Court Opinion

ID: 4647177
Source: CourtListenerOpinion
Date Created: 2020-12-28 21:00:24.183147+00
Date Added: 2024-06-11T08:01:03.939158
License: Public Domain

In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________

Nos. 19-1074, 19-1110, 19-1126, & 19-1188
UNITED STATES OF AMERICA,
                                                 Plaintiff-Appellee,

                                 v.

HECTOR SAUL CASTRO-AGUIRRE, et al.,
                                            Defendants-Appellants.
                     ____________________

        Appeals from the United States District Court for the
          Southern District of Indiana, Indianapolis Division.
      No. 1:16-cr-00123-TWP-DML — Tanya Walton Pratt, Judge.
                     ____________________

 ARGUED SEPTEMBER 15, 2020 — DECIDED DECEMBER 28, 2020
                ____________________

   Before FLAUM, ROVNER, and WOOD, Circuit Judges.
   WOOD, Circuit Judge. Illegal drugs often do not originate in
the community where they are consumed, and so the drug
business—like its legitimate counterparts—commonly in-
cludes a complex distribution network. That was true of the
arrangement before us, which involved large quantities of co-
caine and methamphetamine that moved throughout the
southwestern and northeastern United States. Eventually the
2                                            Nos. 19-1074 et al.

government caught up with the participants. Among those it
indicted were four who chose to go to trial: Jose Manuel Car-
rillo-Tremillo, Hector Saul Castro-Aguirre, John Ramirez-
Prado, and Rafael Rojas-Reyes. These four have joined in the
present appeal, in which they challenge rulings the district
court made at the guilt phase, as well as some of its sentencing
decisions. For the most part, we find no reversible error. The
only exception is Carrillo-Tremillo’s conviction for conspiracy
to launder money, which we set aside.
                               I
                               A
   The defendants before us all played active roles in a cross-
country drug organization: Castro-Aguirre served as the head
of operations; Ramirez-Prado handled logistics, including
providing cars and hotels for distributors and couriers; Rojas-
Reyes coordinated sales in Indianapolis; and Carrillo-Tre-
millo conducted sales in the northeast. To set the stage, we
provide a brief overview of their activities from 2015 to 2016.
   Castro-Aguirre coordinated shipments of methampheta-
mine—usually 30 pounds apiece—from a trailer park in Tuc-
son, Arizona, to Avon, Indiana (a suburb of Indianapolis).
Ramirez-Prado rented SUVs and booked hotels for couriers
along the route. Once the packages reached their destination,
Rojas-Reyes took over and sold the methamphetamine in In-
dianapolis.
    Castro-Aguirre also handled cocaine sales in New Jersey
and New York. Ramirez-Prado and other couriers transported
bulk quantities of cocaine from Arizona and Indianapolis to
New York. There, Castro-Aguirre fronted the drugs to Car-
rillo-Tremillo, who would sell them and remit the proceeds to
Nos. 19-1074 et al.                                          3

Castro-Aguirre. In much the same way, Castro-Aguirre fur-
nished Carrillo-Tremillo with anywhere from 10 to 100 kilo-
grams of cocaine on credit for distribution in Reading, Penn-
sylvania. Castro-Aguirre arranged for couriers to pick up the
proceeds from his various sellers and deliver the cash to him
in Arizona.
    The final trip to Reading proved to be the downfall of the
organization. The deal started out routinely, when Castro-
Aguirre fronted 100 kilograms of cocaine to Carrillo-Tremillo.
The drugs made it to Reading, but alert law enforcement of-
ficers caught up with the couriers and stopped them near the
Illinois-Missouri border. There the agents seized $2,400,000.
    That is just the bare outline of the operation. It had many
moving parts, only some of which are important to this ap-
peal. One key event involved the kidnapping and murder in
2016 of Angel Barrios-Moreno, who supplied the operation
with drugs that he transported across the Mexican-U.S. bor-
der. The evidence indicated that leaders of the infamous Sina-
loa Cartel had ordered the hit. They did so because Barrios-
Moreno failed to pay a debt to the cartel after law enforcement
oﬃcials seized a major drug shipment. The cartel was not for-
giving: during one of Barrios-Moreno’s trips in Mexico from
Nogales to Sinaloa, members of the Sinaloa Cartel kidnapped
Barrios-Moreno and two others—his nephew Adrian Barrios-
Moreno and a friend Luis-Carlos Cebrero-Alvarez—and de-
manded a $500,000 ransom.
    When Castro-Aguirre learned of the kidnapping, he im-
mediately started to raise money for the ransom. He sent cou-
riers to pick up cash and drugs from Rojas-Reyes and
Ramirez-Prado. Once he had collected $250,000, Castro-
4                                                      Nos. 19-1074 et al.

Aguirre sent couriers to make a partial payment on the ran-
som to a cartel member in New York. Despite these eﬀorts, the
cartel ultimately killed Barrios-Moreno, along with the other
two men it had seized.
                                      B
   In January 2018, the government indicted twelve defend-
ants. The four now before us proceeded to trial. The following
chart provides the counts, charges, and verdicts for each one:

                                                     Carrillo-Tre-

                                                                                Rojas-Reyes
                                                                     Ramirez-
                                           Aguirre
                                           Castro-

                                                                      Prado
                                                        millo
#             Charge (Statute)

    Conspiracy to Distribute 500+
1   grams of methamphetamine                G1            G            G            G
    and/or 5+ kilograms of cocaine
    (21 U.S.C. §§ 841(a)(1) & 846)
    Engaging in a Continuing
2   Criminal Enterprise (21 U.S.C.           G
    § 848(a), (b)(1))
    Engaging in a Continuing
3   Criminal Enterprise (21 U.S.C.                                                  G
    § 848(a), (b)(1))
4   Conspiracy to Launder Money              G            G            G            G
    (18 U.S.C. § 1956(h))

