The Honor able Ala n H. Neva s of the United States District Court for the District of * Connecticut, sitting by

desig nation. 06
- 56 48
- cr U SA v. V al ent i ne U N IT E D S T A T E S C O U R T O F A P P E A LS F O R T H E S E C O N D C IR C U IT

_______________________________ August Term, 2007 (Argued: April 4, 2008 Dec ided: August 5, 2008 Amended: August 18, 2008) Docke t No. 06-5648-c r

______________________________ UNI TED STATES OF AMERI CA, Appellee ,

v. LUI S VAL ENTI

NE, Defendant-

Appellant
.

_______________________________ B e fo re : C A LA BR ESI and L EV AL , Circuit Judges , and N EV AS , District Judge
. *

_______________________________ Appea l from an or der of

the District Court for the E astern D istrict of NewYork (D ora Irizarry , District Judge ) deny ing de fenda

nt Luis Valentine’s motion to suppress evide nce se ized in h is a pa rtme nt a ft e r h is a

rr e st a nd fr om t he se nte nc e imp os e d a ft e r V a le nti ne ple a de d guil ty to
on e c ount o f b e inga

fe lon in p os se ssi on

of a fi re arm . V ACAT ED and REMA NDED for f urther pr ocee dings c onsistent with thi s opinion.Va le nti ne a lso c ha lle ng e s a fo ur -l e ve l e nh anc e me nt a pp lie d to his c ri min a l of

fe ns e 1 level. B eca

use we rema

nd to the district court for further proce eding s relatingto the evidenc e supporting his c onviction, we do not consider this challeng e at this time. 2 _______________________ C OL L EE N P. C AS S I DY , Fe dera l Defe nders of New Y ork, Inc., Appe als Bur eau, New Y ork, Ne w York, for De fe nd an t- Ap pe lla nt. E MI L Y B ER GER , Assistant United States Attorney (Da niel A. Spector, A ssistant United States Attorney , on the brief ), for Be nton J . Campbell, United States Attorney for the E astern D istrict of NewYork, Ne w York, N ew Yor k, for Appellee

.

________________________ N EV AS , District Judge, sitting by designation : De fe nd ant L

uis Va le nti ne a

pp e a ls f ro m th e dis tr ic t c ourt ’s de nia l of his mot ion

to suppress evide nce obta ined from his ca r and his re sidence . Valentine c ontends that the district court e rre d in concludingthat (1) his ar rest and the subsequent sea rch of his car w ere leg al and (2) his wife ’s conse nt to searc h their apa rtment was voluntar

y and that the f

irea rms found during the sea rch should not be suppre ssed. 1 I . BA CKGROUND A. The Controlled De livery On Fr id ay , Oc to ber 8 , 2 00 4, mem bers of a d rug enf orce men t t askfor ce bas ed atJ oh n F. Kenne dy Airport in New

York lea rned that box es conta ining a sofa a nd loveseat had ar

rived fr om Puerto Rico, and that appr ox imately 50 kilogr ams of coc aine we re hidde n inside the furniture
. The boxes were shipped via F edEx and addre ssed to Luis L ebron, ba sement apa rtment of 377 Ver non Avenue , Br ookly

n, New Y ork. The ta sk forc e off icer s, consisting of N YPD office rs and DEA a g ents, interce pted the shipment and planne d a contr olled delivery for the f ollowing Monday
.We collectively ref er to the ta sk forc e member s as “of fice rs.” 2 Va le nti ne c onte nd s, and the dis tr ic t c ourt

c on c e de s, tha

t he may have a c tua lly

sa id 3 “Viejo,” which mea

ns “old man” in Spanish, instead of “ Paolo.” No one wa s ever

indicted for the 50 kilogr ams of coc aine c ontained in the fur niture. 4 3 B e c a u s e th e r e w e r e n o F e d E x tr u c k s av a i l a

b l e f o r th e c o n tr o l l e d

d e l i v e r y th atM o n d ay, DEA Spec ial Ag ent Christopher B anzer a nd NYPD Dete ctive Rodney Perez dresse d in FedE x uniforms, rente d a deliver y van and put magnetic F edEx signs on its sides. Another g roup of ag ents and police office rs par ked an unde rcove r surve illance va n acr oss the street f

