United States Court of Appeals

For the First Circuit

No. 09-2252

UNITED STATES OF AMERICA,

Appellant,

v.

FERNANDO CRESPO-RÍOS,

Defendant, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Jay A. García-Gregory, U.S. District Judge]

Before

Lynch, Chief Judge,

Torruella and Stahl, Circuit Judges.

J. Campbell Barker, Attorney, Appellate Section, Criminal

Division, U.S. Department of Justice, with whom Lanny A. Breuer,

Assistant Attorney General, Greg D. Andres, Acting Deputy Assistant

Attorney General, Rosa Emilia Rodríguez-Vélez, United States

Attorney, Nelson Pérez-Sosa, Assistant United States Attorney,

Chief, Appellate Division, and Richard M. Re, Attorney, Criminal

Division, U.S. Department of Justice, were on brief for appellant.

Rachel Brill, for appellee.

June 8, 2011
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TORRUELLA, Circuit Judge. Fernando Crespo-Ríos

("Crespo") was charged with (1) transferring obscene material to a

minor under the age of sixteen in violation of 18 U.S.C. § 1470 and

(2) possession of child pornography in violation of 18 U.S.C.

§ 2252(a)(4)(B). The district court granted his motion to suppress

the child pornography that agents discovered on various digital

media while they were executing a warrant to search for evidence of

(1) transferring obscene material to a minor in violation of

18 U.S.C. § 1470 and (2) enticing or coercing a minor in violation

of 18 U.S.C. § 2422(b). The government now appeals the grant of

the motion to suppress and the denial of its motion for

reconsideration. We reverse and remand with instructions to deny

the motion to suppress.

I. Background

In August 2007, Special Agent Odette D. Tavares of the

Federal Bureau of Investigation entered a Spanish-language chat

room posing as a twelve-year-old Puerto Rican girl. She was part

of a covert online investigation aimed at identifying individuals

attempting to engage in sexual relations with minors. An

individual later identified as Crespo approached Tavares in the

chat room and asked if Tavares had "MSN," referring to an instant

messaging program. Tavares replied affirmatively, and they

continued to chat through MSN's "instant messenger."
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During this first conversation and others that followed

over the course of approximately the next eight months, Crespo

repeatedly communicated with Tavares about matters of a sexual

nature despite being informed that she was only twelve years old

and in seventh grade. During the majority of Crespo's chat

sessions with Tavares, he displayed his bare erect penis to Tavares

at some point. Crespo also repeatedly asked Tavares to meet with

him and discussed the sexual activities that would take place if

they met. He said, among other things, that (1) he would perform

oral sex on Tavares, (2) he and Tavares could watch pornographic

films before having sex, (3) the pair would have sex, (4) he would

teach Tavares how to kiss and how to bathe him, and (5) she could

model a g-string for him. Crespo also displayed two photos of

himself to Tavares and repeatedly asked her to send him photos of

herself.

In addition, Crespo mentioned or suggested at various

points that he had engaged in sexual activities with minors before.

During one chat, he noted that he had had sex with a fourteen-yearold girl. During another conversation, in the context of

encouraging Tavares to shave her genital area, he told her that he

knew of an individual who shaved her genital area as of the age of

eleven.

Based on information learned as a result of the chats

with Crespo, information received from the Puerto Rico Telephone
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Company, and information gleaned from motor vehicle checks, Tavares

submitted an affidavit in support of a search warrant. A

magistrate judge issued a search warrant for a residence in

Mayagüez, Puerto Rico. The warrant authorized agents to search the

residence for evidence, fruits, and instrumentalities of a

violation of 18 U.S.C. § 1470 (transfer of obscene material to a

minor) and 18 U.S.C. § 2422(b) (coercion or enticement of a minor).

The warrant incorporated "Attachment B" of Tavares's affidavit,

which listed, among other items that could be seized, the

following:

2. Records, documents, correspondence

(limited to electronic communications), notes

and/or any other materials relating to

correspondence or contact between [Crespo] and

[Tavares], including but not limited to

electronic mail, chat logs, and electronic

messages.

3. Records, documents, correspondence

(including but not limited to electronic

communications), notes, and/or any other

materials relating to correspondence or

contact between [Crespo] and individuals

purporting to be minors, or any attempt by

[Crespo] to induce any minor to engage in

illegal sexual[] activity, including but not

limited to electronic mail, chat logs, and

electronic messages.

. . . .

10. Any magnetic, electronic or optical

storage device capable of storing data, such

as floppy disks, hard disks, tapes, CD-ROMs,

CD-R[s], CD-RWs, DVDs, optical disks, printer

or memory buffers, smart cards, PC cards,

memory calculators, electronic dialers,
 The magistrate judge did not conduct an evidentiary hearing 1

because she concluded that the defendant's motion to suppress did

not require one.

