United States v. Robert Pennington, Jr.

Opinion

In the

United States Court of Appeals For the Seventh Circuit

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No. 23-3315 UNITED STATES OF AMERICA, Plaintiff-Appellee,

v.

ROBERT L. PENNINGTON, JR., Defendant-Appellant.

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Appeal from the United States District Court for the Central District of Illinois.

No. 2:18-cr-20021 — Sara Darrow, Judge.

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ARGUED JANUARY 17, 2025 — DECIDED SEPTEMBER 4, 2026

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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. Suspecting Pennington had drugs in his vehicle, however, the police 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 eventually 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 selective enforcement, which was also denied without a hearing . On appeal, Pennington challenges the denial of both motions . 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 registration . 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, Sergeant 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 license .

1 District Court Dkt. 17-1, Flack Video at 1:03.

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While running Pennington’s information, Sergeant Flack received a caution message. He contacted dispatch, who advised him that Pennington was possibly affiliated with a street gang, had an unspecified criminal history, and had surrendered his license in 2008. Sergeant Flack then questioned dispatch whether it had received a response yet from Kentucky regarding whether Pennington’s driver’s license was valid, and dispatch responded that it had not.

Immediately, Sergeant Flack returned to the car Pennington was driving, accepted the insurance information that Pennington 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 Pennington ’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 explained that about a year ago he had gotten back his previously 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 Pennington had anything in his car like the drugs from his 4 No. 23-3315

previous drug charges or whether a dog would alert to anything in the car he was driving, to which Pennington responded “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, explained it to him, and returned Pennington’s other documents . 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 Pennington , he asked whether Pennington would consent to a vehicle 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,” because Sergeant Flack “[did not] care about personal use.” Pennington 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 probation , to which Pennington said “no.” Pennington exited Sergeant Flack’s vehicle about three minutes after Sergeant Flack gave him the warning and returned his other documents.2

2 Id. at 24:22.

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Pennington returned to his vehicle and continued up Interstate 57.

Following this interaction, Sergeant Flack sent a message from his in-car computer to the in-car computer used by Illinois State Police Sergeant and canine officer John Lillard. Sergeant 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 leaving 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 spotted the car Pennington was driving and observed him improperly pull in front of a semi-truck. Sergeant Lillard initiated a traffic stop based on improper lane usage. After explaining the reason for the stop, Sergeant Lillard asked Pennington 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 explained 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).

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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 eventually 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.” Sergeant 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 Pennington ’s car while Trooper Dorsey wrote the warning for improper 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 improper 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

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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 vehicle . Sergeant Lillard completed the dog sniff about a minute later.

Once the canine alerted to the presence of controlled substances , Sergeant Lillard conducted a search of Pennington’s vehicle and discovered crack cocaine. Pennington was arrested 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 inception 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 Pennington 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 prolonged 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 pretrial conference and addressed a number of Pennington’s pretrial motions concerning its ruling on the previous motion to suppress. In addition to requesting reconsideration of arguments 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 independent reasonable suspicion for the second stop. Accordingly , the district court denied Pennington’s requests for reconsideration on the motion to suppress.

Before trial, Pennington moved to dismiss the superseding indictment based on vindictive prosecution and selective enforcement . The district court denied that motion without an evidentiary hearing. With respect to the vindictive prosecution claim, the district court found Pennington had not shown he was prosecuted for any impermissible reason. Next, the

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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, reserving his right to appeal the denial of his suppression motions 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 superseding indictment without an evidentiary hearing. We address 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, Pennington ’s term of imprisonment ended on April 17, 2025. His conviction and term of supervised release, however, remained intact. Thus, the commutation 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).

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considering all the evidence, we cannot avoid or ignore a definite 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 determinations 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 Constitutional 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 exemption , 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 circumstances 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 required 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

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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 license , seek the vehicle’s registration, request proof of insurance , 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 related 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 vehicles on the road are operated safely and responsibly.” Rodriguez , 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) (unrelated questioning); Illinois v. Caballes, 543 U.S. 405, 408 (2005) (dog sniff). But if there is no independent reasonable suspicion 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 unrelated 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 unreasonably prolonged. From this, Pennington argues the district court 12 No. 23-3315

should have suppressed the drugs Sergeant Lillard discovered during the second traffic stop.

