United States v. Robert Pennington, Jr.
CourtCourt of Appeals for the Seventh Circuit
Date FiledSeptember 4, 2026
Docket23-3315
JudgeHamiltondissents
StatusPublished
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Full Opinion
In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 23-3315
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
ROBERT L. PENNINGTON, JR.,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Central District of Illinois.
No. 2:18-cr-20021 — Sara Darrow, Judge.
____________________
ARGUED JANUARY 17, 2025 — DECIDED SEPTEMBER 4, 2026
____________________
Before SYKES, HAMILTON, and PRYOR, Circuit Judges.
PRYOR, Circuit Judge. While driving on Interstate 57, Robert
Pennington, Jr. was stopped twice in less than two hours for
minor traffic violations. He was allowed to leave the first stop
with only a warning and without a search of his vehicle. Sus-
pecting Pennington had drugs in his vehicle, however, the po-
lice officer notified a canine officer positioned up the highway
of his suspicions. The canine officer identified Pennington’s
vehicle, observed Pennington commit another traffic
2 No. 23-3315
infraction, and pulled him over. That second traffic stop even-
tually culminated in a dog sniff, leading to the discovery of
drugs in Pennington’s car. Pennington moved to suppress
those drugs, which the district court denied after a hearing.
Pennington then moved to dismiss the indictment filed
against him based on claims of vindictive prosecution and se-
lective enforcement, which was also denied without a hear-
ing. On appeal, Pennington challenges the denial of both mo-
tions. For the reasons provided below, we affirm.
I. BACKGROUND
A. Factual Background
1. First Traffic Stop
On January 23, 2018, Illinois State Police Master Sergeant
Mark Flack observed Pennington driving eight miles per hour
over the speed limit on Interstate 57 near Effingham, Illinois.
Sergeant Flack stopped Pennington’s vehicle and approached
the passenger side window.1
Sergeant Flack explained that he had stopped Pennington
for speeding, and requested his driver’s license and registra-
tion. After Pennington could not readily locate his insurance
information, Sergeant Flack indicated that he would review it
when he returned from his police vehicle. Before leaving, Ser-
geant Flack also told Pennington that he would issue only a
warning if everything checked out. Sergeant Flack then went
back to his squad car with Pennington’s Kentucky driver’s li-
cense.
1 District Court Dkt. 17-1, Flack Video at 1:03.
No. 23-3315 3
While running Pennington’s information, Sergeant Flack
received a caution message. He contacted dispatch, who ad-
vised him that Pennington was possibly affiliated with a
street gang, had an unspecified criminal history, and had sur-
rendered his license in 2008. Sergeant Flack then questioned
dispatch whether it had received a response yet from Ken-
tucky regarding whether Pennington’s driver’s license was
valid, and dispatch responded that it had not.
Immediately, Sergeant Flack returned to the car Penning-
ton was driving, accepted the insurance information that Pen-
nington produced, and requested Pennington to join him in
the front of his squad car so they did not have to shout over
traffic to communicate.
Still waiting for a response from Kentucky on Penning-
ton’s license, Sergeant Flack, once inside the squad car, asked
Pennington about his travel plans and employment. While
Pennington sat beside Sergeant Flack, the dispatcher advised
over the radio that she had received Pennington’s criminal
history, including a 2009 conviction involving 50 pounds of
marijuana and a 2001 conviction for driving with a suspended
license. The dispatcher also noted that she had about 20 more
pages of information which she was reviewing regarding
Pennington’s criminal history. Meanwhile, Pennington ex-
plained that about a year ago he had gotten back his previ-
ously suspended license. The dispatcher then reported that
Pennington had drug trafficking convictions from 2005 and
2011. A short while later, the dispatcher advised that she had
received Pennington’s driver’s license status from Kentucky
and that the license was valid.
At that point, Sergeant Flack questioned whether Pen-
nington had anything in his car like the drugs from his
4 No. 23-3315
previous drug charges or whether a dog would alert to any-
thing in the car he was driving, to which Pennington re-
sponded “no.” Sergeant Flack then stated that Pennington
seemed nervous. Pennington responded that he was nervous
any time he was around police officers because they “kill
Black people.” Sergeant Flack replied that Pennington was
“watching too much TV, that ain’t true.”
Next, Sergeant Flack printed Pennington’s warning, ex-
plained it to him, and returned Pennington’s other docu-
ments. After giving Pennington the warning, Sergeant Flack
again said that Pennington appeared nervous and asked if he
was sure there was nothing in the car. Pennington said no,
and that he is nervous any time he is around police officers.
