Petition for Writ of Certiorari — Daniel Stewart, Petitioner v. United States
Supreme Court briefJan 23, 2019
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For the Seventh Circuit
Chicago, Illinois 60604
CERTIFIED COPY
October 26, 2018
Before
FRANK H. EASTERBROOK, Circuit Judge
ILANA DIAMOND ROVNER, Circuit Judge
J. PHIL GILBERT, District Judge
No. 16-4105
UNITED STATES OF AMERICA
Plain tiff-Appellee,
Appeal from the United States District Court
for the Southern District of Indiana,
Indianapolis Division.
V.
No. 1:15-cr-00024-WTL-DKL-1
DANIEL STEWART,
Defendant-Appellant
William T. Lawrence, Judge.
ORDER
No judge of the court having called for a vote on the Petition for Rehearing En
Banc, filed by Defendant-Appellant on October 10, 2018, and all of the judges on the
original panel having voted to deny the same,
IT IS HEREBY ORDERED that the Petition for Rehearing En Banc is DENIED.
Of the Southern District of Illinois, sitting by designation.
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CERTIFIED COPY
No. 16-4105
UNITED STATES OF AMERICA,
Plain tiff-Appellee,
tu
DANIEL STEWART,
Defendant-Appellant.
Appeal from the United States District Court for the
Southern District of Indiana, Indianapolis Division.
No. 1:15-cr-00024-WTL-DKL-1 William T. Lawrence, Judge.
-
ARGUED MARCH 30, 2018
DECIDED SEPTEMBER 5, 2018
-
Before EASTERBROOK and ROVNER, Circuit Judges, and
GILBERT, District Judge.
ROVNER, Circuit Judge. Daniel Stewart was convicted of
drug trafficking, firearms offenses, and money laundering,
primarily based on evidence gathered as a result of a traffic
Of the Southern District of Illinois, sitting by designation.
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stop and a subsequent confession. We affirm the district court's
denial of Stewart's motion to suppress the traffic stop evidence
and the confession, and we reject Stewart's additional claims
on appeal.
I.
On January 20, 2015, Detectives Jeff Sequin and Ryan
VanOeveren were surveilling the home of Daniel Stewart.
Stewart w as not the main focus of their investigation. For
months, Indianapolis police had been trying to gather evidence
about a large-scale cocaine supplier ultimately identified as
Geraldo Colon. In May 2014, with the assistance of the federal
Drug Enforcement Agency, they arrested three Arizona-based
couriers who were bringing drugs into Indianapolis. One of
those couriers, Juan Lizarraga, began cooperating with the
investigators and provided information that led the officers to
a major customer of Colon. Lizarraga did not know the
customer by name but he knew the apartment complex where
the customer lived, and he had seen Colon deliver drugs to the
customer at that apartment complex and also at Colon's
furniture store. Lizarraga offered the officers a general physical
description of the customer.
Over a period of several months, officers surveilled Colon's
furniture store. During that time, they twice observed Stewart
visit the store, once on October 23, 2014, and once on December
16, 2014. On each occasion, Stewart stayed only a short time
and made no purchase. Through further investigation, the
officers identified Stewart and learned that he lived in the
apartment complex pointed out by Lizarraga. Stewart had a
criminal record that included felony drug offenses. In early
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January 2015, believing that Stewart was the customer identified by Lizarraga, they began to surveil Stewart in an attempt
to connect him to Colon's drug trafficking.
In the early evening of January 20, 2015, Detectives
VanOeveren and Sequin followed Stewart's white Volkswagen
from his apartment complex to a Shell gas station. After
Stewart pulled up to a pump, another man exited a grey car
that was parked at the station, and walked over to the passenger side of Stewart's car. The man got into Stewart's car and
closed the door. A few minutes later, the man exited Stewart's
car and immediately left the station in the grey car. Stewart
then got out of his Volkswagen and pumped gas. Although
they could not see through Stewart's tinted windows from
their vantage point some eighty yards away, based on their
many years of experience investigating drug crimes,
VanOeveren and Sequin believed that they had just witnessed
a drug sale at the gas station.
They decided to watch Stewart's car for traffic violations
and to attempt a traffic stop. Because they were in plain clothes
and unmarked cars, they called Detective Brady Ball to the
scene in his squad car. Detective Ball specialized in drug
interdiction stops, and he traveled with Josie, a dog who had
been trained to detect the scent of illegal drugs. Detective Ball
testified that he arrived in the area in time to see Stewart fail to
stop at a red light when he made a right turn, the same
violation observed by the other detectives.' Detective Ball
The district court found that some ambiguity existed in the record as to
whether Ball himself saw Stewart fail to stop or whether he effected the
(continued...)
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activated his lights and Stewart pulled over in the parking lot
of a Speedway gas station.
Detective Ball recorded the audio of his encounter with
Stewart and so the trial court had a detailed, time-indexed
account of everything that was said during the stop.2 At the
suppression hearing, Detective Ball supplemented this recording with his personal observations and recollection. Detective
Ball explained to Stewart the reason for the stop and asked for
routine information such as license and registration. Stewart
seemed unusually nervous, fidgeting with his wallet and
taking several deep breaths as he complied with Ball's requests. Because the car was registered to a business named
"Eleete Image, Inc." and because Stewart's address was
different from that on the registration, Ball asked for clarification. Ball also asked questions related to officer safety such as
whether Stewart had any guns or knives in the car or on his
person. Stewart denied having any weapons. Ball asked
Stewart to exit the car and sit on the bumper. He noted that
Stewart's tinted windows were "borderline" illegal and asked
(...continued)
stop on the basis of VanOeveren's report that Stewart failed to stop. Under
the collective knowledge doctrine, Ball was entitled to stop Stewart based
on the traffic violation witnessed and reported by VanOeveren. See United
States v. Contreras, 820 F.3d 255, 268 (7th Cir. 2016) (under the collective
knowledge doctrine, the court may attribute facts known to one officer to
other officers).
2
The audio recording was submitted to the district court as an exhibit at
the suppression hearing without a separate record number. Stewart
supplied it to this court as a compact disc attached to his supplemental
appendix.
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if Stewart had ever been arrested. Stewart responded that he
had been arrested on drug charges "a long time ago." Ball
asked for consent to search the car and Stewart declined. Ball
noticed a bulge in Stewart's pocket and asked him what it was.
