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# United States Court of Appeals Forthe Seventh Cir c uit

No. 16-4105

U NI T E D S TAT E S OF A M E RI C A , Plaintiff-Appellee,

v.

D ANI E L S T E W

AR T , Defendant-Appellant.

Appea l fro m the U ni ted S ta tes Di stri ct Co urt fo r the S o uthern Di stri ct o f Indi ana, Indi ana po l i s Di v i si on. No . 1 :1 5-cr-0 0 0 2 4 -WTL-DKL-1 — Willia m T. La wre nce , Judg e.

A RGU E D M ARC H 30, 2018

— D E C I D E D S E PT E MB E R 5, 2018

Befor e E A S T E R

B R OO K a n d R OVN E R

, Circuit Judges , and G I L B E R T , District Judge

. *
R OVN E R , Cir cuit Judge. Dani el Stew ar t w as conv i cted of dr u g tr affi cking, fi r ear ms offenses, and m oney launder ing, pr im a r i ly based on ev i dence gather ed as a r esult of a tr affi c

* Of the S outhern Di stri ct o f Il l i no i s, si tti ng b y desi gna ti on.2 No. 16-4105 stop and a subsequent confessi on. W e affi r m the di s tr i ct cour t’s deni al of S tew ar t’s moti on to suppr ess the tr affi c stop ev i dence and the c onfessi on, and w e r ej ect S tew a r t’s addi ti on a l clai ms on appeal.
I. On Januar y 20, 2015, Detecti v es Jeff S e quin and R y an V a nOev er en w er e sur v ei lling the home o f Dani el S tew a r t. S tew a r t w as not the main focus o f thei r inv esti gati on. For months, Indi anapoli s poli ce had been tr yi n g t o g a th e r ev i dence about a lar ge-scale cocaine suppli er ulti mately i dentif ied as Ger aldo Colon. In May 2014, wi th the assi stance of the feder al Dr ug Enfor cement Agency , they ar r ested thr ee Ar i zona-based

cour i er s wh o w er e br inging dr ugs in to Indi anapoli s. One of those cour i er s, Juan Li zar r a g a, began cooper ati ng w i th the inv esti gator s a nd pr ov i ded infor mati on that led the offi cer s to

a maj or customer of Colon. Li zar r aga di d not k n o w the customer by name but he knew the apar tment c omplex wher e the cu stomer li v ed, and he had seen Colon deli v er dr ugs to the customer at that a par tment complex a n d a lso at Colon’s fur ni tur e s tor e. L iz a r r a g a o ffe r ed the offi cer s a gener al physi cal descr i pti on of the customer

. Ov er a per i od of sev er al months, offi c er s sur v ei lled Colon’s fur ni tur e stor e. Dur ing that ti me, they twi ce obser v ed S tew ar t

v i si t the stor e, once on October 23, 2 014, and once on D ecember 16, 2014. On each o c c asi on, S tew ar t stay ed only a shor t ti me and made no pur chase. Thr ough fur ther inv esti gati on, the offi cer s i denti fi ed Stew ar t and lear ned that h e l iv e d in the apar tment complex poi n ted out b y Li zar r a ga. S tew ar t had a
cr i min al r ecor d that included felony dr ug offenses. In ear lyNo. 16-4105 3 Januar y 2015, beli ev ing that S tew ar t w as the customeri d enti

fi ed by Li zar r aga, they began to sur v ei l S tew a r t in an a ttempt to connect hi m to Colon’s dr ug tr a ffi cking. In the ear ly ev ening of Januar y 2 0, 2 015, Detecti v es V a nOev er en and S equin follow ed S tew ar t’s whi te V olksw agen fr om hi s a p a rtment complex to a S h ell gas stati on. After S tew a r t pulled up to a pu m p , another m an exi ted a gr ey c ar that w as p ar ked a t the stati on, and w alked ov er to the passenger si de of S tew a rt’s car

. The m an got into S tew ar t’ s c a r a nd closed the door

. A few minutes l ater , the man exi ted Stew ar t’s

car and i mmedi a t e l y left the stati on in the gr ey car

. S tew ar t then got out of hi s V

olksw a gen and pumped gas. Alt h o u gh t h e y could not see thr ough S tew ar t’s ti nted win dows fr o m thei r v antage poi nt some ei ghty y ar d s aw ay , based on thei r many y ear s of exper i ence inv esti gati ng dr ug cr i mes, V a nOev er en and S equin beli ev ed that they had j ust wi tnessed a dr ug sale at the gas stati on. They deci ded to w a tch S tew ar t’s car for tr affi c v i olati ons and to attempt a tr affi c stop. B ecause they w er e in plain clothes and unmar ked car s, t hey called Detecti v e Br ady Ball to the

scene in hi s squad car

. Detecti v e Ball speci a li zed in dr ug inter d i c ti on stops, and he tr av eled wi th Josi e, a dog who had been tr ain ed to detect the scent of i llegal dr ugs. Detecti v e Ball testi fi ed that he ar r i v ed in the ar ea in ti me to s ee S tew ar t fai l to stop at a r ed l i ght when he made a r i ght tur n, the same
v i olati on obser v ed by th e o t her detecti v es. 1 Detecti v e Ball

1 The di s tri ct co urt fo und tha t so me a mb i gui ty ex i sted i n the reco rd a s to whether Ba l l hi msel f s a w S t ewa rt fa i l to sto p or whether he e ffected the (co nti nued...)4 No. 16-4105

acti v a ted hi s l i ghts and S tew ar t pulled ov er in the par ki ng lot of a S peedw ay gas stati on. Detecti v e B a ll r ecor ded the audi o of his encounter wi th S tew a r t a nd s o the tr i al cour t had a d e t a i led, ti me-indexed

a ccount of ev er ythi ng that w as sai d dur ing the stop. 2 At t he suppr essi on hear ing, Detecti v e Ball supplemented thi s r ecor ding wi th hi s per sonal obser v ati ons and r ecollecti on. Detecti v e Ball explained to S tew a rt the r eason for the stop a nd asked for

r outine infor mati on such as li cense and r egi str ati on. S tew ar t
se e m e d unusually ner v ous, fi dgeti ng wi th h i s w allet and taki ng sev er al deep br eaths as he compl ie d wi th Ball’s requests. Because the car w as r egi ster ed to a busin ess name d “Eleete Image, Inc.” and because S tew ar t’s a d d r ess w as di ffer ent fr om that on the r egi str ati on, Ball asked for clar i fi cati on. Ball also asked questi ons r elated to offi c er safety such as whether S tew ar t h ad any guns or kni v es in the car o r o n h is per son. S tew a r t deni ed hav ing any w eapons. Ball a sked S t ew ar t to exi t the car and si t on the bumper

. He n oted tha t S tew a r t’s ti nted windows wer e “ b or d er line” i llegal and a sked

1 (...co nti nued) sto p o n the b a si s o f Va nOev eren’s repo rt tha t Stewa rt fa i l ed t o sto p. Under the co ll ecti v e kno wl edge do ctri n e, Ba l l wa s enti tl ed to sto p S tewa rt b a sed

o n the tra ffi c v i o l a t i o n wi tnessed a n d repo rted b y Va nOev eren. See United States v
. Contreras , 8 2 0 F.3 d 2 55 , 2 6 8 ( 7 th Ci r. 2 0 1 6 ) (under the co l l ecti v e kno wl edge do ctri ne, the co urt ma y a ttri b ute fa cts kno wn to o ne o ffi cer to
o ther o ffi cers).

2 The a udi o reco rd i n g w a s sub mi t t ed to the di stri ct co u rt a s a n ex hib i t a t the suppressi o n hea ri ng wi tho u t a sepa ra t e reco rd numb er. S t e wa rt suppl i ed i t to thi s co urt a s a co mpa ct di sc a tta ched to hi s suppl ementa l

a ppendi x

.No. 16-4105 5

i f S tew a r t h a d ev er been ar r ested. S tew ar t responded that he had been ar r ested on dr ug char ges “ a long ti me ag o .” Ball asked for consent to sear ch the car and S tew ar t declin ed. Ball noti ced a b ulge in S tew ar t’s pocket and asked h i m what i t w as. S tew a r t r epli ed that i t w as $700 in c a s h

. B a l l then r etur ned to hi s s quad c ar to r u n the li cense and r egi str ati on infor mati on as
w ell a s a check for outstanding w ar r ant s

. S econds later , Ball

w as back out of hi s car , a gai n asking S tew ar t to si t on the bumper. Fi v e minutes had elapsed at thi s point in the stop.
Moments a fter r etur ning t o t h e squad car , Ball r adi oed a
r equest for backup. H e e xplained that he w as on a n in ter di cti on stop and w an t e d to r un hi s dog a r ound the car

. He

r equested that offi cer s ar r i v e as qui ckly as possi ble. It appear s fr om the a u di o r ec or ding that Ball c onti nued to w or k on the tr affi c v i olati on as he w ai ted fo r a r e sp onse to hi s request for backup, but an e s t im a t e of the ti me attr ibuted to calling for backup w ould be at most sev enty-fi v e seconds. 3
As h e w ai ted for backup to ar r i v e, Detecti v e Ball c onti nued the pr ocess of checking the l i cense and r egi str ati on, r unnin g a

