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United States v. De La Torre

United States Court of Appeals, Seventh Circuit

October 10, 2019

United States of America, Plaintiff-Appellee,
v.
Reynold De La Torre, et al., Defendants-Appellants.

          Argued September 6, 2019

          Appeals from the United States District Court for the Southern District of Indiana, Indianapolis Division. No. l:16-cr-00251-TWP-MJD - Tanya Walton Pratt, Judge.

          Before Flaum, Sykes, and St. Eve, Circuit Judges.

          St. Eve, Circuit Judge.

         The Zamudio drug organization distributed pounds of methamphetamine and cocaine throughout the Indianapolis, Indiana area. At the top sat Jose Zamudio, who imported the drugs from his suppliers in Mexico and oversaw his network of distributors here. Reynold De La Torre, Christian Chapman, Jeffrey Rush, and Adrian Bennett were four of those local distributors. Maria Gonzalez was Zamudio's live-in girlfriend. Besides permitting Zamudio to store and traffic drugs out of her home, Gonzalez helped launder Zamudio's drug money and wired hundreds of thousands 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 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 to this appeal, we use "Zamudio" to refer to Jose Zamudio.) Agents received court authorization to intercept numerous telephone calls between Zamudio and his associates. On November 17, 2016, the FBI executed approximately forty search warrants as a result of its investigation into the Zamudio organization. The warrants led to the seizure of over seventy firearms, approximately fifteen pounds of methamphetamine, smaller quantities of cocaine, heroin, and marijuana, and cash. At least eighteen 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 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 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, 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 21 U.S.C. §§ 841 and 846, and two counts of conspiracy to launder monetary instruments in violation of 18 U.S.C. §§ l956(a)(1)(A)(i), (h) and l956(a)(1)(B)(i), (h). Before sentencing, the government sought to apply an aggravating role enhancement pursuant to § 3B1.1 of the Sentencing Guidelines for Gonzalez's supervisory role in the organization. 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 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 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 between 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 appeal 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 conditions 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 imposed the conditions of supervised release.

         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 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 convictions, one in 2001 for felony dealing in a controlled substance (the "2001 Indiana conviction") and the second in 2010 for felony possession of methamphetamine (the "2010 Indiana conviction"). The two prior felony drug convictions subjected Rush to a mandatory term of life imprisonment without release. 21 U.S.C. § 841(b)(1) (2018).

         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 Federal Rule of Criminal Procedure 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 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 21 U.S.C. §§ 841(a)(1) and 846, and two counts of possession with intent to distribute methamphetamine in violation of 21 U.S.C. § 841(a)(1). The government also filed a § 851 information notifying Chapman that it intended 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 conviction") and two 1993 convictions in Illinois for felony unlawful 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).

         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 government dismissed the remaining two counts of the indictment against Chapman and filed an amended § 851 information 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. ...


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