rom 377 Ve rn on , whe re the y

re c or de d v ide o o f t

he loc atio n a

nd re c e ive d a

ud io t ra ns mis sio ns fr om a wirele ss device w orn by

Det. Pere z. Other offic ers wer e positioned in various locations withi n a 2 few blocks of 377 Ve rnon. As the off

icer s pulled up in the delivery van at a pproxi mately

11:47 a.m., they

saw Valentine g etting out of

a seda n parke d near

the building. Va lentine walke d toward the building and said somethingthat Special Ag ent B anzer interpr eted a s “Paolo, Fe dEx , Fe dEx ,” and waved 3 to a man n ame d Pe dr o Ro dr igue z furt he r d own th e str e e t. D e t. P e re z as ke d V a le nti ne if he c ou ld help unload the he avy

box es and V alentine a g ree d so long a s Det. Pere z paid him. R odriguez then appr oache d the offic ers a nd Valentine a

nd the g roup discussed who w ould sign for the delivery . Valentine the n went inside 377 Ve rnon and c ame out with a man ide ntified only as “Ang el.” Ang el said he w ould call L ebron to a sk him to come home to sign f or the de livery
. Ang el ca lled L ebron a

nd g ave the phone to Det. Per ez. The per son on the phone purpor ting to be L ebron state d that he wa s at work a nd could not leave , but they should leave the delivery on the sidewalk for

him. Valentine wa s not present for the phone c all. Ultimately , no one sig ned for the boxes and Det. Pere z and Special Ag ent B anzer we nt back to their of fice at J FK w ithout
m ak i n gth e d e l i v e r

y. 4Although D et. J ohnson testified that he c ould see Va lentine and the othe rs the entire 5 time they wer e in the lot, the district court found that Det. J ohnson could not see what transpired there
. Of the f

ive people a

rre sted that day , only

Valentine ultimately

was prose cuted. 6 4 After the deliver

y van lef t, severa l of the off

icer s continued surve illing 377 Ver non. Special Ag ent Robert Yoos, a 20-y ear veter an of the DEA, watched the a partment buildingfrom
an unma rk e d p oli c e c ar. NY PD D e te c tiv e Mic ha e l John so n, wi th s e ve n ye ars ’ e xpe ri e nc e wi th the police de partment, c ontinued surveillance from a va n acr oss the street. The office rs observe d Valentine g oing in a

nd out of 377 Ver

non and talkingwith various individuals on the sidewalk. At approximately

1:00 p.m., Valentine, dre ssed in a g ray hooded swe atshirt, came out of 377 Ver non and g estured to other people standingnear

by and proc eede d to walk up the block. Special Ag ent Yoos and D et. J ohnson observe d Valentine a nd the other pe ople enter

a vac ant lot. None of the offic ers c ould see what transpired in the lot. A fe w minutes later, Va lentine 5
rea ppear ed alone at the other end of the block, holding a cup of c offe e or some othe r beve rag e. Valentine w alked ba ck to 377 Ver non and later

remove d his sweatshirt and plac ed it in his car. A supervisingag ent, who wa s not on the scene , authorized Vale ntine’s ar rest base d on inf or matio n f ur nis he d to him

by Spe c ia l A g e nt Y oo s a

nd De t. Johns on . Y oo s th e n to ld N YPD Se rg e ant A lla

n H oe hl a nd NY PD D e te c tiv e Pa

ul C ro c ke tt t o mo ve in a

nd arr e st V a le nti ne , whil e Special Ag ent Yoos wa lked up the stree t to arre st the other people loiteringon the block who ha d enter ed the va cant lot with Valentine. 6 B
. Va le nti ne ’s Ar

re st Valentine ha d stepped out of his ca r and w as wa lking towa

rd the trunk a

rea at
a pp ro ximate ly

1:3 0 p .m. wh e n Se rg e ant H oe hl a nd De t. C ro c ke tt b loc ke d h is c ar w iththe ir unmarke d police ca

rs. The of

fice rs, wea

ringplainclothes and ba dg es, appr oache d Valentine5

from the f ront and re ar of

his car a nd told him t hey

wer e police of

fice rs and that he was unde r
arr est. Vale ntine strug g led with the offic ers, a nd Det. Johnson and at least two other of fice rs ra n over to a ssist i n Valentine’ s arr est. Serg eant Hoe hl stated that bec ause he felt Va lentine re ach f or his gun at on e po int

