UNITED STATES DISTRICT COURT

EASTERN DISTRICT OF NEW YORK

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UNITED STATES OF AMERICA,
MEMORANDUM AND ORDER
-against- Case No. 08-CR-415 (FB)

RALPH CIOFFI and MATTHEW TANNIN,

Defendants.
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Appearances:
For the United States of America: For Defendant Ralph Cioffi:
BENTON J. CAMPBELL, ESQ. DANE BUTSWINKAS, ESQ.
United States Attorney MARGARET A. KEELEY, ESQ.
Eastern District of New York Williams & Connolly LLP
By: JAMES G. MCGOVERN, ESQ. 725 Twelfth Street, N.W.
ILENE JAROSLAW, ESQ. Washington, DC 20005
PATRICK SEAN SINCLAIR, ESQ.
BRIAN SANO, ESQ. For Defendant Matthew Tannin:
Assistant United States Attorneys SUSAN E. BRUNE, ESQ.
271 Cadman Plaza East NINA M. BEATTIE, ESQ.
Brooklyn, NY 11201 MARYANN J. SUNG, ESQ.
THERESA TRZASKOMA, ESQ.
Brune & Richard LLP
80 Broad Street
New York, NY 10004

BLOCK, Senior District Judge:

Defendant Matthew Tannin (“Tannin”) is charged with conspiracy, securities

fraud and wire fraud in connection with two hedge funds he managed for Bear Stearns

Asset Management (“BSAM”). He moves to suppress evidence seized from his personal

email account on the ground that the warrant authorizing the seizure did not comply with
the Warrants Clause of the Fourth Amendment.1 For the following reasons, the motion is

granted.

On July 7, 2009, FBI Special Agent Mark Munster (“Munster”) applied to

Magistrate Judge Cheryl Pollak for a warrant to search Tannin’s personal email account.

See Letter from P. Sinclair (Oct. 12, 2009), Ex. (“Search Warrant”). An affidavit executed by

Munster accompanied the application. See id., Ex. (“Affidavit in Support of a Search

Warrant”).

A. The Affidavit

The Affidavit began with a boilerplate description of the Internet, email and

Google (the company who hosted the targeted account). It then set forth Munster’s

proffered bases for issuing the Warrant.

First, the Affidavit expressly incorporated by reference the 27-page

indictment to demonstrate probable cause that Tannin had committed the charged crimes.

To connect those crimes to Tannin’s personal email account, the Affidavit alluded to

paragraph 41 of the indictment, which excerpted an email sent by Tannin from his personal

account to Cioffi on April 22, 2007 (“the April 22nd Email”):

[T]he subprime market looks pretty damn ugly. . . . If we

believe the [CDO report is] ANYWHERE close to accurate I
think we should close the funds now. The reason for this is
that if [the CDO report] is correct then the entire subprime
market is toast. . . . If AAA bonds are systemically downgraded

1
Defendant Ralph Cioffi (“Cioffi”) is charged with the same crimes as Tannin, in
addition to insider trading; he is not a party to the motion.

2
 then there is simply no way for us to make money – ever.

Indictment ¶ 41 (alterations in original).2

As recounted in the Affidavit, the April 22nd Email was produced to BSAM’s

counsel in the course of an investigation into the funds’ collapse. BSAM turned the email

over to the Securities Exchange Commission (“SEC”) and the United States Attorney’s

Office in November 2007. Munster opined that Tannin’s use of his personal email account,

instead of his Bear Stearns account, to discuss work-related matters made it “likely that

Matthew Tannin purposely used THE SUBJECT E-MAIL ACCOUNT to facilitate the

charged conspiracy” because the conspirators “were able to communicate privately by

using THE SUBJECT E-MAIL ACCOUNT, in that their communications would not be

subject to capture and review by Bear Stearns.” Affidavit ¶ 15.

The Affidavit then quoted at length from the Stored Communications Act,

18 U.S.C. §§ 2701-12. As pertinent here, the Act allows government agents to obtain from

companies such as Google the contents of their subscribers’ accounts pursuant to a warrant

issued by the “court with jurisdiction over the offense under investigation.” Id.

§ 2703(b)(A).

In the Affidavit’s next section, Munster described the procedures necessary

to adequately execute the search. First, he averred that the search would be limited to

emails created on or before August 12, 2007, “the day prior to Tannin’s retention of private

counsel, to prevent the danger of intercepting privileged communications.” Affidavit ¶ 22.

