06-4813-cr

United States v. Delossantos

1 UNITED STATES COURT OF APPEALS

2

3 FOR THE SECOND CIRCUIT

4 

5 -------------

6 

7 August Term 2007

8

9 Argued: May 13, 2008 Decided: July 25, 2008

10

11 Docket No. 06-4813-cr

12

13 --------------------------------------------------X

14

15 UNITED STATES OF AMERICA, 

16

17 Appellant,

18

19 - against -

20

21 MARINO DELOSSANTOS,

22

23 Defendant,

24

25 FRANCISCO RODRIGUEZ,

26

27 Defendant-Appellee.

28

29 --------------------------------------------------X

30

31 Before: FEINBERG, MINER, and B.D. PARKER, Circuit Judges.

32

33 The United States appeals from an order of the district

34 court granting defendant-appellee’s motion to suppress evidence

35 because the police lacked probable cause for his arrest. The

36 order of the district court is reversed. 

37

38 JAMES R. SMART, Assistant United States Attorney

39 (RICHARD J. SCHECHTER, Assistant United

40 States Attorney, WILLIAM J. NARDINI,

41 Assistant United States Attorney, Of

42 Counsel, on the brief), for KEVIN J.

43 O’CONNOR, United States Attorney for the

44 District of Connecticut, New Haven, Conn.,

45 for Appellant.

46
 This summary is drawn from the district court’s findings 1

of fact. United States v. Rodriguez, No. 3:06-cr-57(JCH), 2006

WL 2860633, at *1-4 (D. Conn. Oct. 4, 2006).

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1 SARAH F. RUSSELL, Assistant Federal Defender, for

2 THOMAS G. DENNIS, Federal Defender, New

3 Haven, Conn., for Defendant-Appellee.

4

5 FEINBERG, Circuit Judge:

6 Defendant-appellee Francisco Rodriguez was arrested after

7 driving another man to the scene of a drug deal that turned out

8 to be a police sting. The United States District Court for the

9 District of Connecticut (Janet C. Hall, J.) concluded that the

10 police lacked probable cause to arrest Rodriguez and granted

11 his motion to suppress post-arrest statements and evidence

12 obtained from his apartment and car. For the reasons explained

13 below, we reverse the order of the district court.

14

15 I. BACKGROUND1

16 Defendant Marino Delossantos met an undercover Drug

17 Enforcement Administration (“DEA”) task force agent, Officer

18 Felix Martinez of the Stamford, Connecticut Police Department,

19 in a bar. The two men discussed a possible cocaine deal.

20 At a second meeting, on October 25, 2005, Delossantos told

21 Officer Martinez that he looked familiar and that he suspected

22 Martinez was a Stamford police officer. He nevertheless agreed

23 to “go home” to get a cocaine sample. Agents followed

24 Delossantos’s car to 1315 Howard Avenue, a multifamily
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1 residential building in Bridgeport, Connecticut. Delossantos

2 entered the building for a few minutes; he then left and drove

3 to meet Officer Martinez at a Cumberland Farms grocery store

4 and gas station in neighboring Fairfield. There, Delossantos

5 got in the officer’s car and gave him the cocaine sample,

6 telling him he could also get some heroin. During the meeting,

7 Delossantos also asked Officer Martinez if he knew two people

8 from Stamford; although the officer did know them, he denied

9 it. Because of Delossantos’s evident suspicions, the agents

10 decided that they would arrest him at the next meeting.

11 That night, Officer Martinez called Delossantos and asked,

12 in code, to buy cocaine and heroin. They agreed to meet the

13 next day at the Cumberland Farms. 

14 DEA agents surveilling 1315 Howard Avenue the next morning

15 saw Delossantos and another man, later identified as defendant16 appellee Rodriguez, leave the building’s front porch and get in

17 the car that Delossantos had driven the previous day. Agents

18 saw Rodriguez drive the car toward Interstate 95, then lost

19 sight of it. Half an hour later, at 11:15 a.m., Officer

20 Martinez spoke to Delossantos on his cell phone, and

21 Delossantos asked for more time; Martinez said he could hear

22 “car sounds” and another person in the background. When they

23 spoke again at 12:20 p.m., Martinez could again hear “road
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1 noise” and another person. Both times, Martinez believed

2 Delossantos was in a car.

3 Agents saw both men return in the car to 1315 Howard

4 Avenue at 12:30 p.m. Delossantos entered the building while

5 Rodriguez walked behind the car and disappeared from view. They

6 returned to the car about ten minutes later, and Rodriguez

7 again drove them in the direction of the Cumberland Farms.