duri ngthe sc uf

fl e , Se rg e ant H oe hl h it h im o n th e he a d w ithha nd c uf fs to subdue him. Once the offic ers ha d Valentine ha ndcuff ed, they called a n ambulance to treat Valentine’ s resultinghead w ound. After Valentine’ s arr est, Det. Johnson searche d Valentine’ s car and found the g ray
sweatshirt Valentine had be en we aringear lier in the day . Inside a poc ket of the swe atshirt, he found some g lassine bag s of her oin. No other c ontraba nd was found in the c ar. C. The Sea

rch of Valentine’ s Apartment Special Ag ent Yoos, par

ked up the stre et a f

ew blocks, a

rrived a t 377 Vernon shor

tly afte r Va le nti ne ’s arr e st. Spe c ia l A g e nt Y oo s th e n c a lle d f or Se rg e ant H oe hl a

nd De t. C ro c ke tt t o
acc ompany

him to Valentine’s apa

rtment. When they

knocked on the door, Va lentine’s wife , Annette Pena

Morales, a

nswere d. She appea

red a s though she had just awakened a nd looked nervous, c oncer

ned, but also ca lm. Special Ag ent Yoos told Morales that he and the other of fi c e rs we re wo rk ingon

a na rc oti c s c a se and

that th e y ha d ju st a

rr e ste d V a le nti ne . M or a le s to ld the offic ers that she lived there with Valentine a nd their two childre n. She stated that she ha d been lookingout the window and ha d witnessed Va lentine’s ar rest. Special Ag ent Yoos then a sked Mora les if they could come inside to discuss the matter further . Morales a llowed the off icer s to enter the a

partment. Spec ial Ag ent Yoos informe d her that her husba

nd had just been a

rre sted for a

very serious nar cotics off

ense. H e then a sked Morales if othe r people had bee n in the apar tment ear lier that day , and Mora les said that her da ughte r a nd he r d a ug hte r’ s b oy fr ie nd

ha d v isi te d. Spe c ia l A g e nt Y oo s a sk e d if oth e r p e op le
wer e cur rently in the apar

tment, and Morale s said no.Ac c or din gto M or a le s, sh e g ave c on se nt f or the of fi c e rs to s e arc h th e ho me , b ut o nly to 7 look for people , not contraba nd. She stated that the off icer s had aske d if they

could take a

look inside her a

partment be cause they

had see n two men come out of the apa rtment ea rlier in the da

y . She g ave the office rs per

mission t o look around for the two men they

mentioned, but she denie s that she g ave the m permission to searc h for a ny thing e lse. In a dd iti on , M or a le s st ate d th at th e of fi c e rs did no t pr e se nt t

he c on se nt t o s e arc h f

or m to her until afte r they

had discove red the guns in the bedroom. She said that the of fice rs told her that if she did not sign it, eve ry thing they found would be attributable to her, a nd if she wa s char g ed with any

thing, she would probably lose her c hildren. She stated that she signe d the form beca use they had alr eady

sear ched the apar

tment and she did not think she was a ble to make them le ave . A ft e r s e arc hin ghe r a pa rtme nt f or a pp ro ximate ly

six ho ur s, the of

fi c e rs ins tr

uc te d h e r t o g et dre ssed and then the y arr ested he r. The district c ourt did not credit Mora les' s testimony to the extent itconflicte d with the testimony of the off icer s. See infra p. 9. Af te r t he of fi c e rs ’ i nit ia l e ntr

y , tw o a dd iti on a l of

fi c e rs c ame to t

he a pa rtme nt t o a ssi st i n 8 the sea rch. 6 As to what next transpired, Mora les’s testimony varie s signific antly

from that of the office rs. Acc ordingto the office rs, Special Ag ent Yoos aske d Morales if a ny guns or drug s were 7 in her a partment a

nd she denie d that such items wer e pre sent. She said that she ha d been a sleep until a few moments bef

ore V alentine wa s arr ested. Spec ial Ag ent Yoos then a sked her if they
c ou ld s e arc h th e a

pa rtme nt. Mo ra le s a g re e d, and Spe c ia l A g e nt Y oo s g ave Mo ra le s a c on se nt t o
sear ch for m. He re ad the f

orm to Morales a

nd told her that it allowed the of fice rs to sear ch her
a pa rtme nt. Th e c on se nt f

or m pr ov ide s: 1. Ihave be en aske d to permit special a g ents of the Dr ugEnforc ement Administration to search 377 V ernon A venue, B rookly n, N.Y., apa

