UNITED STATES OF AMERICA, Plaintiff-Appellee, υ. REYNOLD DE LA TORRE, et al., Defendants-Appellants.
Nos. 18-2009, 18-2218, 18-2286, 18-3303, and 19-1299
United States Court of Appeals For the Seventh Circuit
ARGUED SEPTEMBER 6, 2019 — DECIDED OCTOBER 10, 2019
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.
Before FLAUM, SYKES, and ST. EVE, Circuit Judges.
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 sentences 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
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 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 organization 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
Zamudio eventually pleaded guilty to four counts of the indictment that included conspiracy to distribute drugs, unlawful 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 Gonzalez 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 Union to wire drug proceeds from Indiana to Mexico and California. But she did not just launder money herself; Gonzalez 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 possess with intent to distribute and to distribute controlled substances in violation of
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 Guidelines 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 aggravating 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 methamphetamine in violation of
At a combined plea and sentencing hearing, the district court informed De La Torre that it intended to impose the conditions of supervised release that were recommended
De La Torre now challenges two of the conditions of supervised release as vague and unconstitutional:
[1] You shall not knowingly purchase, possess, distribute, administer, or otherwise use any psychoactive substances (e.g., synthetic marijuana, bath salts, Spice, glue, etc.) that impair a person‘s physical or mental functioning, whether or not intended for human consumption.
[2] You shall not be a member of any gang or associate with individuals who are gang members.
He does not, however, challenge any other portion of his sentence, 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 methamphetamine 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
Facing life in prison, Rush opted to plead guilty in exchange for the government dropping one of the two § 851 prior felony convictions. His mandatory minimum sentence was now twenty years’ imprisonment, though he agreed to a binding plea agreement under
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 customers. Chapman also stands in a similar procedural posture to Rush.
Chapman was indicted on one count of conspiracy to possess with intent to distribute and to distribute controlled substances in violation of
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
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 methamphetamine and cocaine directly from Zamudio to then distribute. Bennett was indicted on three counts: one count of conspiracy to possess with intent to distribute and to distribute controlled substances in violation of
He initially entered into a plea agreement, wherein he pleaded guilty to one count of conspiracy to possess with intent to distribute and to distribute controlled substances. The government filed a § 851 information notifying Bennett of its 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 imprisonment range was significantly reduced.
At the sentencing hearing, Bennett moved to withdraw his plea agreement based on the dramatic change in circumstances. 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 characteristics, as well as the serious nature of the offense, by promoting respect for the law, providing
Bennett appealed his sentence as unreasonable.
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 “organizer, leader, manager, or supervisor of one or more other participants.” U.S.S.G. § 3B1.1 n.2. Relevant here, “[i]f the defendant was a manager or supervisor (but not an organizer or leader) and the criminal activity involved five or more participants or was otherwise extensive,” the offense level is increased 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 requirement for the number of participants in the criminal enterprise 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 supervisees qualify as a “participant” under the Guidelines.
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 presented to the district court, and she denied the judge the opportunity 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 proceedings.” 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 participant 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 either, 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 minimum Gonzalez‘s son, whom she trusted, knowingly assisted his mother
Those facts were also set forth in the PSR. Gonzalez objected 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 laundering 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 Guidelines require for the aggravating role enhancement. In overruling 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 release made for the first time on appeal. See United States v. Flores, 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 submitted in this appeal,3 but the law is now clear in this circuit. We will find challenges to supervised release conditions waived when
the defendant has notice of the proposed conditions, 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 otherwise evidences an intentional or strategic decision 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
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
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 increased to a mandatory minimum term of imprisonment of twenty years if the defendant was convicted “after a prior conviction for a felony drug offense.”
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 defined exclusively by § 802(44) ....“). Each of the four categories of covered drugs is also defined in § 802. See
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 recidivism 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, under the categorical approach, it is only the elements that matter, not the defendant‘s underlying conduct.
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
Chapman has two convictions for felony unlawful possession of controlled substances in violation of
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 sentence 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 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
After the briefing was submitted in this appeal, we decided Najera-Rodriguez v. Barr, 926 F.3d 343 (7th Cir. 2019), which held that
3. Chapman‘s guilty plea
We accept the government‘s concession that Chapman‘s plea agreement should be vacated, and offer a brief explanation.
Chapman, the government, and the sentencing judge all erroneously believed that Chapman‘s multiple prior convictions 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 alternative. That was not true.
Without those two prior Illinois convictions, and assuming for the moment that his 2000 Indiana conviction was a qualifying predicate felony drug offense, Chapman‘s mandatory minimum immediately dropped from life to twenty years’ imprisonment. See
Chapman has met his burden of showing that the error regarding 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 calculating the correct Guidelines range affected the defendant‘s substantial rights and warranted relief). Chapman‘s sentencing 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 necessary.” Without correction of this error, Chapman may be unnecessarily deprived of his liberty and may spend more time in jail than necessary, which we find “seriously affects the fairness, integrity or public reputation of judicial proceedings.” Olano, 507 U.S. at 736 (brackets omitted).
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 Indiana conviction for possession of a controlled substance.4 We start with Rush‘s 2001 Indiana conviction because it is dispositive.
Rush was convicted in 2001 of dealing in a schedule I, II, or III controlled substance in violation of
A person who:
(1) knowingly or intentionally:
(A) manufactures;
(B) finances the manufacture of;
(C) delivers; or
(D) finances the delivery of;
a controlled substance, pure or adulterated, classified in schedule I, II, or III, except marijuana, 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 marijuana, hash oil, or hashish;
commits dealing in a schedule I, II, or III controlled substance ....
To demonstrate the overbreadth of the Indiana statute, Rush points to methamphetamine in schedule II. There, schedule II lists “[m]ethamphetamine, including its salts, isomers, and salts of its isomers.”
The federal Controlled Substances Act also specifically defines the term “isomer” to mean “the optical isomer,” except as used in schedule I(c) and schedule II(a)(4), where isomer means “any optical, positional, or geometric isomer.”
The Indiana Code, on the other hand, does not define the term “isomer.” “In Indiana, the lodestar of statutory interpretation is legislative intent, and the plain language of the statute 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 interpreting a statute is to give its words their plain meaning by considering the text and structure of the statute.“). Ascertaining the “ordinary” meaning of isomer might be a fool‘s errand, but it is not one we must undertake here. A statute “should be examined as a whole, avoiding both excessive reliance on strict literal meaning and selective reading of individual words.” Estate of Moreland, 576 F.3d at 695 (quoting Cubel, 876 N.E.2d at 1120). The structure of Indiana‘s Controlled 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 optical isomers.”
The government does not contest that Indiana‘s statute, on its face, is broader than federal law, but contends that geometric 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 juncture. First, the government
No matter, our decision is not solely dependent on the definition of methamphetamine and which of its isomers do or do not exist.
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 felony 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 sentenced in consideration of a Guidelines range of 262 to 327
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
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, appeals his below-Guidelines sentence of 225 months’ imprisonment as unreasonable. “We review a district court‘s choice of sentence in two steps. First, we assess de novo whether the
court followed proper procedures. If the decision below is procedurally sound, then we ask whether the resulting sentence 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 sentence 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
On appeal, Bennett simply attempts to reargue the § 3553(a) factors, and makes substantially the same arguments he did below. But the district court considered all of Bennett‘s arguments at sentencing and took them all into 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 disparity. See
The district judge imposed a sentence that addressed Bennett‘s personal history and characteristics, reflected the seriousness 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-Guidelines 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 affirmed.
***
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.