United States District Court, S.D. New YorkJun 1, 2009
08 Mag. 0017 (HBP) (S.D.N.Y. Jun. 1, 2009)

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08 Mag. 0017 (HBP).

June 1, 2009


I. Introduction

Petitioner Thomas Lee Doane moves for the return of documents seized by the Government on January 10, 2008 from his apartment pursuant to a search warrant. Doane also moves pursuant to Fed.R.Crim.P. 41(h) for the pre-indictment suppression of these documents and the fruits thereof in any future criminal prosecution. The parties have consented to my exercising plenary jurisdiction in this matter pursuant to 28 U.S.C. § 636(c). For the reasons set forth below, Doane's motion is granted in part and denied in part.

II. Facts

In July 2007, Special Agent Lola Fox of the Criminal Investigation Division of the Internal Revenue Service ("IRS-CID") received information from a confidential source that Doane was evading his federal income taxes (Affidavit of Special Agent Lola Fox, sworn to on January 4, 2008 ("Fox Aff.") at 6). According to the confidential source, Doane was operating several profitable construction companies out of his apartment which generated hundreds of thousand of dollars in yearly income that Doane had failed to report to the IRS (Fox Aff. ¶ 8). Doane's tax returns for 2003, 2004, and 2005 indicated yearly income of $7,314, $7,728, $7,728, respectively (Fox Aff. ¶¶ 19-21) and for the 2006 tax year, Doane reported $15 in taxable interest as his sole source of income (Fox Aff. ¶ 18). Doane did not file a tax return for the 2002 tax year (Fox Aff. ¶ 22).

On January 4, 2008, I issued a search warrant for Doane's apartment. The search warrant directed the seizure of

1. Books and records relating to the businesses run by THOMAS LEE DOANE, for the years 2002 to the present, including but not limited to, client addresses, phone records, client receipts, accounts receivable, accounts payable, sales journals, purchase journals, payroll records, petty cash payment records, cash disbursements, general journals, cash receipts, register receipts, work papers, correspondences, copies of tax returns, memoranda, bank records, cash, canceled checks, drafts and money orders.

(Attachment A to the Search Warrant, dated January 4, 2008, at ¶ 1). Before executing the warrant, all of the agents involved in the search of Doane's apartment were given a brief overview of the investigation into Doane and provided with copies of the Fox affidavit and the search warrant (Transcript of Evidentiary Hearing on September 26, 2008 ("Tr.") at 6). The search warrant was executed on January 10, 2008 and approximately eight boxes of documents were taken from Doane's apartment (Inventory Listing of All Items Seized at Search Warrant Site, attached to the Declaration of Caroline Rule, dated August 15, 2008).

On August 18, 2008, Doane filed a motion pursuant to Fed.R.Crim.P. 41(g) seeking the suppression and return of "all originals and duplicates of his records that date from before 2002," which he argued were outside the scope of the warrant and, therefore, seized in violation of the Fourth Amendment (Memorandum of Law in Support of Petitioner Thomas Doane's Motion for the Return of Property Seized in Violation of his Fourth Amendment Rights and the Suppression of Evidence and the Fruits Thereof, dated August 18, 2008, at 5). In support of his motion, Doane submitted an affidavit in which he asserted that "the documents that the Government seized, which predate 2002, were together in a folder of business documents all of which predated 2002, and all of which were clearly so dated." (Declaration of Thomas Lee Doane, dated August 18, 2008, at ¶ 4).

The Government asserts that the pre-2002 documents were intermingled with post-2002 documents and they were lawfully seized "as evidence of criminal wrongdoing in plain view" discovered during the inspection of items within the scope of the warrant (Letter of Assistant United States Attorney Telemachus P. Kasulis, dated September 10, 2008). After oral argument on September 12, 2008, I concluded that an evidentiary hearing was necessary and scheduled the hearing for September 26, 2008.