2
The government has introduced the April 22nd Email as evidence of Tannin’s
knowledge and intent.

3
He then stated that the nature of electronically stored data required “the searching

authorities [to] carefully open and examine all the stored data to determine which of the

various files are evidence, fruits, or instrumentalities of the crime,” and that such a

procedure “would be impractical to do at Google’s offices” and would instead need to be

carried out off-site “in a controlled environment.” Id. ¶ 23. Finally, he averred that

“[f]ederal law enforcement officials will review the records sought by the search warrant

and will segregate any messages and content constituting evidence of violations of federal

criminal law.” Id. ¶ 24.

The final paragraph of the Affidavit recited Munster’s belief, based on the

facts set forth, that “there is probable cause to search THE SUBJECT E-MAIL ACCOUNT

for evidence of activities relating to conspiracy to commit securities fraud and wire fraud,

in violation of 18 U.S.C. § 371; securities fraud, in violation of 15 U.S.C. §§ 78j(b) and 78ff;

and wire fraud, in violation of 18 U.S.C. § 1343.” Id. ¶ 25.

B. The Warrant

Magistrate Judge Pollak signed the Warrant, which authorized a search of

“the premises known and described as electronic mail address ‘[email protected]’.”

The Warrant contained a boilerplate statement reflecting the magistrate judge’s

“satisf[action] that the affidavit(s) and any recorded testimony establish probable cause to

believe that the person or property . . . described is now concealed on the . . . premises

above-described and establish grounds for the issuance of this warrant.”3 The government

3
The Warrant erroneously states that it is based on the affidavit of a “Special Agent
Elizbeth [sic] Brance.”

4
concedes, however, that the Affidavit was not attached to or incorporated by reference into

the Warrant.

The Warrant authorized Munster (or “any Authorized Officer of the United

States”) to seize from Tannin’s email account the items set forth in “Attachment A” to the

Warrant. The attachment listed seven categories of “records and other stored information”

relating to Tannin’s account; the category pertinent here was described as “all e-mail up

through August 12, 2007, including any attachments, and all instant messages, sent by or

received by the accounts [sic], whether saved or deleted, whether contained directly in the

e-mail account or in a customized ‘folder.’”4 There was no provision limiting the emails

to be seized to those containing evidence of the crimes charged in the indictment or,

indeed, of any crime at all.

Attachment A also set forth procedures for obtaining the account from

Google. It directed Google employees to “locate, isolate, and create an exact duplicate” of

all records sought, and to produce the duplicate to the executing officer “in electronic

form.” The attachment did not, however, describe any procedures for the executing officer

to follow in searching the account and seizing particular records.

C. Execution of the Warrant

The Warrant was served on Google. On July 17, 2009, Google wrote to the

government that it was “no longer able to extract the information requested in the Search

Warrant” because Tannin’s account had been “deleted.” Letter from K. Untiedt to I.

4
Broadly speaking, the other categories involved a wide range of information about
the account, such as billing records, activity logs and user preferences.

5
Jaroslaw (July 17, 2009). On the eve of trial, however, Google advised the government that

it had located a copy of the account as it existed on November 7, 2007. Google promptly

sent the government a CD-ROM containing that version of the account.

Members of the prosecution team searched the account. See Letter from I.

Jaroslaw (Oct. 8, 2009) (“Today the government received via Federal Express from Google

the contents of defendant Matthew Tannin’s G-Mail account as it existed on November 7,

2007 on a CD-ROM. We have not had an opportunity to review the account in its

entirety.”). During an “initial look” at the account, the government isolated a November

23, 2006 email from Tannin to himself (“the November 23rd Email”). The lengthy email

is essentially a diary entry, in which Tannin recorded his thoughts about such sundry

matters as recent vacations and medical issues; however, several paragraphs were devoted

to Tannin’s anxiety about work and the state of the market.5

D. The Motion to Suppress

On October 8, 2009, the government informed me and defense counsel that

it intended to offer the November 23rd Email into evidence as bearing on Tannin’s

“knowledge and intent on all the pending charges against him.” Letter from I. Jaroslaw

(Oct. 8, 2009). Tannin moved to suppress the email (which has been marked for

identification as Government Exhibit 100); he argued that the Warrant was “invalid on its

face because it failed to describe with particularity the materials that would be the proper

subject of a search” and that “[s]uch a warrant is unreasonably broad and therefore

5
Since I conclude that the search that yielded the November 23rd Email violated the
Fourth Amendment, it would be inappropriate to repeat the contents of the email.