1. First Traffic Stop Pennington argues Sergeant Flack unreasonably prolonged the first stop by continuing to investigate whether Pennington possessed drugs after Sergeant Flack printed Pennington ’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 Pennington ’s warning, explained it to him, and returned his license 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 camera , 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 demanded ” to support prolonging the stop. Id. at 355.

So, because Sergeant Flack continued to question Pennington after the stop’s mission had concluded, Sergeant Flack unreasonably prolonged the first stop. The government offers two counterarguments, but neither persuade.

First, it contends Pennington’s detention ended once Sergeant Flack printed the warning and handed back his

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documents, so any questioning beyond that point was just a consensual encounter. But the “retention or return of documentation 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 reasonable 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 Sergeant Flack finished his continued questioning. After printing Pennington’s warning, Sergeant Flack continued to ask Pennington 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 vehicle , 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 retained 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.

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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 Sergeant 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 exclusionary rule should operate to suppress the drugs recovered 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 suppression ’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 illegal 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

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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 between the unconstitutional act and the discovery of evidence .” Strieff, 579 U.S. at 238. One such exception is the attenuation doctrine. Id. Under that doctrine, evidence is admissible “when the connection between unconstitutional police conduct and the evidence is remote or has been interrupted by some intervening circumstance, so that ‘the interest protected by the constitutional guarantee that has been violated would not be served by suppression of the evidence obtained .’” Id. (quoting Hudson, 547 U.S. at 593).

To evaluate whether the second stop was sufficiently attenuated 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 factors ). “In the final analysis, however, the question is still whether the evidence came from ‘the exploitation of that illegality 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 Sergeant Flack’s unlawful first stop and Sergeant Lillard’s second stop of Pennington. This is sufficient to support attenuation . Cf. Davis, 44 F.4th at 689 (concluding 45 minutes between initial entry and voluntary consent was sufficient for attenuation ).

Second, the presence of intervening circumstances also favors the government. Sergeant Lillard had independent reasonable 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) (explaining an officer’s reasonable belief that a driver committed even a minor traffic violation supports a traffic stop). Pennington ’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 collectively 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

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after observing a traffic violation. Indeed, Sergeant Lillard testified that he followed Pennington for a while but had no reason to stop Pennington until Pennington’s subsequent traffic violation. And any subjective motivation Sergeant Lillard may have harbored does not undermine his independent justification for stopping Pennington. See United States v. Bass, 325 F.3d 847, 850 (7th Cir. 2003) (“Any ulterior motive an officer 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 inquiry 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 officer ’s initial Terry stop was mistaken, but “his conduct thereafter 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 unreasonably prolonged first stop was not a “wanton and purposeful … 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 deterrence function.

Taken all together, the drugs Sergeant Lillard discovered during the second stop were sufficiently attenuated from Sergeant Flack’s unreasonably prolonged first stop. For that reason , 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 redundant with Sergeant Flack’s checks from an hour earlier. Pennington 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 Pennington to sit in the patrol car or whether he had weapons, to check Pennington’s records again, and to conduct other questioning .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 particularized suspicion of dangerousness,” United States v. Goodwill , 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.

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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]fficers 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 performing 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 information 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 dissent ’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 mission . Those questions were either related to the traffic stop itself 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 permissible 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 continue 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 warning . “An officer may conduct certain unrelated checks—including a dog sniff—during a lawful traffic stop, but he may not do so in a way that prolongs the stop, absent the reasonable suspicion ordinarily demanded to justify detaining an individual .” Lewis, 920 F.3d at 491 (quotation marks omitted). The government does not contend Sergeant Lillard had independent reasonable suspicion to justify the sniff, so the

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“critical question” is whether the sniff prolonged the stop. Rodriguez , 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 Sergeant 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 (quotation marks omitted).

Lastly, Pennington takes issue with Trooper Dorsey subbing 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 delayed ” 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 characterization 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 rejected 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 depend 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 unconstitutionally prolonged beyond the time reasonably required , so suppression of the drugs eventually obtained during 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 review 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 App. Dkt. 25, Pennington Br., at 28– 31; App. Dkt. 39, Pennington Reply Br., at 21–22). Accordingly, we limit our discussion to the selective enforcement theory he maintains on appeal.

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an indictment. United States v. Skoczen, 405 F.3d 537, 546 (7th Cir. 2005). We review the denial of an evidentiary hearing for abuse of discretion. See United States v. Curlin, 638 F.3d 562, 564 (7th Cir. 2011) (reviewing denial of evidentiary hearing on motion to suppress for abuse of discretion).