Stewart replied that it was $700 in cash. Ball then returned to
his squad car to run the license and registration information as
well as a check for outstanding warrants. Seconds later, Ball
was back out of his car, again asking Stewart to sit on the
bumper. Five minutes had elapsed at this point in the stop.
Moments after returning to the squad car, Ball radioed a
request for backup. He explained that he was on an interdiction stop and wanted to run his dog around the car. He
requested that officers arrive as quickly as possible. It appears
from the audio recording that Ball continued to work on the
traffic violation as he waited for a response to his request for
backup, but an estimate of the time attributed to calling for
backup would be at most seventy-five seconds.'
As he waited for backup to arrive, Detective Ball continued
the process of checking the license and registration, running a
All references to the audio recording will be given in the format
minutes:seconds elapsed from the beginning of Detective Ball's encounter
with Stewart. Ball's call for backup began at 5:11. From 5:23 to 6:01, the
recording consists of occasional electronic beeps, undecipherable radio
transmissions and periods of silence. From 6:01 to 6:09, from 6:50 to 7:04,
and from 7:16 to 7:19, Ball supplied additional information about his
location and his need for backup. In the midst of waiting for a reply on his
request, at 6:25, Ball can be heard beginning to run a check on the car's
registration under the name, "Eleete." We estimate that the time spent
calling for backup, excluding audio content clearly related to the traffic
mission of the stop, is at most seventy-five seconds.
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check for outstanding warrants, and beginning to write the
ticket. Approximately thirteen minutes into the stop, while
Detective Ball was still completing tasks related to writing the
ticket, the backup officers arrived. For approximately forty-five
seconds, Detective Ball spoke to the backup officers, explaining
to one officer how to complete the electronic ticket-writing
process (which was apparently new), and asking the other
officer to keep a watch over Stewart. Ball then removed Josie
from his car and walked her around Stewart's car. On her
second pass around the Volkswagen, Josie alerted to the
driver's side door. The entire process of Josie exiting the squad
car, sniffing, and then alerting took one minute and forty-five
seconds. The backup officer was still working on the ticket
when Josie alerted. Detective Ball offered further advice on
completing the ticket, and then approached Stewart.
He explained to Stewart that Josie had alerted to the odor
of illegal drugs, and he handcuffed Stewart, clarifying that he
was not under arrest. Detective Ball explained at the suppression hearing that he felt this was necessary for officer safety
based on the description of the suspected gas station drug
transaction, Josie's alert, and the background information that
he had learned about Stewart prior to making the stop.
Believing he now had probable cause to search the car, he
began to inspect the interior of Stewart's Volkswagen. See
Florida v. Harris, 568 U.S. 237, 246-47 (2013) (certification of a
dog by a bona fide organization after testing the dog's reliability in a controlled setting or successful completion of a recent
training program that evaluated the dog's proficiency in
locating drugs creates a rebuttable presumption that the dog's
alert provides probable cause to search). Almost immediately,
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Detective Ball found a handgun in the center console area,
within reach of the driver's seat. Knowing that Stewart was a
convicted felon, he now had probable cause for an arrest. See
18 U.S.C. § 922(g)(1). He placed Stewart under arrest and gave
him Miranda warnings. He then continued his search of the car.
Although he found no drugs in the passenger compartment of
the car, he found a bag in the trunk containing approximately
102 grams of crack cocaine, 250 grams of powder cocaine, 241
grams of heroin, 19 grams of methamphetamine, and a digital
scale. He also found $7,420 in cash. The purported $700 in
Stewart's pocket turned out to be $1,904, for a total of $9,324 in
cash.
Detective Ball approached Stewart again and said, "That's
a lot of drugs, bud. You want to talk to a detective?" Stewart
appeared to shake his head to indicate "no." Ball clarified,
"You do not want to talk to a detective? Well, you understand
I gotta have one come out." Stewart replied, "Can you put me
in the car? It's kind of cold out."' Ball said, "Yes, they're going
to talk to you regardless so you'll get in the car at that point. I
have a dog in my car." Ball then radioed for narcotics officers
to come to the scene. We will discuss that call and the subsequent interchange between Ball and Stewart more completely
below when we address Stewart's motion to suppress his
confession. Eventually Stewart was placed in the car of the
narcotics officers when they arrived on the scene.
Temperatures hovered between thirty-eight and forty-one degrees on this
January day, and Stewart was wearing pants, a sweatshirt and tennis shoes.
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VanOeveren and Sequin were the officers who arrived to
transport Stewart. VanOeveren reminded Stewart of his
Miranda rights and asked if Stewart wanted to talk about the
gun, narcotics and cash found in his car. Stewart first tried to
talk the detectives into releasing him for a short period,
promising to meet them later to assist them in their investigation. The officers declined and gave Stewart two options: come
with the detectives to the police station to discuss his situation
or go straight to the Marion County Jail. Stewart opted to go to
the police station with the detectives. Once there, officers
brought Stewart into an interview room and Detective Ryan
Clark gave Stewart his Miranda rights. Stewart indicated that
he understood his rights and he signed a written waiver of
those rights. He then made incriminating statements that were
video-recorded. In the meantime, officers obtained a search
warrant for his residence. The affidavit supporting the warrant
detailed the cash, drugs and gun found in the car. The search
of Stewart's home yielded an additional 1650 grams of cocaine;
1005 grams of methamphetamine; 1500 grams of heroin; four
more handguns; and $487,542 in cash.
Stewart was charged in a six-count indictment with
possession with intent to distribute controlled substances, in
violation of 21 U.S.C. §§ 841 and 851; possession of a firearm by
a felon, in violation of 18 U.S.C. § 922(g)(1); possession of a
firearm in furtherance of a drug trafficking crime, in violation
of 18 U.S.C. § 924(c); engaging in monetary transactions in
property derived from specified unlawful activity, in violation
of 18 U.S.C. § 1957; and two counts of money laundering, in
violation of 18 U.S.C. § 1956(a)(1). The district court denied
Stewart's motion to suppress the evidence obtained during and
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as a result of the traffic stop and the confession he gave at the
police station. The district court also denied Stewart's pre-trial
motion in limine to prevent or limit the use of evidence that he
had twice visited Colon's furniture store. After a four-day trial
that included testimony about Colon's criminal activities, a
jury convicted Stewart on all counts. Because Stewart had two
qualifying prior felony drug convictions, his sentence on the
drug possession count was life imprisonment without parole.