3 A l l references to the a udi o rec o r d i ng wi l l b e gi v en in the fo rma t mi nutes:seco nds el a psed fro m the b egi nni ng o f Detecti v e Ba ll ’s enco unter wi th S tewa rt. Ba l l ’ s ca ll fo r b a ckup b ega n a t 5 :1 1. Fro m 5 :2 3 to 6 : 0 1 , the

reco rdi n g co nsi s ts of o cca si o na l el ectro ni c b eeps, un d eci pherab le ra di o tra nsmi s si o ns and peri o ds of si l ence. Fro m 6 :0 1 to 6 :0 9 , fro m 6 : 5 0 t o 7 :0 4 , a nd fro m 7 :1 6 to 7 :1 9 , Ba l l s u p pl i ed a ddi ti o na l info rma ti o n ab o u t hi s l o ca ti o n a nd hi s need fo r b a ckup. In the mi dst o f wa i t i ng fo r a repl y on hi s request, a t 6 :2 5, Ba l l ca n b e hea rd b egi n n i n g t o r u n a check on the ca r’s regi s tra ti o n under the na me, “El eete.” We esti ma te tha t the t i m e spent
ca ll i n g fo r b a ckup, ex cl udi ng a u d i o co n t ent cl ea rl y rel a t ed to the t ra ffi c mi ssi o n o f the sto p, i s a t mo st sev enty-fi v e seco nds.6 No. 16-4105
check for outstanding w ar rants, a nd begin ning to wr i te the ti cket. Appr o x im a tely thi r teen m inutes into the stop, whi le Detecti v e Ball w as sti ll c ompleti ng tasks r elated to wr i ting the t i ck e t , th e b a c ku p o ffi cer s ar r i v ed. For appr oxi mately for ty-five seconds, D etecti v e B all spoke to the backup offi cer s, e x p laining to one offi cer how to complete the electr oni c ti cket-wr i ti ng pr ocess (whi ch w as appar ently n ew), and a sking the other offi cer to keep a w a tch ov er S tew ar t. Ball then r em o v e d J osi e fr om hi s car a nd w alked her a r o u nd S tew ar t’s car

. On her second p a s s ar ound the V olksw agen, Josi e aler ted to the dr i v er ’s si de door

. The enti r e pr ocess of Josi e exi tin g the squad

car , sni ffing, and then a ler ti ng took one m inute and for ty-fi v e seconds. The backup offi cer w as sti l l w or king on the ti cket when J osi e al e r ted. Detecti v e B a ll offer ed fur ther adv i ce on completing the ti cket, and then appr oached S tew ar t. He explai ned to S tew ar t that Josi e had aler ted t o the odor of i llegal dr ugs, and he handcuffed S tew a r t, clar i fying that he

w as not under ar r est. Detecti v e Ball explai ned at the suppr essi on hear in g that he felt thi s w as n ecessary for offi cer safety based on the descr i pti on of t h e s uspected gas stati on dr ug tr ansacti on, Josi e’s aler t, and the backgr ound infor mati on that he had l e a r ned about S tew ar t pr i or to making the stop. Beli ev ing he n ow had pr obable cause to sear ch the car , he began to inspect the inter i or of S tew ar t’s V olksw agen. See Florida v
. Harris , 5 68 U.S

. 237, 246–47 ( 2013) ( c e r ti fi c ati on of a dog by a bona fi de or gani zati on after testi ng the dog’s r eli ab i li ty i n a contr olled setti ng or successful completion of ar ecent tr ain ing pr ogr am that ev aluated the dog’s p r ofi c i ency in locati ng dr ugs cr eates a rebuttable pr esumpti on that the dog’s aler t p r ov i des pr obable cause to sear ch). Almost i mmedi ately ,No. 16-4105 7

Detecti v e B a ll found a handgun in the cen t e r c o n sole ar ea, wi thin r each of the dr i v er ’s seat. Knowing that S tew a r t w as a
c o nv i cted felon, he now had pr obable cause for an a r r e s t

. S e e 18 U.S .C. § 922(g)(1). He placed S tew ar t under ar r est and gav e hi m Miranda w ar nin gs. He then c onti nued hi s sear ch of the car

. Although he found no d r u gs in the passenger compar tment of the car , h e found a bag in the tr unk containin g appr oxi mately 102 gr ams of cr a ck cocaine, 250 gr ams of powder cocaine, 241 gr ams of her oi n, 1 9 gr ams of methamphetamine, and a di gi tal scale. H e also found $ 7 ,420 in ca sh

. T h e pur por ted $700 in S tew a r t’s pocket tur ned out to be $1,904, for a total of $9,324 in cash.
Detecti v e Ball appr oached S tew ar t agai n a nd sai d, “ That’s

a l ot of dr ugs, bud. Y

ou w ant to talk to a de t e ct iv e?” S tew ar t appear ed to shake hi s h e a d to indi cate “no.” B all clar i fi ed, “Y ou do not w ant to talk to a detecti v e? W ell, y ou under stand I gotta hav e one come out.” S tew ar t r epli ed, “Can y ou put me in the car ? It’s ki nd of cold out.” 4 Ball sai d, “Y es, they’r e goi ng to talk to y ou r egar dless so y ou’ll get in the car a t that poi nt. I hav e a dog i n my c ar .” Ball then r adi oed for nar c oti c s offi cer s to come to the scene. W e wi ll di scuss that call and t h e s u bsequent inter change betw een Ball and S tew ar t m or e completely below when w e addr ess S tew ar t’s moti on to suppr ess hi s confe s sion. Ev entually S tew ar t w a s placed in the car of the

nar coti c s offi cer s when they ar r i v ed on the scene.

4 Tempera tures ho v ered b etween thi rty-ei ght an d fo rty-o ne degrees o n thi s Ja nua ry da y, a nd S tewa rt wa s wea ri ng pa nts, a swea tshi rt a nd t enni s sho es.8 No. 16-4105

V a nOev er en and S equin w er e the offi cer s who a r r iv e d to tr anspor t S tew a r t. V

anOev er en r e minded Stew ar t of hi s Miranda ri ghts and asked i f Stew ar t w ante d t o talk ab out the gun, n a r coti cs and cash found in hi s car

. Stew a r t fi r st tr i ed to t a l k the detecti v es into r eleasing hi m for a shor t per i od , pr omi sing to meet them l ater to assi st them in thei r inv esti gati on. The offi cer s declined and gav e S tew ar t tw o opti ons: come wi th the detecti v es to the poli ce stati on to di scuss hi s s i tuati on
or go str a i ght to the Mar i on County Jai l. S tew ar t opted to go to the poli c e stati on w it h the detecti v es. Once ther e, offi cer s br o ug h t S tew a r t in to an inter v i ew r oom a nd Detecti v e R y an Clar k gav e Stew ar t hi s Miranda r i ghts. S te w a r t in di cated that he under stood hi s r i ghts and h e s igned a wr i tten w a i v er of those r i ghts. He then made incr i minatin g statements that w er e
v i deo-r ecor d ed. In the m eanti me, offi cer s obtain e d a sear ch

w ar r ant for hi s r esi dence. The affi dav i t suppor ti ng the w a r r ant detai led the cash, dr ugs a nd gun found in the car

. The sear ch of S tew ar t’s home yi elded an a ddi ti onal 1650 gr ams of cocaine; 1005 gr ams of methamphetamine; 1 500 gr ams of her oin ; four

mor e handguns; and $487,542 in cash. S tew a r t w as char ged in a si x-count indi ctment wi th p o s s e ssi on w i th intent to di str ibute contr olled substances, in
v i olati on of 21 U.S .C. §§ 841 a nd 851; possessi on of a fi r ear m b y
a felon, in v i olati on of 18 U.S .C. § 922(g)(1); possessi on of a fi r ear m in fur ther ance of a dr ug tr a ffi ckin g cr i me, in v i olati on of 1 8 U.S .C. § 9 24(c); engagi n g in mo ne t a r y tr ansacti ons in pr oper ty der i v ed fr om s peci fi ed u nlawful acti vi ty , in v i olati on of 18 U.S

. C

. § 1 9 57; and tw o counts of money launder ing, in
v i olati on o f 1 8 U.S .C. § 1956(a)(1). The di str i c t c our t deni ed S te wa r t ’ s m o t i o n t o s u ppr ess the ev i dence obtai n ed dur in g andNo. 16-4105 9

as a result of the tr affi c stop and the confessi on he gav e at the poli ce stati on. The di str i ct cour t also deni ed S tew ar t’s pr e-tr i al moti on in limine to pr ev ent or li mi t the use of ev i dence that he had twi ce v i s i ted Colon’s fur ni tur e stor e. After a four -day tr i al that incl uded testi m ony about Colon’s cr i minal acti v i ti es, a j ur y conv i cted S tew ar t on a ll counts. Because S tew ar t h ad tw o quali fyin g pr i or felony dr ug conv i cti ons, hi s sentence on the dr ug possessi on count w as li fe i mpr i sonment wi thout par ole. See 21 U