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unconstitutional.” Tannin’s Mem. of Law at 2.6 The government has filed a series of letter

memoranda in response.

Taken collectively, the parties’ submissions frame the following three issues

for my determination:

1. Did the Warrant violate the Warrants Clause of the

Fourth Amendment?

2. If so, is the November 23rd Email nevertheless

admissible under the “good-faith exception” of United
States v. Leon, 468 U.S. 897 (1984)?

3. If not, is the November 23rd Email nevertheless

admissible under the “inevitable discovery” doctrine?

I address these issues in turn.7

6
Tannin also moved to exclude the November 23rd Email under Federal Rule of
Evidence 403. As I explained in open court, I agree with the government that the email is
relevant because it tends to show Tannin’s knowledge of potential problems with the funds
and its investments; although the email predates the dates of the crimes charged in the
indictment (March-June 2007) by several months, it is not implausible that a jury could
reasonably conclude that Tannin’s knowledge of problems in November 2006 spurred him
to enter into a conspiracy to cover up those problems in March 2007.
7
One preliminary matter is not in question: The government does not dispute that
Tannin has a reasonable expectation of privacy in the contents of his personal email
account. See United States v. Zavala, 541 F.3d 562, 577 (5th Cir. 2008) (“[C]ell phones contain
a wealth of private information, including emails, text messages, call histories, address
books, and subscriber numbers. [The defendant] had a reasonable expectation of privacy
regarding this information.”); United States v. Forrester, 512 F.3d 500, 511 (9th Cir. 2008)
(“E-mail, like physical mail, has an outside address ‘visible’ to the third-party carriers that
transmit it to its intended location, and also a package of content that the sender presumes
will be read only by the intended recipient. The privacy interests in these two forms of
communication are identical. The contents may deserve Fourth Amendment protection, but
the address and size of the package do not.”).

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 II

A. The Warrants Clause

The Fourth Amendment’s Warrants Clause provides that “no Warrants shall

issue, but upon probable cause, supported by Oath or affirmation, and particularly

describing the place to be searched, and the persons or things to be seized.” The clause was

intended as a bulwark against “the ‘general warrant’ abhorred by the colonists” and

protects against “a general, exploratory rummaging in a person’s belongings.” Coolidge v.

New Hampshire, 403 U.S. 443, 467 (1971). Its overarching purpose is to ensure that “those

searches deemed necessary should be as limited as possible.” Id.

To achieve its goal, the Warrants Clause requires particularity and forbids

overbreadth. “Particularity is the requirement that the warrant must clearly state what is

sought. Breadth deals with the requirement that the scope of the warrant be limited to the

probable cause on which the warrant is based.” United States v. Hill, 459 F.3d 966, 973 (9th

Cir. 2006). Thus, as I recently explained in United States v. Cohan, 628 F. Supp. 2d 355

(E.D.N.Y. 2009), a warrant can violate the clause “either by seeking specific material as to

which no probable cause exists, or by giving so vague a description of the material sought

as to impose no meaningful boundaries.” Id. at 359.

A warrant is sufficiently particular if it “enable[s] the executing officer to

ascertain and identify with reasonable certainty those items that the magistrate has

authorized him to seize.” United States v. George, 975 F.2d 72, 75 (2d Cir. 1992). “Courts

tend to tolerate a greater degree of ambiguity where law enforcement agents have done the

best that could reasonably be expected under the circumstances, have acquired all the

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descriptive facts which a reasonable investigation could be expected to cover, and have

insured that all those facts were included in the warrant.” United States v. Buck, 813 F.2d

588, 590 (2d Cir. 1987) (quoting United States v. Young, 745 F.2d 733, 759 (2d Cir. 1984)); see

also United States v. Spilotro, 800 F.2d 959, 963 (9th Cir. 1986) (“Warrants which describe

generic categories of items are not necessarily invalid if a more precise description of the

items subject to seizure is not possible.”). Nevertheless, “[a] failure to describe the items

to be seized with as much particularity as the circumstances reasonably allow offends the

Fourth Amendment because there is no assurance that the permitted invasion of a suspect’s

privacy and property are no more than absolutely necessary.” George, 975 F.2d at 76.