See 21 U.S.C. § 841(b). For four of the remaining counts, the
court sentenced Stewart to terms of imprisonment between five
and fifteen years' imprisonment to be served concurrent with
the life sentence. The sentence for possession of a gun in
furtherance of a drug trafficking crime tacked on a gratuitous
five consecutive years to the sentence of life imprisonment.
Stewart appeals.
II.
On appeal, Stewart contends that the evidence gained
through the traffic stop should have been suppressed because
Detective Ball unconstitutionally prolonged the stop in order
to conduct the dog sniff procedure. Stewart also asserts that the
prolonged detention due to the sniff was not otherwise
supported by reasonable suspicion. Any evidence obtained
after the search of his car, he argues, should be suppressed as
the fruit of the poisonous tree. Stewart maintains that the
incriminating statements he made following his arrest should
also have been suppressed because investigators violated his
invocation of his right to remain silent. He also submits that the
district court erred in admitting substantial amounts of
prejudicial and irrelevant evidence of prior bad acts. And
finally, he asserts that the government failed to present
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sufficient evidence in support of the money laundering
convictions, rendering them infirm as a matter of law. He seeks
to have the convictions on every count vacated and the case
remanded for further proceedings. But he also contends that
his convictions for money laundering should be reversed
outright. Because some of these objections were preserved and
others were not, we will address the standard of review as we
turn to each issue.
A.
Josie conducted her life-altering sniff of Stewart's car on
January 20, 2015. The next day, the Supreme Court heard
argument in Rodriguez v. United States, 135 S. Ct. 1609 (2015).
The Court decided Rodriguez on April 21, 2015, some three
months before Stewart filed his motion to suppress and five
and a half months before the district court held the suppression
hearing. In Rodriguez, the Supreme Court considered "whether
police routinely may extend an otherwise-completed traffic
stop, absent reasonable suspicion, in order to conduct a dog
sniff." 1355. Ct. at 1614. The Court concluded that a traffic stop
may become unlawful if it is prolonged beyond the time
reasonably necessary to complete the traffic-related mission of
the stop. 135 S. Ct. at 1614-15. Unrelated inquiries may not
measurably prolong a traffic stop, although an officer may
conduct ordinary inquiries incident to the stop such as questions involving the driver's license, the vehicle's registration,
and whether there are outstanding warrants for the driver. 135
S. Ct. at 1615. These activities are all related to the mission and
objective of enforcing the traffic code, and "ensuring that
vehicles on the road are operated safely and responsibly." 135
S. Ct. at 1615. Because traffic stops are "especially fraught with
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danger to police officers," an officer may also take "certain
negligibly burdensome precautions in order to complete his
mission safely." Rodriguez, 135 S. Ct. at 1616 (citing Arizona v.
Johnson, 555 U.S. 323, 330 (2009)). Dog sniffs, the Court said,
may not be fairly characterized as part of the officer's traffic
mission, and so dog sniffs may not prolong or add time to the
stop unless supported separately by individualized, reasonable
suspicion. Rodriguez, 135 S. Ct. at 1616-17.
On appeal, Stewart first argues that Detective Ball unreasonably lengthened the stop in order to conduct the dog sniff.
Such a delay was unconstitutional under Rodriguez, he continues, and no reasonable suspicion supported lengthening the
stop in order to conduct the sniff. Moreover, Stewart contends
that the government failed to argue below that the evidence
obtained from the stop was admissible under any exception to
the exclusionary rule, and so the government forfeited any
such claim on appeal. See United States v. Leo, 792 F.3d 742,
748-49 (7th Cir. 2015). In considering a district court's denial of
a motion to suppress, we usually review findings of fact for
clear error and questions of law de novo. United States v.
Borostowski, 775 F.3d 851, 863 (7th Cir. 2014). However, the
government asserts that Stewart did not preserve the issue that
he raises on appeal because he failed to make a timely and
specific objection in the district court. Because Stewart forfeited
the issue, the government argues, we should review the district
court's decision for plain error only. See United States v. Olano,
507 U.S. 725, 731 (1993); United States v. Hamad, 809 F.3d 898,
904 (7th Cir. 2016); Fed. Rule Crim. P. 52(b). The government
also contends that this court should consider its claim that
Detective Ball conducted the dog sniff in good faith reliance on
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then-binding circuit precedent. United States v. Leon, 468 U.S.
897, 909 (1984) (unlawfully obtained evidence should not be
suppressed when the police act on an objectively good-faith
belief that their conduct is lawful); Davis v. United States, 564
U.S. 229, 241 (2011) (when binding appellate precedent
specifically authorizes a particular police practice, the
exclusionary rule should not apply if that precedent is later
overruled by the Supreme Court); United States v. Jenkins, 850
F.3d 912, 918 (7th Cir. 2017) (same). Stewart responds that he
adequately preserved the argument by raising it in a letter to
the court after the suppression hearing, and that, in any case,
the district court addressed the issue on the merits and did not
treat it as forfeited. See R. 69 (Supplemental Authority In
Support of Defendant's Motion to Suppress). By Stewart's
measure, this court should therefore apply the usual standard
of review and the government should be precluded from
raising an exception to the exclusionary rule.
In his Motion to Suppress Evidence, Stewart challenged
only whether Josie's sniff of the car provided probable cause to
conduct a search. Specifically, Stewart complained that (1) Josie
is not a reliable dog; (2) Josie was subjected to handler error;
and (3) the drugs were planted in his car by police officers after
Josie performed the sniff. R. 33 and 33-1. At the suppression
hearing, Stewart made no mention of a claim that extra time
was taken to conduct the sniff. After the suppression hearing,
Stewart filed a supplemental memorandum where he contended for the first time that Ball was not entitled to conduct
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the sniff at all.' Stewart argued that VanOeveren's testimony
that he had observed Stewart engage in a drug sale at the Shell
station was unreliable and not entitled to any weight in
determining probable cause or reasonable suspicion to conduct
the sniff. Stewart also argued in his supplemental memorandum that the sniff could not be justified by his apparent
nervousness, and that Josie was unreliable because there was
testimony that she had alerted in the past on occasions when
drugs were not found. Stewart thus made no claims about the
sniff improperly lengthening the stop before, during or after
the suppression hearing. His only reference to Rodriguez came
after he filed a post-hearing supplemental memo, where he
submitted a copy of Rodriguez to the district court as supplemental authority. The letter accompanying the copy of the
Rodriguez decision read, in its entirety:
Enclosed please find a case entitled Rodriguez v.