    1   The letter “G” indicates guilty.
Nos. 19-1074 et al.                                              5

  Distributing 500+ Grams of
5 Methamphetamine Mixture (21                                G
  U.S.C. § 841(a)(1))
  Distributing 50+ Grams of
6 Methamphetamine Mixture                                    G
  (21 U.S.C. § 841(a)(1))
  Possession of 50+ Grams of
8 Methamphetamine Mixture (21                                G
  U.S.C. § 841(a)(1))

    The jury found each defendant guilty of conspiracy to dis-
tribute the controlled substances and conspiracy to launder
money. As the chart indicates, Castro-Aguirre and Rojas-
Reyes were also convicted on several additional charges. The
district court sentenced all the defendants to lengthy terms in
prison.
    The defendants have appealed from their convictions,
their sentences, or both. We have organized their contentions
as follows: Section II addresses evidentiary rulings, Section III
resolves challenges to the underlying convictions, and Sec-
tion IV briefly discusses the sentencing arguments.
                      II. Evidentiary Rulings
    The defendants raise two primary evidentiary points: the
first concerns the district court’s decision to admit evidence of
cell-site locations collected pursuant to the Stored Communi-
cations Act (“the Act”); and the second relates to the court’s
decision to allow the jury to hear about the Barrios-Moreno
kidnapping and murder. The standard of review for both
points is generally deferential. To the extent the court made
legal determinations, our review is de novo, United States v.
6                                             Nos. 19-1074 et al.

Figueroa-Espana, 511 F.3d 696, 701 (7th Cir. 2007), but we re-
view decisions whether to admit or exclude evidence only for
abuse of discretion, United States v. Johnson, 916 F.3d 579, 586–
87 (7th Cir. 2019) (quoting United States v. Causey, 748 F.3d 310,
316 (7th Cir. 2014)).
            A.      Cell-Site Location Information
    The defendants argue that the district court erred by deny-
ing their motion to suppress cell-site location information
(commonly called CSLI) that the government obtained using
the procedures set out in the Act. They contend that this in-
formation was collected in violation of the Fourth Amend-
ment, because, midway through the trial, the Supreme Court
ruled that the government must obtain a warrant if it wishes
to obtain some CSLI. See Carpenter v. United States, 138 S. Ct.
2206 (2018).
    “CSLI is location information generated by cellular phone
providers that indicates which cell tower a particular phone
was communicating with when a communication was made.”
Orin S. Kerr, The Eﬀect of Legislation on Fourth Amendment Pro-
tection, 115 MICH. L. REV. 1117, 1128 (2017). Any cell phone
with a functioning battery regularly communicates with cell
towers. The phone leaves behind a trail, which is refreshed
“as frequently as several times per minute,” showing its
rough location (within 50 meters or so of the actual spot).
United States v. Curtis, 901 F.3d 846, 847 (7th Cir. 2018) (quot-
ing Carpenter, 138 S. Ct. at 2219–21). With this information, the
government has a near-perfect record of the phone’s location
(and thus, presumptively, that of the user). Carpenter, 138 S.
Ct. at 2217–21.
Nos. 19-1074 et al.                                              7

    The Act permits the government to obtain a court order
authorizing the collection of “non-content information.” 18
U.S.C. § 2703(c). Before Carpenter, the government could ei-
ther seek a warrant for this information or it could “obtain[] a
court order for such disclosure under subsection (d) of this
section.” Id. at § 2703(c)(A), (B). Subsection (d) specified that a
court order could issue “only if the governmental entity oﬀers
specific and articulable facts showing that there are reasona-
ble grounds to believe that ... the records or other information
sought, are relevant and material to an ongoing criminal in-
vestigation.” Id. at § 2703(d). That standard is significantly
lower than the probable-cause requirement for a warrant. See,
e.g., Terry v. Ohio, 392 U.S. 1 (1968). The defendants here do
not contend that the government failed to present “specific
and articulable facts” for its order. Instead, relying on Carpen-
ter, they contend that they have a reasonable expectation of
privacy—protected by the Fourth Amendment—in their
CSLI, the government failed to obtain a warrant before it
seized those records, and so suppression is called for.
    The district court did not disagree with the need for a war-
rant, nor could it after Carpenter. But it recognized that this is
not the end of the inquiry. The dispositive question, it held,
was whether the government acted in good faith when, in-
stead of securing a warrant, it relied on the court order. See
United States v. Leon, 468 U.S. 897, 919 (1984); Heien v. North
Carolina, 574 U.S. 54 (2014). If it acted in good faith, then sup-
pression is not required. The district court found the good-
faith rule applicable to these cases: at the time that the gov-
ernment obtained the court order in July 2016, no court of ap-
peals had concluded that CSLI could be collected only with a
warrant, and the government had relied on the procedures set
8                                              Nos. 19-1074 et al.