After Sergeant Flack explained again why he stopped Pen-
nington, he asked whether Pennington would consent to a ve-
hicle search due to his nervousness. Pennington said no, and
Sergeant Flack agreed not to search the car but noted that he
believed Pennington was “up to something.”
Sergeant Flack insisted that Pennington was nervous, and
after Pennington defended himself, Sergeant Flack asked
whether he had “a little bit of personal use or … a lot,” be-
cause Sergeant Flack “[did not] care about personal use.” Pen-
nington explained that he had nothing and asked whether he
could continue on his way. Sergeant Flack did not respond
and instead asked Pennington if he was on parole or proba-
tion, to which Pennington said “no.” Pennington exited Ser-
geant Flack’s vehicle about three minutes after Sergeant Flack
gave him the warning and returned his other documents.2
2 Id. at 24:22.
No. 23-3315 5
Pennington returned to his vehicle and continued up Inter-
state 57.
Following this interaction, Sergeant Flack sent a message
from his in-car computer to the in-car computer used by Illi-
nois State Police Sergeant and canine officer John Lillard. Ser-
geant Flack explained to Sergeant Lillard that Pennington had
denied his request for a search, described the make and model
of the car Pennington was driving, and shared Pennington’s
drug-related criminal history. Sergeant Lillard told Sergeant
Flack that he would “keep an eye out for it,” and Sergeant
Flack shared which direction Pennington traveled after leav-
ing the first stop.
2. Second Traffic Stop
About an hour after Pennington had been released from
the first traffic stop with Sergeant Flack, Sergeant Lillard spot-
ted the car Pennington was driving and observed him im-
properly pull in front of a semi-truck. Sergeant Lillard initi-
ated a traffic stop based on improper lane usage. After ex-
plaining the reason for the stop, Sergeant Lillard asked Pen-
nington to exit his vehicle. Sergeant Lillard had Pennington
raise his shirt to ensure he was not carrying a weapon, then
directed Pennington to his squad car.3 Sergeant Lillard ex-
plained the traffic violation to Pennington and indicated that
he would issue Pennington a warning. Sergeant Lillard had
3 The first seven minutes of the video lack audio, so we rely on Sergeant
Lillard’s testimony from the motion to suppress hearing for the beginning
of the stop. At the hearing, Sergeant Lillard stated that the first few
minutes of audio were not recorded due to user error, but he manually
turned on his microphone about six minutes and fifty seconds into the
video. (District Court Dkt. 17-4, Lillard Video; Dkt. 24 at 71–72).
6 No. 23-3315
trouble, however, logging into the in-car computer database
system to complete the written warning, which delayed the
stop.
Sergeant Lillard’s computer issues persisted, so he even-
tually called the Illinois State Police help desk for assistance.
The call lasted for approximately four minutes, and Sergeant
Lillard’s computer issues were eventually resolved. During
the wait time, Sergeant Lillard inquired about Pennington’s
trip and criminal history. Sergeant Lillard also explained
again why he stopped Pennington and that he was going to
issue Pennington a warning for improper lane usage. Not
long after, Trooper Luke Dorsey, whom Sergeant Lillard had
radioed for assistance, also arrived on the scene.
After terminating the call to the help desk, Sergeant Lillard
asked Pennington if he had any guns, drugs, or large sums of
money in the car, to which Pennington responded “no.” Ser-
geant Lillard then asked if there was anything illegal in the
vehicle, which Pennington again denied. Sergeant Lillard said
“okay,” and that he would take his canine around Penning-
ton’s car while Trooper Dorsey wrote the warning for im-
proper lane usage. Pennington then asked what the purpose
of the dog sniff was, and Sergeant Lillard responded that it
was because he could conduct the sniff and because he was
not prolonging the traffic stop as Trooper Dorsey would be
writing the warning.
When Pennington prodded further about the purpose of
the dog sniff when he had been pulled over for only an im-
proper lane usage, Sergeant Lillard explained that every so
often he would run his canine during a traffic stop, especially
when he has help from another officer. Sergeant Lillard and
Trooper Dorsey switched places. After allowing the canine to
No. 23-3315 7
relieve itself, Sergeant Lillard began walking the dog around
Pennington’s vehicle. About 90 seconds later, and before
Trooper Dorsey issued the warning to Pennington, the canine
alerted to the presence of controlled substances within the ve-
hicle. Sergeant Lillard completed the dog sniff about a minute
later.
Once the canine alerted to the presence of controlled sub-
stances, Sergeant Lillard conducted a search of Pennington’s
vehicle and discovered crack cocaine. Pennington was ar-
rested on scene.