rtment 2. 2
. I h av e n o tb e e nth r e at e n e d o r f o r c e d i nan y w ay. 3. Ifre ely

consent to the sea

rch. Mo ra le s si g ne d th e fo rm . Morales initially

denied that ther e wa s any contra band in the apa

rtment as the of

fice rs be g an to se arc h. Spe c ia l A g e nt Y oo s w arn e d h e r t hat if the y fo un d a gun that sh e ha d n ot t old 8 them about, she would be in trouble. Eventually , she told the offic ers that ther e wa s a gun in a7

corne r closet a

nd two guns in a locked box. Det. Crocke tt discovered a shotgun inside a dr aws tr ingba gha

ng ingon a do or in t he be dr oo m. I

n th e up pe r c or

ne r o f t he be dr oo m c los e t, Det. Crocke tt found a locke d firepr oof box. After he f ound the key

and unlocke d it, he dis c ov e re d tw o p ist ols ins ide the bo x. Mo ra le s to ld t he of fi c e rs that th e gun s b e lon g e d to Valentine. D et. Crocke tt also found a fe w g lassine bag s of her oin in a bedside table draw er. The office rs then ar

rested Mor ales. When the office rs later

questioned Va lentine at their of fice , he told them that Morales was not involved and that he took responsibility for the e vidence seized in the apar tment. D. Ind ic tme nt a

nd Mo tio n to Sup pr e ss A g rand jury

char g ed Va lentine with one count of beinga fe lon in possession of a fire arm
and on e c ount o f p os se ssi nghe ro in w ithint e nt t o d istri bute . V a le nti ne fi le d a mot ion to s up pr e ss the evidenc e re lied upon by the g rand jury , arguing that law enf orce ment office rs had a

rre sted him without probable ca

use, that the wa

rra ntless searc hes of his ca

r and his apa

rtment wer e ta int e d b y his un lawf

ul a rr e st, and that hi s w if

e did no t c on se nt t o th e se arc h o f t he ir a pa rtme nt. The district cour

t held a suppre ssion hearingon Valentine’ s motion on S eptember 13 and 27, 2005. At the hea

ring , the g overnme nt presente d five witnesse s: Special Ag ents Ba nzer and Yo os , D e ts. John so n a

nd Cr oc ke tt, and

Se rg e ant H oe hl. Va le nti ne pr e se nte d M or a le s a s h is witness. The district cour

t denied Va lentine’s motion to suppress. Thoug h the district court found that Valentine’ s actions duringthe attempted F edEx delivery wer e too ambiguous to provide probable cause for his ar

rest, the c ourt found that Va lentine’s entr y into the vaca

nt lot with ot her individuals and rea

ppear ance with a beve rag e a f ew minutes later

was suff icient to provide probable cause for the of

fice rs to arr est him. The cour t relied on the te stimony

of De t. J ohnson
and Spe c ia l A g e nt Y oo s th at, i n th e ir e xpe ri e nc e , V a le nti ne ’s a c tio ns we re c on sis te nt w iththo se8

of a na rc oti c s d e a le r. Spe c if

ic a lly , D e t. Johns on

state d th at se lli ngdr

ug s to a g ro up of pe op le
s i mu l t an eo u s l y

m i n i m i z edth e c h an ce s o f ge t t i n g cau gh t , an d Va l en t i n e’ s p urc h as e o f ab ev er age
a f t e r w ar d s w a s th e w ay dr

u gd e a l e r s typ i c a l l y r i d

th e m s e l v e s o f

p o s s i b l y m ar

k e d “ b uy m o n e y” used by underc over a g ents. Special Ag ent Yoos stated that, in his experience , Valentine’ s actions we re c onsistent with a drugsale. The court e x plained its finding of probable cause as fo llo ws : Whil e the c ourt

a g re e s w iththe de fe ns e that, s tand inga lon e , d e fe nd ant’ s c on du c t, up until the fa ile d c ontr oll e d d e liv e ry , w a s to o ambi guo us to g ive ri se to p ro ba ble cause for a

n arr est, the totality

of the c ircumstance s, including de fenda nt’s conduct a fter the delivery attempt, amply

supports the court’ s conclusion that the re wa s p ro ba

ble c a us e fo r d e fe nd ant’ s a

rr e st. (A .3 61 ). Th e c ourt

the n c on c lud e d th at th e se arc h o f V a le nti ne ’s c ar w a s in c ide nt t o h is a rr e st and ther efor e lawf