The level of specificity required by the Warrants Clause depends on many

factors. The nature of the crime, for example, may require a broad search. See, e.g.,

Andresen v. Maryland, 427 U.S. 463, 481 n.10 (1976) (“Like a jigsaw puzzle, the whole

‘picture’ of petitioner’s false-pretense scheme . . . could be shown only by placing in the

proper place the many pieces of evidence that, taken singly, would show comparatively

little.”); United States v. Regan, 706 F. Supp. 1102, 1113 (S.D.N.Y. 1989) (“The degree to

which a warrant must state its terms with particularity varies inversely with the complexity

of the criminal activity investigated.”). The type of evidence sought is also relevant; in

particular, courts have recognized that documentary evidence may be difficult to describe

ex ante with the same particularity as a murder weapon or stolen property. See, e.g., United

States v. Riley, 906 F.2d 841, 845 (2d Cir. 1990) (“It is true that a warrant authorizing seizure

of records of criminal activity permits officers to examine many papers in a suspect’s

possession to determine if they are within the described category. But allowing some

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latitude in this regard simply recognizes the reality that few people keep documents of

their criminal transactions in a folder marked ‘drug records.’”); United States v. Zanche,

541 F. Supp. 207, 210 (W.D.N.Y. 1982) (“Unlike other forms of property, business records

are often incapable of being itemized one by one, particularly when their existence, but not

their precise names or quantity, is all that is known.”).

Document searches pose unique Fourth Amendment concerns. As the

Supreme Court noted more than 30 years ago:

[T]here are grave dangers inherent in executing a warrant

authorizing a search and seizure of a person’s papers that are
not necessarily present in executing a warrant to search for
physical objects whose relevance is more easily ascertainable.
In searches for papers, it is certain that some innocuous
documents will be examined, at least cursorily, in order to
determine whether they are, in fact, among those papers
authorized to be seized. . . . [R]esponsible officials, including
judicial officials, must take care to assure that they are
conducted in a manner that minimizes unwarranted intrusions
upon privacy.

Andresen, 427 U.S. at 482 n.11. The dawn of the Information Age has only heightened those

concerns. The risk of exposing intimate (and innocent) correspondence to prying eyes is

magnified because “[c]omputers . . . often contain significant intermingling of relevant

documents with documents that the government has no probable cause to seize.” United

States v. Vilar, 2007 WL 1075041, at *35 (S.D.N.Y. 2007) (citation and internal quotation

marks omitted); see also United States v. Comprehensive Drug Testing, Inc., 579 F.3d 989, 1005

(9th Cir. 2009) (“Seizure of . . . Google’s email servers to look for a few incriminating

messages could jeopardize the privacy of millions.”). However, “it is precisely because

computer files can by intermingled and encrypted that the computer is a useful criminal

10
tool.” Vilar, 2007 WL 1075041, at *35.

Courts and commentators have wrestled with how best to balance privacy

interests and legitimate law-enforcement concerns in the context of computer searches.

One approach would require law-enforcement officials to specify a search protocol ex ante

and to use, whenever possible, “key word searches . . . to distinguish files that fall within

the scope of a warrant from files that fall outside the scope of the warrant.” Raphael

Winick, Searches and Seizures of Computers and Computer Data, 8 Harv. J.L. & Tech. 75, 108

(1994). Another would require the creation of “firewalls” to prevent investigators and

prosecutors from obtaining the results of a computer search until documents within the

scope of the warrant had been segregated by a third party. The Ninth Circuit recently

endorsed variants of both procedures, among others, to minimize the intrusiveness of

computer searches. See Comprehensive Drug Testing, 579 F.3d at 1006 (“Segregation and

redaction must be either done by specialized personnel or an independent third

party. . . . The government’s search protocol must be designed to uncover only the

information for which it has probable cause, and only that information may be examined

by the case agents.”). As Judge Karas noted in Vilar, however, the majority of courts to

have considered the question have not required the government to specify its search

protocol in advance. See 2007 WL 1075041, at 37-38 (citing cases); see also Orin S. Kerr,

Searches and Seizures in a Digital World, 119 Harv. L. Rev. 531, 572 (2005) (“[T]he [computer]

forensics process is too contingent and unpredictable for judges to establish effective ex

ante rules.”).