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electronic notebooks, cellular telephones, and

personal digital assistants[.] 

. . . . 

12. Any computer equipment used to encode

or store data . . . .

The main text of Tavares's affidavit referred to child pornography

when it described the parameters of the potential search as

including, among other things, "any and all chat logs, child

pornography, child erotica, information pertaining to the sexual

interest in children, [and] images depicting sexual contact between

adults and minors." "Attachment B" authorized agents to search for

"[c]orrespondence . . . which refers to . . . child pornography"

and "sex toys to include but not limited to pornographic videos."

When Tavares executed the search warrant, she seized,

among other things, a computer system, an external hard drive, and

a number of CDs. The government forensically analyzed the seized

items and discovered child pornography. The record is not clear as

to exactly where and how each item of child pornography was

discovered, or which items were photographs as opposed to videos.1

According to Crespo's appellate brief, however, some of the child

pornography was found on the external digital media. At oral

argument, Crespo's counsel explained that child pornography images

were found on both the computer Crespo used for his chats and on
 As the government noted in its response in opposition to the 2

motion to suppress, Crespo failed to state specifically which items

he sought to suppress.

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the external hard drive. Crespo's counsel also mentioned, in

responding to a question about the location of the child

pornography, that there was a video that was found on the external

hard drive and also on a CD.

Crespo was ultimately charged with (1) knowingly

possessing both still images and movie files of actual minors

engaging in sexually explicit conduct, in violation of 18 U.S.C.

§ 2252, and (2) attempting to transfer obscene matters to someone

who was apparently under the age of sixteen, in violation of

18 U.S.C. § 1470. Following his indictment, Crespo filed a motion

to suppress the child pornography evidence on the ground that the

search warrant was impermissibly general and authorized government

agents to search for items without probable cause to believe those

items would be present.2

A magistrate judge recommended that the court deny

Crespo's motion to suppress, concluding that there was probable

cause to search for child pornography. The magistrate judge also

noted that the good faith exception to the exclusionary rule, see

United States v. Leon, 468 U.S. 897 (1984), applied, and that the

doctrine of inevitable discovery, see Nix v. Williams, 467 U.S. 431

(1984), might apply.
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The district court rejected the magistrate's

recommendation, concluding that Tavares's affidavit did not provide

probable cause to believe that Crespo's digital media would contain

child pornography. The district court also concluded that the good

faith exception to the exclusionary rule did not apply. Addressing

the magistrate's inevitable discovery argument, the district court

noted that it believed that the plain view doctrine would be a more

appropriate framework than the inevitable discovery doctrine, and

concluded that the government ultimately could not prevail under

the plain view doctrine. In a later order denying the government's

motion for reconsideration, the district court clarified its

reasoning on this point. According to the second order, because

there was no probable cause to search for child pornography, the

law enforcement officers who conducted a forensic examination of

Crespo's digital media were not conducting a lawful search, and

thus were not entitled to avail themselves of the plain view

exception to the warrant requirement. The government now appeals.

II. Standard of Review

In assessing a district court's decision to grant a

motion to suppress, "[w]e review 'the court's findings of fact for

clear error and the application of the law to those facts de

novo.'" United States v. Siciliano, 578 F.3d 61, 67 (1st Cir.

2009) (quoting United States v. Vilches-Navarrete, 523 F.3d 1, 12

(1st Cir. 2008)).
 The government did not expressly advance an argument under the 3

inevitable discovery doctrine on appeal, and it is unclear whether

it did so below. However, the magistrate judge addressed the

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III. Discussion

The government makes three alternative arguments: (1)

probable cause supported the warrant's authorization to search

Crespo's computer for child pornography, (2) suppression was

inappropriate given the good faith doctrine because the agents

acted in objectively reasonable reliance on the warrant, and (3)

the child pornography evidence should not be suppressed because it

was discovered in plain view during a lawful search. Crespo

responds, first, that there was no probable cause to seize and

search all of Crespo's digital media in order to look for child

pornography because Tavares's affidavit did not allege any nexus

between Crespo's behavior and possession of child pornography and

because the warrant application was overly broad. In addition,

Crespo contends that the good faith exception is inapplicable

because Tavares, who executed the warrant, could not have

reasonably believed that there was probable cause to search for

child pornography. Finally, Crespo argues that the plain view

exception does not apply because the government had no probable

cause to search the external hard drive or CDs at all.