B. Procedural Background
A federal grand jury returned a superseding indictment
charging Pennington with one count of possessing with the
intent to distribute 28 grams or more of a mixture or substance
containing cocaine base, in violation of 21 U.S.C. § 841(a)(1),
(b)(l)(B)(iii).
Pennington moved to suppress the drugs found during
Sergeant Lillard’s traffic stop. He made four arguments in
support: (1) Sergeant Lillard lacked reasonable suspicion to
stop Pennington; (2) Sergeant Lillard unreasonably delayed
writing Pennington’s warning so he could conduct a dog
sniff; (3) the two traffic stops were impermissibly coordinated
to circumvent Rodriguez v. United States, 575 U.S. 348 (2015),
and United States v. Rodriguez-Escalera, 884 F.3d 661 (7th Cir.
2018); and (4) Sergeant Lillard had no independent probable
cause to justify prolonging the traffic stop.
At the conclusion of the evidentiary hearing on the motion
to suppress, the district court denied Pennington’s request. It
first concluded Sergeant Lillard’s stop was justified at its in-
ception because the officer had probable cause, or at least
8 No. 23-3315
reasonable suspicion, to stop Pennington for improper lane
usage. The court credited Sergeant Lillard’s testimony and
video evidence as supporting this conclusion. The court then
reasoned that the first stop conducted by Sergeant Flack was
irrelevant to the lawfulness of Sergeant Lillard’s subsequent
stop because Sergeant Lillard independently observed Pen-
nington commit a traffic violation. The court next found that
the dog sniff did not unreasonably prolong Sergeant Lillard’s
stop because the stop “didn’t extend beyond the purpose of
writing the written warning,” and that the stop was not pro-
longed just to conduct the dog sniff. The court also found the
total duration of Sergeant Lillard’s stop was reasonable given
the technical difficulties he encountered.
In preparation for trial, the district court conducted a pre-
trial conference and addressed a number of Pennington’s pre-
trial motions concerning its ruling on the previous motion to
suppress. In addition to requesting reconsideration of argu-
ments he had made previously, Pennington argued Sergeant
Flack unlawfully prolonged the first traffic stop, rendering
evidence obtained from Sergeant Lillard’s subsequent stop
the “fruit of a poisonous tree.” The district court rejected that
argument, reasoning Sergeant Lillard had developed inde-
pendent reasonable suspicion for the second stop. Accord-
ingly, the district court denied Pennington’s requests for re-
consideration on the motion to suppress.
Before trial, Pennington moved to dismiss the superseding
indictment based on vindictive prosecution and selective en-
forcement. The district court denied that motion without an
evidentiary hearing. With respect to the vindictive prosecu-
tion claim, the district court found Pennington had not shown
he was prosecuted for any impermissible reason. Next, the
No. 23-3315 9
court rejected the selective enforcement claim, providing two
reasons: (1) the officers developed sufficient objective reasons
to stop Pennington, so any pretextual motivations the officers
may have harbored were irrelevant; and (2) Pennington failed
to show he was treated differently than similarly situated
members of a protected class.
Pennington then entered a conditional plea agreement, re-
serving his right to appeal the denial of his suppression mo-
tions and his motion to dismiss the superseding indictment.
The district court sentenced Pennington to a term of ten years’
imprisonment followed by eight years of supervised release.4
He now appeals.
II. ANALYSIS
Pennington challenges both the denial of his motion to
suppress and the denial of his motion to dismiss the super-
seding indictment without an evidentiary hearing. We ad-
dress each in turn.
A. Motion to Suppress
“When reviewing the denial of a suppression motion, we
assess conclusions of law de novo and findings of fact for clear
error.” United States v. Avila, 106 F.4th 684, 692 (7th Cir. 2024).
“A factual finding is clearly erroneous only if, after
4 After oral argument, former President Biden granted Pennington clem-
ency and commuted his sentence of imprisonment. Accordingly, Penning-
ton’s term of imprisonment ended on April 17, 2025. His conviction and
term of supervised release, however, remained intact. Thus, the commu-
tation of Pennington’s prison term did not moot his appeal—he could still
benefit from success on appeal because his term of supervised release
could still be affected. See Pope v. Perdue, 889 F.3d 410, 414 (7th Cir. 2018);
United States v. Raney, 797 F.3d 454, 461 n.6 (7th Cir. 2015).
10 No. 23-3315
considering all the evidence, we cannot avoid or ignore a def-
inite and firm conviction that a mistake has been made.”