To date, the Second Circuit has not taken sides in the debate on the

11
particularity required for computer searches. There is, however, one form of particularity

whose absence the Second Circuit has unequivocally and unqualifiedly condemned:

“[A]uthorization to search for ‘evidence of a crime,’ that is to say, any crime, is so broad as

to constitute a general warrant.” George, 975 F.2d at 76. “[A] fortiori a warrant not limited

in scope to any crime at all is . . . unconstitutionally broad.” Id. at 77. George represents not

simply a majority view, but the unanimous view of courts across the nation. See Spilotro,

800 F.2d at 964 (“The use of generic descriptions in the . . . warrant still might not have been

fatal had the warrant more specifically identified the alleged criminal activities in

connection with which the items were sought.”); cf. United States v. Maxwell, 920 F.2d 1028,

1033 (D.C. Cir. 1990) (“References to broad statutes realistically constitute no limitation at

all on the scope of an otherwise overbroad warrant and therefore cannot save it.”); United

States v. Roche, 614 F.2d 6, 8 (1st Cir. 1980) (“[S]ection 1341 makes illegal all frauds that

utilize the mails; limitation by so broad a statute is no limitation at all.” (footnote omitted)).

Thus, whatever new challenges computer searches pose in terms of particularity, it is

always necessary -- and hardly onerous -- to confine any search to evidence of particular

crimes. See, e.g., United States v. Riccardi, 405 F.3d 852, 862 (10th Cir. 2005) (“[W]arrants for

computer searches must affirmatively limit the search to evidence of specific federal crimes

or specific types of material.”).

B. Reliance on Affidavits

In George, the government attempted to save the fatally overbroad warrant

by relying on the probable-cause affidavit to show a connection between the warrant and

a particular crime. See 975 F.2d at 76. The Second Circuit rejected the attempt:

12
 A sufficiently specific affidavit will not itself cure an overbroad
warrant. Resort to an affidavit to remedy a warrant’s lack of
particularity is only available when it is incorporated by
reference in the warrant itself and attached to it.

Id.

The circuit court confronted the same argument less than a year later in

United States v. Bianco, 998 F.2d 1112 (2d Cir. 1993). The search warrant at issue in Bianco

authorized officers to search a defendant’s home and seize, without limitation, “[N]otes,

Ledgers, Envelopes, Papers, and Records Containing Initials, Names, Addresses, Dollar

Amounts, Codes, Figures, and the Like: United States Currency.” Id. at 1115. The affidavit

supporting the warrant explained that the search was for evidence of the defendant’s

loansharking activities. See id. William Hutton, an FBI agent who supervised the search

team and decided which items were to be seized, “had familiarized himself with the

warrant and its supporting affidavit, and was aware that he was looking for evidence of

loansharking.” Id. In addition, the defendant was made aware of the purpose and

limitations on the search. See id. at 1117.

The Second Circuit began by “focusing solely on the warrant itself,” and

concluded that it was overbroad because “when viewed by itself, [it] describe[d] neither

the precise items to be seized nor the possible crimes involved.” Id. at 1116. The court

then noted that the supporting affidavit was neither expressly incorporated into nor

physically attached to the warrant; nonetheless, it allowed the affidavit’s limitations on the

search to be read into the warrant, eschewing the “formal requirements of incorporation

and attachment” in favor of a “commonsense” approach because “the functional purposes

13
of those two requirements -- to insure that all parties involved are informed of the scope

of and limits upon the authorized search -- were fully satisfied,” id. at 1117:

In this case, it is clear that both the federal agents and [the
defendant] were apprised of [the scope of and limitations on
the search.] The affidavit was present at the time of the search,
and spells out quite clearly the nature and purpose of the
proposed search. It explains in detail the motivation behind
the search and the nature of the documents sought. When the
warrant and affidavit are read together, there is no ambiguity.
Moreover, although the warrant may not have explicitly
incorporated the affidavit, the presence and activity of agent
Hutton, who had read the affidavit and who approved each
seizure, satisfies us that the limitations included in the affidavit
were observed.

Id.

However, as I explained in Cohan, the exception carved out in Bianco can no

longer be viewed as the law of the Second Circuit in light of the Supreme Court’s

subsequent decision in Groh v. Ramirez, 540 U.S. 551 (2004). Two of my colleagues have

reached the same conclusion. See Vilar, 2007 WL 1075041, at *22 n.13 (“Bianco is of

questionable use to the Government [because Groh’s] holding sheds doubt on whether an

unincorporated document may ever be used to satisfy the particularity requirements of the

Fourth Amendment.”); United States v. Ryan, 2008 WL 901538, at *2 (D.Vt. Mar. 31, 2008)

(“[Bianco] does not survive the Supreme Court’s decision in Groh.”).