8 Agents followed the car.

9 Delossantos called Officer Martinez en route and told him,

10 in Spanish, to follow his car to another location when he

11 arrived. The phrase Delossantos used was variously translated

12 as “I don’t want to do it there” or “Let’s go some place else”

13 (by Martinez) and “I don’t want to be there” (by defendants’

14 translator). During the call, Martinez could hear Delossantos

15 speaking to another person in Spanish. Martinez asked

16 Delossantos to wait for him at the Cumberland Farms. When the

17 car pulled into the gas station, agents immediately surrounded

18 it and arrested both Delossantos and Rodriguez. 

19 In response to questioning, Rodriguez told the agents that

20 he lived at 1315 Howard Avenue. He further consented to a

21 search of his apartment and car, which revealed drugs and other

22 evidence. Delossantos independently told the agents that he

23 shared an apartment with Rodriguez and that the drugs were his,

24 not Rodriguez’s. Delossantos also told the agents that
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1 Rodriguez agreed to drive Delossantos knowing Delossantos was

2 engaged in drug dealing.

3 A federal grand jury returned an indictment against

4 Delossantos and Rodriguez in March 2006, charging them with

5 conspiracy to distribute 500 or more grams of cocaine and 100

6 or more grams of heroin, and charging Delossantos with

7 substantive possession counts. Delossantos pled guilty to the

8 conspiracy counts in July 2006. In August 2006, the grand jury

9 returned a superseding indictment that added substantive

10 possession counts against Rodriguez.

11 Rodriguez moved to suppress his post-arrest statements and

12 the evidence seized from his apartment and car. He was granted

13 leave to file a late motion to suppress evidence. The district

14 court held an evidentiary hearing on the suppression motion on

15 August 23, 2006. By order dated October 4, 2006, the district

16 court granted the suppression motion. The Government timely

17 brought this interlocutory appeal. Rodriguez’s trial has been

18 stayed pending this appeal; he is currently on pretrial

19 release.

20

21 II. DISCUSSION

22 A. Governing Law

23 On appeal from the grant of a suppression motion, we

24 review the district court’s factual findings for clear error,
 The Government does not contest the district court’s 2

conclusion that the evidence against Rodriguez would not have

been inevitably discovered absent his arrest.

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1 viewing them in the light most favorable to the Government, but

2 we analyze de novo the existence of probable cause. United

3 States v. Howard, 489 F.3d 484, 490-91 (2d Cir. 2007). The

4 Government bears the burden of proof as to establishing

5 probable cause. United States v. Elgisser, 334 F.2d 103, 110

6 (2d Cir. 1964).

7 The main question we must resolve is whether Rodriguez was

8 legally arrested. If he was not, the evidence derived from his

9 post-arrest statements and the consensual search of his

10 apartment and car must be suppressed as the fruit of an

11 unlawful arrest. Wong Sun v. United States, 371 U.S. 471, 485-

12 86 (1963).2

13 Rodriguez argues that his arrest was invalid under the

14 Fourth Amendment, which protects “[t]he right of the people to

15 be secure in their persons . . . against unreasonable searches

16 and seizures.” A warrantless arrest is unreasonable under the

17 Fourth Amendment unless the arresting officer has probable

18 cause to believe a crime has been or is being committed.

19 Devenpeck v. Alford, 543 U.S. 146, 152 (2004); United States v.

20 Watson, 423 U.S. 411, 417 (1976). Probable cause exists where

21 the arresting officer has “‘knowledge or reasonably trustworthy

22 information of facts and circumstances that are sufficient to
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1 warrant a person of reasonable caution in the belief that the

2 person to be arrested has committed or is committing a crime.’”

3 Walczyk v. Rio, 496 F.3d 139, 156 (2d Cir. 2007) (quoting

4 Weyant v. Okst, 101 F.3d 845, 852 (2d Cir. 1996)).

5 The Supreme Court has repeatedly stated that the probable6 cause standard is “a ‘practical, nontechnical conception’ that

7 deals with ‘the factual and practical considerations of

8 everyday life on which reasonable and prudent men, not legal

9 technicians, act.’” Maryland v. Pringle, 540 U.S. 366, 370

10 (2003) (quoting Illinois v. Gates, 462 U.S. 213, 231 (1983)).

11 Because the standard is fluid and contextual, a court must

12 examine the totality of the circumstances of a given arrest.

13 Id. at 371; Panetta v. Crowley, 460 F.3d 388, 395 (2d Cir.

14 2006). These circumstances must be considered from the

15 perspective of a reasonable police officer in light of his

16 training and experience. United States v. Moreno, 897 F.2d 26,

17 31 (2d Cir. 1990), abrogated on other grounds by Horton v.