United States v. Devalois, 128 F.4th 894, 899 (7th Cir. 2025)
(quoting United States v. Yang, 39 F.4th 893, 899 (7th Cir.
2022)). We also afford “special deference to credibility deter-
minations made by the district court.” Avila, 106 F.4th at 692.
The Fourth Amendment prohibits unreasonable searches
and seizures. U.S. CONST. amend. IV. “Because of this Consti-
tutional protection, police officers ordinarily need probable
cause to stop someone for the seizure to be reasonable.” Avila,
106 F.4th at 693. The Supreme Court has carved out an exemp-
tion, however, for routine traffic stops. Id. For an initial traffic
stop to pass constitutional muster, the officer must reasonably
believe that he observed a traffic violation. Id. (citing United
States v. Cole, 21 F.4th 421, 427 (7th Cir. 2021) (en banc) (noting
that because traffic stops are typically brief detentions they
require only reasonable suspicion of a traffic violation—not
probable cause)).
A traffic stop is reasonable only if it was “justified at its
inception, and reasonably related in scope to the circum-
stances which justified the interference in the first place.” Cole,
21 F.4th at 427 (quoting Hiibel v. Sixth Jud. Dist. Ct. of Nev., 542
U.S. 177, 185 (2004)). “A traffic stop may, however, ‘become
unlawful if it is prolonged beyond the time reasonably re-
quired to complete the mission of’ the stop.” Avila, 106 F.4th
at 693 (quoting Rodriguez, 575 U.S. at 354–55). “‘Authority for
the seizure thus ends’ when the mission is ‘or reasonably
should have been’ accomplished.” Devalois, 128 F.4th at 898
(quoting Rodriguez, 575 U.S. at 354).
“The mission of a traffic stop … is ‘to address the traffic
violation that warranted the stop and attend to related safety
No. 23-3315 11
concerns.’” Cole, 21 F.4th at 428 (quoting Rodriguez, 575 U.S. at
354). Part of this mission includes “ordinary inquiries incident
to [the traffic] stop.” Rodriguez, 575 U.S. at 354 (alteration in
original). For example, “[p]olice may check the driver’s li-
cense, seek the vehicle’s registration, request proof of insur-
ance, and investigate whether there are warrants out for the
driver’s arrest.” Devalois, 128 F.4th at 898–99 (citing United
States v. Gholston, 1 F.4th 492, 496 (7th Cir. 2021), and Yang, 39
F.4th at 903). The officer may also typically ask questions re-
lated to the stop, such as questions about the driver’s travel
plans. See Cole, 21 F.4th at 430. “These checks serve the same
objective as enforcement of the traffic code: ensuring that ve-
hicles on the road are operated safely and responsibly.” Ro-
driguez, 575 U.S. at 355.
Officers may also “engage in certain additional activities”
beyond the stop’s mission, “as long as they do ‘not prolong
the traffic stop.’” Devalois, 128 F.4th at 899 (quoting Cole, 21
F.4th at 429). This includes asking questions unrelated to the
stop’s mission and conducting a dog sniff. Cole, 21 F.4th at
429; see also Arizona v. Johnson, 555 U.S. 323, 333 (2009) (unre-
lated questioning); Illinois v. Caballes, 543 U.S. 405, 408 (2005)
(dog sniff). But if there is no independent reasonable suspi-
cion to justify those activities, they are lawful only if they do
not prolong the traffic stop. See Rodriguez-Escalera, 884 F.3d at
668 (“Absent reasonable suspicion … , law enforcement may
not extend a traffic stop with measures like a dog sniff unre-
lated to the mission of the stop.”).
Pennington maintains that both the first stop by Sergeant
Flack and the second stop by Sergeant Lillard violated his
Fourth Amendment rights because each stop was unreasona-
bly prolonged. From this, Pennington argues the district court
12 No. 23-3315
should have suppressed the drugs Sergeant Lillard discov-
ered during the second traffic stop.
1. First Traffic Stop
Pennington argues Sergeant Flack unreasonably pro-
longed the first stop by continuing to investigate whether
Pennington possessed drugs after Sergeant Flack printed Pen-
nington’s warning and handed back his documents.
