torre waived challenge. He on notice now challenged conditions since disclosure initial PSR, proposed both conditions verbatim. He did le any objections. Any doubt that De La Torre have su ffi cient advance notice challenged conditions erased sentencing. Counsel told sentencing judge De La Torre “carefully” reviewed proposed conditions had no objections, then waived formal reading. De La Torre had ample opportunity raise objections to any conditions knew could imposed passed chance. We are satis ed record De La Torre intentionally waived appellate challenge conditions supervised release. C. Chapman’s and Rush’s predicate felony drug enses
Chapman and Rush challenge validity their guilty pleas based perceived errors applicable mandatory minimum sentences. For both defendants, government led an information pursuant U.S.C. § 851(a) alleging that prior state law convictions were each a “felony drug fense” 841. As result enhance ments, Chapman and Rush each faced mandatory minimums life prison. Both opted reach plea agreement ex change for amending information allege only prior felony conviction, low ered mandatory minimum sentence. Because, they argue, their plea agreements were based errors regarding mandatory minimum sentences they would have otherwise faced, pleas entered into knowingly and intelligently should vacated. There no contention that either Chapman Rush objected predicate fenses requested vacate their pleas, thus our review for plain error. ultimately agree there error ected their substantial rights, thus vacate both Chapman’s Rush’s agreements remand for further proceedings. Predicate enses
Section 841(b)(1)(A), applicable penalty provision Chapman’s Rush’s federal convictions, provided time ten year mandatory minimum sentence creased mandatory minimum imprisonment twenty years if defendant convicted “after 2009, . conviction felony drug o ff ense.” U.S.C. § 841(b)(1)(A) term “felony drug o ff ense” is de fi ned U.S.C. § 802(44) mean:
an o ff ense is punishable by imprisonment more than year under any law the United States or State or foreign country prohibits or restricts conduct relating narcotic drugs, marihuana, anabolic steroids, or depressant or stimulant substances.
See Burgess v. United States , U.S. (2008) (“The ‘felony drug o ense’ contained § 841(b)(1)(A)[] … is de fi ned exclusively by § 802(44) ….”). Each the four catego ries covered drugs also de fi ned § See U.S.C. § 802(17) (de fi ning “narcotic drugs”); id . § 802(16) (de fi ning “marihuana”); id . 802(41)(A) (de fi ning “anabolic steroid”); id . 802(9) (de ning “depressant or stimulant substance”). led information identifying prior convictions pursuant 851(a). must, then, determine whether Chapman’s Rush’s
prior convictions state law meet federal de nition “felony ense.” To do so, apply categorical approach, requires us compare elements state statute conviction elements federal recid ivism statute. United States Elder F.3d (7th Cir. 2018). If, only if, elements state law mirror are narrower federal statute can conviction qualify predicate ense. Id Importantly, un der categorical approach, only elements mat ter, defendant’s underlying conduct.
16 18 Chapman’s Illinois convictions begin with Chapman’s two 1993 Illinois convictions because, although Illinois convictions relied upon as prior felony enses §§ 841(b)(1)(A) 851 purposes binding plea agreement, all parties now agree these convictions do qualify as predicate enses error requires vacating agreement.
Chapman has two convictions unlawful posses sion controlled substances in violation ILCS 570/402(c) Subsection (c) broad residual provision applies possession “a controlled or counterfeit substance set forth in subsection (a) (d).” Id The Illinois statute de nes “controlled substance” “a drug, substance, immediate precursor Schedules Article II Act.” ILCS 570/102(f). The Schedules, turn, are found ILCS 570/204 (Schedule I), id. § (Schedule II), id. § (Schedule III), id. (Schedule IV), id. § (Sched ule V). government rst led information identifying
three convictions—these two Illinois convictions conviction—that increased Chapman’s statutory minimum sentence life prison. agreed withdraw information Illinois convictions, reducing Chapman’s mandatory minimum sen tence twenty years prison, if Chapman pleaded guilty. Chapman reluctantly accepted pleaded guilty.
Two our recent decisions bear directly outcome Chapman’s appeal. Shortly after Chapman pleaded sentenced, held Elder Arizona statute included propylhexedrine mismatched al federal de nition felony drug o ff ense 802(44), which does not cover propylhexedrine. Elder , F.3d at 501. Because Illinois schedules listed propylhexedrine Schedule V controlled substance, s ee ILCS 570/212(d) (1993), follows that Illinois’s 402(c) is also categorically broader federal de nition felony o ff ense. government not contest this point, but instead argued that Illinois statute was divisible thus we could look elements Chapman’s actual convictions.