Three of the agents who participated in the search of Doane's apartment testified at the September 26 hearing. On direct examination Special Agent Nick Silva, who was responsible for searching the bedroom, the main living room area, and Mr. Doane's desk, testified as follows regarding the organization of Doane's files:

Q: To the best of your recollection, what kind of documents were you looking for?
A: In a brief overview, I was looking for any tax documents, financial documents, work-related documents . . . through our set time frame.
Q: Do you recall what that time frame was as you sit here today?
A: Yes. It was 2002 to present.
Q: Now, I know it was awhile ago, but if you could speak generally about how Mr. Doane organized his documents in the areas of his apartment that you searched.
A: Well, when I searched in the bedroom directly where I was, I didn't really find anything. It was more on the living room table. There was a table right in the center, and you just pretty much had a bunch of documents all over the table. And then the computer desk where I also searched, there were documents on top, and there were filing cabinets to the side.
Q: In the filing cabinets, how were the documents organized?
A: Yes. In the filing cabinets, when you pulled out the filing cabinet, it had a hanging folder in there with a manila folder in each hanging folder as well.
Q: So there was a series of folders, is that what you mean?
A: Yes. Yes.
Q: Did the folders have labels on them?
A: Yes
Q: What did those labels say?
A: Some had subject matters, some had individuals' names and some had addresses as well.
Q: Do you recall seeing any labels on the folders that spoke only of dates?
A: Only dates? No.
* * *
Q: Do you recall deciding not to search the contents of any folder because of what the label said?
A: No, I wouldn't do that because — just because a label says something doesn't mean that inside that folder that's what's there. So I would have taken a quick look at everything just to make sure.
Q: So describe the process you used to examine and search the documents in a folder once you opened it up to see its contents.
A: Ok, Again. I would open up the folder, and I would just take a quick look at the front of every page — every set of documents to see if I could tell if it was, again, a financial document, tax-related document, work document, and after I found that out, I would then look at the dates.
Q: Tell me, when you decided that there were a number of documents in a folder that you felt were financial documents, tax documents, business documents, the examples you've given that were within the date range, did you then examine every document in that folder or no?
A: No.
Q: Why not?
A: Well, the biggest reason is that it would be extremely time-consuming, and I would have to stay at Mr. Doane's apartment for a long time.
Q: So, once you determined that there were a number of documents in a folder that were responsive, what did you do then? Did you just take those documents or did you take the whole folder?
A: I would have most likely taken the whole folder.
* * *
Q: Where you aware at the time that you were . . . in fact taking pre-2002 documents?
A: During some instances, yes.
Q: Why were you taking these documents?
A: I would have taken those documents because I had looked inside the folders again, and I would have seen that there were a majority of current records in there, being 2002 to the present, and if there were some pre-2002 documents, for example, if it was a contract that was made pre-2002, I would have thought that it's relevant to take because it substantiates what happened in 2002 and thereafter.

(Tr. 9-13).

Special Agent Madeline Gorra also testified regarding the procedures employed to search Doane's apartment:

Q: Talk to me about the procedures that you would use to quickly look at the documents inside a folder once you opened it up?
A: I would open up a folder. I would thumb through the different pieces of paper in the folder. I would, you know, scan them quickly to see — nor-mally a financial document is pretty evident that its a financial document. We're trained to iden-tify these things in a pretty quick period of time. So I take a peek, did it look like an income item, did it look like an expense item. I take a quick scan of the date. It appeared to be intact, and I'd thumb through, not looking at every piece of paper carefully, but thumb through at least a huge portion of that — after I looked at a huge portion of it, that it would indeed fit into the scope of the warrant.
Q: . . . . Lets say that you looked at a huge portion of the documents in a given folder and found a lot of them to be responsive to the warrant. Would you then just take those documents or would you take the entire folder?
A: Since we're only looking at a certain number of documents, we would just take the whole folder.
Q: Did you know at the time of the search that you were seizing some pre-2002 documents?
A: I didn't, no.
Q: When did you realize that you some pre-2002 documents had been seized?
A: When I was notified that there was a suppression hearing on items prior to 2002?
* * *
Q: It was a while ago I know, but can you ballpark how much was taken versus how much was left . . .?
A: For the items I looked at, and I know that a good portion of the stuff came from the places I looked, I would say we took maybe 80 percent of the documents that he had.

(Tr. 45-48). On cross-examination, Gorra was shown the file labeled William Knight and questioned regarding the documents contained therein, to wit, (1) a receipt from "Sleepy's" dated April 8, 1999 (Government's Exhibit ("GX") 2G), (2) a letter from William Knight to an individual named Marty, dated February 20, 2004 (GX 2H), (3) pictures of two different rugs (GX 2J and GX 2K), (4) a picture of a mirror (GX 2M), (5) a note from Knight to "Tom" (GX 2N), (6) a photograph of a lamp shade (GX 20), and (7) a partial photocopy of a note from Knight to "Tom" dated May 3, 2001 (GX 2Q).