. S .C. § 841(b). For four of the r emainin g counts, the

cour t sentenced S t e wa r t t o t e r m s o f i m pr i sonment betw een fi v e and fi fteen y ear s’ i m pr i sonment to be ser v ed c oncur r ent wi th the li fe s e n t e n ce. The sentence for p ossessi on of a gun in fur ther ance of a dr ug tr affi cking cr i me tacked on a gr atui tous fi v e c onsecuti v e y ear s to the sentence of li fe i mpr i s onment. S tew a r t appeals.
II. On app e a l , S tew ar t contends that the ev i dence gai ned thr ough the tr a ffi c stop should hav e been suppr essed because Detecti v e Ball unconsti tuti onally pr olonged t he stop in or der to conduct the dog s ni ff pr ocedur e. S t ew a r t also asser ts that the pr olonged d etenti on due to the sni ff w as not other wi se suppor ted by r easonable su spi ci on. Any ev i d ence obtai ned after the sear ch of hi s car , he ar gues, should be suppr essed as the fr ui t of the poi sonous tr ee. S tew a r t main tai ns that the incr i minating statements h e made followin g h i s ar r est should also hav e been suppr essed because inv esti gator s v i olated hi s inv ocati on of h i s ri ght to r emain s i lent. He also submi ts that the di str i ct cour t er r ed in admi tti ng s ubstanti al a m o un ts of pr ej udi ci al a n d i r r elev ant ev i dence of pr i or bad acts. And finally , h e asser ts that the g o v er nment f ai led to pr esent10 No. 16-4105
suffic ie nt ev i dence in suppor t of the money launder ing
conv i cti ons, r ender ing them infi rm as a matter of law

. He seeks to hav e the conv i cti ons on e v e r y co unt v a cated and the case
r emanded for f

ur ther pr oceedings. But he also contends that hi s conv i cti ons for money l aunder ing s hould be r ev er s ed outr i ght. Because some of these obj ecti ons w er e pr eser v ed and other s w er e not, w e wi l l addr ess the standar d of rev i ew as w e tur n to each i s sue. A. Josi e conducted her li fe-alter ing sniff o f S tew ar t’s car on Januar y 20, 2015. The n e x t d ay , the S upr eme Cour t h ear d

ar gumen t i n Rodriguez v
. United States , 135 S

. Ct. 1 609 (2015). The Cour t d eci d ed Rodriguez on A p r il 21, 2015, some thr ee months befor e S t ew ar t fi led h i s moti on to suppr ess and fi v e and a half m onths befor e the d i s tr i ct c our t held the suppr essi on hear ing. In Rodriguez , the S upr eme Cour t consi der ed “whether poli ce r outi nely may extend an o t her wi se-completed tr affi c
s t o p , absent r easonable suspi c i on, in or der to conduct a d o g sni ff.” 135 S. Ct. at 1614. The Cour t concluded that a tr affi c stop may become u n l a wful i f i t i s pr olonged bey ond the ti me
r easonably necessary to complete the tr affi c-r elated mi ssi on of the stop. 135 S

. Ct. at 1 614–15. Unr elated inqui r i es m a y no t
measur ably pr olong a t r affi c stop, although an offi cer may conduct or dinar y inqui r i es in ci dent to the st o p su c h a s questi ons inv olv ing the dr i v er ’s li cense, the v ehi cle’s r egi s tr a t io n, and whether ther e ar e outstanding w ar r ants for the dr i v er

. 135 S

. Ct. at 1615. Th ese acti v i ti es ar e all r elated to the mi ssi on and obj e c ti v e of enfor cing the tr a ffi c code, and “ensur in g that

v ehi cles on the r oad ar e oper a ted safely and r esponsi bly .” 135 S

. Ct. at 1615. Because tr affi c stops ar e “especi a lly fr aught wi thNo. 16-4105 11 danger to poli ce offi cer s,” a n o f f i cer may also take “cer tai n
n e gli gibly bur densome pr ecauti ons in or der to complete hi s
m is s ion safely

.” Rodriguez , 135 S

. Ct. at 1616 ( ci ti ng Arizon a v
. Johnson , 555 U.S

. 323, 330 (2009)). Dog sni ffs, the Cour t sai d, may not be fai r ly char acter i zed as par t of the offi cer ’ s tr affi c mi ssi on, and so dog sni ffs may not pr olong or add ti me to the

s t o p unl e s s s u p p o r t e d s epar a tely by indi v i duali ze d, r e a s o n ab l e suspi ci on. Rodriguez , 135 S . Ct. at 1616–17. On appeal, S tew ar t fi r st ar gues that Detect iv e Ball unr easonably lengthened the stop in or d er to conduct the dog s ni ff. S uch a delay w a s u nconsti tuti onal under Rodriguez , he continues, an d n o r easonable suspi ci on suppor ted lengtheni n g the stop in or der to conduct the sni ff. Mor eov er , S tew ar t contends that the gov er nment fai led t o ar gue below that the ev i dence obtai n ed fr om the stop w as admi s si b le under any excepti on to the exclusi onar y r ule , a n d s o the gov er nment for fei ted any such clai m on appeal. See United Sta te s v
. L e o , 7 92 F .3d 742, 748–49 (7th Ci r
. 2015). In consi der ing a di s tr i ct cour t’s deni al of

a moti on to suppr ess, w e u s u a lly r ev i ew findings of fact for clear er r or and questi ons of law de novo

. United States v
. Borostowski

, 775 F .3d 8 5 1, 863 (7th Ci r
. 2014). H ow ev er , the gov er nment asser ts that S tew ar t di d not pr eser v e the i ssue that he r ai ses on a ppeal because he fai led t o make a ti mely and speci fi c obj ecti on in the di str i ct c o u r t

. B ecause S tew ar t for fei ted the i ssue, the gov er nment a rgues, we should rev i ew the di s tr i ct
cour t’s deci s i on for plain er r or only

. See United States v
. Olano , 507 U.S

. 725, 731 (1993); Uni t e d S t a tes v
. Hamad, 809 F .3d 898, 904 (7th Ci r
. 2016); Fed. Rule Cr i m. P

. 52(b). The gov er nment also contends that thi s cour t s hould consi d er i ts c lai m that Detecti v e B all conducted the dog sni ff in good fai th r eli ance on12 No. 16-4105
then-bin d ing ci r cui t pr ecedent. United States v
. Leon , 468 U.S

. 897, 909 (1984 ) ( u n l awfully obtai ned ev i dence should not be suppr essed when the poli ce a ct o n a n obj ecti v ely good-fai th beli ef that thei r conduct i s lawful); Davis v
. United States , 564 U.S

. 2 29, 241 (2011) (when b inding a ppellate pr ecedent speci fi cally author i zes a par ti cular poli ce pr acti ce, the exclusi onar y rule s hould not apply i f that p r e cedent i s later

ov er r uled by the S upr eme Cour t); United States v
. J enkins , 850 F .3d 912, 9 18 (7th Ci r
. 2017) (same). S tew ar t r esponds that he adequately pr eser v e d t h e a rgument by r a i sing i t in a l etter to the c our t after the suppr ess i on h ear in g, and that, in any c ase, the d i str i c t cour t addr essed the i ssue on the mer i ts and di d not tr eat i t a s for fei t e d

. S e e R. 6 9 (S upplemental Author i ty In S uppor t of Defendant’s Moti on to S uppr ess). By Stew ar t’s

measur e, thi s cour t should ther efor e apply the usual standar d of r e v i ew a n d the gov er nment should be pr ecluded fr om
r a i sing an excepti on to the exclusi onar y r ule.
In hi s M o t io n to S uppr ess Ev i dence, S tew ar t challenged only whether Josi e’s sni ff of the car pr ov i d ed p r obable cause to conduct a sear ch

. S peci fi cally , S tew a r t complained that ( 1) Josi e i s not a r elia ble dog; (2) Josi e w as subj ected to handler er r or ; and (3) the dr ugs wer e planted in hi s car by poli ce offi cer s after Josi e per for med the sni ff. R. 33 and 33-1. At t h e s up p r essi on hear ing, S tew a r t made no menti on of a clai m that extr a ti me
w as taken to conduct the sni ff. After the s uppr essi on hear ing, S tew a r t fi led a s u p p l e mental memor andum wher e he contended for the fi r s t ti me that Ball w as n ot enti tled to conductNo. 16-4105 13
the sni ff at all. 5 S tew ar t a r g u ed that V anOev er en’s testi m ony that he had obser v ed S tew ar t engage in a dr ug sale at the S hell stati on w as u nr eli able a nd n ot enti tled to any wei ght in det e r m inin g p r ob a

b l e cause or r easonable suspi ci on to conduct t h e sni ff. S tew ar t also ar gued in hi s supplemental memor andum that the s n i ff could not be j usti fi ed by hi s appar ent
ner v ousness, and that Josi e w as unr e l ia b l e because ther e w as testi mony that s he had aler ted in the p ast on occ asi ons when dr ugs wer e not found. Stew ar t thus made no clai ms about the sni ff i mpr oper l y l engthening the s top befor e, dur ing or after the suppr essi on hear ing. Hi s only r efer ence to Rodriguez came after h e fi led a post-hear ing supplemental memo, wher e he submi tted a copy of Rodriguez to the di str i c t cour t as s upplemental a u t h o r i ty

. The letter a ccompanying the copy of the Rodriguez deci si on r ead, in i ts enti r ety: Enclosed p lease fin d a case enti tled Rodr i guez v
. Uni ted S tates, No. 13-9972. Ar gu e d J anu a r y 2 1 , 2 015- Deci ded Apr i l 21, 2015 in the S upr eme Cour t of the Uni ted S tates. Please gi v e consi der ati on to thi s deci si on in r ev i ewing Mr

. S tew ar t’s Moti on to S uppr ess Ev i d ence. R. 69.
In d enying the Moti on to S uppr ess, the d i str i ct cour t

r ej ected any ar gument that Josi e w as unr eli able or that handler

er r or contr ib u t e d t o her aler t, clai ms whi ch S tew ar t has n ow

5 By o rder o f the di stri ct co urt, the pa rti es were a l lo wed to fi l e suppl ementa l m emo r a n d a si mul ta neo usl y, three da ys a fter the suppressi o n hea ri ng. R . 8 7, a t 8 4

.14 No. 16-4105 abandoned on appeal. 6 The cour t also br i efly addr essed what i t char acter i z ed as S tew ar t’s challenge to the reasonableness of the length of ti me he w a s d etai ned for the tr affi c stop. Ci ti ng Rodriguez , the cour t noted that poli ce offi cer s may n ot extend

an other wi se-completed tr affi c stop, absent r easonable suspi

ci on, in or der to conduct a dog sni ff. After a br i ef di scussi on of gov er nin g law

, the di str i ct cour t conclud ed that Ball di d not unconsti tuti onally pr olong the stop: Appr oxi mately fi fteen minutes elapsed betw een the ti me B a ll pulled S tew ar t ov er and J o s i e’s aler t.