After brie ng was submi ed this appeal, de cided Najera Rodriguez Barr F.3d (7th Cir. 2019), held that ILCS 570/402(c) divisible. In light this holding, government conceded oral argument that Chapman’s Illinois convictions do qualify prior enses purposes enhancement. Accord ingly, agreed that error ected Chap man’s substantial rights that his plea agreement must be set aside. Chapman’s plea accept government’s concession Chapman’s
plea agreement should vacated, er brief explana tion.
Chapman, government, sentencing judge all erroneously believed Chapman’s multiple prior convic tions subjected him mandatory life sentence. record abundantly clear Chapman only agreed agreement because believed life prison was only ternative. That true.
Without those Illinois convictions, assum ing moment conviction *18 18 18 2009, qualifying predicate felony ff ense, Chapman’s manda ‐ tory minimum immediately dropped life twenty years’ imprisonment. See U.S.C. 841(b) (2018). Yet Chap man agreed a binding term of imprisonment of twenty fi ve years—a far greater prison sentence than could have been sentenced without any plea agreement at all. And this is all notwithstanding presence of his conviction, absence which would cut his mandatory minimum incarceration half, down ten years. See 841(b) (2018).
Chapman has met burden showing that error re garding use Illinois convictions enses prejudicial. See United States v. Olano , U.S. An error such we have here “establishes reasonable probability that a defendant will serve prison sentence more than ‘necessary’ ful ll purposes incarceration.” Rosales Mireles United States , S. Ct. (2018) (holding plain error cal culating correct range ected defendant’s substantial rights warranted relief). Chapman’s sentenc ing transcript re fl ects more than reasonable probability additional jail time. In accepting binding agreement, sentencing judge expressed concern over length sentence stated “di ffi cult nd this month sentence imprisonment greater than neces sary.” Without correction error, Chapman may un necessarily deprived liberty may spend more time jail necessary, nd “seriously ects fair ness, integrity public reputation judicial proceedings.” Olano U.S. (brackets omi ed). 18 ‐ 19 Rush’s 2001 Indiana conviction government’s initial 851 informations identi ed
three Indiana convictions as felony drug enses: Rush’s 2001 Indiana conviction for dealing schedule I, II, or III controlled substance; Rush’s 2010 Indiana conviction for possession methamphetamine; Chapman’s 2000 Indi ana conviction for possession controlled substance. [4] start with Rush’s 2001 Indiana conviction because it is dispos itive.
Rush convicted 2001 dealing schedule I, II, or III controlled substance violation Indiana Code 35 48 ‐ 4 ‐ 2 That statute provides, pertinent part, that:
A person who:
(1) knowingly intentionally: (A) manufactures;
(B) nances manufacture of; (C) delivers;
*20 20 18 ‐ 2009,
(D) fi nances delivery of; controlled substance, pure or adulterated, classi fi ed in schedule I, II, or III, except mariju ana, hash oil, or hashish; or (2) possesses, intent to: (A) manufacture;
(B) fi nance manufacture of; (C) deliver; or
(D) fi nance delivery of; controlled substance, pure or adulterated, classi ed schedule I, II, or III, except mariju ana, hash oil, hashish;
commits dealing schedule I, II, III con trolled substance ….
Ind. Code 35 ‐ 48 ‐ 4 ‐ 2(a) The schedule I, II, III con trolled substances are found Indiana Code §§ ‐ ‐ 2 ‐ 4, 35 ‐ ‐ ‐ ‐ ‐ 8, respectively.
To demonstrate overbreadth statute, Rush points schedule II. There, schedule II lists “[m]ethamphetamine, including its salts, iso mers, salts its isomers.” Ind. Code 6(d)(2). federal statute similarly controls “methamphetamine, cluding its salts, isomers, salts isomers.” See Schedule II(c), Schedule III(a)(3). A seeming match. But closer look reveals otherwise. federal Controlled Substances Act also speci cally de nes “isomer” mean “the optical isomer,” except used schedule I(c) schedule II(a)(4), where isomer 18 ‐ 2009, 21 means “any optical, positional, or geometric isomer.” 21 802(14). Methamphetamine is listed sched ‐ ule I(c) schedule II(a)(4) thus, purposes of federal enses, includes only its optical isomers.