Q: . . . . There's nothing incriminating on the face of these documents, is there?
A: That's a hard question to answer. Can you restate it?
Q: Well, if you were to walk into someone's apartment and see a gun, that would be incriminating, correct?
A: Correct.
Q: There is nothing incriminating about these documents on their face, is there?
A: Knowing that he was accused of tax evasion and it could be potential expenses or a potential job, it's hard question to answer. I mean, it's not direct evidence of anything. . . .
The Court: Is there anything about these documents that suggested that they had evidentiary value in an investigation for tax evasion?
A: Looking through this, I would — and this is just my looking at it now, because I don't even know how much I looked at it in the past, but looking at it now, it looks like William Knight could have been a client. If he was a client, he could have been someone who was paying Mr. Doane to do some sort of work. Therefore, that would be income.
The Court: Is there anything in here that indicates Mr. Doane was doing some work for Mr. Knight?
A: Ok. Looking at this letter, I mean, its hard to kind of look at everything at one time, but looking at this letter, it appears to be that Mr. Knight was selling him an Oriental rug. I'm assuming that this is it in the photos; that maybe he was selling him — I don't know who William Knight is, but maybe he was selling him a glass mirror. That would be — you know, that would be other photos. These notes are very vague as to exactly who they are. . . . I mean, if its items that person is going to purchase — it could be income he's hiding — I mean, there's so many different things it could be and you're talking about one day.
* * *
Q: But a mattress sold to William Knight wouldn't be incriminating on its face, now, would it?
A: You know, again, one piece of paper if its incriminating or not, that's why you investigate. I mean, I don't know how William Knight — I don't even know who William Knight is, so I don't know how he interacts and how he comes into play with this investigation. . . .

(Tr. 57-59). Fox also testified regarding the seizure of pre-2002 documents.

Q: Now, at the time the warrant was being executed, did you know that pre-2002 documents were being seized by the IRS?
A: No.
* * *
Q: How did you eventually realize that some pre-2002 documents were seized during the execution of the warrant on Mr. Doane's apartment?
A: I started trying to identify clients and witnesses that were involved in the corporation or the business — rather, the construction business that Tom Doane was operating. So I was going through, and . . . in the folders with those clients I realized that there were pre-2002 documents.
* * *
Q: Could you explain why you felt that [the pre-2002 documents] were relevant?
A: Well, we were looking at two different things. First, we aren't sure whether or not there's a conspiracy involving our witnesses in regard to this tax charge. . . . But even more importantly, I noticed that if you take a look at some of the documents that were post 2002 its difficult to understand them in context without looking at the pre-2002 documents.
Q: Can you give an example of [] that connectedness that you're speaking about there?
A: Sure. We had one client that we noticed, she had large bill — statement billings that she paid to Thomas Doane, large amounts of money, and then she had a monthly payment that's being made that we noticed in the invoices and the checks that were being allocated. We couldn't really determine what those were for . . . but there was correspondence prior to 2002 from the client which explained (A) that there was a relationship where Thomas Doane was acting as a super, and also where she explains all the different projects she would like Tom Doane to work on.

(Tr. 72-73). On cross-examination, Fox was shown the folder labeled "9 Bank Street" and asked to elaborate on the allegedly incriminating nature of one those documents:

Q: Even though the search warrant told you only to search for and seize things from 2002 onwards, that was the only authority you had under the search warrant, you would still look at and take notes off of documents that were pre-2002, correct?
A: I did, yes.
Q: When you seized these documents, you had no idea that there was a potential conspiracy, did you?
A: No.
* * *
Q: . . . . I'm going to show you a document that's marked . . . Government Exhibit 2B. Can you read the top line of this document?
A: Thomas Doane, August 1 through December 23, 2000.
Q: Is there anything on the face of that document that suggests it's incriminating in any way?
A: Incriminating towards tax — potential tax charges, is that what you're asking me?
Q: Just saying on the face of the document, is there anything on the face of that document that indicates to you that crime has been committed?
A: There is a suggestion that there are payments being made.
Q: . . . . Is there something on that document that suggests that a crime has been committed?
A: In and of itself, no.
The Court: Let me ask you a question. You said in and of itself no was your answer. Is there anything about that document in relationship to other documents that leads you to conclude that GX-2B is evidence of a crime?
A: Yes. It outlines payments in that there are payments that are not being made, and I'm not sure when those payments are going to be made and whether or not they impact —
The Court: Where does it indicate payments not being made?
A: Owing. It says due $385,015.45.
* * *
The Court: Well, how is the existence of a debt evidence of the existence of a crime?
A: Well, actually it would limit the — if somebody owed you money and it was a loan, it's different than income in terms of calculating potential tax loss to the Government, and I need to determine whether or not it's a loan that's being repaid or if that's income that's being incurred in terms of the $385,000.