forth in the Act. See, e.g., United States v. Thousand, 558 F.
App’x 666, 670 (7th Cir. 2014).
    The defendants present a bold theory in an eﬀort to obtain
suppression of the CSLI. They contend that Carpenter itself
was a deviation from precedent. At the time, courts consist-
ently held that a person has no reasonable expectation of pri-
vacy in information held by third parties; they relied on
United States v. Miller, 425 U.S. 435 (1976) (no reasonable ex-
pectation of privacy in bank-held financial records), and Smith
v. Maryland, 442 U.S. 735 (1979) (no reasonable expectation of
privacy in phone-provider-held call logs). Carpenter held for
the first time that this third-party rule had its limits and in
particular did not apply to cell phones. 138 S. Ct. at 2217. De-
fendants contend that the rationale of Carpenter—namely, that
CSLI is uniquely expansive and invasive—also calls for us to
override the good-faith exception and order suppression
here.
     But it is one thing to speak of the scope of a rule, such as
the third-party doctrine, and quite another to ask whether the
purpose of the rule will be served by its application to good-
faith missteps. We recognized just two years ago that the mis-
taken use of the Act’s procedures, rather than a warrant, to
collect CSLI is eligible for the good-faith exception to the or-
dinary practice of suppression. See Curtis, 901 F.3d at 848 (cit-
ing Krull, 480 U.S. at 349); see also Herring v. United States, 555
U.S. 135, 140 (2009). We recognized the deterrent role the ex-
clusionary rule is designed to play, but we found no evidence
that “legislators are inclined to subvert their oaths and the
Fourth Amendment” when passing laws such as the Act. Cur-
tis, 901 F.3d at 849 (quoting Krull, 480 U.S. at 349). Nor did we
see any reason why the application of the exclusionary rule to
Nos. 19-1074 et al.                                           9

evidence seized before Carpenter was decided, in good-faith
reliance on a court order pursuant to the Act, would provide
additional deterrence. Id.
   We are not inclined to revisit Curtis. We thus find that the
CSLI obtained in this case was properly admitted, because the
government, following the procedures set forth in the Act,
gathered it in good faith.
                      B.   Motion in Limine
    We turn next to the defendants’ challenge to the district
court’s denial of their motion in limine to suppress evidence
of their gang membership and evidence that the Sinaloa Car-
tel was behind Barrios-Moreno’s kidnapping and murder.
Once again, they face an uphill battle, as we defer to the dis-
trict court’s assessments both of relevance and potential inap-
propriate prejudice. United States v. Johnson, 916 F.3d 579, 588
(7th Cir. 2019).
                      1.   Gang Membership
    The defendants first contend that their relationship to the
Sinaloa Cartel was irrelevant to show that they participated in
the charged oﬀenses. At trial, Yesenia Samaniego, an admitted
participant in their drug-distribution network, testified that
Castro-Aguirre indicated to her that he was involved with a
cartel. Her husband, Jesus Samaniego, corroborated this ac-
count, explaining that Castro-Aguirre “basically” told him
that these defendants were working for the Sinaloa Cartel.
   In their motion in limine, the defendants argued that the
proposed evidence of gang aﬃliation was inadmissible to
show involvement in the conspiracies at issue. The district
10                                            Nos. 19-1074 et al.

court, however, rejected their argument and allowed its ad-
mission. Its decision to do so was not an abuse of discretion.
    We have long held that “‘[e]vidence of gang aﬃliation is
admissible in cases in which it is relevant to demonstrate the
existence of a joint venture or conspiracy and a relationship
among its members’ and each defendant’s knowledge of and
participation in the drug conspiracy.” United States v. Alviar,
573 F.3d 526, 536 (7th Cir. 2009) (alteration in original) (quot-
ing United States v. Westbrook, 125 F.3d 996, 1007 (7th Cir.
1997)). The critical distinction is between use of gang aﬃlia-
tion for the limited purpose of showing the existence of the
conspiracy and the connections among the various actors
(which is permissible), and use of gang aﬃliation to show ac-
tual involvement in the conspiracy (which is not). See United
States v. Suggs, 374 F.3d 508, 517 (7th Cir. 2004). The district
court here respected that line. The evidence of the defendants’
loose aﬃliation to the Sinaloa Cartel was relevant to show
their association and the existence of a drug-distribution con-
spiracy.
     2.     Kidnapping and Murder of Barrios-Moreno
    In contrast, we are troubled by the district court’s decision
to admit the evidence of the kidnapping and murder of Bar-
rios-Moreno and his colleagues. This was explosive material,
and it had little to do with the conduct for which the defend-
ants were being tried. At trial, the government elicited testi-
mony from Yesenia that Angel Barrios-Moreno, a supplier for
the defendants, was kidnapped by the Sinaloa Cartel for a
debt he had accrued after the government seized drugs that
had been bound for him. The cartel demanded a $500,000 ran-
som. The government’s theory was that this ransom moti-
vated certain of the defendants’ actions in the ensuing days.
Nos. 19-1074 et al.                                          11

The ransom, prosecutors urged, put pressure on the defend-
ants to collect cash to free Barrios-Moreno. Yesenia testified
that they managed to raise $250,000 in relatively short order.
But the government did not link that eﬀort to the operation of
the drug organization that lay at the heart of this case.
    Even less relevant was the government’s decision to try to
supplement the ransom testimony with copies of a news arti-
cle that included pictures of the three dead men: Barrios-
Moreno and his two colleagues. The government contended
that the jury needed to understand that Barrios-Moreno was
brutally murdered by cartel members who were not part of
this case, because the jury would otherwise be at a loss to ex-
plain why the defendants stopped using Barrios-Moreno as a
drug source and found a new seller. But the government
never explained why the identity of the drug source mattered
to the charges in this case.
    The defendants requested that the district court allow
them to stipulate that Barrios-Moreno was killed, and they
asked that the photos not be admitted because they were
gruesome and had no eﬀect apart from “inflam[ing] the jury.”
The court compromised, keeping out one of the photos and
admitting the other two. In so ruling, it commented that
“there’s nothing gruesome. It’s just three bodies.” It then gave
a limiting instruction to the jurors, telling them that the evi-
dence was admissible “solely as background material to es-
tablish the eﬀect that the kidnapping and murder of these in-
dividuals in Mexico had on the alleged drug traﬃcking and
money laundering activities of the defendants in the United
States.”
   Yesenia was not the only witness to address the kidnap-
ping and homicide. The government also asked a DEA agent,
12                                            Nos. 19-1074 et al.