ul. Wit h respe ct to the sea

rch of Valentine’ s apar

tment, the court he ld that the g overnme nt’s witnesses we re c redible, a nd Morales’ s testimony

was incr edible to the extent that it differe d from that of the office rs. The c ourt found that Mora les consente d to the sear ch and signed the consent for

m before the sea

rch be g an. The court a lso found that Morales’ s consent wa s g iven fre ely and that she ne ver obje cted to the of fice rs’ sea

rch. Finally , the cour

t found that Vale ntine’s statements to the off icer s after his arre st were
vo luntary be c a us e Va le nti ne wa ive d h is Miranda ri g hts and did no t c la im that he wa s f

or c e d to provide stateme nts to the office rs. E. Valentine’ s Conditi onal Guilty Plea and Sentenc ing On F e br ua ry 28 , 2 00 6, Va le nti ne ple a de d guil ty to C ount O ne of

the ind ic tme nt, name ly beinga fe lon in possession of a fire arm, pursua nt to a written plea

ag ree ment. Although the plea
a g re e me nt c onta ine d a

pr ov isi on

by wh ic h V a le nti ne wa ive d h is r ig ht t o a pp e a l or oth e rw ise challeng e his conviction or se ntence if the district court imposed a term of imprisonment of 1209

months or

le ss, the ple a

a g re e me nt p e rm itt e d V a le nti ne to a pp e a l th e de nia l of

his mot ion

to suppress phy sical evide nce. There afte r, the district cour t sentence d Valentine to 120 months of imprisonment. Va le nti ne no w b ri ng s th is a pp e a l. I I . STANDARD OF REVI EW “O nan ap p ea l fr o ma r

u l i n g o na m o t i o nt o s u

p p re s s , we re v i ew a d i s tri ctco urt 's fi n d i n gs of historical fa ct for c lear err or, but ana ly

ze de novo the ultimate deter mination of such leg al issues as proba

ble ca use . . . ,” United States v. Smith, 9 F .3 d 1 00 7, 10 11 (2 d Ci r. 19 93 ); ac c or d Ornelas v. United States , 517 U.S. 690, 695 n.4 (1996), includingwhether the exception for a
sear ch incident to that ar

rest is applica

ble, United States v. Gagnon , 373 F.3d 230, 235 ( 2d Cir. 2004). I I I . DI SCUS SI ON A. Va le nti ne ’s Ar

re st Wa s N ot S up po rt e d b y Pr ob a ble Ca us e The off icer s arr ested Va lentine without a war rant. Such a

n arr est must be supported by probable cause or else it violates the F ourth Amendment. Be c k v . O hio , 379 U.S. 89, 91 (1964); United States v. Fisher , 702 F.2d 372, 375 ( 2d Cir. 1983). Vale ntine argues on appe al that the district court incorr ectly

conclude d that his arre st was supported by probable cause . He f

urther
co n t en d s th atth e p h y s i ca l ev i d en ce s u b s equ en t l y

fo un d b y th e o ff i ce rs af t er h i s arre s t–

th ro u gh the sea rch of his car a nd apar tment – were the fruits of that illeg al ar rest. Thus, the f

irst issue
ra ise d b y his a pp e a l is wh e the r t

he fa c ts a s f

ound by the dis tr ic t c ourt

we re su ff

ic ie nt t o e sta

bli sh probable cause to arre st Valentine. “Probable cause to arre st a person e x ists if the law enfor ceme nt official, on the ba sis of the totality

of the c ircumstance s, has suffic ient knowledg e or r easona bly trustworthy

information to justi fy a per son of re asonable caution in believingthat an off ense ha s been or

is being10

committed by

the per son to be arr ested.” United States v. Patrick, 899 F.2d 169, 171 ( 2d Cir. 1 9 9 0 ) ( ci t i n g Brinegar v. United States , 3 38 U. S. 1 60 , 1 75 -7 6 ( 19 49 )) ; Bec k, 379 U.S. at 91. Whil e proba

ble ca use “r equire s only

a proba bility or substantial cha

nce of criminal ac tivity , not
an ac tual showingof such a ctivity ,” mer e suspicion is not enoug h. Illinois v. Gates , 4 62 U. S. 213, 244 n.13 (1983). In deter mining whe ther proba

ble ca use exists to arre st a suspect, “ [t ]he experience of a police office r is a fa ctor to be c onsidered . . . but the r eleva nce of the suspect’ s
co n d u cts h o u l d