United States, No. 13-9972. Argued January 21,2015Decided April 21, 2015 in the Supreme Court of the
United States.
Please give consideration to this decision in reviewing Mr. Stewart's Motion to Suppress Evidence.
R. 69.
In denying the Motion to Suppress, the district court
rejected any argument that Josie was unreliable or that handler
error contributed to her alert, claims which Stewart has now
By order of the district court, the parties were allowed to file supplemental memoranda simultaneously, three days after the suppression hearing.
R.87,at84.
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abandoned on appeal.6 The court also briefly addressed what
it characterized as Stewart's challenge to the reasonableness of
the length of time he was detained for the traffic stop. Citing
Rodriguez, the court noted that police officers may not extend
an otherwise-completed traffic stop, absent reasonable suspicion, in order to conduct a dog sniff. After a brief discussion of
governing law, the district court concluded that Ball did not
unconstitutionally prolong the stop:
Approximately fifteen minutes elapsed between the
time Ball pulled Stewart over and Josie's alert.
During that fifteen-minute period, Ball was actively
engaged in conducting the traffic stop. When other
officers arrived, Ball directed one officer to continue
writing the ticket while Ball had Josie conduct an
open air sniff. Thus, Ball did not prolong or extend
the traffic stop beyond the time necessary to effectuate its purpose. Once Josie alerted, the encounter
moved beyond that of a mere traffic stop, as probable cause to search the vehicle was established.
R. 70, at 6 (footnotes omitted).
Stewart is correct, in a sense, that the district court addressed the merits of the issue of whether the sniff prolonged
the stop. The court, as we have just seen, found that Detective
Ball did not, as a matter of fact, prolong the stop beyond the
6
The district court also noted that Stewart presented no evidence or
argument in support of his claim that police officers planted drugs in his
trunk after the sniff was completed. The court found no reason to give the
claim any credence and rejected it. That claim has also been abandoned on
appeal.
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time necessary to effectuate the traffic purpose of the stop
when he conducted the sniff procedure with Josie. On appeal,
Stewart now challenges this fact-finding by parsing the time
line of the stop. He faults Ball for taking the time to call for
backup, complains about the forty-five second delay in
explaining the electronic ticket process to the backup officer,
and objects to the actual time taken to run Josie around the car.
According to Stewart, the only conclusion is that "[t]he
resulting stop was longer than if Ball had simply written
Stewart a traffic citation," rendering the stop unconstitutional
under Rodriguez. Opening Brief, at 8.
Although Stewart has correctly identified the key question
under Rodriguez, prior to the appeal, Stewart never raised an
objection that would have alerted the government to the need
to make a record on this very point. In seeking to use evidence
obtained without a warrant, the government bore the burden
of proving by a preponderance of the evidence at the suppression hearing that an exception to the warrant requirement
applied. United States v. Basinski, 226 F.3d 829, 833 (7th Cir.
2000). At that hearing, the government presented evidence
relevant to Stewart's stated objections. That is, the government
provided evidence that Josie is a well-trained and reliable dog
with a proven track record of detecting the odor of illegal
drugs. The government also presented evidence that Detective
Ball was a highly trained handler and that no handler error
was involved in this search. Finally, the government presented
evidence that Detective Ball found the drugs in the trunk
during the search, negating the contention that the drugs were
planted in the truck after the fact.
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The government had no reason to ask Detective Ball why
he took the time to call for backup, and so the record is silent
on whether he summoned backup both for officer safety and
in order to conduct the sniff. He testified that safety was on his
mind when he asked backup officers to watch Stewart after
Josie alerted because he knew from his fellow officers that
there were "some pretty serious allegations" of drug dealing
by Stewart. Because Stewart failed to object specifically to the
time taken for calling for backup, the court had no occasion to
rule on whether the seventy-five seconds' used for that task
should be attributed to the dog sniff or to some other proper
purpose of the traffic stop such as officer safety. From the
record that was developed, the government (had it been
alerted to this objection) could have made a non-trivial
argument that the call for backup was related as much to
officer safety as to conducting the dog sniff. Detective Ball
knew he was being asked to stop a felon suspected of selling
drugs moments earlier. As the stop properly progressed, Ball
saw that Stewart was unusually nervous, and learned that the
bulge in Stewart's pocket was a notably large amount of
currency, lending credence to the charge of recent drug
dealing. Ball had to twice direct Stewart to sit on the bumper
As we noted above, seventy-five seconds is the maximum amount of time
taken to call for backup and respond to questions regarding the need for
backup. That includes periods of near-silence. Because Stewart failed to
alert the government and the court that he challenged this period of time,
the record is undeveloped on what Ball was doing during that quiet period.
For at least part of the gaps, he was audibly engaged in tasks related to the
traffic violation. The district court, of course, found that Ball was actively
engaged in conducting the traffic stop throughout the challenged period.
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of his car while Ball worked on the ticket. And as soon as the
two backup officers arrived, Ball asked one officer to watch
Stewart, which would seem to indicate that he was concerned
for his safety even before conducting the sniff. But the government had no opportunity to present evidence or argument on
this point because Stewart failed to timely and specifically
object to this part of the time line.
Nor did Stewart alert the court or the government to his
ultimate claim that "[t]he resulting stop was longer than if Ball
had simply written Stewart a traffic citation," the salient
question under Rodriguez. And so the government had no
reason or opportunity to ask Detective Ball if he could have
finished writing the ticket himself in less time than it took to
conduct the sniff. Again, by listening to the time-indexed
audio, we know that Detective Ball took approximately fortyfive seconds to hand off the ticket to the backup officer (who
was not fully familiar with the new electronic system), and
roughly ninety seconds to run Josie around the car. The officer
working on the ticket was not finished writing it when Josie
alerted. That suggests that some additional amount of time was
needed for any officer to complete the ticket. We are left with
more questions than answers. Was the backup officer diligently
working on the ticket while Detective Ball ran the dog around
the car? Could Detective Ball have completed the ticket in less
time than it took to call for backup, hand off the ticket and run
the dog? Was any of that time attributable to tasks permissibly
related to the mission of the traffic stop? And if so, could
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Detective Ball have completed the ticket more quickly than the
time attributed solely to the dog sniff?'