Matthew Holbrook, to review the same news articles. During
the direct examination, the government placed the photo-
graphs of the three dead bodies on display, as well as multiple
photos of Barrios-Moreno’s gravesite. The government even
asked the district court to permit it to circulate physical copies
of the photographs of Barrios-Moreno’s gravesite to the jurors
because they “were a little fuzzy when you place them on the
projector.” The district court obliged.
    The government asked two other witnesses to add context
to Barrios-Moreno’s death. First, Jesus Samaniego testified
that Barrios-Moreno was kidnapped because he owed a debt
to the cartel. This was supposedly to provide context for the
Castro-Aguirre group’s need for a new supplier after Barrios-
Moreno was killed. The government asked Jesus if he knew
who killed Barrios-Moreno, and Jesus responded that the son
of Joaquin (“El Chapo”) Guzmán—the head of the Sinaloa
Cartel—was behind the killing. Jesus also provided details
about the eﬀorts to repay the ransom.
   Shortly after Jesus testified, and well after the district
court’s limiting instruction to the jurors specifically informing
them that none of the defendants participated in these mur-
ders, the district court informed counsel that multiple ju-
rors—fearing for their safety—asked whether the defendants
had access to their personal information. The district court
brushed their concerns aside, suggesting that the fear likely
arose “because weʹve talked about the cartel and things like
that.” Over the defendants’ renewed objection, it found that
the evidence was relevant and not prejudicial, and it ex-
pressed the view that “this type of question is normal in al-
most every jury trial.”
Nos. 19-1074 et al.                                          13

    Even then, the testimony about the murders did not stop.
The government next presented Julio Cesar Cebrero-Alvarez,
a taxi driver in Nogales (Mexico) who had driven Castro-
Aguirre and Barrios-Moreno. Cebrero-Alvarez stated that he
was present for the events that led to Barrios-Moreno’s mur-
der and retold the story in great detail. He told the jury that
he took a trip to Sinaloa from Nogales with several people:
Barrios-Moreno, Angel’s nephew Adrian, and Cebrero-Alva-
rez’s brother Luis Carlos. At the outset he was in a car with
Barrios-Moreno, while Luis Carlos and Adrian rode in a sep-
arate car. At some point Barrios-Moreno switched to the other
car, and Cebrero-Alvarez, now driving alone, periodically
called the other car to check in. Cebrero-Alvarez became con-
cerned when Barrios-Moreno stopped answering. This
prompted him to visit Barrios-Moreno’s wife, who told him
that Barrios-Moreno’s sister Elvia had just called and in-
formed her that her husband and the others had been kid-
napped. Cebrero-Alvarez concluded by reporting that the po-
lice informed him that they had found the bodies and asked
him to identify them, but that he turned around when he was
within 10 kilometers of the meeting place because he was
“afraid maybe it was a trick” and that he would be killed too.
    We struggle to see the relevance of this highly prejudicial
evidence, particularly in light of the jurors’ expressed concern
about their safety. No one ever accused the defendants who
were on trial with any of these murders, or even with violent
histories. More troubling still, the jurors voiced their concern
after receiving the limiting instruction designed to mitigate
any undue prejudice from the evidence of Barrios-Moreno’s
kidnapping and murder. We see no reason why the govern-
ment needed to elicit testimony from at least four witnesses
explaining in great detail how these men were kidnapped and
14                                            Nos. 19-1074 et al.

murdered, why it needed to introduce multiple photographs
of the deceased bodies or the gravesite, or why it would not
have been suﬃcient for the court simply to tell the jury that
Barrios-Moreno had left the conspiracy, or disappeared, or
was killed.
    We are not impressed with the government’s arguments
that the jury would have been left with an evidentiary gap
without this extensive evidence. The government contends
that the evidence explains certain travel to pay oﬀ the ransom
and that the jurors would have been unable to figure out why
the defendants would seek a new source and recruit new cou-
riers without it. It relies on a 25-year-old case from this court
in which we held that the government could introduce evi-
dence of a triple murder in which no defendant participated,
committed by the Zapata organization, because that incident
explained why a participant “ended up cooperating with the
government after being an active, loyal member of the con-
spiracy himself.” United States v. Pulido, 69 F.3d 192, 200 (7th
Cir. 1995).
    We have no quarrel with the result in Pulido, but it was
based on significantly diﬀerent facts. There, the government
showed how the murders of the three men prompted their as-
sociate to cooperate with the government. Here, no such link
exists among the contested evidence, the defendants, and the
charges.
    The government contended in the district court that any
prejudice from this evidence is mitigated because Yesenia Sa-
maniego testified that she feared for her life if she returned to
Mexico, but it did not raise this argument in its appellate brief.
In any event, this theory is not particularly persuasive. Only
after the district court denied the defendants’ motion in limine
Nos. 19-1074 et al.                                            15

did the defendants ask Yesenia whether she was afraid of be-
ing killed for her testimony by members of the Sinaloa Cartel
if she returned to Mexico, or if the government oﬀered to “get
[her] a visa to stay in the United States” in exchange for her
testimony. Yesenia answered that she was afraid of Sinaloa
members in Mexico, not any of the defendants, who are in the
United States.
    In light of the tenuous connection between this evidence
and the case before us and the prejudice reflected in the jurors’
concerns for their safety, we find that the district court abused
its discretion by admitting this evidence.
     This finding is not, however, an automatic ticket to rever-
sal. We also must decide whether the error was harmless.
United States v. Vasquez, 635 F.3d 889, 898 (7th Cir. 2011). “The
test for harmless error is whether, in the mind of the average
juror, the prosecution’s case would have been ‘significantly
less persuasive’ had the improper evidence been excluded.”
Id. (quoting United States v. Emerson, 501 F.3d 804, 813 (7th Cir.
2007)).
    Given the overwhelming nature of the evidence presented
at trial regarding the defendants’ guilt, we cannot say that the
jury would have found the prosecutor’s case significantly less
persuasive had the court kept out the evidence relating to Bar-
rios-Moreno. Yesenia and Jesus Samaniego provided uncon-
troverted testimony connecting Castro-Aguirre, Ramirez-
Prado, and Rojas-Reyes to multiple large drug transactions
and identifying Carrillo-Tremillo as a major distributor.
These two testified about each of the trips from Arizona to In-
dianapolis, as well as the trips from Arizona and Indianapolis
to New York, New Jersey, and Pennsylvania. The government
presented travel and financial records tying Carrillo-Tremillo
16                                            Nos. 19-1074 et al.