... Dur ing that fi fteen-minute per i od, Ball w as acti v ely engaged i n conducting the tr affi c stop. When other offi cer s ar ri v ed, Ball di r ected one offi cer to continue
wr i ting the ti cket w h i le Ball h ad Josi e conduct an open ai r sni ff. Thus, Ball d i d not pr olong or extend the tr affi c stop bey ond the ti me n ecessar y to effectuate i ts pur pose. Once Josi e aler ted, the encounter
mov ed bey ond that of a mer e tr affi c stop, as pr obable cause to sear ch the v ehi cle w as establi shed. R. 70, at 6 (footnotes omi tted). S tew a r t i s cor r ect, in a sen s e , t h at the di str i ct cour t a ddr essed the mer i ts of the i ssue of whether the sni ff p r olonged the stop. The cour t, as w e hav e j ust seen, found that Detecti v e Ball di d not, a s a matter of fact, pr olong the s top bey on d the

6 The di stri ct co u rt a l so no ted tha t S tewa rt pr e s e n t e d n o ev i dence o r
a rgument i n suppo rt o f hi s cl a i m tha t po l i ce o ffi cers pl a nted drugs i n hi s trunk a fter the sni ff w a s co m pl eted. The co urt fo und no rea s o n to gi v e the cl a i m any credence a nd rej ected i t

. Tha t cl a i m ha s a l so b een ab a n do ned o n
a ppea l

.No. 16-4105 15

ti me necess a r y t o effectuate the tr affi c pur p ose of the stop when he conducted the sni ff p r ocedur e w i th Josi e. On a ppeal, S tew a r t now challenges thi s f act-finding by par sing the ti me lin e of the stop. He faults Ball for taki ng t h e t i me to call for b a c k u p, complains about the for ty-fi v e second delay in explai ning the electr oni c ti cket pr ocess to the backup offi cer , and obj ects to the actual ti me taken to r un Josi e ar ound the car

. Accor d in g to S tew ar t, the only conclusi on i s that “[t]he

r esulting stop w as longer than i f Ball had si mply wr i tten S tew a r t a tr affi c c i tati on,” render ing the s top unconsti tuti onal under Rodriguez . Opening Br i ef, at 8. Although S tew ar t has cor rectly i denti fi ed the key questi on under Rodriguez , p r i or to the appeal, S tew a r t nev er r ai sed an obj ecti on that w ould hav e aler ted the gov er n ment to the need to make a r ecor d on thi s v er y poi nt. In seeking to use ev i dence obtai n ed wi thout a w ar r ant, the gov er nment bor e the bur den of pr ov ing by a p r eponder ance of the ev i dence at the suppr essi on h ear ing that an exc e pti on to the w a r r ant requi r ement appli ed. United S t a t e s v
. Basinski, 226 F

. 3d 829, 833 ( 7th Ci r
. 2000). At t h a t h ear ing, the gov er n m ent p r esented ev i dence

r elev a nt to S tew ar t’s stated obj ecti ons. That i s, the gov er nment pr ov i d ed ev i d ence that Josi e i s a well-tr ain ed and reli able d og wi th a pr ov en tr ack r ecor d of d etecti ng the odor o f il l e gal dr ugs. The gov er nment also pr esented ev i dence that Detecti v e Ball w a s a h i ghly tr ain e d h a n d l er and that no handler er r or
w as inv olv ed in thi s sear ch. Fi n ally , the gov er nment pr esented

ev i dence that Detecti v e B all found the dr ugs in the tr unk dur ing the sear ch, negati ng the contenti on that the dr ugs w er e planted in the tr uck after the fact.16 No. 16-4105
The gov er nment had no r eason to ask D etecti v e B all why he took the ti me to call for back u p, and s o the r ecor d i s si lent

on whether h e summoned backup both for offi cer s afety and in or der to conduct the sni ff. He testi fi ed that safety w a s on hi s
m ind when he asked backup offi cer s to w atch S tew ar t a f t e r Josi e aler ted because he knew fr om hi s fellow offi cer s that ther e w er e “some pr etty ser i ous all egati ons” of dr ug dealing by S tew ar t. Because S tew ar t fai led to obj ect speci fi cally to the ti me taken for calling for backup, the cour t had no occasi on to

r u le on whether t h e sev enty-fi v e seconds 7 used for that task should be attr ibuted to th e d o g sni ff or to some other pr oper pur pose of the tr affi c stop s uch as offi cer sa f e t y
. Fr om the

r ecor d that w as dev eloped, the gov er nment (had it b een aler ted to thi s obj ecti on ) could h av e made a non-tr i v i al

ar gument that the call for backup w a s r elated a s m u c h to offi cer safety as to cond u c t in g the dog sni ff. Detecti v e Ball knew he w as being asked to s top a felon suspected of selling dr ugs moments ear li er

. As the stop pr oper ly pr ogr essed, Ball

saw that S tew ar t w as unusually n er v ous, and lear ned that the bulge in Stew ar t’s pocket w as a notably lar ge a mount of

cur rency , lending cr edence to the char ge of r ecent dr u g dealing. B a ll had to twi ce di r ect S tew ar t to si t on the bumper

7 A s we no ted ab o v e, sev enty-fi v e seco nds i s the ma x i mum a mo unt o f ti me ta ken t o c a l l fo r b a ckup a nd respo nd to q uesti o ns rega rdi ng the need fo r b a ckup. Tha t i ncl udes peri o ds o f nea r-si l ence. Be c au s e S tewa rt fa i l ed t o
a l ert the go v ernment a nd the co urt tha t he cha l l enged thi s peri o d o f ti m e, the reco rd is undev el o ped o n wha t Ba l l wa s do i ng duri ng tha t qui et peri o d. Fo r a t l ea st pa rt o f the ga ps, he wa s a udi b l y enga ged i n t a sks rel a ted to the tra ffi c v i o l a ti o n. The di stri ct co urt, o f co urse, fo und tha t Ba l l wa s a cti v el y enga ged i n co nducti ng the tra ffi c sto p thro ugho ut the cha l l enged peri od.No. 16-4105 17
of hi s car whi le Ball w or ked on the ti cket. And a s so on a s the tw o backup offi cer s ar r i v ed, B all asked one offi cer to w atch S tew a r t, whi ch w ould seem to indi cate that he w a s concer ned for hi s safety ev en befor e conducting the sni ff. But the gov er nment had no oppor tuni ty to pr esent ev i d ence or ar gument on thi s poi nt because S t e w a r t f ai led to ti mely and speci fi cally obj ect to thi s par t of the ti me line. Nor di d S tew ar t aler t the c our t or th e g o v er nment to hi s ulti mate clai m that “[t]he r esulting stop w as l onger than i f Ball had si mply wr itten S tew ar t a tr affi c ci tati on,” the sali ent questi on under Rodriguez

. And so the gov er nment h a d no
r eason or oppor tuni ty to a sk Detecti v e B a l l i f he could hav e fini shed wr i ti ng the ticket hi mself in less ti me than i t took to conduct the sni ff. Agai n, by li stenin g t o the ti me-indexed audi o, w e know that Detecti v e Ball took a ppr oxi mately for tyf iv e s e c o n ds to hand off the ti cket to the backup offi cer (who

w as n ot fu l ly fami li ar wi th the new electr oni c system), and

r oughly ninety seconds to r un Josi e ar ound the car

. The offi cer
w or ki ng on the t ic k e t w as not fin i shed wr i tin g i t when Josi e aler ted. That suggests that some addi ti on a l a m o unt o f ti me w as needed for any offi c er to complete the ti cket. W e ar e left wi th

m o r e qu e s ti o n s than answer s. W as the backup offi cer di l i gentl y
w or ki ng on the ti c ket whi le Detecti v e Ball r a n the dog ar ound the car ? Could D etecti v e Ball hav e completed the ti c ket in less ti me than i t took to call for b ackup, h and off the ti cket and run the dog? W

as any of that ti me attr i

butable to tasks per mi ssi bly

r elated t o t h e mi ssi on of the tr affi c stop? And i f so, could18 No. 16-4105

Detecti v e B all hav e completed the ti cket mor e qui ckly than the ti me attr i

buted solely to the dog sni ff ? 8
The r eason w e h av e no answer s to these questi ons i s that S tew a r t fai led to r ai se thi s speci f ic o bj e cti on in a ti mely

manner , when t h e gov er nment could hav e dev eloped the

r ecor d and t h e c o u r t could hav e r uled on the i ssue wi th full knowledge of the ci r cumstances. Fr om the moment the stop began to the moment Josi e aler ted, fewer than si xteen minutes h a d elapsed, not an unr easonable amount of ti me in t he abstr act for a ti cket for r unning a r ed li ght. W e know fr om the audi o r ecor ding t h a t t h e v ast maj or i ty of that ti me w as spent di li gently completing tasks r elated solely to the mi ssi on of the stop. Any uncer tai nty about the r emaining few minutes can be attr ibuted only to the defendant’s fai lur e to r ai se thi s obj ecti on in a ti mely ma n n er