The reason we have no answers to these questions is that
Stewart failed to raise this specific objection in a timely
manner, when the government could have developed the
record and the court could have ruled on the issue with full
knowledge of the circumstances. From the moment the stop
began to the moment Josie alerted, fewer than sixteen minutes
had elapsed, not an unreasonable amount of time in the
abstract for a ticket for running a red light. We know from the
audio recording that the vast majority of that time was spent
diligently completing tasks related solely to the mission of the
stop. Any uncertainty about the remaining few minutes can be
attributed only to the defendant's failure to raise this objection
in a timely manner. Rodriguez had been on the books for
months, and so the defendant had every opportunity to raise
the issue before the suppression hearing. We will therefore
treat the issue as forfeited and review for plain error.
In order to reverse for plain error, we must find (1) error
(2) that is plain, and (3) that affects the defendant's substantial
rights. Olano, 507 U.S. at 732; Hamad, 809 F.3d at 904. An error
is plain if it is clear or obvious. Olano, 507 U.S. at 734; Hamad,
809 F.3d at 904. And an error affects the defendant's substantial
8
By analyzing Stewart's claim in this fashion, we do not mean to imply
that certain tasks will automatically count against the length of the mission
of a traffic stop so as to prohibit a dog sniff in future cases. We simply
cannot tell on this record how to allocate these tasks because the defendant
failed to timely and specifically object. We leave that analysis for another
day where the parsing of the time line matters to the outcome.
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rights when it is prejudicial, that is, when it has affected the
outcome of the district court proceedings. Olano, 507 U.S. at
734. Finally, "Rule 52(b) leaves the decision to correct the
forfeited error within the sound discretion of the court of
appeals, and the court should not exercise that discretion
unless the error 'seriously affect[s] the fairness, integrity or
public reputation of judicial proceedings." Olano, 507 U.S. at
732 (quoting United States v. Young, 470 U.S. 1, 15 (1985)).
To state the standard is to demonstrate that Stewart cannot
meet it here. He challenges the district court's factual finding
that the sniff did not lengthen the stop. The court determined
that Ball was actively engaged in conducting the traffic stop
before handing off the ticket, and that another officer continued that mission while Ball ran Josie around the Volkswagen.
In other words, the sniff was conducted contemporaneously
with the traffic mission of the stop. Based on the evidence that
the district court had before it, there is no reason to conclude
that this finding was in error. Nothing in the record calls the
court's finding into question, and to the extent that we simply
do not know whether every moment was spent in trafficrelated tasks, the fault for those omissions lies with Stewart.
The district court did not address whether any lengthening
of the stop to conduct the dog sniff was otherwise supported
by reasonable suspicion or probable cause. See R. 70, at 9 n.10
(declining to decide whether Ball independently had probable
cause to search). Because we have concluded that there was no
plain error in the court's finding that the stop was not unconstitutionally lengthened, we need not address whether Detective Ball possessed reasonable suspicion that would have
allowed lengthening the stop in any case. Nonetheless, for the
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sake of completeness we note that, at the time Detective Ball
decided to conduct the sniff, he knew that Stewart was a felon
and a drug trafficker who was being investigated for additional
trafficking and an association with Colon. He knew that,
moments earlier, his fellow officers witnessed Stewart engaged
in an encounter that, in their extensive experience, they
believed to be a drug sale. He knew that Stewart was unusually nervous when stopped for running a red light. And he
knew that Stewart admitted to having $700 in cash in his
pocket. It would be difficult to say that this information would
not supply reasonable suspicion to support a delay of a few
minutes to conduct a dog sniff. In short, the court did not err,
much less plainly err, when it denied Stewart's motion to
suppress the evidence found in the Volkswagen.
Stewart also contends that all evidence obtained as a result
of the traffic stop should have been excluded as the fruit of the
poisonous tree. See Utah v. Strieff, 136 S. Ct. 2056, 2061 (2016)
(the exclusionary rule encompasses both the primary evidence
obtained as a direct result of an illegal search or seizure and
evidence later discovered and found to be derivative of an
illegality, the so-called fruit of the poisonous tree). Obviously,
if the original search was not unlawful, there is no basis to
exclude evidence derived from the original search. The
contraband found in the car formed the basis of a request for
a warrant to search Stewart's home. Because there is no basis
to exclude the evidence found in the car, there is no basis to
exclude the evidence found in the home. Stewart also asserts
that his confession was obtained as a result of the unlawful
search of the car. Again, because there is no reason to exclude
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the evidence found in the car, that search cannot provide a
foundation for excluding Stewart's confession.
B.
We turn to Stewart's contention that the court erred when
it refused to suppress his confession on the separate ground
that it was obtained when the officers ignored his invocation of
his right to remain silent and continued to question him.
Stewart preserved this argument and so we review findings of
fact for clear error and questions of law de novo. United States v.
Wysinger, 683 F.3d 784, 793 (7th Cir. 2012). The Fifth Amendment provides that no person "shall be compelled in any
criminal case to be a witness against himself." Police officers
must warn suspects prior to questioning that they have a right
to remain silent, and if the suspect indicates that he wishes to
remain silent, the interrogation must cease. Maryland v. Shatzer,
559 U.S. 98, 103-04 (2010); Miranda v. Arizona, 384 U.S. 436,
444-45, 473-74 (1966). A person who wishes to invoke his or
her right to remain silent must do so unambiguously. Berghuis
v. Thom pkins, 560 U.S. 370,381-82(2010). "If an ambiguous act,
omission, or statement could require police to end the interrogation, police would be required to make difficult decisions
about an accused's unclear intent and face the consequence of
suppression 'if they guess wrong." Berghuis, 560 U.S. at 382
(quoting Davis v. United States, 512 U.S. 452, 458-59 (1994)).
Stewart asserts that he unambiguously invoked his right to
remain silent by shaking his head "no" in response to a
question from Detective Ball regarding whether he wanted to
talk to a detective. The district court found that "Stewart never
affirmatively and unequivocally invoked his right to remain
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silent." R. 70, at 10. The court noted that Stewart appeared to
shake his head, and that when Ball twice tried to clarify the
meaning of that gesture, Stewart responded by twice asking to
be placed in a car because it was cold outside.
Such responses were not an unambiguous invocation of Stewart's right to remain silent such that
officers were precluded from further questioning
him. Stewart did not tell Ball that he no longer
wished to answer Ball's questions. Nor did he
explicitly state that he did not want to speak with
detectives. As such, Stewart's argument on this
ground must fail.