b e s u ff i ci en t l y art i cu l ab l e t h ati t s i mp o rtca nb e u n d er s t o o d b y th e a v er age
rea sonably

prudent pe rson.” Fisher , 702 F.2d at 378. Ba sed on evide nce he ard at the suppression hea ring , the district court c oncluded that Va le nti ne ’s a c tio ns pr ior

to t he fa ile d c ontr oll e d d e liv e ry did no t e sta bli shpr ob a

ble c a us e to
arr est him. The district court noted that Valentine mer ely talked to Rodriguez in front of the apar tment, entere d and exited both his car and the apar tment building seve ral times, ca lled Rodrigue z when the under cover office rs ar

rived with the fur

niture for the controlled de livery , and told Det. Perez that he would he lp car ry the furniture if compensated. Relying on Fisher , 702 F.2d at 377, where we he ld that probable c ause to a rre st was not prese nt where the suspect
emer g ed fr om a house in the vicinity of a house under obse rvation by the offic ers, he sitated and then re -ente red the house, the district cour t concluded that Valentine' s conduct up to this point
wa s to o ambi guo us to g ive ri se to p ro ba ble c a us e to a rr e st. We ag ree that Valentine' s conduct prior to the controlled de livery did not support probable cause . The unde rcove r off icer s had neve r met Va lentine bef ore the y arr ived for the controlled de livery

and had no inf

ormation from whic h they could conc lude that Vale ntine was involved in the sale of na rcotics. And while they

suspected that L ebron, the intended re cipient of the deliver

y , was involved in nar cotics traf ficking , nothing Va lentine had done g ave the m an articula ble basis for c oncludingthat Valentine w as assoc iated with L ebron. A t most, a11

rea sonably

prudent pe rson could conc lude that Vale ntine was fa miliar with other re sidents of the
a pa rtme nt b uil din g , b ut n ot t hat he wa s a sso c iate d w ithL e br on or anyon e e lse inv olv e d in
c r i m i n a l a c t i v i ty. Th e dis tr ic t c ourt

we nt f ur the r, ho we ve r, and

c on c lud e d th at V a le nti ne ' s c on du c t after the failed c ontrolled delivery , coupled with his ac tions prior to the controlled deliver y , g ave the office rs proba

ble ca use to believe that he had sold na rcotics to a group of unidentifie d males loiteringnear

the apa rtment building. In particula r, the district cour

t relied on the f

act that Valentine e x ited his apartment buildingafte r cha ng ing into a sw eatshirt; that he g estured to the unidentified men standingoutside his apartment building , conver sed with them, and wa lked toge ther with them into an adja cent va cant lot throug h a fe nce, where the offic ers c ould not see wh att o o k p l ac e; th ath e r e- em er geda f ew m i nu t es l at er

fr o ma d i ff

er en td i re ct i o n , ca rryi n g a be ve ra g e ; and

that he e nte re d a

nd e xite d h is c ar. B a se d o n th is c on du c t and the of fi c e rs ’ interpre tation of it – that a dea ler, in their e x perie nce, w ould “come down and do eve ry body at
on c e be c a us e it w a s le ss c ha

nc e of him g e tti ngc a

ught b y the po lic e ” and

the n p ur c ha se something to g et rid of the mone y used by the buy ers in ca se that money was mar ked – the dis tr ic t c ourt

fo un d th at pr ob a

ble c a us e e xiste d to arr e st V a le nti ne fo r t he sa le of na rc oti c s. With that conclusion, we respe ctfully disag ree . We have pr eviously

held that no proba

ble ca use exists to arre st where a suspec t’s actions
are too ambiguous to ra ise more than a g ener alized suspicion of involvement in criminal activity
. InUnited States v. Ceballos , for e x ample, police of fice rs monitoring the residenc e of a suspected drugdeale r obser

ved Ceba llos, who was not the targ et of the inve stigation at that time, drive up and par k in front of the suspe cted dr ugdeale r’s home. 654 F .2d 177, 179 (2d Cir. 1981). Ceballos exit ed a c ar, g lance d around in what an offic er de scribed a s a “c urious manner ,” and enter ed the r esidenc e empty -hande d. Id. Five to ten minutes late r, Ceballos eme rg ed fr om the12

residenc e ca

rry ing a small brown pape r bag , ag ain looked ar ound, enter ed the c ar, a nd then drove
awa y . Id. The off

icer s followed Ceba llos, pull ed him over at a stop light, orde red him out of the
car with guns dr awn, a

nd discovere d that the pape r bagcontained na rcotics. Id. at 18 0- 81 . T his court c oncluded that the of fice rs’ seizure of