The district court did not reach whether Sergeant Flack
unreasonably prolonged the first traffic stop, but we have no
trouble concluding he did. First, Sergeant Flack printed Pen-
nington’s warning, explained it to him, and returned his li-
cense and insurance documents. These actions concluded the
mission of the traffic stop: issuing a warning to Pennington
for speeding. Rodriguez, 575 U.S. at 354. But Sergeant Flack,
suspecting Pennington was “up to something,” continued to
question Pennington. Sergeant Flack asked why Pennington
appeared to be nervous; whether he had drugs in the car;
whether he would consent to a search of the car; and whether
he was on parole or probation. From the police vehicle’s cam-
era, it is clear this line of questioning lasted approximately
three minutes after Sergeant Flack issued Pennington the
warning. And the record does not suggest Sergeant Flack, at
that point, had “the reasonable suspicion ordinarily de-
manded” to support prolonging the stop. Id. at 355.
So, because Sergeant Flack continued to question Penning-
ton after the stop’s mission had concluded, Sergeant Flack un-
reasonably prolonged the first stop. The government offers
two counterarguments, but neither persuade.
First, it contends Pennington’s detention ended once Ser-
geant Flack printed the warning and handed back his
No. 23-3315 13
documents, so any questioning beyond that point was just a
consensual encounter. But the “retention or return of docu-
mentation is not dispositive” in evaluating when a seizure
ends. United States v. Finke, 85 F.3d 1275, 1281 (7th Cir. 1996).
“In assessing whether a person has been seized, we look to
the totality of the circumstances and ask whether ‘a reasona-
ble person would feel free to terminate the encounter.’”
United States v. Lopez, 907 F.3d 472, 487 (7th Cir. 2018) (quoting
United States v. Drayton, 536 U.S. 194, 201 (2002)).
Here, a reasonable person in Pennington’s position would
not have felt free to leave Sergeant Flack’s squad car until Ser-
geant Flack finished his continued questioning. After printing
Pennington’s warning, Sergeant Flack continued to ask Pen-
nington whether he had illegal drugs in the car, whether he
was on parole or probation, and whether he would consent to
a search of the car. See United States v. Borys, 766 F.2d 304, 311
(7th Cir. 1985) (explaining consensual encounter ripened into
investigative stop when agents told defendant they suspected
him of transporting drugs and sought permission to search
his luggage). During that continued questioning, Pennington
asked if he was free to leave but did not receive an answer.
And this questioning occurred in Sergeant Flack’s police ve-
hicle, an enclosed space he controlled. See United States v.
Smith, 794 F.3d 681, 685 (7th Cir. 2015) (explaining police
questioning in an enclosed space like an alley is less likely to
be consensual than questioning in “open, populated spaces”);
cf. Lopez, 907 F.3d at 487 (explaining detention continued
while multiple officers blocked the defendant’s exit and re-
tained his vehicle, keys, and phone). No reasonable person in
Pennington’s shoes would have felt free to ignore Sergeant
Flack’s continued questioning and leave the vehicle without
responding.
14 No. 23-3315
Second, the government argues Pennington’s nervousness
justified Sergeant Flack’s continued questioning, as the stop’s
officer-safety purpose remained intact until Pennington left
Sergeant Flack’s vehicle. But the “officer safety interest stems
from the mission of the stop itself.” Rodriguez, 575 U.S. at 356.
As explained above, the stop’s mission concluded once Ser-
geant Flack printed Pennington’s warning and returned his
documents. Sergeant Flack’s continued questioning, even if
taken as safety precautions, detoured beyond that mission.
See id. The government’s interest in officer safety does not
save Sergeant Flack’s post-mission questioning.
But even though Sergeant Flack unreasonably prolonged
the first stop in violation of Pennington’s Fourth Amendment
rights, that alone is not enough to justify suppression here.
Recall that Pennington ultimately seeks to suppress the drugs
found during the second traffic stop; Sergeant Flack did not
recover any drugs during the first stop. To show that the ex-
clusionary rule should operate to suppress the drugs recov-
ered during the second stop based on the illegality of the first
stop, Pennington must demonstrate the first stop’s illegality
tainted the second stop. His challenge to the first stop falters
at this step.
The exclusionary rule requires suppression of evidence
seized in violation of the Fourth Amendment when suppres-
sion’s deterrence benefits outweigh its substantial social costs.
United States v. McGill, 8 F.4th 617, 624 (7th Cir. 2021) (citing
Utah v. Strieff, 579 U.S. 232, 237 (2016)). The rule “encompasses
both the primary evidence obtained as a direct result of an il-
legal search or seizure and … evidence later discovered and
found to be derivative of an illegality, the so-called fruit of the
poisonous tree.” Strieff, 579 U.S. at 237 (quotation marks
No. 23-3315 15
omitted). Suppression is a “last resort,” not a “first impulse.”
Hudson v. Michigan, 547 U.S. 586, 591 (2006).