Selective enforcement occurs when police investigate people with one protected characteristic but do not investigate similarly-situated people without that protected characteristic . See Conley v. United States, 5 F.4th 781, 789 (7th Cir. 2021). Such a protected characteristic includes one’s exercise of his constitutional rights. See United States v. Kerley, 787 F.2d 1147, 1148 (7th Cir. 1986) (per curiam). Because selective enforcement is an equal protection claim,7 it requires proof that a law enforcement officer’s “actions had a discriminatory effect and were motivated by a discriminatory purpose.” Conley, 5 F.4th at 789. “A plaintiff must show discriminatory purpose ‘in his case.’” Id. (quoting McCleskey v. Kemp, 481 U.S. 279, 292 (1987)). “And discriminatory purpose implies more than … awareness of consequences. It implies that the decisionmaker … selected or reaffirmed a particular course of action at least in part because of, not merely in spite of, its adverse effects upon an identifiable group.” Id. (quotation marks omitted).

To obtain an evidentiary hearing on a selective enforcement claim, Pennington initially had to make “a prima facie case based on facts sufficient to raise a reasonable doubt” about the officers’ purpose. Kerley, 787 F.2d at 1148 (citation

7 “The Equal Protection Clause of the Fourteenth Amendment applies

only to the States, but it has been ‘reverse-incorporated’ to apply to the federal government as a component of the Fifth Amendment’s Due Process Clause.” Conley, 5 F.4th at 788 n.1 (citing Bolling v. Sharpe, 347 U.S. 497, 498–500 (1954)).

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modified). Pennington contends that because Sergeant Lillard stopped him for refusing Sergeant Flack’s requested consent search, he met his prima facie burden of showing the Sergeants singled him out and enforced traffic laws against him for exercising his constitutional rights.

The record, however, belies that contention. Pennington does not contest on appeal that Sergeant Lillard independently observed him commit a traffic violation. And even though Sergeant Lillard may have been looking for Pennington ’s car based on Sergeant Flack’s suspicions and could have pulled over other vehicles while looking for Pennington, Pennington has not shown the drivers of those vehicles were otherwise similarly situated to him. Nor has Pennington shown that Sergeant Lillard pulled him over “at least in part because of, not merely in spite of,” Pennington’s exercise of his constitutional rights, not the traffic violation. Conley, 5 F.4th at 789 (citation modified). For these reasons, Pennington has not raised a reasonable doubt about whether the Sergeants acted with a discriminatory purpose.

Resisting this conclusion, Pennington argues the record developed during the evidentiary hearing on his motion to suppress was insufficient to evaluate the Sergeants’ subjective intent for purposes of his selective enforcement claim. Not so. It is true that the district court did not rely on the Sergeants’ subjective intent when it denied Pennington’s motion to suppress . But the record is still more than sufficient to evaluate whether Pennington met his burden of raising a reasonable doubt about the Sergeants’ purpose. As shown above, he did not meet that burden.

No. 23-3315 25

Thus, the district court did not abuse its discretion when it denied an evidentiary hearing on Pennington’s motion to dismiss the superseding indictment against him.

III. CONCLUSION

For these reasons, we AFFIRM.

26 No. 23-3315

HAMILTON, Circuit Judge, dissenting. I respectfully dissent.

Defendant Pennington was subjected to two unreasonable stops that went beyond even the wide latitude given to police officers in traffic stops. The two officers coordinated their stops and engaged in redundant records checks that prolonged the second stop beyond what was needed to carry out the permissible mission, contrary to Rodriguez v. United States, 575 U.S. 348 (2015).

Before explaining my disagreement, I must note my agreement with the majority on two key issues. First, I agree that Sergeant Flack unreasonably prolonged the first traffic stop by continuing to question Pennington after he had issued the warning citation that was the ostensible purpose of the stop. Second, I agree that Pennington was not free to leave during that questioning. Ante at 12–14. By now virtually all litigated traffic stops have audio and video recordings. If the government wants to show that detention has ended, courts should reasonably expect the recording to include an express statement by the officer that the suspect is now free to go. (Such verbal assurances may sometimes be meaningless, though. For example, in United States v. Lopez, 907 F.3d 472, 487 (7th Cir. 2018), one officer assured the detained suspect that he was “free to go” while other officers still had his vehicle, his keys, and his cellphone.)