R. 70, at 10.
We begin with the context of that incident. Wysinger, 683
F.3d at 793-94 (in determining whether a suspect clearly
invoked his or her right to counsel, we consider the circumstances in which the statement was made as well as the words
employed); United States v. Hampton, 675 F.3d 720, 727 (7th Cir.
2012) (objective inquiry into whether suspect invoked right to
counsel includes review of not only the words the suspect used
but also the circumstances in which the statement was made).
See also Berghuis, 560 U.S. at 381-82 (the standards which apply
in determining whether a person has unambiguously invoked
the right to counsel also apply in determining whether a
person has invoked the right to remain silent). As soon as
Detective Ball found a gun in the Volkswagen, he placed
Stewart under arrest and read him his Miranda rights. He then
began asking Stewart about the gun. Stewart freely answered
these questions, telling Ball that his "girl" left the gun in the
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car, denying that his fingerprints or DNA would be found on
the gun, and then changing his story to indicate that he had
fired it at a gun range and that his prints might be on it.
Detective Ball then searched the rest of the car and found the
bag in the trunk that contained drugs and cash. Ball approached Stewart again and said, "That's a lot of drugs, bud.
You want to talk to a detective?" Stewart appeared to shake his
head to indicate "no." Ball clarified, "You do not want to talk
to a detective? Well, you understand I gotta have one come
out." Stewart replied, "Can you put me in the car? It's kind of
cold out." Ball said, "Yes, they're going to talk to you regardless so you'll get in the car at that point. I have a dog in my
car." After this, Ball called for narcotics officers to come to the
scene. In the course of that call, Ball said over the radio:
He's going to need to talk to a narcotics detective at
some point. I don't know if he's going to talk but
maybe if we sit him in a car and explain the seriousness of it, he'll talk to somebody but I've explained
to him that, regardless, when we find the stuff, we
have to have a detective. I don't mean to waste
your time but he doesn't seem like he wants to talk
out in the open. Maybe if we sit him in a car, he'll
want to talk. He originally said he didn't. He's been
Mirandized and everything. But you know our
protocols on the street. We have to call for a detective regardless.
...
Supplemental Appendix, audio disc at 28:25-29:26.
Detective Ball then returned to Stewart and said, "A
detective is going to talk to you. If you want to talk to him, it's
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up to you. I have a protocol to follow. You understand that? I
wear this uniform. I may have a drug dog. I can do all this stuff
but we have to follow our procedures, okay?" Stewart responded, "Can I sit in somebody's car? It's cold out here." Ball
again told him that he had a dog in his squad car. The narcotics
detectives then arrived and Stewart was placed in their car.
Those officers delivered Miranda warnings again, and Stewart
freely spoke to them as he tried to convince them to release
him. He gave a video-recorded statement after being taken to
the police station where he was given his Miranda warnings yet
again and then signed a written waiver before making the
video-recorded statement.
Stewart relies on the head nod as the unambiguous invocation of his right to remain silent. He argues that it is clear from
the audio recording that Detective Ball understood that nod to
mean that he did not wish to speak to the officer. Stewart
contends that Ball was not asking for clarification when he
said, after the head nod, "You do not want to talk to a detective." To Stewart, there is a period on the end of that sentence.
The government contends that it is a question mark. The
district court found that it was a question, a request for
clarification. After listening to the recording, we can find no
clear error in that conclusion. Detective Ball also indicated to
other officers that he was not sure if Stewart would talk, that
he appeared not to want to talk out in the open but that he
might be willing to speak with officers if they sat him in a car.
In context, none of Detective Ball's ensuing comments convince
us that the district court clearly erred.
But in any case, Detective Ball's subjective beliefs do not
govern the outcome here. The inquiry into whether a person
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has actually invoked the right to remain silent is an objective
one. Davis, 512 U.S. at 458-59; Wysinger, 683 F.3d at 793. When
a person "appears" to nod in the negative and then refuses to
clarify the meaning of that gesture, there is no clear error in
concluding that the nod was not an unambiguous invocation
of the right to remain silent. This is especially true in the
circumstances here. Stewart freely spoke to Ball after Miranda
warnings and before the head nod. He refused to clarify the
meaning of the nod and asked to sit in a car because of the
cold. An ambiguous or equivocal reference that causes a
reasonable officer to understand only that the suspect "might
be invoking the right" to remain silent is not enough to require
the cessation of questioning. Davis, 512 U.S. at 459. A reasonable officer would have understood Stewart's apparent nod to
mean that he might be invoking his right to remain silent, and
such an officer would not be required to cease questioning if
the suspect refused to clarify.
C.
Stewart also contends that his convictions for money
laundering must be reversed because the evidence was
insufficient as a matter of law. "Ordinarily, we review a
challenge to the sufficiency of the evidence to determine only
whether any rational trier of fact could have found the essential elements of the crime beyond a reasonable doubt, viewing
the evidence in the light most favorable to the government."
United States v. Webster, 775 F.3d 897,904-05 (7th Cir. 2015). But
Stewart failed to raise this objection in the district court and so
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we review this forfeited claim only for plain error.' Fed. R. Civ.
Proc. 52(b); Olano, 507 U.S. at 731; Webster, 775 F.3d at 905;
United States v. Esterman, 324 F.3d 565, 569-70 (7th Cir. 2003).
Counts V and VI of the indictment charged Stewart with
laundering of monetary instruments in violation of 18 U.S.C.
§ 1956(a)(1)(B)(i).1° Count V specifically charged that, on July
29, 2014, Stewart deposited $2,040 in currency into an Eleete
Image, Inc. account at Chase Bank; that this money was the
proceeds of ongoing narcotics trafficking; that he made the
deposit knowing that the transaction was designed in whole or
in part to "conceal and disguise the nature, location, source,
ownership, and control of the proceeds" of that unlawful
At oral argument, defense counsel confirmed that Stewart had no
objection to the jury instructions, and so any claim regarding the jury
instructions has been waived. United States v. Locke, 759 F.3d 760, 763 (7th
Cir. 2014) (when a defendant intentionally relinquishes or abandons a
known right, the issue has been waived and cannot be reviewed on appeal,
not even for plain error); United States v. Asian, 644 F.3d 526, 540 (7th Cir.