In Groh, -- a Bivens action -- the defendant, an ATF agent, applied for a

warrant to search the plaintiff’s ranch. The application was supported “with a detailed

affidavit, which [the defendant] also prepared and executed, that set forth the basis for his

belief that [weapons] were concealed on the ranch.” Id. at 554. The warrant, however,

14
“failed to identify any of the items that [the defendant] intended to seize” and “did not

incorporate by reference the itemized list contained in the application.” Id. at 554-55. The

defendant led the search team executing the warrant. See id. at 555.

In the Supreme Court, the defendant conceded that the warrant was invalid

on its face, but argued that it was saved by the limitations contained in his supporting

affidavit. The Court squarely rejected that argument: “The fact that the application

adequately described the ‘things to be seized’ does not save the warrant from its facial

invalidity. The Fourth Amendment by its terms requires particularity in the warrant, not

in the supporting documents.” Id. at 557. The Court recognized that “most Courts of

Appeals have held that a court may construe a warrant with reference to a supporting

application or affidavit if the warrant uses appropriate words of incorporation, and if the

supporting document accompanies the warrant.” Id. at 557-58. Since the affidavit at issue

had not been attached and formally incorporated by reference, the Court did not “further

explore the matter of incorporation.” Id. at 558.

Therefore, as I explained in Cohan, Bianco’s “commonsense” exception to

formal incorporation and attachment did not survive Groh. See 628 F. Supp. 2d at 363.

After noting that my conclusion was in accord with Vilar and Ryan, I pointed out that the

Second Circuit recently held in United States v. Waker, 534 F.3d 168 (2d Cir. 2008), that Groh

did not preclude reliance on the supporting affidavit since it was attached to the search

warrant and the warrant contained “deliberate and unequivocal language of

incorporation.” Id. at 172. I then clearly summarized my view of the state of the law:

15
 [I]n light of Groh and Waker, the Government cannot rely on
language in a warrant simply referencing the underlying
affidavit to satisfy the particularity prong of the Fourth
Amendment; rather, it must attach the affidavit to the warrant
and incorporate it by reference using “deliberate and
unequivocal language.”

Cohan, 628 F. Supp. 2d at 363 (quoting Waker, 534 F.3d at 172).

In addition to the clarity of Groh’s holding, the factual similarity between Groh

and Bianco now reinforces my conclusion. As Justice Thomas noted in dissent, the

defendant -- who had prepared the supporting affidavit -- had “briefed the search team

and provided a copy of the search warrant application, the supporting affidavit, and the

warrant for the officers to review.” Id. at 576 (Thomas, J., dissenting). The defendant and

the search team “then conducted the search entirely within the scope of the warrant

application and warrant; that is, within the scope of what the Magistrate had authorized.”

Id. If anything, the facts of Groh present a stronger case for excusing the lack of formal

incorporation and attachment than Bianco. The majority, however, thought those facts

irrelevant and made no exception for situations in which the executing officer was aware

of the affidavit’s contents.

C. Application

The Warrant did not, on its face, limit the items to be seized from Tannin’s

personal email account to emails containing evidence of the crimes charged in the

indictment, or, indeed, any crime at all. It was, therefore, unconstitutionally broad under

George.

Before 2004, the Affidavit might have saved the Warrant under Bianco. It

16
clearly shows that Munster was seeking authority to seize only “evidence of activities

relating to conspiracy to commit securities fraud and wire fraud, in violation of 18 U.S.C.

§ 371; securities fraud, in violation of 15 U.S.C. §§ 78j(b) and 78ff; and wire fraud, in

violation of 18 U.S.C. § 1343.” Affidavit ¶ 25. Both Munster and the prosecution team were

undoubtedly aware that they were to search Tannin’s personal email account only for

evidence relating to those crimes. Because, however, the Affidavit was not attached to or

formally incorporated into the Warrant, Groh renders it an irrelevancy.

My conclusion that the Warrant violates the Fourth Amendment does not end

the inquiry. The remedy for an overbroad search and seizure is suppression of the

resulting evidence. See United States v. Matias, 836 F.2d 744 (2d Cir. 1988).8 The

government, however, invokes two exceptions to that rule: the “good faith” exception and

the “inevitable discovery” doctrine.

III

In United States v. Leon, 468 U.S. 897 (1984), the Supreme Court held that a

violation of the Fourth Amendment does not justify exclusion of the resulting evidence

“when an officer acting with objective good faith has obtained a search warrant from a

judge or magistrate and acted within its scope.” Id. at 920. The good-faith inquiry “is

8
In that regard, it bears noting that, under the doctrine of severance, only the
evidence seized pursuant to the invalid portions of the warrant are suppressed; evidence
seized under any valid portions of the warrant remains admissible. See George, 975 F.2d at
79 (“When a warrant is severed (or redacted) the constitutionally infirm portion -- usually
for lack of particularity or problem cause -- is separated from the remainder and evidence
seized pursuant to that portion is suppressed; evidence seized under the valid portion may
be admitted.”). Here the lack of particularity pervades the entire Warrant; there is,
therefore, no valid portion under which the November 23rd Email could have been seized.