and Ramirez-Prado to the major drug routes the conspirators
used, records from phones the DEA lawfully seized contain-
ing photographs and evidence of other connections among
the defendants, drugs and cash seized from the defendants’
cars and homes, and cell-site location data corroborating the
other evidence showing the defendants’ proximity during the
relevant events. We therefore find that the evidentiary error
we have addressed is harmless. See FED. R. EVID. 103(a); FED.
R. CRIM. P. 52(a).
             III. Carrillo-Tremillo’s Convictions
    We next address Carrillo-Tremillo’s appeal of the district
court’s denial of his motion under Federal Rule of Criminal
Procedure 29 for acquittal on Count 1 (conspiracy to distrib-
ute) and Count 4 (conspiracy to launder money). We review
the denial of a motion for judgment of acquittal de novo, ask-
ing only “whether evidence exists from which any rational
trier of fact could have found the essential elements of a crime
beyond a reasonable doubt.” United States v. Johnson, 874 F.3d
990, 998 (7th Cir. 2017). We conclude that the district court
correctly denied the motion to dismiss with respect to
Count 1, because there was suﬃcient evidence to prove a con-
spiracy, rather than a simple buyer-seller arrangement. In
contrast, we reverse the district court’s denial of the motion to
dismiss with respect to Count 4, because we can find no evi-
dence that would permit a rational trier of fact to connect Car-
rillo-Tremillo to a conspiracy to launder money.
               A.     Conspiracy to Distribute
   To prove a conspiracy to distribute a controlled substance,
the government must show “that (1) two or more people
agreed to commit an unlawful act, and (2) the defendant
Nos. 19-1074 et al.                                             17

knowingly and intentionally joined in the agreement.” United
States v. Johnson, 592 F.3d 749, 754 (7th Cir. 2010) (citing United
States v. Rollins, 544 F.3d 820, 835 (7th Cir. 2008)). We have
identified five commonly occurring facts that permit the in-
ference of a conspiracy to distribute: “[1] sales on credit or
consignment, [2] an agreement to look for other customers, [3]
a payment of commission on sales, [4] an indication that one
party advised the other on the conduct of the other’s business,
or [5] an agreement to warn of future threats to each other’s
business stemming from competitors or law-enforcement au-
thorities.” Johnson, 592 F.3d at 755–56. Among these, fronting
(i.e. supplying on credit, for later reimbursement), has become
the most telling factor. Id.
    Fronting, which occurs only if the supplier and the next-
level distributor have a shared economic stake in the ultimate
transaction, is a sign that we are looking at a conspiracy, not
two independent actors pursuing their own ends. A typical
buyer-seller relationship—even one involving a long history
of transactions—involves one or more on-the-spot exchanges
of cash for drugs. United States v. Lechuga, 994 F.2d 346, 349
(7th Cir. 1993) (en banc) (lead opinion); United States v. Colon,
549 F.3d 565, 567 (7th Cir. 2008). In contrast, the prosecution
can establish a conspiracy by proving that a larger agreement,
including a sale on credit, links the initial sale to the down-
stream distribution eﬀorts. United States v. Avila, 557 F.3d 809,
816 (7th Cir. 2009). This type of evidence tends to show a mu-
tual interest in the success of each party’s operations.
    Carrillo-Tremillo contends that the district court improp-
erly denied his motion for judgment of acquittal on the drug
conspiracy charge because, as he sees it, the government pro-
vided only circumstantial evidence of a simple buyer-seller
18                                           Nos. 19-1074 et al.

relationship. But first, there is nothing wrong with circum-
stantial evidence. And second, there was more to the govern-
ment’s case than he suggests.
    At trial, Yesenia Samaniego testified that she saw Carrillo-
Tremillo enter a hotel room with a small suitcase. She was in
the room with Castro-Aguirre. She then left the room and
waited outside for ten minutes, during which time she did not
see anyone else enter or leave the room. She returned to the
room after Carrillo-Tremillo left and saw a large pile of
money that was not there before on the bed. She concluded by
stating that Castro-Aguirre told her that Carrillo-Tremillo
was a courier for their cocaine distribution.
     Jesus Samaniego corroborated his wife’s account. He tes-
tified that he watched Carrillo-Tremillo walk into a hotel in
Scottsdale, Arizona. Carrillo-Tremillo was carrying the same
duﬄe bag that Castro-Aguirre had filled with cocaine, as Je-
sus watched. Jesus also reported seeing a large pile of money
on the bed in the hotel room after Carrillo-Tremillo visited
Castro-Aguirre there. Like Yesenia, Jesus testified that Castro-
Aguirre specifically told him that Carrillo-Tremillo gave him
the money. The government also presented evidence, includ-
ing airline and hotel receipts from Arizona, Pennsylvania,
New York, and New Jersey, linking Carrillo-Tremillo to the
distribution routes.
    Carrillo-Tremillo attacks the evidence provided by the Sa-
maniegos as unreliable, because neither of them personally
saw him deliver the money. He also contends that without
more context, their testimonies can prove only that he had a
buyer-seller relationship with Castro-Aguirre, not a conspira-
torial one. He believes that the bank and travel records do not
help either. He relies on our decision in Colon, where we held
Nos. 19-1074 et al.                                           19

