Opinion ID: 4445950
Heading Depth: 2
Heading Rank: 2

Heading: De La Torre’s conditions of supervised release

Text: 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.
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.
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.
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
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:
(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
(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).
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.