The Indiana Code, other hand, does de ne “isomer.” “In Indiana, lodestar of statutory interpre ‐ tation is legislative intent, plain language stat ‐ ute is ‘best evidence ... [that] intent.’” Estate Moreland v. Dieter , 576 F.3d 691, 695 (7th Cir. 2009) (quoting Cubel v. Cubel , 876 N.E.2d 1120 (Ind. 2007)); see also Johnson State , N.E.3d (Ind. 2017) (“Our rst task when terpreting statute is give its words their plain meaning by considering text structure statute.”). Ascertain ing “ordinary” meaning isomer might be fool’s er rand, but it must undertake here. A statute “should examined whole, avoiding both excessive re liance strict literal meaning selective reading indi vidual words.” Estate Moreland , F.3d at (quoting Cubel N.E.2d 1120). structure Indiana’s Con trolled Substances Act guides conclusion case.
When Indiana intended limit speci c isomer drug, expressly so. Indiana’s schedule II controls “[a]mphetamine, its salts, optical isomers, salts its op tical isomers.” Ind. Code ‐ ‐ ‐ 6(d)(1) (2000). Elsewhere, legislature uses certain language part of the statute di ff erent language another, court assumes di ff erent meanings were intended.” Sosa Alvarez Machain U.S. n.9 According to Rush, then, Indiana’s generic use “isomer” relation methamphetamine must be broader than optical isomers. agree. Because federal de nition methamphetamine includes only its optical iso mers whereas Indiana de nition includes something more than just optical isomers methamphetamine, mismatch renders statute overbroad.
The government does not contest Indiana’s statute, its face, is broader federal law, but contends geomet ric isomers do not exist real world, thus statutes actually mirror each other. The government’s argument su ers few fatal fl aws at junc ture. First, asks us take judicial notice expert declarations from di erent cases di erent courts discuss isomer forms methamphetamine. These declarations were not before court are proper subject judicial notice. Federal Rules Evidence permit take judicial notice fact is “not subject reasonable dispute” because “generally known” “can be accurately readily determined sources whose accuracy cannot reasonably questioned.” Fed. R. Evid. 201(b). isomeric nature methampheta mine “generally known,” least us. Nor are dec larations incontrovertible—the declarants subjected Daubert challenges, cross examined, tested compet ing expert testimony. None defendants had ability 18 ‐ 23 challenge these declarations in the district court. [5] Second, the declarations crafted other cases an eye ‐ wards the issues at hand those cases. It seems, example, the declarations are primarily focused on proving that geometric isomers methamphetamine do not exist because the state statute speci cally included both optical geo metric isomers methamphetamine. For our purposes, the declarations do not tell us whether any other types isomers methamphetamine could possibly exist. That issue is the heart dispute here. In short, content the declara tions is “arguably subject reasonable dispute therefore not proper subject judicial notice.” Tobey Chibucos 890 F.3d 648 (7th Cir. 2018). Finally, notwithstanding declarations, do not think government’s theoreti cal challenges are pertinent here when plain language chosen by Indiana legislature dictates Indiana statute is categorically broader federal de nition ense.
No ma er, our decision not solely dependent def inition which its isomers do do exist. Indiana Code ‐ ‐ ‐ reaches least other substances are included 802(44). Speci cally, lists “[p]arahexyl” as schedule I “combination product containing tiletimine zolazepam (Telazol)” schedule III drug. Ind. Code §§ ‐ ‐ 4(d)(16), 8(c)(12) Neither substance covered *24 24 18 ‐ under de nitions in § 802(44). To put it succinctly, Rush could have been convicted under § 35 48 ‐ 4 ‐ 2 for dealing a controlled substance that would not be a felony drug o ff ense under § 802(44). Indiana law categorically broader.
Rush’s Indiana conviction dealing a schedule I, II, III controlled substance cannot serve as a predicate fel ony drug o ff ense 841(b)(1)(A) 802(44). Rush’s plea
Having found that Rush’s Indiana conviction does qualify a predicate felony drug o ff ense, error clearly a ff ected Rush’s substantial rights. If Rush had known Indiana conviction qualifying felony ense, it would have changed calculus likely would have proceeded di erently. Without prior felony enses, Rush face potential mandatory minimum life sentence instead would have been sen tenced consideration Guidelines range months’ imprisonment. binding plea agreement called sentence middle range, months, imposed. In doing so, sentencing judge noted month term imprisonment “might greater than necessary” but “the minimum [c]ourt [could] give defendant” because agreement.
Although Rush received within Guidelines sentence— otherwise presumed reasonable review—given facts sentencing judge’s statements record, Rush has 18 ‐ 25 met his burden under the plain error standard. He has shown reasonable probability that, but for the error regarding the 2001 Indiana conviction, the outcome of the proceeding may have been di erent and that may have received less prison time absent the error. See Molina ‐ Martinez United States , 136 S. Ct. 1343 “Any amount actual jail time is signi cant has exceptionally severe consequences for incarcerated individual society bears direct indirect costs incarceration.” Rosales ‐ Mireles , 138 S. Ct. 1907 (cleaned up). That error, ecting Rush’s fundamental rights, left uncorrected would undermine integrity fairness judicial proceedings.