We need not decide whether there was probable cause to

search any of Crespo's digital media for child pornography because

we resolve this appeal based on the inevitable discovery doctrine.3
inevitable discovery doctrine, and Crespo therefore had the

opportunity to argue that it was inapplicable. The inevitable

discovery doctrine we employ here is similar in reasoning to the

government's plain view argument, and it is clear that whether or

not computer files fall under the plain view doctrine, "the

independent source and inevitable discovery doctrines apply to the

contents of the files." United States v. Stabile, 633 F.3d 219,

237 (3d Cir. 2011). We may exercise some latitude as to our

grounds of decision where related doctrines are at issue. See,

e.g., United States v. Sánchez, 612 F.3d 1 (1st Cir. 2010)

(utilizing plain view doctrine rather than community caretaker

doctrine).

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Under the inevitable discovery doctrine, "evidence that 'would

inevitably have been discovered without reference to the police

error or misconduct' may be admitted at trial." United States v.

Hughes, No. 09-1646, 2011 WL 1332061, at *11 (1st Cir. Apr. 8,

2011) (quoting Williams, 467 U.S. at 448). "Such evidence is

admissible 'so long as (i) the lawful means of its discovery are

independent and would necessarily have been employed, (ii)

discovery by that means is in fact inevitable, and (iii)

application of the doctrine in a particular case will not sully the

prophylaxis of the Fourth Amendment.'" Id. (quoting United States

v. Zapata, 18 F.3d 971, 978 (1st Cir. 1994)).

In addressing the first prong of the inevitable discovery

standard, we divide our analysis in order to explain why agents

could have lawfully searched (1) Crespo's computer, (2) the

external hard drive, and (3) the CDs, provided they were searching

those digital media for certain categories of evidence. As

explained below, these searches would have been lawful because
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there was probable cause to believe that at least some of the

evidence listed in the warrant application's "Attachment B" would

have been found on these digital media. Probable cause exists

when, "given all the circumstances set forth in the affidavit[,]

. . . there is a fair probability that contraband or evidence of a

crime will be found in a particular place." United States v.

Hicks, 575 F.3d 130, 136 (1st Cir. 2009) (quoting United States v.

Feliz, 182 F.3d 82, 86 (1st Cir. 1999) (quoting Illinois v. Gates,

462 U.S. 213, 238 (1983))) (internal quotation marks omitted).

There was certainly probable cause to believe that

"records, documents, [and electronic] correspondence . . . relating

to correspondence or contact between" Crespo and Tavares -- the

second category of evidence in "Attachment B" -- would be found on

Crespo's computer, because the affidavit included extensive

documentation of online chats between Crespo and Tavares. This

conclusion is not disputed. Thus, agents' search of Crespo's

computer for this evidence would have been lawful.

The matter of the external hard drive is slightly more

complicated because, according to Crespo's counsel's statements at

oral argument, the hard drive had not been accessed in four years

at the time of the search. Even crediting this statement as true,

however, there was still probable cause to believe that evidence of

similar interactions with other minors or purported minors -- the

third category of evidence listed in "Attachment B" -- would be on
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the external hard drive. This is so because Crespo had told

Tavares that he had had sex with a fourteen-year-old girl and

mentioned knowing someone who had shaved her genital area as of the

age of eleven. Furthermore, Crespo cannot argue that records of

these conversations would not constitute evidence of the crime

charged because such records, if found, could be used to prove

Crespo's intent. See United States v. Wolford, 386 F. App'x 479,

484 (5th Cir. 2010) (chat transcripts with anonymous parties found

on defendant's computer admissible during trial for enticement of

a minor to show motive and intent); United States v. Chase, 367 F.

App'x 979, 982 (11th Cir. 2010) (transcript of chat in which

defendant described molestation of a child admissible to show

intent to entice a minor); United States v. McDarrah, 351 F. App'x

558, 563 (2d Cir. 2009) ("other act" evidence admissible during

trial for attempted enticement because it was relevant to knowledge

and intent and could be used to show that conduct was not a mistake

or accident). Thus, the warrant here also properly authorized

agents to search the external hard drive for, at the very least,

evidence related to Crespo's contacts with other minors or

purported minors. Similarly, even assuming that the searched CDs

had also not been accessed for a number of years, there was

probable cause to believe that, at the very least, evidence of

these older communications would be on the CDs.
 Although there may be limitations on how government agents may 4

search digital media in a case like this one, we need not address

those limitations here.

