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.
Flaum, Sykes, and St. Eve, Circuit Judges.
Eve, Circuit Judge.
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.
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. 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.
Factual and Procedural Background
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.
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.
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
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.
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.
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
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.
Reynold De La Torre
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.
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.
Torre now challenges two of the conditions of supervised
release as vague and unconstitutional:
 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.
 You shall not be a member of any gang or associate with
individuals who are gang members.
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).
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
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)
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.
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.
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.
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).
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.
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