. Rodriguez had b een on the books for months, and so the defendant had ev er y oppor tuni ty t o r ai se the i ssue befor e the suppr essi on hear in g. W e wi ll ther efor e tr eat the i ssue as for fei ted and r ev i ew for plain er r or

. In or d e r t o rev er se for plain er r or , w e must find ( 1 ) er r or (2) that i s plain, and (3) that affects the defendant's substanti al

r i ghts. Olano , 5 07 U.S

. at 732; Hamad, 809 F

. 3d a t 904. An er r or i s plain i f i t i s clear or o b v io u s

. Olano , 507 U.S

. at 734; Hamad, 809 F .3d at 904. And an er r or a ffects the defendant’s substanti al

8 By ana l y z ing S tewa rt’s cl a im i n thi s fa s hi o n, w e do no t mea n to impl y tha t certa i n t a sks wi l l a uto ma ti ca l l y co unt a ga i nst the length o f the mi ssi o n
o f a tra ffi c sto p s o a s to pr o h i bi t a do g sni ff i n future ca ses. We si mpl y
ca nno t tel l o n thi s reco rd ho w to a l l o ca te these ta sks b eca u se the defenda nt fa il e d t o ti mel y a nd speci fi ca l l y o bj ect. We lea v e tha t a na l ysi s fo r a no th er da y where the pa rsi ng o f the ti me l i ne ma tters to the o utco me.No. 16-4105 19

r i ghts when i t i s pr ej udi ci a l, that i s, when i t has affected the outcome of the di str i ct cour t pr oceedings. O l a n o , 507 U.S

. a t 734. Fi nally

, “ Rule 52(b) leav es the decisi on to cor r ect the for fei ted er r or wi thin the sound d i scr eti on of t he cour t of appeals, and the cour t should not exer ci se that di scr eti on
u nless the er r or ‘ser i ously affect[s] the fai rness, integr it y o r p ubli c reputati on of j udi c i al pr oceedin gs.’” Olano , 5 07 U

. S

. a t 732 (quoting United States v. Y oung, 470 U.S . 1, 15 (1985)).
T o state the s tandar d i s to demonstr ate that S tew ar t c annot meet i t h e r e

. He challenges the di str i ct cour t’s factual fin ding that the sni ff di d not lengthen the stop. The cour t deter mined that Ball w as acti v ely engaged in c o nducting the tr affi c stop befor e handing off the ti cket, a n d t h a t another offi cer continued that mi s si on whi le Ball r an J osi e ar ound the V olksw a gen. In other w or ds, the sniff w as conducted contempor aneously wi th the tr affi c mi ssi on of the stop. Based on the ev i dence that the d i str i ct cour t h ad befor e i t, ther e i s no r easo n t o c o n c lude that this f in d in g w as in er r or

. N othi ng in the r ecor d calls the

cour t’s finding into questi on, a nd to the extent that w e si m p ly do not know whe t h er ev er y moment w as s p ent in tr affi cr elated tasks, the fault for those omi ssi ons li es wi th S tew a r t. The di str i ct cour t di d not addr ess whether any lengtheni ng of th e st o p t o conduct the dog sni ff w as other wi se suppor ted by r easonable suspi ci on or pr obable cause. See R. 70, at 9 n.10 (declining to deci d e whether B a ll independently had pr obable

cause to sear ch). Because w e hav e concluded that ther e w as no plain er r or in the cour t’s finding that the stop w as not unconsti tuti onally lengthened, w e n eed not addr ess whether Detecti v e Ball possessed r easonable suspi ci on that w ould hav e allow ed lengtheni ng the stop in any case. Nonetheless, for the20 No. 16-4105
sake of completeness w e note t h a t, at the ti me D etecti v e Ball deci ded to conduct the sni ff, he knew that S tew ar t w as a felon and a dr ug tr affi cker wh o wa s b e ing inv esti gated for addi ti onal tr affi cking and an associ ati o n wi th Colon. He knew that, moments ear l i er

, h i s fell o w o ffi cer s wi tnessed S tew ar t engaged in a n encounter that, in thei r extensi v e exper i ence, they beli ev ed to b e a dr ug sale. He kn e w t h a t S tew ar t w as unusua l l y n er v ous when stopped for r unning a r ed li ght. And he knew that Stew ar t admi tted t o hav ing $700 in cash in hi s pocket. It w ould be di ffi cult to say that thi s infor mati on w ould not supply r easonable suspi ci on to sup por t a delay of a few minutes to conduct a dog sni ff. In shor t, the cour t d i d not er r , much less plainly er r

, when i t deni ed S te w ar t’s moti on to suppr ess the ev i dence found in the V olksw agen. S tew a r t also contends that all ev i dence obtai n ed as a r esult of the tr a ffi c stop s hould hav e been excluded as the fr ui t of the poi sonous tr ee. See Utah v
. Strieff , 136 S

. Ct. 2056, 2 0 61 (2016) (the exclusi onar y r ule encompasses both the pr i mar y ev i dence obtai n ed as a d ir e ct r esult of an i llegal sear ch or sei z ur e and

ev i dence later di scov er ed and f o u n d to b e der i v ati v e of an i llegali ty , the so-called fr ui t of the poi s onous tr ee). Obv i ously , i f the or i gi nal sear ch w as n o t u n lawful, ther e i s no basi s to exclude ev i dence der i v ed fr om the o r ig inal sear ch. The contr aband found in the car for med the basi s of a r e qu e s t f o r
a w a r r a n t to sear ch S tew ar t’s home. Because ther e i s no basi s to exclude the ev i dence found in the ca r , t her e i s no b asi s to exclude t h e e v i d ence found in the home. S tew ar t also asser ts that h i s confessi on w a s obtained a s a r esult of the unlawful

sear ch of the car

. Again, because ther e i s no r eason to excludeNo. 16-4105 21

t h e e vi dence found in the car , that sear ch cannot pr ov id e a foundati on for excluding S tew ar t’s confessi on. B

. W e tur n to S tew ar t’s contenti on that the cour t er red when i t r efused to suppr ess hi s confessi on on the s ep a r ate gr ound that i t w as obtained when the offi cer s i gnor ed hi s inv ocati on of hi s r i ght to r emain sil e n t and continued to questi on hi m. S tew a r t pr eser v ed thi s ar gument and so w e rev i ew findings of fact for clear er r or and questi ons of law de novo

. United States v
. W ysinger, 683 F .3d 7 84, 793 (7th Ci r
. 2012). The Fi fth Ame ndment pr ov i des that no per s o n “ shall be compelled in any
cr i min al c a s e to be a wi tness agai n st h i m s elf.” P oli c e offi cer s must w ar n suspects pr i or to questi oning that they hav e a r i ght to r emain si l ent, and i f the suspect indi cates that he wi shes to

r emain si lent, the inter r ogati on m ust cease. Maryland v
. Shatzer , 559 U.S

. 98, 103–04 (2010); Miranda v
. A rizona, 384 U.S

. 436, 444–45, 4 7 3

– 74 (1966). A per s on who wi shes to inv oke hi s or her r i ght to r emain si lent must do so unambi guously

. Ber ghuis

v
. Thompkins , 5 60 U.S

. 370, 381–82 (2010). “If an ambi guous act, omi ssi on, or statement could r equi r e poli ce to end the inter r ogati on, poli ce w ould be r equi r ed to make di f fic ult deci si ons about an accused’s unclear intent and face the consequence of suppr essi on ‘i f they guess wr ong.’” Ber gh uis , 560 U.S

. at 382 (quotin g Davis v. United States , 512 U.S . 452, 458–59 (1994)). S tew a r t asser ts that he unambi guously inv oked hi s r i ght to

r emain s il e nt by shaking hi s head “ no” in r esponse to a questi on fr om Detecti v e Ball r egar ding whether he w anted to talk to a detecti v e. The di str i ct c our t found that “S tew ar t nev er affi rmati v ely a nd une qu iv ocally inv oked hi s r i ght to remain22 No. 16-4105

si len t

. ” R

. 70, at 10. The c our t noted that Stew ar t appear ed to shake hi s head, and that when Ball twi ce tr i ed to clar i f y the meaning of that gestur e, S tew ar t r esponded by twi ce a sking to be placed in a car b ecause i t w a s cold outsi d e. S uch r esponses w er e not a n u n a mbi guous inv ocat ion of S tew ar t’s r i ght to r emain si l ent such t h a t offi cer s wer e pr ecluded fr om fur th e r questi oning hi m. S tew ar t di d not tel l B a l l that he no longer wi shed to answer Ball’s questi ons. Nor d id he

e x p l ic i tly state that he di d not w ant to speak wi th detecti v es. As such, S tew ar t’s ar gum e n t on thi s gr ound must fai l. R. 70, at 10.
W e begin wi th the con t e x t o f that inci dent. W ysinger, 683 F .3d at 793–94 ( in deter mining whether a suspect clear ly inv oked hi s o r he r r i ght to c ounsel, w e consi der the ci r cumstances in whi ch the statement w as m ade as w ell as the w or ds employ ed); United States v
. Hampton , 675 F .3d 720, 727 (7th Ci r
. 2012) (obj ecti v e inqui r y into whether s u spect inv oked r i ght to counsel includes r ev i ew of not only the w or ds the s uspect used but also the ci r cumstances in whi ch the statement w a s made). See a lso Ber