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Regarding the second prong, we conclude that in the

course of searching Crespo's computer for evidence of his

interactions with Tavares and searching the external hard drive and

CDs for evidence of similar interactions with other individuals,

government agents would have inevitably discovered the child

pornography. When searching digital media for "chats" and other

evidence of enticement, government agents cannot simply search

certain folders or types of files for keywords. First, like paper 4

files, digital files may be mislabeled. See, e.g., United States

v. Highbarger, 380 F. App'x 127, 130 (3d Cir. 2010) ("Suspects can

easily hide information by mislabeling files, and, therefore, law

enforcement officials are not required to accept a suspect's

designation of what is contained in a particular file."); United

States v. Williams, 592 F.3d 511, 522 (4th Cir. 2010) ("Surely, the

owner of a computer, who is engaged in criminal conduct on that

computer, will not label his files to indicate their

criminality."); United States v. Hill, 459 F.3d 966, 978 (9th Cir.

2006) ("Forcing police to limit their searches to files that the

suspect has labeled in a particular way would be much like saying

police may not seize a plastic bag containing a powdery white

substance if it is labeled 'flour' or 'talcum powder.'" (quoting

United States v. Hill, 322 F. Supp. 2d 1081, 1090 (C.D. Cal.
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2004))). The suffixes or extensions of file names, which generally

indicate file types, may be manipulated to disguise the true file

types. See Hill, 322 F. Supp. 2d at 1090 ("Criminals will do all

they can to conceal contraband, including the simple expedient of

changing the names and extensions of files to disguise their

content from the casual observer."); United States v. Harding, 273

F. Supp. 2d 411, 424 (S.D.N.Y. 2003) ("Files containing graphical

images may be assigned file extensions, including 'TXT', that

typically are assigned to text files. Files containing text may be

assigned file extensions, including 'JPG' or 'GIF', that typically

are given to graphical image files."); United States v. Gray, 78 F.

Supp. 2d 524, 529 (E.D. Va. 1999) ("While the '.jpg' suffix

generally denotes a picture file, there is no requirement that it

do so, and, as a result[,] [the agent] could not be certain that

files with the '.jpg' suffix did not contain the materials for

which he was authorized to search."). Furthermore, a chat

transcript, which begins as text, could be converted into an image

and saved as an image file. See Harding, 273 F. Supp. 2d at 424

("Text files . . . are readily scanned and converted into graphical

image files."). Thus, in searching for evidence of Crespo's

interactions with Tavares and other purported minors, forensic

experts would have thoroughly combed through files and would have
 The district court acknowledged as much in its opinion and order 5

responding to the government's motion for reconsideration when, in

its discussion of the plain view exception to the warrant

requirement, it noted that if agents had not been searching for

child pornography, "the alleged child pornography found in

Defendant's digital media would have been seized pursuant to a

search for evidence of enticement and transfer of obscene material

to a minor."

 Crespo also argues that we should dismiss this appeal because 6

the United States Attorney did not personally certify, pursuant to

18 U.S.C. § 3731, that the appeal was not taken for the purpose of

delay and that the evidence suppressed is substantial proof of a

material fact. Instead, an Assistant United States Attorney

("AUSA") electronically signed the required notice of appeal after

consulting with the United States Attorney, who verified that the

requirements of § 3731 were met.

We reject Crespo's argument. Given the process here -- which

included review by the United States Attorney and then by the

Solicitor General -- and the fact that the statute itself notes

that its "provisions shall be liberally construed to effectuate its

purposes," 18 U.S.C. § 3731, we conclude that the AUSA's submission

of the notice of appeal satisfies the statute. See United States

v. Lazar, 604 F.3d 230, 242 n.11 (6th Cir. 2010) ("As to

defendant's contention that certification signed by an AUSA . . .

-- as opposed to the United States Attorney -- cannot satisfy

§ 3731, we reject such a requirement, especially in light of the

review process outlined above [i.e., the process in which the

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inevitably discovered the child pornography that Crespo now seeks

to suppress.5

Finally, "bear[ing] . . . in mind the social costs of the

exclusionary rule," United States v. Scott, 270 F.3d 30, 45 (1st

Cir. 2001), we consider the final prong of the inevitable discovery

test. We conclude that the application of the doctrine here will

not "provide an incentive for police misconduct or significantly

weaken fourth amendment protection." United States v. Silvestri,

787 F.2d 736, 744 (1st Cir. 1986).6
Solicitor General makes a final decision about whether to

appeal]."); United States v. Wolk, 466 F.2d 1143, 1146 n.2 (8th

Cir. 1972) ("While [18 U.S.C. § 3731] refers to the 'United States

attorney[,]' the appellee cites no cases nor suggests any

compelling reasons which justify a decision that would so

needlessly circumscribe the ability of the United States Attorney

to delegate responsibility. We recognize that the statute is to be

'liberally construed to effectuate its purposes', 18 U.S.C. § 3731,

and[] we can unearth no reason to disregard that direction in this

case.").

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IV. Conclusion

For the reasons stated, we reverse the district court's

order and remand with instructions to deny the motion to suppress.

Reversed and Remanded.