18 California, 496 U.S. 128 (1990). 

19

20 B. Analysis

21 The district court found that at the time of the arrest

22 the agents knew or had reasonably trustworthy information as to

23 the following facts: (1) Delossantos had suspicions about the

24 undercover officer’s true identity; (2) the morning of the
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1 planned drug buy, Rodriguez drove Delossantos from 1315 Howard

2 Avenue, where the agents reasonably believed Delossantos was

3 storing drugs, towards Cumberland Farms, the agreed-on meeting

4 place; (3) Rodriguez and Delossantos were the only people in

5 the car; (4) shortly afterwards, Delossantos asked for more

6 time while another person was audible in the background; (5)

7 after the request for more time, Rodriguez drove Delossantos

8 back to 1315 Howard Avenue; (6) shortly afterwards Rodriguez

9 drove Delossantos a third time from 1315 Howard Avenue to the

10 Cumberland Farms; and (7) while the car was en route,

11 Delossantos called the undercover officer to express discomfort

12 with the chosen meeting place.

13 We think the agents had probable cause to arrest Rodriguez

14 based on these facts. The Supreme Court has said that it is

15 reasonable to believe that “a car passenger . . . will often be

16 engaged in a common enterprise with the driver, and have the

17 same interest in concealing the fruits or the evidence of their

18 wrongdoing.” Wyoming v. Houghton, 526 U.S. 295, 304-05 (1999);

19 see also United States v. Patrick, 899 F.2d 169, 172 (2d Cir.

20 1990) (holding that after drugs were discovered in defendant’s

21 backpack, agents had reasonable basis to believe that co22 defendant “was not just a mere innocent traveling companion but

23 was traveling and acting in concert” with defendant). Here,

24 Rodriguez drove Delossantos on multiple trips, including the
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1 final trip to the drug-buy location. More specifically, the

2 Supreme Court has also said that it is reasonable to infer that

3 if one person in a vehicle is engaged in drug dealing, so are

4 the other passengers, because drug dealing is “an enterprise to

5 which a dealer would be unlikely to admit an innocent person

6 with the potential to furnish evidence against him.” Pringle,

7 540 U.S. at 373. Here, the agents could have reasonably

8 inferred that Delossantos was unlikely to be accompanied by an

9 innocent person because Delossantos was already suspicious and

10 thus had reason to worry about the prospect of a witness

11 against him.

12 We disagree with Rodriguez and the district court that

13 this case is analogous to United States v. Di Re, 332 U.S. 581

14 (1948), which also involved the attempted sale of contraband

15 (in Di Re, counterfeit gas ration coupons) from a car. The

16 police in Di Re, acting on an informant’s tip, arrested all

17 three occupants of the car –- the driver, the informant sitting

18 in the back seat, and the defendant Di Re in the passenger

19 seat. Id. at 583. The Supreme Court held that the officers

20 lacked probable cause to arrest Di Re for either possession or

21 conspiracy, because while the informant held counterfeit

22 coupons in his hand and told the officers he got them from the

23 driver, Di Re was neither seen holding coupons nor named by the

24 informant as having any. Id. at 592. 
 Rodriguez’s argument that Officer Martinez effectively 3

singled out Delossantos but not Rodriguez, because he “knew that

Delossantos was the guilty person,” is specious. In Di Re, the

informant had reason to know whether Di Re was guilty, so his

silence concerning Di Re was properly understood as exculpatory.

Here, Officer Martinez did not have preexisting information

about Rodriguez’s involvement.

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1 We think Di Re is distinguishable from the facts here. The

2 Court in Di Re was careful to note that “[t]he argument that

3 one who ‘accompanies a criminal to a crime rendezvous’ cannot

4 be assumed to be a bystander” is indeed “forceful enough in

5 some circumstances.” Id. at 593. The Court said this argument

6 was “farfetched” with respect to Di Re because (among other

7 reasons) the informant fingered the driver, but not Di Re, as a

8 culprit prior to the arrests. Id. at 593-94. There was no

9 equivalent singling out of Delossantos but not Rodriguez. See 3

10 Pringle, 540 U.S. at 374 (distinguishing Di Re on the sole

11 basis that “[n]o such singling out occurred in this case”).

12 Furthermore, the evidence against Rodriguez at the time of his

13 arrest was stronger than that against Di Re. Whereas Di Re was

14 merely seen sitting in the suspect’s vehicle when officers

15 approached, the agents here saw Rodriguez ferry Delossantos

16 between the likely drug-stash location and the transaction

17 point and heard Delossantos discuss details of the transaction
 Two other Supreme Court cases cited by Rodriguez, Ybarra 4

v. Illinois, 444 U.S. 85 (1979), and Sibron v. New York, 392

U.S. 40 (1968), are even less relevant. In Ybarra, police

obtained a warrant to search a bar and its bartender yet decided

to additionally search all the patrons inside, 444 U.S. at 88-

89; in Sibron, police stopped the defendant simply after

observing him speaking with known heroin addicts, 392 U.S. at

45. These cases establish that a person’s presence at a crime

scene or association with criminal suspects do not, without

more, amount to probable cause to arrest. But as we have

explained above, the agents’ suspicions of Rodriguez were not

based solely on his association with Delossantos but on the

objective likelihood that the two men were engaged in a common

criminal endeavor.