ghuis , 560 U.S

. at 3 8 1–82 (the standar ds whi ch apply in deter min ing whether a per s on has unambi guously inv oked the r i ght to c ounsel also apply in d eter mining whether a per son has inv oked the r i ght to remain si lent). A s s oon as D e t e cti v e Ball found a gun in the V olksw a gen, he p la c e d S tew a r t under ar r est and r ead h i m hi s Miranda r i ghts. He then began asking S tew a r t ab out the gun. S tew ar t fr eely answ er ed t h e s e questi ons, telli ng Ball that h i s “gi r l” left the gun in t heNo. 16-4105 23

car , denyin g that hi s finger pr ints or DNA w ould be found on the gun, and then changin g h is stor y to indi cate that he had fi r ed i t a t a gun r ange and that hi s pr ints m i ght be on i t. Detecti v e Ball t h e n sear ched the r est of the car and found the b a g in the tr unk that contained dr ugs and cash. Bal l a p
pr oached S tew ar t agai n and s a id , “ That’s a lot of dr ugs, bud. Y ou w ant to talk to a detecti v e?” S tew a r t appear ed to shake hi s h ead to indi c a te “ no.” Ball c lar i fi ed, “ Y ou do not w ant to ta l k to a detect iv e ? W

e ll, y ou under stand I gotta hav e one come out.” S tew ar t repli ed, “Can y ou put me in the car ? It’s ki nd of cold out.” Ball s ai d, “Y

es, they’r e goi ng to talk to y ou r egar dless so y ou’ll get in the car a t t h a t p o in t. I hav e a dog in m y
car .” After thi s, Ball called for n ar coti cs offi cer s to come to the scene. In the cour se of that call, Ball sai d ov er the r adi o: He’s goi ng to need to talk to a nar coti cs detecti v e a t
some poi nt. I don’t know i f he’s goin g to talk b ut maybe i f w e si t hi m in a car a nd explai n the ser i ousness of i t, he’ll talk to somebody but I’v e explai ned to hi m that, r egar d less, when w e f in d t he s tuff, w e hav e to hav e a detecti v e.
... I don ’ t mean to w aste y our ti me but he doesn’t seem li ke he w ants to talk out in the open. May b e if w e si t hi m in a car , he’ll

w ant to talk. He or i gi nally sai d he d i d n ’t. He’s b een Mirandized and ev er ythi n g. But y o u know our p r o t o cols on the str eet. W e hav e to call for a d e t e c
ti v e r egar dless. S upplemental Appendi x, audi o di sc at 28:25–29:26.
Detecti v e Ball then r e t u r ned to S tew ar t and sai d , “A detecti v e i s goi ng to talk to y ou. If y ou w ant to talk to hi m, i t’s24 No. 16-4105

up to y ou. I h av e a pr otocol to follow. Y ou under stand that? I

w ear thi s uni for m
. I may hav e a dr ug dog. I can do all thi s stuff but w e ha v e to follow our pr ocedur es, okay?” S tew ar t responded, “Can I si t in somebody’s car ? It’s cold out h er e.” Ball agai n told hi m that he had a dog in hi s squad car

. The nar coti cs detecti v es then ar r i v ed and S tew ar t w as placed in thei r car

. Those offi cer s deli v er ed Miranda w ar n ings agai n, and S tew ar t f r eely spoke to them as he tr i ed to conv ince them t o r e l e a s e hi m. He gav e a v i deo-r ecor ded statement after bein g taken to the poli ce stati on wher e he w as gi v en hi s M iranda w ar nin gs y et agai n and then si gn e d a wr i tten w ai v er befor e makin g the

v i deo-r ecor d ed statement. S tew a r t r eli es on the head nod as the unambi guous inv ocati on of hi s ri ght to r emain si lent. He a r gues that i t i s c lear fr om the a udi o r ecor ding that Detecti v e B a ll under stood that nod to
mean that he di d n o t w is h to speak to the offi cer

. S tew ar t contends th a t B a l l w a s not asking for clar i fi c ati on when he sai d, after the head no d, “Y ou do not w ant to talk to a detecti v e.” T o S tew ar t, ther e i s a per i od on the end of that sentence. The gov er nment c ontends th a t i t i s a questi on mar k. The di str i ct cour t found that i t w as a questi on, a r e qu e s t for clar i fi cati on. After li stening to the r e c o r d ing, w e can find no clear er r or in that co n c l u s i on. Detecti v e Ball also indi cated to other offi cer s that he w as not sur e i f S tew ar t w ould t a l k, t hat he appear ed not to w a n t to talk out in the open b ut that he mi ght be wi lling to speak wi th offi c er s i f they sat hi m in a car

. I n c o nt e x t, none of Detecti v e Ball’s ensuing comment s c o nv in c e us that the di str i ct cour t clear ly er r ed.
But in any case, Detecti v e B a ll’s s ubj ecti v e belie f s d o not gov er n the outcome her e. The in quir y into whether a per sonNo. 16-4105 25
has a ct u a l l y inv oked the r i ght to r emain si lent i s an obj ecti v e
one. Davis , 512 U.S

. at 458–59; W ysinger, 683 F .3d at 793. When

a per son “appear s” to nod i n the negati v e and then r efuses to clar i fy the meanin g of that ges t ur e , t h e re i s no clear er r or in concluding that the nod w a s not an unambi guous inv ocat ion of the r i ght to r emain s i lent

. Thi s i s especi ally tr ue in the ci r cumstances her e. S tew ar t fr eely spoke to Ball after Miranda

w ar nings and befor e the head nod. He r efused to clar ify t he meaning of t h e n o d and asked to si t in a car because of the cold. An amb iguous or equi v ocal r efer ence that causes a
r easonable offi cer to under stand only that the s uspect “ might be inv oki ng the r i ght” to r emain s i lent i s not enough to r equi r e the c essati on of questi oning. Davis , 512 U.S

. a t 4 5 9

. A r easonable offi cer w ould hav e under stood S tew ar t’s appar ent nod to
mean that he m i ght be inv oki ng hi s r i ght to r emain si lent, and such an offi cer w ould not be r equ ir e d t o c ease questi oning i f the suspect r efused to clar i fy

. C. S tew a r t also conte n ds that hi s conv i cti ons for money la u n d e r ing must be r ev er s ed because the ev i d ence w as insuffi c i ent as a matter o f l aw
. “Or dinar i l y

, w e r ev i ew a challenge to the suffi ci ency of the ev i d ence to deter m ine only whether any r ati onal tr i er of fact could hav e found the essenti al elements of the cr i me bey ond a r easonable doubt, v i ewing the ev i d ence in the li ght most f av or a b le to the gov er nment.” United States v
. W

ebster , 775 F .3d 897, 904–05 (7th Ci r
. 2015). But S tew a r t f a i led to rai se thi s obj ecti on in the di str i ct cour t and s o26 No. 16-4105

w e r ev i ew thi s for fei ted clai m only for plain er r or

. 9 Fed. R. Ci v
. Pr oc. 52(b); Olano , 507 U.S

. at 731; W ebster , 775 F .3d at 9 0 5 ; United States v
. Esterman , 324 F .3d 565, 5 6 9

– 7 0 ( 7 t h Ci r
. 2003). Counts V a nd VI o f the indi ctment char ged Stew ar t wi th l a u n d e r ing of monetar y instr uments in v i olati on of 18 U.S

. C. § 1 956(a)(1)(B)(i ). 1 0 Count V speci fi cally char ged that, on July 29, 2014, S tew ar t deposi ted $ 2,0 4 0 in cur r ency into an Eleete Image, Inc. account at Chase B a nk; that thi s mo ney w as the pr oceeds of ongoi n g nar coti cs tr affi cking; that he made the deposi t knowing that the tr ansacti on w as desi gned in whole or in par t to “con c e a l a n d d i s gui s e the natur e, locati on, sour ce,
owner s hi p, and contr ol of the pr oce e d s ” of that unlawful

9 A t o ra l a rgument, defense co unsel co nfi rmed tha t Stewa rt ha d no
o bj ecti on t o the j ury i nstructi ons, a nd s o a ny cl a i m rega rdi ng the j ury i nstructi o ns h a s b een wa i v ed. United States v
. Locke, 7 5 9 F.3 d 7 6 0 , 7 6 3 (7 th Ci r. 2 0 1 4 ) (when a defenda nt i ntenti o na l l y rel i nqu i s hes o r aba n do ns a kno wn ri ght, the i ssue ha s b een w a i v ed a nd ca nno t b e rev i ewed o n a ppea l,

no t ev en fo r pl a in erro r); United S tate s v
. Aslan , 6 4 4 F.3 d 52 6 , 5 40 (7 th Ci r. 2 0 1 1 ) (where a defenda nt seeks to o v erturn a v erdi ct fo r i nsuffi ci ency o f the

ev i dence b ut di d no t cha l l enge h i s co nv i cti o n fo r mo ney la underi ng i n the di s tri ct co urt a n d di d no t o bj ect to the j ury i n s t ructi o ns on thi s co unt, we
rev i ew the co nv i cti o n fo r pl a i n erro r).