17
confined to the objectively ascertainable question whether a reasonably well trained officer

would have known that the search was illegal despite the magistrate’s authorization.” Id.

at 922 n.23. In that regard, it “requires officers to have a reasonable knowledge of what the

law prohibits.” Id. at 919 n.19. Thus, the exception will not apply if the warrant is “so

facially deficient -- i.e., in failing to particularize the place to be searched or the things to

be seized -- that the executing officers cannot reasonably presume it to be valid.” Id. at

923.9

As noted, there many unresolved questions regarding the parameters of a

search for computer documents. See supra Part II. In light of the Second Circuit’s silence

on these thorny issues, an officer could reasonably believe that search protocols and similar

procedures are not constitutionally mandated.

This case, however, is not about search terms or firewalls. It is, rather, about

the fundamental and venerable prohibition on general warrants. Since “it is obvious that

a general warrant authorizing the seizure of evidence without mentioning a particular

crime or criminal activity to which the evidence must relate is void under the Fourth

Amendment,” “no reasonably well-trained officer could believe otherwise.” George, 975

F.2d at 77.

9
The exception will also not apply (1) “if the magistrate or judge in issuing a warrant
was misled by information in an affidavit that the affiant knew was false or would have
known was false except for his reckless disregard of the truth”; (2) “in cases where the
issuing magistrate wholly abandoned his judicial role”; or (3) if the warrant is “based on
an affidavit so lacking in indicia of probable cause as to render official belief in its existence
entirely unreasonable.” Leon, 468 U.S. at 923 (citation and internal quotation marks
omitted). Those circumstances are not present here.

18
 Before Groh, an executing officer might reasonably (and correctly) believe that

his or her knowledge of the probable-cause affidavit would, under Bianco, cure a facially

overbroad warrant. But Groh has been on the books since 2004. Indeed, the Supreme Court

believed no reasonable officer could question its holding even then. Since Groh was a civil

case, the Court was not called upon to directly apply Leon’s good-faith exception; however,

it did address -- and reject -- the defendant’s claim of qualified immunity, the doctrine

upon which Leon was based:

Given that the particularity requirement is set forth in the text

of the Constitution, no reasonable officer could believe that a
warrant that plainly did not comply with that requirement was
valid . . . . [A]s we observed in [Leon], “a warrant may be so
facially deficient – i.e., in failing to particularize the place to be
searched or the things to be seized – that the executing officers
cannot reasonably presume it to be valid.” This is such a case.

540 U.S. at 564-65 (quoting Leon, 468 U.S. at 923).

IV

The government has also invoked the “inevitable discovery” doctrine, under

which unlawfully seized evidence is not suppressed if “the prosecution can establish by

a preponderance of the evidence that the information ultimately or inevitably would have

been discovered by lawful means.” Nix v. Williams, 467 U.S. 431, 444 (1984). The Second

Circuit has held that “[t]he exception requires the district court to determine, viewing

affairs as they existed at the instant before the unlawful search, what would have happened

had the unlawful search never occurred.” United States v. Eng, 997 F.2d 987, 990 (2d Cir.

1993) (emphasis in original).

The government does not -- and could not -- argue that the November 23rd

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Email would have been discovered by lawful means had the Warrant never been executed.

Rather, it argues that the email could lawfully be obtained through another, more

particularized warrant now that the Warrant has been invalidated. This distinction is

dispositive because for purposes of the doctrine, timing is everything.