that the government merely “describe[d] a routine buyer-
seller relationship” when it presented evidence of routine
cash purchases of distribution quantities of drugs. 549 F.3d at
567.
    Carrillo-Tremillo’s reliance on Colon is mistaken. There we
held that the government would have successfully proven a
conspiracy if it had provided evidence that the supplier
“‘fronted’ cocaine to the defendant (a factor mentioned in al-
most all the cases) rather than being paid in cash at the time
of sale. With fronting, the seller becomes the buyer’s creditor,
adding a dimension to the relationship that goes beyond a
spot sale for cash.” Id. at 569.
    In the present case, the government did just what we had
called for in Colon. The jury was entitled to conclude that the
Samaniegos’ testimony and the physical evidence connecting
Carrillo-Tremillo to the defendants were enough to prove
fronting, which in turn can be used to prove a conspiracy.
Carrillo-Tremillo’s theory is not completely improbable, but
it was the jury’s job to decide what happened, and this jury
drew inferences favorable to the government. We do not ask
whether a rational trier of fact could agree with the defend-
ant’s construction of the evidence. Rather, we ask whether a
rational trier of fact could find that Carrillo-Tremillo partici-
pated in the conspiracy to distribute. We conclude that it
could, and so we aﬃrm the district court’s denial of Carrillo-
Tremillo’s motion for judgment of acquittal on Count 1.
            B.        Conspiracy to Launder Money
   A charge of conspiracy to launder money requires proof
that the defendant knowingly was involved with “at least one
other person [who has] agreed with him to commit” an act of
20                                            Nos. 19-1074 et al.

money laundering, United States v. McBride, 724 F.3d 754, 756
(7th Cir. 2013), and that the defendant “knew the proceeds
used to further the scheme were derived from illegal activity,”
United States v. Arthur, 582 F.3d 713, 718 (7th Cir. 2009). Proof
of the underlying oﬀense of money laundering requires “that
a rational trier of fact could have concluded from the record
that [the defendant] knowingly used the proceeds from a
specified unlawful activity in financial transactions that [1]
were intended to promote the continuation of the unlawful
activity, or [2] were designed to conceal or disguise the pro-
ceeds of the unlawful activity.” Id. (quoting United States v.
Turner, 400 F.3d 491, 496 (7th Cir. 2005); 18 U.S.C. § 1956(a)(1),
(h)).
    There must be evidence of activity that is separate from
the underlying predicate oﬀense that generates proceeds to be
laundered, in order successfully to charge a defendant with
involvement in a conspiracy to commit money laundering.
The point of the money-laundering oﬀense is to “criminalize[]
a transaction in proceeds, not the transaction that creates the
proceeds.” United States v. Mankarious, 151 F.3d 694, 705 (7th
Cir. 1998) (emphasis added). Even when “the predicate of-
fense and the conspiracy to launder money cannot be sepa-
rated with surgical precision, they are clearly distinct.” United
States v. Diamond, 378 F.3d 720, 727 (7th Cir. 2004). The evi-
dence against a defendant will not support a conviction for
conspiracy to commit money laundering when it demon-
strates involvement only in a conspiracy that generated pro-
ceeds but does not demonstrate involvement in any subse-
quent conspiracy to launder those proceeds.
   We pause here to clarify the kinds of activity that signals
involvement in a conspiracy to commit money laundering.
Nos. 19-1074 et al.                                           21

We have never provided an exhaustive list of the transactions
that give rise to a money laundering conspiracy, and we de-
cline to do so now. But we have explained that “certain types
of transactions may be indicative of a design to conceal,” in-
cluding, for example, “transactions surrounded in unusual
secrecy, structured transactions, depositing ill-gotten funds
into another’s bank accounts, using third parties to conceal
the real owner, or engaging in unusual financial moves which
culminate in a transaction.” Turner, 400 F.3d at 497. In Dia-
mond, we upheld a conviction for conspiracy to launder
money where the evidence showed that the defendant en-
dorsed checks that a coconspirator deposited into his personal
accounts, repeatedly purchased cashier’s checks with fund
money (often to evade IRS reporting), withdrew fund money
in cash because cash is untraceable, wired money to an oﬀ-
shore bank account to purchase an oil refinery, and wired
money to her own oﬀshore bank account. Diamond, 378 F.3d
at 727–28. In contrast, in United States v. Malone, the defendant
received payment for sending drivers with vans full of drugs
stuﬀed in band equipment, so that he could arrange for the
delivery of the drugs, receive cash payments for them, and
return the funds to a drug-distribution group. 484 F.3d 916,
921–22 (7th Cir. 2007). We held that the evidence was insuﬃ-
cient to support a conviction for conspiracy to launder money
because the defendant was a mere conduit; he did not partic-
ipate in any transactions designed to conceal the proceeds
that were intended to promote the continuation of the unlaw-
ful activity. Id.
   The government argues that Carrillo-Tremillo is guilty of
participating in the conspiracy to launder money because he
knowingly conducted financial transactions with the intent to
22                                            Nos. 19-1074 et al.