1 0 Tha t sta t u t e p r o v i des, i n rel ev a nt pa rt, “ Who ev er, kno wi ng tha t the pro perty i nv o lv ed in a fin an c ia l tra nsa cti o n represents the pro ceeds o f so me fo rm o f unl a wful a cti v i ty, co nducts o r a ttempts to co nduct such a fi nanci a l tra nsa cti o n whi ch in fa ct i nv o l v es th e pro ceeds o f s peci fi ed u nl a w ful

a cti v i ty ... kno wi ng tha t the tra nsa cti o n i s desi gned i n who l e o r i n pa rt

... to co ncea l o r di sgui se the na ture, the l oca ti o n, the so u rce, the ownershi p, o r the co ntro l o f t h e pro ceeds o f speci fi ed unl a wful a cti v i ty

... sha l l b e sentenced to a fi ne
... o r i mpri so nment

... o r b o th.” 1 8 U

. S .C. § 1 9 5 6 (a )(1 )(B)(i ).No. 16-4105 27

acti v i ty; and that whi le conducting and a ttempti ng to conduct thi s tr ansacti on, S tew ar t knew that the pr oper ty in v olv ed

r epr esented t he pr oceeds of ongoi ng contr olled substances tr affi cking a cti vi ty

. 1 1 Count VI char ged the same conduct,

c h a n ging only the date and the amount of the deposit : o n August 4, 2 014, S tew ar t deposi ted $2350 into the Eleete Image bank account.
W e p r ev i ously menti oned Eleete Image, Inc. only once. The

car that S tew ar t w as dr i v ing when he w as ar r ested w as
r egi ster ed to that co mpany and the li cense p lates bor e the

name “ Eleete.” In or der to addr ess the suffi ci ency o f t he

ev i dence clai m o n the money launder ing counts, some backgr o un d o n Eleete i s necessary
. The ev i dence at tr i al demonstr a ted that, in 2012, S tew ar t hi r ed Rosema r ie Br own to incor por ate a business for h i m in the name “ Eleete Image, Inc.” Br own fi led the necessary paper w o r k wi th the state to cr eate th e c o r p o r a t i o n and also appli ed for an Employ er Identi fi c a t i o n Number wi th the Inter nal Rev enue S er v i ce. S he li sted S tew ar t
as the business owner in the cor por ate documents but substi

tuted her own addr ess for the business addr ess on the in cor p o1 1 Al tho u gh S tewa rt po i ntedl y di d no t cha l l enge the j ury i n structi o ns h ere, i t i s hel pful t o n o t e tha t the j ury wa s i nstructed, co nsi stent wi th the l a ngua ge o f the indi ctment a nd wi th the S eventh Ci rcui t pa ttern i nstructi ons, tha t the go v ernment must pro v e b eyo nd a rea so nab l e do ub t tha t

“ [t]he D efenda nt knew tha t the tra nsa cti o n wa s desi gned i n who le o r in pa rt to co n cea l a nd [si c] di s gui se the na ture, the l o c a t io n , the so urce, the

o wnershi p, or the co ntro l o f the pro ceed s o f o n g o i ng drug tra ffi cki ng
a cti v i ty.

... The t erm ‘ c o n cea l o r di s gui se’ mea ns to hi de the na ture, the l o ca ti o n, the s o urce, the o wner s h i p , o r the co ntro l o f the pro ceeds o f speci fi ed unl a wful a cti v i ty.” R . 1 37

.28 No. 16-4105

r a ti on paper s. S he also cr eat ed a w ebsi te for Eleete, and testi fi ed that S tew ar t told her that he intended to r un a number of businesses under the “Eleete” name including a food tr uck and a cleaning ser vi ce, among other t h i n g s

. S tew a r t opened b a n k accounts in the company name, including a check i n g account wi th an associ ated d e b i t car d. He w as the only si gnator y li sted on these accounts. S tew a r t n ev er r an any legi ti mate business under the Eleete

name. He had no legi ti mate s our ce of income, 1 2 and the gov er nm ent w as able to demonstr ate at tr i al that most of the money that flow ed thr ough the Eleete accounts came fr om the

s ale of i llegal dr ugs. S tew ar t p ur chased the V olksw agen he

w a s d r i v in g at the ti me of hi s ar r est wi th a check fr om the Eleete account. On the m emo line, he n oted that the check w as for a “company car

,” and the c ar w as in fact r egi st er ed to the company

. H e a lso used the Eleete a ccount debi t car d to make pur chases at r etai l establi shments. For example, the gov er nment intr oduced ev i dence that S tew ar t s pent appr oxi mately $7400 at S aks Fi fth A

v enue, including a s ingle pur chase of $1200, a ll u sing the Eleete Image debi t c ar d r a ther than l ar ge amounts of cash that mi ght hav e r a i sed suspi ci on. Money enter ed and left the Eleete accounts in u nusual

w a y s. For example, S tew ar t gav e $10,000 in cash to a fri end , pur por tedly to enable the fr i end t o buy a car on Stew ar t’s behalf. Th e fr i end nev er pur chased a car , how ev er

, and instead

1 2 Testi mo ny a t tr i a l s h o w ed tha t, in the fi v e yea rs precedi ng hi s a rrest, S tewa rt ha d ga mb li ng wi nni ngs o f $ 1 4 0 0 , a nd tha t he so l d a few pa i nti ngs fo r less than $ 1 0 0 0 to ta l . Tha t wa s the ex tent o f a ny i denti fi ab l e l egi t i ma te i nco me duri ng tha t ti me peri o d.No. 16-4105 29

r etur n ed the m oney t o S tew ar t by wr i ti ng thr ee checks to Eleete Image, including a t le a st one check fr om the fr i end’s business account. S tew ar t also deposi ted into the Eleete accounts thi r d p ar ty checks totali ng mor e th a n $ 6 6,000 in a t h r ee-y ear p er i od. These checks, made out to other s a nd endor sed ov er to S tew ar t, outw ar d ly a p pear ed to be paychecks.
At tr i al, the gov er nment ar gued that Eleete Image w a s a “fr ont company

,” “ a scam and a sham.” R. 202, a t 645–46. The gov er nment contended that S tew ar t cr eated Eleete Image and tr i ed to make i t look li ke a legi ti m ate company in or d er to hav e
a place to deal wi th the cash he ear ned fr om dr ug sales. P ossessing and us in g l a r ge amounts of cash, the gov er nment

ar gued, w ould p otenti ally dr aw scr utiny , but u sing a business
a c count and a business debi t car d helped pr ev ent susp ic io n that the funds w er e i llegi ti mate. When seeking a bank loan in 2014, for example, S tew ar t n oted on the appli cati on that he had been “employ ed” by E l eete Image for fi v e y ear s and had an income of $6700 permonth.
In c losing ar guments, the gov er nment w ent t h r ough the elements of mone y launder in g one by one, associ ati ng ev i

d e n c e fr om the tr i al wi th pr oof of those elements. For t he f o u r th element of money l aunder in g, whether the defendan t “knew that the tr ansacti on w as desi gned in whole or in par t to conceal or di sgui se the natur e, the l ocati on, the sour c e, the

ow ne r s h i p , or the contr ol of the pr oceeds of ongoi n g dr ug tr affi cking acti v i ty

,” the gov er nment ar gued in closing that the Eleete business account w as desi gned to h i de the natur e of the funds as dr ug money and to di s tance S tew ar t fr om owner shi p of the funds:30 No. 16-4105 Why does ma ki n g cash deposi ts into the Eleete Image bank account—why does i t m eet that last element? W

ell, as w e’v e di scussed, what i s the whole poi nt of thi s Eleete Image bank account? The whole poi nt is n ot to conduct any legi ti mate busi

ness. He had m or e than tw o y ear s to do that or to make something of a star t of i t. The poi nt w a s he i s a dr ug tr affi cker

. Th at i s what he does for a li v ing. That i s what he’s done for a li v ing for y ear s, and he needs to fin d a w ay to spend and

use h i s money in a w ay that’s not goi n g to r a i s e ey ebr ows. S o, concealing or di sgui sing the n atur e or sour ce of that cash, w ell, once the cash—we d o that financi al tr ansacti on, p ut that somewhat small a mount, couple thousand dollar s—once we put that—r un i t thr ough into the business a ccoun t, now w e’r e not j ust w alki n g a r ound w i th sev er al thousand dollar s in our pockets. It’s a business a ccount. I t l o o k s li ke business-r elated money

. I t can be spent li ke business-r elated m oney thr ough the Eleete Image

car d s. Then, of cour se, i t a l s o goes to the owner shi p or contr ol, the a ttempt to hi de the owner shi p or contr ol. It’s not D ani e l S tew ar t w alki ng ar ound. It i s Eleete Image who now has the money

. W e know i t i s di ffi cult—cer tai nly the detecti v es di d i t; but i t i s somewhat di ffi cult to m a ke that l eap fr om Eleete Image at Dowit ch Lane, whi ch w e know i sNo. 16-4105 31

associ ated wi th Rosemar i e Br own, to Dani el S tew ar t at 4523 Eagle Cr eek P ar kw ay; but that w as the poi nt. R. 202, at 656–57. S tew a r t n ow c lai ms that thi s ev i d ence w a s insuffi ci ent as a matter of law to pr ov e money launder ing. Ci ti ng Esterman , S t e w a r t contends that the gov er nment w as r equi red to pr ov e that the char ged tr ansacti ons wer e sp e c i f i c a l ly d e s i gned to h i de the pr ov enance of the f unds inv olv ed. The gov er nment fai led to do so her e, he ar gues, because he di d nothi n g mor e than deposi t money into account s that he opened, accounts that could be tr aced easi ly back to hi m. He asser ts that the facts of hi s case a r e r emar kably si mi l ar to the facts in Esterman , wher e thi s cour t r ev er s ed a conv i cti on for money l a u n de r ing on the

same for fei t e d in s u ffi c i e n cy - o f

- th e
- e v i d e n c e c l a i m th a t h e r ai ses her e. He notes that hi s name i s on the incor por ati on paper s for Eleete, and that he i s the si gnator y on the Eleete bank a ccounts. Hav ing made no attempt to h i d e behin d the Eleete a ccount, the facts cannot s u ppor t a finding of concealment under Esterman , he ar gues. S o w e tur n to E sterman