In United States v. Whitehorn, 829 F.2d 1225 (2d Cir. 1987), FBI agents

conducted a warrantless “bomb sweep” of the defendant’s apartment; during the sweep,

they found a false passport and driver’s license. Prior to the sweep, however, other agents

had begun preparing a search-warrant application for the same premises; the warrant,

which was issued later the same day, authorized the seizure of, inter alia, “false identities

of federal fugitives.” Id. at 1228. In those circumstances, the Second Circuit held, the

doctrine was applicable:

Agents at the F.B.I. office actually began the warrant

application process over an hour before the illegal bomb sweep
of [the defendant’s] apartment occurred. They had already
pinpointed the apartment to be searched. Through interviews
with neighbors as well as prior extensive investigation, they
knew that two of the apartment’s occupants, Evans and Buck,
had a history of trafficking in false identification documents,
weapons, and explosives; indeed, the night before Evans and
Buck had been arrested carrying all but the latter. In short, the
agents had overwhelming probable cause before the bomb
sweep to search the apartment in the belief that it was being
used . . . as a “safe house” for federal fugitives in which false
identification documents and other types of information
detected by the bomb sweep reasonably could be expected to
be found. Under these circumstances, and given that the
agents were then proceeding to secure a warrant which
specifically authorized the seizure of the challenged evidence,
we conclude that the district court properly denied
Whitehorn’s motion to suppress the evidence first detected by
the bomb sweep.

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Id. at 1231. By contrast, in United States v. Cabassa, 62 F.3d 470 (2d Cir. 1995), the circuit

court rejected the doctrine in a case in which the application process had begun, but no

warrant had been issued:

In cases in which a claim of inevitable discovery is based on

expected issuance of a warrant, the extent to which the warrant
process has been completed at the time those seeking the
warrant learn of the search is of great importance. First, the
extent of completion relates directly to the question of whether
a warrant would in fact have issued; ultimate discovery would
obviously be more likely if a warrant is actually obtained.
Second, it informs the determination of whether the same
evidence would have been discovered pursuant to the warrant.
If the process of obtaining a search warrant has barely begun,
for example, the inevitability of discovery is lessened by the
probability, under all the circumstances of the case, that the
evidence in question would no longer have been at the location
of the illegal search when the warrant actually issued.

Id. at 473.

The specific concerns raised in Cabassa are not present here. There is little

doubt that the government could now obtain a warrant authorizing a search that would

yield the November 23rd Email, and that the email would still be found on Google’s server.

Nevertheless, the government’s timing still presents a problem: Having seen the November

23rd Email, the government is now in a position to obtain a warrant with perfect

particularity. There is, in other words, no way to purge the taint of its unconstitutionally

overbroad search.

Even if I were to restrict the government to the facts set forth in the Affidavit,

a more fundamental problem would remain. The “inevitable discovery” doctrine is

essentially a rule of harmless error. See Nix, 467 U.S. at 443 n.3 (“The ultimate or inevitable

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discovery exception to the exclusionary rule is closely related in purpose to the

harmless-error rule[.]”). No court has ever endorsed the view that it would allow the

government to retroactively cure a Fourth Amendment violation, and it is easy to see why.

The violation is not the discovery of incriminating evidence, but the invasion of the

searchee’s privacy. Since such a violation is inherently irremediable, the exclusionary rule

exists to deter violations in the first instance. See Elkins v. United States, 364 U.S. 206, 217

(1960) (“The [exclusionary] rule is calculated to prevent, not to repair. Its purpose is to

deter -- to compel respect for the constitutional guaranty in the only effectively available

way -- by removing the incentive to disregard it.”). It is one thing to say that there is no

need to deter by suppressing evidence that would have been discovered regardless of

unconstitutional conduct; it is quite another to allow the government a second chance to

fix a problem that never should have arisen.

In concluding, I note that my observation in Cohan -- that, in light of Groh, a

facially invalid warrant cannot be salvaged unless a particularized affidavit is attached to

the warrant and incorporated into the warrant by reference -- was technically dicta since

I found that the warrant there was sufficiently particular. See 628 F. Supp. 2d at 362.

Nonetheless, I thought that this dicta was appropriate to alert the government that if it did

not heed Groh’s holding in the future, it would risk the suppression of evidence that it

wished to introduce at trial.

I have been the assigned judge on this case since its inception over a year ago.

Cohan was issued this past June, two weeks before the Warrant was sought. The

22
government was, therefore, on explicit notice that my understanding of the Supreme

Court’s holding in Groh would undoubtedly oblige me to strike down a facially invalid

warrant in the absence of incorporation and attachment of the supporting affidavit.

CONCLUSION

Tannin’s motion to suppress is granted. The government is barred from

introducing the November 23rd Email into evidence in its case-in-chief.10

SO ORDERED.

_____________________________________
FREDERIC BLOCK
Senior United States District Judge
Brooklyn, New York
October 26, 2009

10
The exclusionary rule does not bar the prosecution from using illegally obtained
evidence to impeach the defendant’s own testimony. See James v. Illinois, 493 U.S. 307, 308-
09 (1990).

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