2011) (where a defendant seeks to overturn a verdict for insufficiency of the
evidence but did not challenge his conviction for money laundering in the
district court and did not object to the jury instructions on this count, we
review the conviction for plain error).
10
That statute provides, in relevant part, "Whoever, knowing that the
property involved in a financial transaction represents the proceeds of some
form of unlawful activity, conducts or attempts to conduct such a financial
transaction which in fact involves the proceeds of specified unlawful
activity knowing that the transaction is designed in whole or in part
to conceal or disguise the nature, the location, the source, the ownership, or
the control of the proceeds of specified unlawful activity
shall be
sentenced to a fine
or imprisonment
or both." 18 U.S.C.
§ 1956(a)(1)(B)(i).
...
...
...
..
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activity; and that while conducting and attempting to conduct
this transaction, Stewart knew that the property involved
represented the proceeds of ongoing controlled substances
trafficking activity.11 Count VT charged the same conduct,
changing only the date and the amount of the deposit: on
August 4, 2014, Stewart deposited $2350 into the Eleete Image
bank account.
We previously mentioned Eleete Image, Inc. only once. The
car that Stewart was driving when he was arrested was
registered to that company and the license plates bore the
name "Eleete." In order to address the sufficiency of the
evidence claim on the money laundering counts, some background on Eleete is necessary. The evidence at trial demonstrated that, in 2012, Stewart hired Rosemarie Brown to
incorporate a business for him in the name "Eleete Image, Inc."
Brown filed the necessary paperwork with the state to create
the corporation and also applied for an Employer Identification
Number with the Internal Revenue Service. She listed Stewart
as the business owner in the corporate documents but substituted her own address for the business address on the incorpo11
Although Stewart pointedly did not challenge the jury instructions here,
it is helpful to note that the jury was instructed, consistent with the
language of the indictment and with the Seventh Circuit pattern instructions, that the government must prove beyond a reasonable doubt that
"[t]he Defendant knew that the transaction was designed in whole or in
part to conceal and [sic] disguise the nature, the location, the source, the
ownership, or the control of the proceeds of ongoing drug trafficking
activity.
The term 'conceal or disguise' means to hide the nature, the
location, the source, the ownership, or the control of the proceeds of
specified unlawful activity." R. 137.
...
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ration papers. She also created a website for Eleete, and
testified that Stewart told her that he intended to run a number
of businesses under the "Eleete" name including a food truck
and a cleaning service, among other things. Stewart opened
bank accounts in the company name, including a checking
account with an associated debit card. He was the only
signatory listed on these accounts.
Stewart never ran any legitimate business under the Eleete
name. He had no legitimate source of income, 12 and the
government was able to demonstrate at trial that most of the
money that flowed through the Eleete accounts came from the
sale of illegal drugs. Stewart purchased the Volkswagen he
was driving at the time of his arrest with a check from the
Eleete account. On the memo line, he noted that the check was
for a "company car," and the car was in fact registered to the
company. He also used the Eleete account debit card to make
purchases at retail establishments. For example, the government introduced evidence that Stewart spent approximately
$7400 at Saks Fifth Avenue, including a single purchase of
$1200, all using the Eleete Image debit card rather than large
amounts of cash that might have raised suspicion.
Money entered and left the Eleete accounts in unusual
ways. For example, Stewart gave $10,000 in cash to a friend,
purportedly to enable the friend to buy a car on Stewart's
behalf. The friend never purchased a car, however, and instead
12
Testimony at trial showed that, in the five years preceding his arrest,
Stewart had gambling winnings of $1400, and that he sold a few paintings
for less than $1000 total. That was the extent of any identifiable legitimate
income during that time period.
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returned the money to Stewart by writing three checks to
Eleete Image, including at least one check from the friend's
business account. Stewart also deposited into the Eleete
accounts third party checks totaling more than $66,000 in a
three-year period. These checks, made out to others and
endorsed over to Stewart, outwardly appeared to be paychecks.
At trial, the government argued that Eleete Image was a
"front company," "a scam and a sham." R. 202, at 645-46. The
government contended that Stewart created Eleete Image and
tried to make it look like a legitimate company in order to have
a place to deal with the cash he earned from drug sales.
Possessing and using large amounts of cash, the government
argued, would potentially draw scrutiny, but using a business
account and a business debit card helped prevent suspicion
that the funds were illegitimate. When seeking a bank loan in
2014, for example, Stewart noted on the application that he had
been "employed" by Eleete Image for five years and had an
income of $6700 per month.
In closing arguments, the government went through the
elements of money laundering one by one, associating evidence from the trial with proof of those elements. For the
fourth element of money laundering, whether the defendant
"knew that the transaction was designed in whole or in part to
conceal or disguise the nature, the location, the source, the
ownership, or the control of the proceeds of ongoing drug
trafficking activity," the government argued in closing that the
Eleete business account was designed to hide the nature of the
funds as drug money and to distance Stewart from ownership
of the funds:
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Why does making cash deposits into the Eleete
Image bank account—why does it meet that last
element? Well, as we've discussed, what is the
whole point of this Eleete Image bank account? The
whole point is not to conduct any legitimate business. He had more than two years to do that or to
make something of a start of it.
The point was he is a drug trafficker. That is what he
does for a living. That is what he's done for a living
for years, and he needs to find a way to spend and
use his money in a way that's not going to raise
eyebrows.
So, concealing or disguising the nature or source of
that cash, well, once the cash—we do that financial
transaction, put that somewhat small amount,
couple thousand dollars—once we put that—run it
through into the business account, now we're not
just walking around with several thousand dollars
in our pockets. It's a business account. It looks like
business-related money. It can be spent like
business-related money through the Eleete Image
cards.
Then, of course, it also goes to the ownership or
control, the attempt to hide the ownership or control. It's not Daniel Stewart walking around. It is
Eleete Image who now has the money.
We know it is difficult—certainly the detectives did
it; but it is somewhat difficult to make that leap from
Eleete Image at Dowitch Lane, which we know is
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associated with Rosemarie Brown, to Daniel Stewart
at 4523 Eagle Creek Parkway; but that was the point.