Ceballos was a

de fa cto ar

rest and that the totality

of the circ umstances did not establish proba ble ca use. Id. at 181, 185. In particula r, this court found that eve n though the office rs, base d on their experienc e, we re suspicious that Ceba llos had purcha sed nar cotics, proba ble ca use re quired somethingmore than g ener alized suspicion before the offic ers c ould have a

rre sted him. Id. L ike Ceballos , a re asonably prudent pe rson, base d on the information known by experience d office rs, would not believe that Valentine ha d committed a cr ime. L ackingany information that Vale ntine was involved in sellingnarc otics, that he wa s associate d with the intended re cipient of the na rcotics- packe d furniture , or that the unidentified me n with whom Valentine e ntere d the vac ant lot had soug ht to purchase narc otics, the offic ers c oncluded that Valentine ha d consummated a drugdeal. This infe renc e wa s based pr imarily on the fa ct that he called some unidentified men tog ether , disappea red w ith them through a

vacant lot, and ree me rg e d a

fe w m inute s late r c arr

yinga be ve ra g e . Su c h n on -c ri min a l c on du c t, w ith out mo re , is too ambi guo us to s up po rt pr ob a ble c a us e . Wh ile the of

fi c e rs ’ e xpe ri e nc e may

have le d th e m to suspect Va lentine’s socia l interac tion with the men and his decision to purcha se a be vera g e as consistent with the actions of dr ugdeale rs, they

never observe d any

transac tion between Valentine a

nd the men. Indeed, the rec ord does not indicate that, prior to the ar rest, the of

fice rs observe d any

evidenc e of na

rcotics tra ffickingat the apa rtment building, e x cept f

or the shipment of fur niture to another

person in a dif

fer ent apa rtment in the building. Thus, Va lentine’s conduc t
c ou ld n ot h ave g e ne rate d a ny thi ngmor e tha

n a g e ne ra lize d s us pic ion

that he wa s invo lve d in criminal conduc t. Such suspicions do not create probable cause to arre st. See, e .g., W ong Sun v.Al tho ug h w e ho ld t hat th e fa c ts a s f

ound by the dis tr ic t c ourt

did no t g ive ri se to 9 probable cause to arre st Valentine, we rec og nize that Valentine’s c onduct may have g iven the office rs some g rounds for suspicion. We express no view, how ever , as to whethe r such suspicion was suff icient to stop Valentine unde r Te rry v . O hio , 392 U.S. 1 (1968), bec ause the rec ord indisputably

reve als that the off

icer s arr ested Va lentine and made no attempt to stop him for questioning. A s the district court’s f indings re veal, two of

fice rs, ac ting unde r a supe rior’s ins tr uc tio ns , a pp ro a c he d V a le nti ne , to ld h im tha t he wa s und e r a

rr e st, and or de re d h im t o p ut h is hands behind his bac k. Ba sed on “the deg ree of intrusion, the amount of for ce use d, and the 13 United States , 371 U.S. 471, 479 (1963) (“ I t is basic that an ar rest . . . must stand upon firmer g ro un d th an me re su sp ic ion .” ); c om pa re United States v. Ingrao , 897 F.2d 860, 863- 65 (7th Cir. 1990) (f inding no pr obable c ause where a suspec t car ried a n opaque ba gdown a g ang way previously

used by a nar cotics suspec t, looked around while crossingthe stree t, and then drove
car efully awa y while fre quently

looking in his rea

rview mirr or), with Un ite d S tates v . R os ar io , 638 F.2d 460, 462 ( 2d Cir. 1980) (findingprobable cause wher e off icer s observe d a plastic ba g containinga substance which looked like c ocaine , which wa s furtively car ried fr om house to car and exhibited to two men for inspection). The off icer s’ interpre tation of Vale ntine’s ac tions seems to have be en lar g ely informed by his presenc e at the sur

veilled apa

rtment building a

nd his familiarity

with other men who kne w the intended r ecipient of

the Fe dEx delivery . “[I ]n order to find proba ble ca use base d on association with per sons eng ag ing in c riminal activity , some additional circ umstances f rom which it is reasona