My disagreement focuses on the length of the second stop. That second stop was carried out by Sergeant Lillard in coordination with Sergeant Flack, who had been frustrated by Pennington’s lawful choice not to consent to a search of his vehicle at the first stop. Based on information from Sergeant Flack before even making the second stop, Sergeant Lillard knew everything he needed to issue the planned warning

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except Pennington’s name. He found the name in just a few moments. Yet Sergeant Lillard repeated the same records checks that Sergeant Flack had conducted just an hour earlier, and he found out just what Sergeant Flack had found out. Those redundant records checks prolonged the second stop by roughly ten minutes and seem to have enabled the dog sniff that led to the discovery of the contraband. 1 Given the coordination between the officers, we should recognize that the delay violated Pennington’s rights under Rodriguez, much as the Ninth Circuit concluded in a similar case. In United States v. Gorman, 859 F.3d 706 (9th Cir. 2017), as in this case, one officer conducted an unlawfully prolonged traffic stop but let the driver go without searching his vehicle. Id. at 715. As in this case, the first officer alerted other officers ahead on the road that they should look for that vehicle and try to search it. Id. at 717. And as in this case, a second officer made a second stop and conducted redundant records checks

1 The majority reads the testimony of Sergeant Lillard differently, ante

at 19, but makes its own findings to the effect that the redundant records checks did not delay the second stop. That theory differs from the district court’s. In my view, the district court erred by disregarding both the link between the two stops and the effects of Sergeant Lillard’s redundant records checks. The district court did not make the finding the majority makes for itself. See A141-44. The court said that information Sergeant Lillard already had “really isn’t relevant because everything that Trooper Lillard did during the course of his traffic stop that was supported by probable cause was in the normal course of things.” A141. When Sergeant Lillard stopped Pennington, he already had vehicle registration and insurance information and Sergeant Flack’s report on the driver’s criminal history . The only new information Sergeant Lillard needed was Pennington’s name. There was thus no need to take up the usual time that would be needed for an independent stop where the officer starts without any driver and vehicle information.

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that unnecessarily prolonged that second stop. The delay enabled a dog sniff of the vehicle, and an eventual search that turned up $167,000 in hidden cash that had been in contact with illegal drugs. The Ninth Circuit reasoned that the two coordinated stops needed to be evaluated together, and the court held that the currency had been seized in violation of the Fourth Amendment. Id. at 718–19. We should follow that reasoning and apply the exclusionary rule here.

The majority asserts, though, that there was sufficient “attenuation” between Sergeant Flack’s first illegal stop and Sergeant Lillard’s second stop prolonged by the redundant records checks. See ante at 15–17, applying factors from Brown v. Illinois, 422 U.S. 590, 603–04 (1975). That analysis asks the reader to squint and wear blinders at the same time, rewarding gamesmanship by law enforcement. See Gorman, 859 F.3d at 719; United States v. Foreste, 780 F.3d 518, 525–26 (2d Cir. 2015) (“looking only to whether independent traffic violations support successive traffic stops would create a rule subject to … gamesmanship”).

It is true, as the majority says, that the lane change provided the pretext that could authorize the second stop. See Whren v. United States, 517 U.S. 806 (1996). But it is naïve to suggest that the second stop was not caused by the first stop and Sergeant Flack’s frustrated request for other officers to make a further stop. Contrary to the majority’s analysis, the issue here is not whether Sergeant Lillard could lawfully stop Pennington at all. The problem is the way he carried out the stop, prolonging it unnecessarily with the redundant records checks that he did not need because of the coordination with Sergeant Flack. See Gorman, 859 F.3d at 716 & n.5; Foreste, 780

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F.3d at 525–26; United States v. Ilazi, 730 F.2d 1120, 1125 (8th Cir. 1984) (noting need to consider successive stops together).

As for “the purpose and flagrancy of the officers’ conduct,” the officers were obviously well trained in Fourth Amendment law and the Rodriguez limits on traffic stops. They chose to push those boundaries past the breaking point. Their purposes had nothing to do with traffic safety and everything to do with drug interdiction. Under Whren they were empowered to use traffic stops as pretexts for drug investigations, but only within Fourth Amendment standards of reasonableness. Enforcing the exclusionary rule here would promote both the purpose of the Fourth Amendment and the exclusionary rule itself. We should reverse Pennington’s conviction.