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1 (albeit in veiled terms) with Rodriguez evidently sitting

2 beside him.4

3 We are also unpersuaded by Rodriguez’s attempts to

4 minimize, qualify, or explain away individual facts that tend

5 to establish his participation in the crime. Rodriguez argues,

6 among other things, that he and Delossantos might have returned

7 to 1315 Howard before the meeting not to retrieve drugs but

8 simply because Delossantos may have “had other things to do”;

9 that Rodriguez might not have been in the car when Delossantos

10 spoke to the undercover officer; that while Rodriguez was

11 spotted on the building’s front porch, there was no evidence he

12 had ever been inside; and that Rodriguez might have been

13 unaware of the purpose of the trip and the meaning of

14 Delossantos’s comments, having been brought along as nothing

15 but an “innocent dupe.” These omissions and hypothetical
 Although Arvizu involved the existence of reasonable 5

suspicion to make a traffic stop rather than of probable cause

to arrest, the opinion is relevant here because both standards

require us to examine the totality of the circumstances. See

United States v. Yusuf, 461 F.3d 374, 390 n.15 (3d Cir. 2006).

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1 explanations are persuasive in varying degrees, but they do not

2 alter the existence of probable cause. 

3 First, the Supreme Court has instructed us not to consider

4 individual facts in isolation but to examine the totality of

5 the circumstances. Pringle, 540 U.S. at 371. In United States

6 v. Arvizu, 534 U.S. 266 (2002), a border patrol agent who

7 stopped defendant’s vehicle testified about a number of small

8 details that might have each been explained away but that

9 collectively aroused his suspicions. The Court held that, in

10 declining to give weight to any observation “that was by itself

11 readily susceptible to an innocent explanation,” the lower

12 court engaged in erroneous “divide-and-conquer analysis.” Id. 5

13 at 274; see also United States v. Fama, 758 F.2d 834, 838 (2d

14 Cir. 1985) (“The fact that an innocent explanation may be

15 consistent with the facts alleged . . . does not negate

16 probable cause.”). For the same reason, we cannot discount

17 facts one by one simply because Rodriguez has suggested

18 hypothetical explanations for them that are consistent with his

19 innocence.

20 Second, although Rodriguez posits innocent explanations

21 for his conduct, we must evaluate the facts in light of the
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1 training and experience of the arresting agents. See Moreno,

2 897 F.2d at 31. “‘[S]ome patterns of behavior which may seem

3 innocuous enough to the untrained eye may not appear so

4 innocent to the trained police officer who has witnessed

5 similar scenarios numerous times before.’ As long as the

6 elements of the pattern are specific and articulable, the

7 powers of observation of an officer with superior training and

8 experience should not be disregarded.” United States v. Price,

9 599 F.2d 494, 501 (2d Cir. 1979) (alteration in original)

10 (quoting United States v. Oates, 560 F.2d 45, 61 (2d Cir.

11 1977)); see also United States v. $557,933.89, More or Less, in

12 U.S. Funds, 287 F.3d 66, 85 (2d Cir. 2002). In this case, the

13 agents testified that, in their experience, a drug dealer

14 rarely brings along an uninvolved bystander during drug deals

15 or speaks about the details of transactions in the presence of

16 a bystander, even in code. The agents also testified that a

17 dealer who is uneasy about a transaction will often bring an

18 associate for assistance and protection. We are bound to give

19 these observations, which are supported by the agents’ training

20 and experience, their due weight. 

21 Finally, while Rodriguez’s explanations might well be

22 plausible enough to engender reasonable doubts about his guilt,

23 the standard for probable cause is lower than that for

24 conviction. United States v. Juwa, 508 F.3d 694, 701 (2d Cir.
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1 2007); United States v. Fisher, 702 F.2d 372, 375 (2d Cir.

2 1983). Thus, “innocent behavior frequently will provide the

3 basis for a showing of probable cause; to require otherwise

4 would be to sub silentio impose a drastically more rigorous

5 definition of probable cause than the security of our citizens

6 demands.” Gates, 462 U.S. at 244 n.13. We think the arresting

7 agents had reason to think Rodriguez’s involvement in the drug

8 deal was, at minimum, probable. See id. at 231 (emphasizing

9 that probable cause deals in “probabilities” rather than “hard

10 certainties” (internal quotation marks omitted)).

11

12 III. CONCLUSION

13 Because we find that the agents had probable cause to

14 arrest Rodriguez, there was no reason to suppress the evidence

15 against him. The order of the district court is reversed, and

16 the case is remanded for further proceedings consistent with

17 this opinion.