ble to infer pa

rticipation in criminal enter prise must be shown.” Ingrao , 897 F.2d at 864 (quotation marks omitted). Nothingin the rec ord linked Va lentine to L ebron’ s suspected na

rcotics a ctivity

or the F edEx delivery , and without more, his pre sence at the intended
s i t e o f th e c o n tr o l l e d

d e l i v e r y – w h i c hw a s a l s o h i s r e s i d e n c e – c an n o ts u

p p o rtp r o b a

b l e c a u s e . It is for these r easons that we disag ree with the conclusion of the district c ourt and find that the cumulative re cord is insuffic ient as a matter of law to “war rant a man of re asonable caution in the belief” that Valentine c ommitt ed a c rime. Carroll v. United States , 267 U.S. 132, 162 (1925). 9extent to which appellant' s fre edom of moveme nt was cur tailed,” Ceballos , 654 F.2 at 183, nothing a bout the office rs’ c onduct indicates that this was a Te rry stop. There fore , to the extent that the g overnme nt argues that the off icer s only require d rea sonable suspicion of Va lentine’s criminal ac tivity

to stop him , we r ejec t that argument as unsupported by the re cord. 14 Given that Va lentine’s ar rest wa s not supported by probable cause , we a lso cannot agree with the district court’s c onclusion that the war rantless sea

rch of Valentine' s car , wher ein the
narc otics were found, wa s a valid sea rch inc ident to arre st under New Y ork v. Be lton , 4 53 U. S. 454, 460 (1981) ( holding that “ when a policeman ha s made a

lawful c ustodial arre st of the occupa nt of an a utomobile, he may , as a c ontemporane ous incident of that ar rest, sea rch the pa sse ng e r c omp artme nt o f t hat a uto mob ile ” ). Whil e po lic e of fi c e rs may

c on du c t a

wa rr antl e ss
se arc h o f a

n in div idu a l' s p e rs on a l pr op e rt y if the se arc h is inc ide nt t o a lawf ul c us tod ia l arr e st, of fi c e rs la c kin gpr ob a

ble c a us e to a rr e st a su sp e c t ne c e ssa

ri ly la c k p ro ba

ble c a us e to c on du c t a
sear ch incident to that ar

rest. See id.; United States v. Pe rea, 986 F.2d 633, 642- 43 (2d Cir. 1993). Given that the se arc h of Va lentine’s ca r stemmed fr om an illeg al ar rest and the g overnme nt has not prese nted any alternative g rounds that would support a f inding that the office rs had pr obable c ause to c onduct a wa rra ntless searc h of Va lentine’s vehic le, the evide nce seized from that sea

rch must nec essar ily

be suppre ssed as the f

ruit of the poisonous tree
. See Ingrao , 897 F.2d at 866. This does not end the ne cessa ry inquiry . Valentine w as convic ted, not for the posse ssion of nar cotics found in the se arc h of his sedan, but for the fire arms found in his apa rtment. The
rec ord indicate s that the illeg al ar rest and se arc h of the c ar pr ompted the offic ers to sea rch Valentine’ s apar

tment with Morales’s c onsent and to ultimately discover the firea

rms. Howeve r, under Brown v . I

lli no is , 422 U.S. 590 (1975) and its prog eny , unless Morales’ s consent to sea rch the apa rtment “ha d become so attenuate d as to dissipate the taint” fr om the illega l acts lea ding up to that searc h, the fire arms found inside the a partment must also be suppre ssed as the f ruit of theOn re mand , th e dis tr ic t c ourt sh ou ld, if

ne c e ssa ry , c on du c t a dd iti on a l f

a c t f ind ingto 10 further develop the r ecor d on this iss ue. 15 poisonous tree. Id. at 599 (quotation marks omitted). B eca use the district cour

t found that Valentine’ s arr est was law ful, it never c onsidered the question of attenuation. W e ther efor e
rema nd for the district c ourt to consider that question. 10 I V. CONCLUSI ON F or the fo re g oin gre a so ns , th e dis tr ic t c ourt ’s de nia l of Va le nti ne ’s mot ion

to s up pr e ss i s he re by va c ate d a nd re mand e d w ithins tr

uc tio ns to c on du c t f

ur the r p ro c e e din g s c on sis te nt w ith this opini on. Any

further appea l from the rulingof the district cour t, pursuant to this remand, sh a ll b e re fe rr e d to thi s p ane l of jud g e s.