Not every error relating plea agreement will demand correction plain error. But based facts this case, Rush has satis ed burden. We, therefore, vacate Rush’s agreement remand district further proceedings.
D. Reasonableness Benne tt ’s below ‐ Guidelines sentence
Our nal co ‐ defendant appeal, Adrian Benne ap peals below ‐ sentence months’ imprison ment as unreasonable. “We review court’s choice sentence two steps. First, we assess de novo whether *26 26 18 ‐ 2009, 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 sen tence imposed is inside outside Guidelines range, review sentence abuse discretion. Gall v. United States , 552 U.S. 38, 51 “A below guidelines sentence, like within guidelines one, is presumed reasonable against defendant’s challenge too high.” United States v. Poe tz , F.3d 835, (7th Cir. 2009). A defendant can only rebut presumption reasonableness “by showing sentence does comport factors outlined 3553(a).” United States v. Patel , F.3d (7th Cir. 2019) (quoting United States Solomon F.3d (7th Cir. 2018)).
Benne tt does identify any procedural errors. Nor could he. The district judge’s sentencing procedurally sound. judge correctly calculated Guidelines range, consid ered all 3553(a) factors, adequately explained reasons sentence. district court then sentenced Benne tt months incarceration, thirty seven months below low end Guidelines range months’ imprisonment. Our only task, then, review whether district court abused its discretion sentencing Benne tt months prison, below range. It did not.
On appeal, Benne tt simply tt empts reargue 3553(a) factors, makes substantially same argu ments below. But considered all Benne ’s arguments sentencing took them all into account crafting an appropriate sentence. It our job reweigh 3553(a) factors. For example, Benne tt argues his sentence creates unwarranted sentencing dispar ‐ ity. See 3553(a)(6). But other than giving aver ‐ age sentence tra ffi cking ense Southern Dis ‐ trict and nationally across United States, Ben ne tt provides nothing more. As district stated sen tencing, Benne tt distributed signi cant quantities metham phetamine and cocaine throughout Indianapolis and sur rounding communities. harmful e ects conduct cannot go understated. judge imposed sentence addressed Ben
ne tt ’s personal history characteristics, re fl ected seri ousness ense, su ffi cient, but greater necessary. In sum, Benne tt fails identify speci c reason question substantive reasonableness below Guide lines sentence. A below sentence will almost never unreasonable, United States Trudeau , F.3d (7th Cir. 2016), here. Benne tt ’s sentence af rmed.
* * * AFFIRM sentences Gonzalez, De La Torre,
Benne VACATE Chapman’s Rush’s pleas REMAND further proceedings.
[1] Counsel Zamudio filed Anders brief address Zamudio’s appeal, No. separate order issued today.
[2] Despite Gonzalez’s initial confusion, she no longer disputes Zamudio trafficking enterprise involved five more participants.
[3] In light our circuit’s recent decisions, De La Torre’s appellate counsel moved waive oral argument cede time remaining co defendants. permitted counsel appear by telephone none theless gave counsel opportunity make respond any argu ments behalf De La Torre.
[4] Because we already vacated Chapman’s agreement based disqualified Illinois convictions, we do reach Indiana conviction relied upon purposes plea. analysis Indiana conviction possession controlled substance Indiana Code would largely track analysis Rush’s Indiana conviction due significant similarities between stat utes respect their coverage controlled substances. As we will see next, Rush’s Indiana conviction qualifying predicate felony offense. Without deciding question, we think it unlikely Chapman’s conviction qualifies predicate offense, though leave parties appropriately address remand necessary.
schedule III lists certain stimulants preamble notes each substance “includ[es] its salts, isomers (whether op tical, position, geometric), salts such isomers.” Ind. Code 8(b) legislature knew how limit listed include only its optical isomers. It general rule statutory construction “when
[5] Granted, Rush Chapman challenge their convic tions below, deprived opportunity intro duce evidence court. Our opinion takes no position scientific merits, nor should read limiting government’s ability present such argument future proceedings.
[6] Even only conviction, such conviction, Rush would have been subject mandatory minimum imprisonment ten years, less range. See 841(b)
[7] We do not need address Rush’s Indiana conviction because inclusion Indiana conviction qualifying predicate fense plain error requires remand. We note, however, that Rush treated definition methamphetamine identical between Code §§ 6.1 ‐ ‐ ‐ are convinced assump tion correct, but raise argument differ ent definitions applied sections, thus likely waived argument appeal. Regardless, do need de cide issue.