The Supreme Court has recognized multiple exceptions to
the exclusionary rule involving “the causal relationship be-
tween the unconstitutional act and the discovery of evi-
dence.” Strieff, 579 U.S. at 238. One such exception is the at-
tenuation doctrine. Id. Under that doctrine, evidence is admis-
sible “when the connection between unconstitutional police
conduct and the evidence is remote or has been interrupted
by some intervening circumstance, so that ‘the interest pro-
tected by the constitutional guarantee that has been violated
would not be served by suppression of the evidence ob-
tained.’” Id. (quoting Hudson, 547 U.S. at 593).
To evaluate whether the second stop was sufficiently at-
tenuated from the first, three factors guide our analysis:
(1) the temporal proximity between the two stops, (2) the
presence of intervening circumstances, and, particularly,
(3) the purpose and flagrancy of the official conduct. United
States v. Davis, 44 F.4th 685, 689 (7th Cir. 2022); see also Brown
v. Illinois, 422 U.S. 590, 603–04 (1975) (identifying these fac-
tors). “In the final analysis, however, the question is still
whether the evidence came from ‘the exploitation of that ille-
gality or instead by means sufficiently distinguishable to be
purged of the primary taint.’” United States v. Green, 111 F.3d
515, 521 (7th Cir. 1997) (quoting Wong Sun v. United States, 371
U.S. 471, 488 (1963)).
Here, the discovery of drugs during the second stop was
sufficiently attenuated from the unlawful first traffic stop.
First, the amount of time that passed between the two stops
favors the government. The temporal proximity factor weighs
in favor of attenuation only if “substantial time” passes
16 No. 23-3315
between the unlawful act and when the evidence is found.
Strieff, 579 U.S. at 239. About an hour passed between Ser-
geant Flack’s unlawful first stop and Sergeant Lillard’s sec-
ond stop of Pennington. This is sufficient to support attenua-
tion. Cf. Davis, 44 F.4th at 689 (concluding 45 minutes between
initial entry and voluntary consent was sufficient for attenua-
tion).
Second, the presence of intervening circumstances also fa-
vors the government. Sergeant Lillard had independent rea-
sonable suspicion to pull Pennington over for the second stop,
as he observed Pennington improperly pull in front of a semi-
truck and initiated the second traffic stop on that basis. See
United States v. Jackson, 962 F.3d 353, 357 (7th Cir. 2020) (ex-
plaining an officer’s reasonable belief that a driver committed
even a minor traffic violation supports a traffic stop). Pen-
nington’s independent traffic violation—unrelated from the
first stop’s justification—severed the causal chain between the
two stops.
Pennington resists this conclusion, arguing both stops col-
lectively constitute a single, coordinated investigative effort
by both officers. He relies on United States v. Gorman, 859 F.3d
706 (9th Cir. 2017), where the Ninth Circuit held the fruit of
the poisonous tree doctrine applied when officers’ first illegal
stop “significantly directed” law enforcement’s actions in
conducting the second stop that yielded the evidence. See id.
at 716–17.
The same cannot be said here. Gorman is not persuasive as
applied to this case’s facts because even though Sergeant
Lillard knew Pennington had not consented to Sergeant
Flack’s earlier request to search, Pennington’s refusal did not
taint Sergeant Lillard’s decision to initiate a second traffic stop
No. 23-3315 17
after observing a traffic violation. Indeed, Sergeant Lillard tes-
tified that he followed Pennington for a while but had no rea-
son to stop Pennington until Pennington’s subsequent traffic
violation. And any subjective motivation Sergeant Lillard
may have harbored does not undermine his independent jus-
tification for stopping Pennington. See United States v. Bass,
325 F.3d 847, 850 (7th Cir. 2003) (“Any ulterior motive an of-
ficer may have for making the stop is irrelevant.” (citing
Whren v. United States, 517 U.S. 806, 813 (1996))). Simply put,
Pennington’s intervening traffic violation severed the causal
connection between the two stops.
The final attenuation factor—the purpose and flagrancy of
the officers’ conduct—also favors the government. This in-
quiry centers on “whether law enforcement acted in bad
faith.” Davis, 44 F.4th at 689. This matters “because we do not
employ the exclusionary rule when ‘suppression would do
nothing to deter police misconduct.’” Id. (quoting Davis v.