. In that case, Gar y Ester man opened a bank acc o unt a t Edens Bank in S koki e, Illinoi s, wi th a Russi an busin ess par tner in or der to facil it a te the financing for a pr oj ect that the tw o
w e r e planning in Russi a
. The b usiness par tner retur n ed to Russi a and money b egan flowing into the E d ens Bank a ccount. Almost as qui ckly

, E ster man began wi thdr awing money fr om the a c count and tr ansfer r ing i t to hi s G.E. Inter nati onal Account at Mi chi gan A v e nue Nati onal Bank. Contr a ry to hi s agr eement wi th hi s Russi a n busin ess par tner , E s ter m an engaged in at l east thi r ty-thr ee separ a te tr ansacti ons including32 No. 16-4105

wi r e tr ansf e r s a nd wi thdr aw als to r emov e the money fr om Edens Bank, taki ng the money fo r h is own per s onal use. Ester man then spent t h e money in the G.E. a ccount by wi thdr awing cash or wr i ti ng checks di r ectly for p ur chases. 324 F .3d at 567–68. Assessing these facts, w e noted that we hav e str uggled “to define pr eci sely what amount of c oncealment must o ccur befor e mer e use of i ll-gotten gai ns becomes money launder ing pr ohibi ted b y subpar t (B)(i ) of the s tatute.” 324 F .3 d a t 5 7 0. T w o pr inci ples emer ged fr om the cases:
Fi r st, w e hav e tr ie d to maintain some separ ati on b e t w een the ini ti a l tr ansacti on fr om whi ch i llegal pr oceeds w er e der i v ed and fur ther tr ansacti ons desi gned to conceal the sour ce of those pr oceeds.

... S econd, we hav e str essed that the mer e tr ansfer and spending of funds i s not enough to sweep conduct wi thin the money launder ing statute ; instead, subsequent tr ansacti on s must be speci fi cally desi gned to hi de the pr ov enance of the funds inv olv ed.
Esterman , 324 F .3d at 570 (inter nal ci t a t io ns and quotati on
mar ks omi tted). T

o r estate the fi r st pr in ci p le, “money launder

ing cr i minali zes a tr ansacti on in pr oceeds, not the tr ansacti on that cr eates the pr oceeds.” United States v
. Mankarious , 151 F .3d 694, 7 05 (7 th Ci r
. 1998). The gov er nment’s p r oof in Esterman fai led b ecause the defendant made no effor t to dis g u ise or conceal e ither hi s wi thdr aw als fr om E dens Bank or the destinati on of the funds. He si mply made d eposi ts in t o o t h er bank a c c o u nts that w er e cor r ectly i denti fi ed as hi s and then spent the money i n r etai l tr ansacti ons.No. 16-4105 33

W e r ej ected the gov er nment’s ar gument that, because the Russi an business par tner w as unaw a r e of the exi stence of the G.E. account, Ester man’s use of that a c count establi shed an intent to conceal:
But thi s i s j ust another w ay of descr ibin g Ester man’s ini ti al f r audulent scheme, wher eby he took the money a w ay fr om [ t he Russi an busin ess p ar tner ]. Most fr aud v i cti ms pr obably assume that thei r money has ei ther been spent or placed in an account
o f s o m e s or t, ev en i f they do not know the speci fi c destinati on of the funds. If that w er e eno u gh to show money launder ing at the s ame t im e , ther e
w ould be no d i stin cti on left betw een money launder ing and t he under lyi ng fr aud, a nd indi v i duals who per p etr a te si mple fr aud b y tr ansfer ring i ll-gotten fun d s into a per sonal account w ould alw ays be tr i able as money launder er s. Esterman , 324 F .3d at 571–72. The pr oceeds a t i ssue in Esterman wer e gener ated by fr a ud. That i s, fr aud w a s the “speci fi ed unlawful acti v i ty” menti oned in secti on 1956(a)(1)(B)(i ). In addi ti on to the ini ti a l tr ansacti on whe r e E s ter man took the money by fr aud, the gov er nment fai led to pr ov e that he engaged in an addi ti onal tr an s a cti on t h a t w as d esi gned “to hi de the pr ov enance of the funds inv olv ed.” Instead, he si mply d eposit e d the money that he took by fr aud in to an easi ly i denti fi able account and began to spend i t. In S tew ar t’ s c a s e , the pr oceeds w er e cr eated b y the speci

fi ed unlawful a c t i v i ty of dr ug tr affi cking. In tr ansacti ons that34 No. 16-4105

ar e r eadi ly i denti fi able as s e p ar a te fr om the or i ginal cr i me, S tew a r t took the c ash gener ated fr om that dr ug tr affi cking and engaged in a ser i es of steps d esi gned to conceal or di sgui se that money as business pr oceeds r a t h e r than dr ug money

. Wi th those same steps, he sought to di stance h i m s elf fr om per sonal

owner s hi p of th e funds. He in cor p or ated a business using a false addr ess and then took sev er al steps to make the business
a ppear legi ti mate. He obtai ned an Employ er Identi fi c atio n Number fr om the IRS and cr eated a w ebsi te. He opened a b ank account in the name of the business and enli sted other s to h elp hi m deposi t dr ug pr oceeds into the a cc o u n t in a manner that

w ould cause outsi der s to beli ev e the money w as income to the business. O n the tw o char ged occasi ons, he si mply deposi ted

r e l ati v ely small amounts of cash into the business account a t A T Ms. He then spe n t that money , someti mes on i tems that

c o u l d p r ob a

b ly b e i d enti fi ed as s tr i ctly per sonal and someti me s
on i tems, li ke h i s c a r

, that he ti tled in the name of hi s sham business. In shor t, thi s w as not an Esterman -style scheme, wher e the defendant di d li ttle mor e than take money , stor e i t a nd spend i t. Esterman requi red “concr ete ev i dence of intent to di s gui se or conceal tr ansacti ons, whether that ev i dence comes di r ectly fr om statements by the defendant that indi c ate a n in t e nt to conceal, or fr om ci r cumstanti al ev i dence li ke unusual secr ecy
sur r oundin g tr ansacti ons, car eful s t r u c tu r in g o f tr ansacti ons to

av oi d attenti on, folding or other wi s e d eposi ti ng i llegal pr ofi ts into the bank account or r ecei pts of a legi ti mate business, use
o f thi r d par ti es to conceal the r eal owner , or engagi n g in unusual financi al mov es culmina t in g in a t r an s a cti on.” 324 F .3d at 573. S tew ar t’s machinati ons sur r ou n ding the E l eete b ankNo. 16-4105 35

account supply the necessary ci r cumstanti a l ev i d ence. Under the u sual s tandar d for a suffi ci ency of the ev i dence c laim, w e
can easi ly conclude that a rati onal jur y could hav e f o u nd the essenti al eleme nt o f c o n c e a l m e nt (the only element challenged) bey ond a r easonable doubt, v i ewing the ev i dence in the li ght most fav or able to the gov er nment. W ebster , 775 F

. 3d at 904–05; Aslan , 644 F .3d at 5 40. Under the ev en m or e s tr ingent standar d of plain er ror

, thi s i s not a close case, and the money launder

ing conv i cti ons must be affir med.
III.
Fi nally , we note that S tew ar t r ai sed a number of challenges to th e a d m i s s i o n o f ev i dence that he char acter i z es as p r ej udi ci al and i r r elev ant “bad acts” ev i dence. S tew ar t asks us to r ev i ew the admi ssi on of most of that ev i dence for plain er r or and s ome of i t for abuse of di scr eti on, depending on whether he pr eser v ed the p ar ti cu lar obj ecti on in the di s tr i ct cour t. The gov er nment asser ts both that the ev i denc e w a s pr oper ly admi tted and that, in any ev ent, i f ther e w as er r or , i t w as har mless. W

e agr ee that any er r or in admi tti ng the challenged

ev i dence was har mless. “The test for har mless er r or i s whether , in the mind of the av er age j ur or , the pr osecuti on’s case w ould hav e been s i gni fi cantly le s s p er suasiv e h ad the i mpr oper
ev i dence been excluded.” United States v. Curtis , 781 F .3d 904, 9 1 1 (7th Ci r
. 2015). The ev i dence a gainst S tew ar t w as ov er
whelming. United States v
. G o n zalez, 863 F .3d 576, 588–89 (7th Ci r
. 2017) (ev i denti ar y er r or found har mless wher e ther e w as
ov er whelming admi ssi b le ev i dence of gu il t). The admi ssi ble

ev i dence included ki logr am quanti ti es of dr ugs, fi v e fi r ear ms, and near ly half a m i lli on dollar s in cash. The pr osecuti on’s case36 No. 16-4105

w o uld hav e been no less p er suasiv e had the challenged

ev i dence been excluded.
AFFIRMED