promote the continuation of the unlawful activity. Its evi-
dence is scant. All we see is that Carrillo-Tremillo paid Castro-
Aguirre the proceeds he collected from drugs that had been
fronted to him. The government argues that this payment ad-
vanced the conspiracy because it kept Carrillo-Tremillo’s
credit good with Castro-Aguirre, thereby ensuring a contin-
ual flow of additional supplies.
    This evidence falls short. The evidence of a conspiracy to
commit money laundering cannot be identical to the evidence
of the underlying oﬀense that generated the proceeds that
need laundering. As we have noted in connection with
Count 1, the government proved that Carrillo-Tremillo par-
ticipated in a conspiracy to distribute controlled substances:
Castro-Aguirre gave Carrillo-Tremillo drugs on credit, Car-
rillo-Tremillo distributed those drugs, and Carrillo-Tremillo
paid Castro-Aguirre back. It is precisely this element of front-
ing that diﬀerentiates these transactions from a simple buyer-
seller relationship. Now the government wants to say that the
same evidence of fronting and reimbursement qualifies as
money laundering, in the sense of financial transactions in-
tended to promote the unlawful activity.
    What is missing here is any kind of transaction in the drug
proceeds, as opposed to the actions that generate the pro-
ceeds. The government did not prove that Carrillo-Tremillo
conducted a financial transaction with those proceeds over
and beyond paying his debt for the fronted drugs. In addition,
it needed to point to an independent transaction that was (1)
intended to promote the continuation of the unlawful activity
or (2) designed to conceal or disguise the proceeds. Evidence
of fronting, standing alone, is insuﬃcient for purposes of this
Count. The government’s theory would erase the distinction
Nos. 19-1074 et al.                                           23

between the conspiracy to distribute controlled substances
and money laundering. We have not accepted this approach,
nor do we see any sign that Congress meant to create this per-
fect overlap. We conclude, therefore, that the district court
erred when it denied Carrillo-Tremillo’s motion for judgment
of acquittal with respect to the conspiracy to commit money
laundering.
                           IV. Sentences
   We turn finally to the defendants’ challenges to their sen-
tences. The challenges fall within two categories. First, Rojas-
Reyes attacks his concurrent life sentences on constitutional
grounds. Second, Ramirez-Prado and Carrillo-Tremillo argue
that their below-guideline sentences are substantively unrea-
sonable.
                      A.       Rojas-Reyes
    We review constitutional challenges, including challenges
to the constitutionality of sentences, de novo. United States v.
Figueroa-Espana, 511 F.3d 696, 705 (7th Cir. 2007); United States
v. Nagel, 559 F.3d 756, 759 (7th Cir. 2009). The Eighth Amend-
ment’s Cruel and Unusual Punishment Clause “prohibits sen-
tences that are grossly disproportionate to the crime commit-
ted.” Nagel, 559 F.3d at 762. Proving that a life sentence is
grossly disproportionate to the crime committed is a difficult
task, United States v. Brucker, 646 F.3d 1012, 1019 (7th Cir.
2011), because that standard is met only in “exceedingly rare”
cases, Harmelin v. Michigan, 501 U.S. 957, 963 (1991); see also
United States v. Gross, 437 F.3d 691, 692 (7th Cir. 2006). Three
factors shed light on the question: “(i) the gravity of the of-
fense and the harshness of the penalty; (ii) the sentences im-
posed on other criminals in the same jurisdiction; and (iii) the
24                                            Nos. 19-1074 et al.

sentences imposed for commission of the same crime in other
jurisdictions.” Nagel, 559 F.3d at 762 (quoting Solem v. Helm,
463 U.S. 277, 292 (1983)).
    As our earlier chart illustrated, the jury found Rojas-Reyes
guilty on six counts. The district court sentenced him to four
concurrent life sentences for Counts 1, 3, 5, and 8. Count 3 car-
ried a mandatory life sentence, and the district court applied
the maximum sentence of life for Counts 1, 5, and 8. The court
then imposed concurrent sentences of 240 months in prison
for Count 4 and 480 months in prison for Count 6. Rojas-
Reyes argues that his four concurrent life sentences are
grossly disproportionate to the offenses charged because he
was only 38 years old at the time of sentences, had no prior
criminal history, and was sentenced for only non-violent of-
fenses.
    Rojas-Reyes’s constitutional challenges are without merit.
We have “repeatedly upheld mandatory life sentences im-
posed pursuant to § 841(b)(1)(A) against Eighth Amendment
challenges.” United States v. Ousley, 698 F.3d 972, 975 (7th Cir.
2012) (finding that mandatory life sentences for possession of
more than 50 grams of crack cocaine with the intent to distrib-
ute with at least two prior drug felonies does not constitute
cruel and unusual punishment); see also United States v. Car-
raway, 612 F.3d 642, 644–46 (7th Cir. 2010) (same); United States
v. Strahan, 565 F.3d 1047, 1052–53 (7th Cir. 2009) (rejecting
Eighth Amendment challenges to statutorily prescribed man-
datory-minimum life sentences). The Supreme Court has like-
wise explained that even mandatory minimums without con-
sideration for “mitigating factors such as … the fact that [a
defendant] had no prior felony convictions” do not violate the
Nos. 19-1074 et al.                                            25

Eighth Amendment because “they are not unusual in the con-
stitutional sense.” Harmelin, 501 U.S. at 994–95. Our sister cir-
cuits have also upheld multiple concurrent life sentences
against Eighth Amendment challenges. See Virgin Islands v.
Gereau, 592 F.2d 192 (3d Cir. 1979); United States v. Anderson,
561 F.2d 1301 (9th Cir. 1977); United States v. Williams, 576 F.3d
1149 (10th Cir. 2009); United States v. Rolon, 511 F. App’x 883
(11th Cir. 2013).
    Our task is not to determine whether we, sitting in the seat
of the district court, would have given a person in his late thir-
ties with no prior record multiple concurrent life sentences for
non-violent drug offenses. Instead, we ask only whether the
district court’s sentencing decisions violate the Eighth
Amendment. They did not.
                      B.    Ramirez-Prado
    Despite the fact that Ramirez-Prado received a sentence
below the level suggested by the advisory Federal Sentencing
Guidelines, he argues that it was unreasonably long. This is a
hard case to make. When, as here, there is no procedural chal-
lenge to a sentence, we ask only whether the sentence selected
by the district court is substantively reasonable. United States
v. Warner, 792 F.3d 847, 856 (7th Cir. 2015). In this connection,
we must be “mindful that substantive reasonableness occu-
pies a range, not a point, and that the sentencing judge is in
the best position to apply the § 3553(a) factors to the individ-
ual defendant.” Id. (quotation marks and citations omitted).
As a result, we evaluate sentencing challenges for abuse of
discretion and recognize that “sentence[s] within [guideline]
range [are] presumptively reasonable.” United States v. Wal-
lace, 531 F.3d 504, 507 (7th Cir. 2008).
26                                                   Nos. 19-1074 et al.