United States, 564 U.S. 229, 232 (2011)). Although Sergeant
Flack’s continued questioning unreasonably prolonged the
first stop, Sergeant Lillard’s initial decision to pull Pennington
over was lawful. And, as discussed below, Sergeant Lillard’s
initial determination and conduct during the second traffic
stop was also lawful. See Strieff, 579 U.S. at 241–42 (holding
this factor “strongly favor[ed]” the government when of-
ficer’s initial Terry stop was mistaken, but “his conduct there-
after was lawful”). There’s also “no indication” that Sergeant
Flack’s prolonged questioning “was part of any systemic or
recurrent police misconduct.” Id. at 242. Sergeant Flack’s un-
reasonably prolonged first stop was not a “wanton and pur-
poseful … Fourth Amendment violation,” Brown, 422 U.S. at
602–03, so suppressing the drugs Sergeant Lillard discovered
18 No. 23-3315
in the second stop would not serve the exclusionary rule’s de-
terrence function.
Taken all together, the drugs Sergeant Lillard discovered
during the second stop were sufficiently attenuated from Ser-
geant Flack’s unreasonably prolonged first stop. For that rea-
son, suppression based on the first stop is not warranted.
2. Second Traffic Stop
Pennington also argues suppression is warranted because
Sergeant Lillard unreasonably prolonged the second traffic
stop. We disagree.
Pennington first argues Sergeant Lillard unreasonably
prolonged the stop by conducting checks that were redun-
dant with Sergeant Flack’s checks from an hour earlier. Pen-
nington contends Sergeant Lillard already knew Pennington
had no outstanding warrants and had insurance, a license,
and registration, so Sergeant Lillard did not need to ask Pen-
nington to sit in the patrol car or whether he had weapons, to
check Pennington’s records again, and to conduct other ques-
tioning.5
None of those actions, however, unreasonably prolonged
the stop. Sergeant Lillard could ask Pennington “to sit in the
police car for the duration of [the] traffic stop without any par-
ticularized suspicion of dangerousness,” United States v. Good-
will, 24 F.4th 612, 615 (7th Cir. 2022), as a request to move into
the squad car was “reasonably incidental” to the stop, United
States v. Lewis, 920 F.3d 483, 492 (7th Cir. 2019). Sergeant
Lillard also appropriately “attend[ed] to … safety concerns”
related to the stop by asking Pennington whether he had any
5 Sergeant Lillard did not conduct a protective frisk for weapons.
No. 23-3315 19
weapons. Cole, 21 F.4th at 428 (quoting Rodriguez, 575 U.S. at
354); see also Goodwill, 24 F.4th at 615 (explaining that “[o]ffic-
ers reasonably fear for their safety during traffic stops” for
many reasons, including because “a driver can have a hidden
weapon”). And when officers conduct a traffic stop, “they are
entitled to demand the driver’s identification, of course, and
it is routine to check the driver’s record for active warrants,
driving history, and criminal history. Those checks are done
for important reasons, including officer safety.” United States
v. Simon, 937 F.3d 820, 833 (7th Cir. 2019) (quoting Swanigan v.
City of Chicago, 881 F.3d 577, 586 (7th Cir. 2018)); see also United
States v. Sanford, 806 F.3d 954, 956 (7th Cir. 2015) (“The trooper
checked the occupants’ criminal histories on the computer in
his car—a procedure permissible even without reasonable
suspicion … .”). Sergeant Lillard did not have to rely on the
check run earlier that afternoon; he was entitled to conduct
his own check of Pennington’s records and criminal history.
Relying on the Ninth Circuit’s decision in United States v.
Gorman, 859 F.3d at 717–19, the dissent argues that Sergeant
Lillard impermissibly extended the second stop by perform-
ing redundant database checks. We respectfully disagree. The
mission of the second stop was to issue Pennington a warning
for improper lane usage. As Sergeant Lillard prepared that
warning—which was delayed by a software malfunction—he
simultaneously accessed Pennington’s background infor-
mation through a separate software program. Because these
checks occurred while he was preparing the warning and did
not divert from the stop’s mission, we cannot accept the dis-
sent’s view that they unreasonably prolonged the stop.
Next, despite Pennington’s contention otherwise, most of
Sergeant Lillard’s questioning before the dog sniff—like his
20 No. 23-3315
questions about Pennington’s travel plans, criminal history,
and gang involvement—fall squarely within the stop’s mis-
sion. Those questions were either related to the traffic stop it-
self or to safeguarding Sergeant Lillard’s safety during the
stop. See Rodriguez, 575 U.S. at 354; Cole, 21 F.4th at 429–30.
And even if some of Sergeant Lillard’s other questioning did
not relate to the stop’s mission, that questioning was still per-
missible unless it prolonged the stop. See Cole, 21 F.4th at 429.