R. 202, at 656-57.
Stewart now claims that this evidence was insufficient as a
matter of law to prove money laundering. Citing Esterman,
Stewart contends that the government was required to prove
that the charged transactions were specifically designed to hide
the provenance of the funds involved. The government failed
to do so here, he argues, because he did nothing more than
deposit money into accounts that he opened, accounts that
could be traced easily back to him. He asserts that the facts of
his case are remarkably similar to the facts in Esterman, where
this court reversed a conviction for money laundering on the
same forfeited insufficiency-of-the-evidence claim that he raises
here. He notes that his name is on the incorporation papers for
Eleete, and that he is the signatory on the Eleete bank accounts.
Having made no attempt to hide behind the Eleete account, the
facts cannot support a finding of concealment under Esterman,
he argues. So we turn to Esterman.
In that case, Gary Esterman opened a bank account at
Edens Bank in Skokie, Illinois, with a Russian business partner
in order to facilitate the financing for a project that the two
were planning in Russia. The business partner returned to
Russia and money began flowing into the Edens Bank account.
Almost as quickly, Esterman began withdrawing money from
the account and transferring it to his G.E. International
Account at Michigan Avenue National Bank. Contrary to his
agreement with his Russian business partner, Esterman
engaged in at least thirty-three separate transactions including
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wire transfers and withdrawals to remove the money from
Edens Bank, taking the money for his own personal use.
Esterman then spent the money in the G.E. account by withdrawing cash or writing checks directly for purchases. 324 F.3d
at 567-68.
Assessing these facts, we noted that we have struggled "to
define precisely what amount of concealment must occur
before mere use of ill-gotten gains becomes money laundering
prohibited by subpart (B)(i) of the statute." 324 F.3d at 570.
Two principles emerged from the cases:
First, we have tried to maintain some separation
between the initial transaction from which illegal
proceeds were derived and further transactions
designed to conceal the source of those proceeds.
Second, we have stressed that the mere transfer and
spending of funds is not enough to sweep conduct
within the money laundering statute; instead,
subsequent transactions must be specifically designed to hide the provenance of the funds involved.
Esterman, 324 F.3d at 570 (internal citations and quotation
marks omitted). To restate the first principle, "money laundering criminalizes a transaction in proceeds, not the transaction
that creates the proceeds." United States v. Mankarious, 151 F.3d
694, 705 (7th Cir. 1998). The government's proof in Esterman
failed because the defendant made no effort to disguise or
conceal either his withdrawals from Edens Bank or the
destination of the funds. He simply made deposits into other
bank accounts that were correctly identified as his and then
spent the money in retail transactions.
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We rejected the government's argument that, because the
Russian business partner was unaware of the existence of the
G.E. account, Esterman's use of that account established an
intent to conceal:
But this is just another way of describing Esterman's
initial fraudulent scheme, whereby he took the
money away from [the Russian business partner].
Most fraud victims probably assume that their
money has either been spent or placed in an account
of some sort, even if they do not know the specific
destination of the funds. If that were enough to
show money laundering at the same time, there
would be no distinction left between money laundering and the underlying fraud, and individuals
who perpetrate simple fraud by transferring
ill-gotten funds into a personal account would
always be triable as money launderers.
Esterman, 324 F.3d at 571-72.
The proceeds at issue in Esterman were generated by fraud.
That is, fraud was the "specified unlawful activity" mentioned
in section 1956(a)(1)(B)(i). In addition to the initial transaction
where Esterman took the money by fraud, the government
failed to prove that he engaged in an additional transaction
that was designed "to hide the provenance of the funds
involved." Instead, he simply deposited the money that he
took by fraud into an easily identifiable account and began to
spend it.
In Stewart's case, the proceeds were created by the specified unlawful activity of drug trafficking. In transactions that
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are readily identifiable as separate from the original crime,
Stewart took the cash generated from that drug trafficking and
engaged in a series of steps designed to conceal or disguise that
money as business proceeds rather than drug money. With
those same steps, he sought to distance himself from personal
ownership of the funds. He incorporated a business using a
false address and then took several steps to make the business
appear legitimate. He obtained an Employer Identification
Number from the IRS and created a website. He opened a bank
account in the name of the business and enlisted others to help
him deposit drug proceeds into the account in a manner that
would cause outsiders to believe the money was income to the
business. On the two charged occasions, he simply deposited
relatively small amounts of cash into the business account at
ATMs. He then spent that money, sometimes on items that
could probably be identified as strictly personal and sometimes
on items, like his car, that he titled in the name of his sham
business.
In short, this was not an Esterman-style scheme, where the
defendant did little more than take money, store it and spend
it. Esterman required "concrete evidence of intent to disguise or
conceal transactions, whether that evidence comes directly
from statements by the defendant that indicate an intent to
conceal, or from circumstantial evidence like unusual secrecy
surrounding transactions, careful structuring of transactions to
avoid attention, folding or otherwise depositing illegal profits
into the bank account or receipts of a legitimate business, use
of third parties to conceal the real owner, or engaging in
unusual financial moves culminating in a transaction." 324 F.3d
at 573. Stewart's machinations surrounding the Eleete bank
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account supply the necessary circumstantial evidence. Under
the usual standard for a sufficiency of the evidence claim, we
can easily conclude that a rational jury could have found the
essential element of concealment (the only element challenged)
beyond a reasonable doubt, viewing the evidence in the light
most favorable to the government. Webster, 775 F.3d at 904-05;
Asian, 644 F.3d at 540. Under the even more stringent standard
of plain error, this is not a close case, and the money laundering convictions must be affirmed.
III.
Finally, we note that Stewart raised a number of challenges
to the admission of evidence that he characterizes as prejudicial
and irrelevant "bad acts" evidence. Stewart asks us to review
the admission of most of that evidence for plain error and some
of it for abuse of discretion, depending on whether he preserved the particular objection in the district court. The
government asserts both that the evidence was properly
admitted and that, in any event, if there was error, it was
harmless. We agree that any error in admitting the challenged
evidence was harmless. "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." United States v. Curtis, 781 F.3d 904,
911 (7th Cir. 2015). The evidence against Stewart was overwhelming. United States v. Gonzalez, 863 F.3d 576, 588-89 (7th
Cir. 2017) (evidentiary error found harmless where there was
overwhelming admissible evidence of guilt). The admissible
evidence included kilogram quantities of drugs, five firearms,
and nearly half a million dollars in cash. The prosecution's case
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would have been no less persuasive had the challenged
evidence been excluded.
AFFIRMED
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This is a copy of a public record, reproduced as it was published. It is not legal advice, and it may not be the version a court would rely on. Check the official source before you cite it.