   After the jury returned a verdict of guilty against Ramirez-
Prado, the district court held a sentencing hearing for him.
When all was said and done the district court calculated his
recommended guideline range for Count 1 as 324 to 405
months; for Count 4, his “range” was 120 months.2 The court
then applied a seven-year reduction below the low end of the
Count 1 range, sentencing Ramirez-Prado to 240 months for
Count 1 and a concurrent sentence of 120 months on Count 4.
    Ramirez-Prado contends that his sentence should have
been lower yet—no more than a total of 120 months. We take
this as an admission that 120 months was reasonable for
Count 4, and so we focus on Count 1. Emphasizing that he
had no prior criminal history, Ramirez-Prado contends that
the sentence was improper because other defendants who
confessed to their involvement in the conspiracy and testified
at trial garnered lower sentences. Yesenia Samaniego received
60 months, and Jesus Samaniego, who had a higher criminal
history, received 230 months. Ramirez-Prado argues that 18
U.S.C. § 3553(a)(6) requires the district court to consider sen-
tencing disparities among defendants with similar records.
He contends that the district court failed to do so.
   We are not persuaded. “Unlike the sentencing judge, we
may presume on appeal that a within-guidelines sentence is
reasonable.” United States v. Warner, 792 F.3d 847, 855–56 (7th

     2We read the district court’s determination that the recommended
sentencing range was a 120-month point as an acknowledgement of a stat-
utory maximum. But 18 U.S.C. § 1956(a), (h) prescribes a 20-year (240-
month) maximum, not 120 months (or 10 years). The government, how-
ever, does not challenge the district court’s sentencing decision or take a
cross-appeal, and so we evaluate the sentencing decisions as presented on
the record below.
Nos. 19-1074 et al.                                             27

Cir. 2015) (quoting United States v. Nania, 724 F.3d 824, 830
(7th Cir. 2013); Rita v. United States, 551 U.S. 338, 341 (2007)).
Precisely because sentences that fall within the guidelines are
presumptively reasonable, sentences that fall below the rec-
ommended sentencing range are presumptively reasonable as
well. See United States v. Anderson, 580 F.3d 639, 651 (7th Cir.
2009) (citing United States v. Wallace, 531 F.3d 504, 507 (7th Cir.
2008)). Indeed, we have never “deemed a below-range sen-
tence to be unreasonably high.” United States v. Brown, 932
F.3d 1011, 1019 (7th Cir. 2019). Moreover, while we have rec-
ognized that the district court must account for unwarranted
sentencing disparities between codefendants, we have also
found that (1) cooperation is a relevant and appropriate factor
in sentencing disparities between codefendants and (2) “a dis-
trict court that sentences within the Guidelines necessarily
gives weight and consideration to avoiding unwarranted dispari-
ties.” United States v. Pulley, 601 F.3d 660, 668 (7th Cir. 2010)
(emphasis added).
    Here, the district court explicitly accounted for the dispar-
ity in sentences between the Samaniegos and Ramirez-Prado,
noting that the Samaniegos received larger downward vari-
ances for their cooperation. Moreover, just as a district court
sentencing within the guideline range necessarily is taking
steps to avoid unwarranted disparities, so too does a district
court that sentences below the guideline range. Cf. United
States v. Anderson, 580 F.3d 639, 651 (7th Cir. 2009).
   This case is not destined to be the first one in which we
find that a sentence substantially below the recommended
guideline range is nonetheless unreasonably high. We there-
fore affirm Ramirez-Prado’s sentence.
28                                             Nos. 19-1074 et al.

                   C.      Carrillo-Tremillo
    Carrillo-Tremillo’s situation is a bit more complex. The
district court found that the recommended guideline range
for Count 1 was 235 to 293 months and the statutory maxi-
mum for Count 4 was 240 months pursuant to 18 U.S.C.
§ 1956(a), (h). It sentenced Carrillo-Tremillo to 215 months for
Count 1 and 120 months for Count 4.
    Carrillo-Tremillo attempts to chart the same course as
Ramirez-Prado, challenging the reasonableness of his 215-
month sentence because of the sentencing disparity between
himself and the Samaniegos, one of whom received a larger
term than he. As with Ramirez-Prado, these arguments are
without merit. But there’s more. The district court’s sentence
of 215 months’ imprisonment for Count 1 was based on the
offense level of 38, which in turn took into account its im-
proper conviction with respect to Count 4, which we vacate
today. Looking at Count 1 alone, the district court found that
Carrillo-Tremillo’s offense level was 36. On remand, Carrillo-
Tremillo is entitled to be resentenced solely on the basis of his
conviction on Count 1. His sentence on Count 4 must be set
aside in light of our ruling on the merits of that conviction.
                               V
    In the end, the outcome of this complex prosecution re-
mains largely undisturbed. We AFFIRM the convictions of all
the defendants, except for Carrillo-Tremillo’s conviction on
Count 4 for conspiracy to launder money. We also AFFIRM the
sentences of all the defendants, once again with the exception
of Carrillo-Tremillo. We VACATE Carrillo-Tremillo’s sentence
in appeal No. 19-1110, and REMAND his case for further pro-
ceedings consistent with this opinion.