The district court found Sergeant Lillard’s questioning did
not fall within this category, and we agree. This questioning
occurred while Sergeant Lillard was still trying to log into his
computer and write the warning. This alone distinguishes
Sergeant Lillard’s actions from scenarios where officers con-
tinue to question and investigate the suspect after the Terry
stop’s justification had already evaporated, like Sergeant
Flack engaged in during the first stop. See Lopez, 907 F.3d at
475, 486 (holding officers unreasonably prolonged stop when
they suspected the defendant of drug trafficking based on an
informant’s tip, opened the defendant’s bags, and found no
contraband, but continued to detain and question him). From
this, we cannot say the district court clearly erred in finding
Sergeant Lillard’s questioning did not prolong the stop.
Pennington also argues Sergeant Lillard unreasonably
prolonged the stop when he conducted a canine sniff while
Trooper Dorsey finished writing Pennington’s traffic warn-
ing. “An officer may conduct certain unrelated checks—in-
cluding a dog sniff—during a lawful traffic stop, but he may
not do so in a way that prolongs the stop, absent the reasona-
ble suspicion ordinarily demanded to justify detaining an in-
dividual.” Lewis, 920 F.3d at 491 (quotation marks omitted).
The government does not contend Sergeant Lillard had inde-
pendent reasonable suspicion to justify the sniff, so the
No. 23-3315 21
“critical question” is whether the sniff prolonged the stop. Ro-
driguez, 575 U.S. at 357.
The district court found Sergeant Lillard did not delay the
stop by conducting the dog sniff. This is a factual finding we
review for clear error. See Gholston, 1 F.4th at 497. The district
court credited the officers’ testimony that it takes between 10
to 15 minutes to enter a written warning. The court also found
that the additional four minutes of technical difficulties Ser-
geant Lillard endured while trying to write the ticket was not
a purposeful delay. And because Sergeant Lillard completed
the dog sniff about 20 minutes after initiating the traffic stop,
the court found the stop was not delayed to conduct the sniff
and the stop’s overall duration was not too long. Given the
officers’ credible testimony and the video evidence, these
findings do not leave us with a “definite and firm conviction
that a mistake has been made.” Devalois, 128 F.4th at 899 (quo-
tation marks omitted).
Lastly, Pennington takes issue with Trooper Dorsey sub-
bing in to finish writing the warning while Sergeant Lillard
conducted the dog sniff, contending this swap unreasonably
added time to the stop. But “so long as the transfer of duties
does not prolong a traffic stop, the officer who begins to write
a citation need not be the one to complete it.” Devalois, 128
F.4th at 900. And the court found the stop “wasn’t even de-
layed” by the officers trading duties. This factual finding was
not clearly erroneous. Sergeant Lillard messaged Trooper
Dorsey to assist with the traffic stop. Nothing in the record
shows Sergeant Lillard stopped working on the warning until
the officers switched places in Sergeant Lillard’s vehicle.
This is also why the district court’s alternative characteri-
zation of any delay from this tradeoff as “de minimis” does not
22 No. 23-3315
carry the day for Pennington. He is correct that Rodriguez re-
jected a de minimis rule for extensions of a stop. See 575 U.S. at
356–57; see also Lopez, 907 F.3d at 486 (explaining the question
of whether a stop was unreasonably prolonged “does not de-
pend on exactly how many minutes the stop lasts,” as “a 15-
minute stop would be too long if the investigation justifying
the stop finished at the 14-minute mark”). But in evaluating
the district court’s factual findings, we look to the substance
of those findings and may still affirm when the court did not
clearly err in finding the stop was not extended at all. See
Gholston, 1 F.4th at 497–98 (holding that although the district
court “chose[] imperfect language” in characterizing officer’s
delays as de minimis, it nonetheless stayed within the bounds
of Rodriguez because “the court found that [the officer] did not
extend the stop at all, not that any delay was permissibly de
minimis”). That’s what happened here. In short, the officers
switching roles did not render the stop here unreasonable.
In sum, the second stop by Sergeant Lillard was not un-
constitutionally prolonged beyond the time reasonably re-
quired, so suppression of the drugs eventually obtained dur-
ing that stop was not warranted.
B. Motion to Dismiss
Pennington also challenges the district court’s decision to
deny without an evidentiary hearing his motion to dismiss
the superseding indictment for selective enforcement.6 We re-
view de novo a district court’s denial of a motion to dismiss
6 Pennington appears to have abandoned on appeal the vindictive prose-
cution theory he pressed below. (See