(Tr. 78-82). Finally, Fox testified that she had showed the pre-2002 documents to three witnesses, Jennifer Curran, Stephen Culhane and Susanna Culhane (Tr. 76). Fox also explained that she did not discover the names of any witnesses from pre-2002 documents and she would have interviewed these three individuals, even absent the seizure of the pre-2002 document, in light of the extensive post-2002 correspondence between these three individuals and Doane (Tr. 75-76).

After the evidentiary hearing, the Government decided that it would agree to the return and suppression of all but 32 pages of documents. The Government subsequently divided these 32 pages into six categories. After reviewing the documents produced at the hearing, "petitioner realized that there were many undated documents seized by the Government which were [allegedly] outside the limitations of the warrant" (Memorandum of Law in Opposition to the Government's Letter Brief, dated October 31, 2008 ("Pet. Mem."), at 6). Petitioner now seeks the suppression of these undated documents as well.

III. Analysis

Doane now moves for the return and suppression of (1) the undated documents and (2) the pre-2002 documents. The Government argues (1) that the undated documents were within the scope of the warrant and (2) the pre-2002 documents were legally seized under the plain-view doctrine. In addition, the Government argues that suppression of these documents would be improper at this time because Doane has not yet been indicted and Doane cannot demonstrate that he would suffer any irreparable injury if the suppression motion were to be deferred until trial.

A. Pre-Indictment Consideration of Doane's Motions

The threshold issue, presented by the Government, is whether I can rule on Doane's motions prior to indictment. Rule 41 of the Federal Rules of Criminal Procedure provides in pertinent part:

(g) Motion to Return Property. A person aggrieved by an unlawful search and seizure of property or by the deprivation of property may move for the property's return. The motion must be filed in the district where the property was seized. The court must receive evi-dence on any factual issue necessary to decide the motion. If it grants the motion, the court must return the property to the movant, but may impose reasonable conditions to protect access to the property and its use in later proceedings.
(h) Motion to Suppress. A defendant may move to suppress evidence in the court where the trial will occur, as Rule 12 provides.

As the foregoing language suggests, Rule 41(g) (h) permit courts to order the return of illegally seized property without granting a motion for suppression. Under the version of Rule 41 in effect from 1944 to 1989, this was not the case, and granting a motion for the return of property required the suppression of that property at any subsequent hearing or trial. As a result, many courts deferred pre-indictment Rule 41(e) motions unless a movant could show (1) the search was illegal, (2) that he is without an adequate remedy at law, and (3) that he would suffer some irreparable injury if relief is not granted. Premises Known Described as 55 West 47th Street, Suites 620 650 v. United States, 712 F. Supp. 437, 440-41 (S.D.N.Y. 1989);Matter of Search of Premises Known Described as 6600 Long Island Expressway, Suites 104 and 105, Maspeth, N.Y., 88-0906 M (CBA), 1988 WL 142662 at *2 (E.D.N.Y. Dec 28, 1988);In re Two Search Warrants Issued March 14, 1986, 110 F.R.D. 354, 356 (E.D.N.Y. 1986); Jordache Enters., Inc. v. United States, 86 Cr. 1 (LLS), 1987 WL 9705 at *2 (S.D.N.Y. April 14, 1987); In the Matter of the Application of John Campola, 543 F. Supp. 115, 117 (S.D.N.Y. 1982); Application of Sentinel Gov't Sec., 530 F. Supp. 793, 796 (S.D.N.Y. 1982). The principal reason offered by these courts for engrafting an irreparable harm requirement onto the language of Rule 41(e) was that a pre-indictment suppression motion would unduly interfere with the function of the grand jury. See e.g. Matter of Search of Premises Known and Described as 6600 Long Island Expressway, Suites 104 and 105, Maspeth, NY, supra, 1988 WL 142662 at *1 ("the cases reason that to grant the motion pre-indictment would have the effect of suppressing evidence before the grand jury in derogation of the holding inUnited States v. Calandra, 414 U.S. 338 (1974). . . .");Jorda-che Enters., Inc. v. United States, supra, 1987 WL 9705 at *2 (the minimal deterrence gained by allowing pre-indictment suppression motions would be outweighed by the interference that such motions would cause with the role of the grand jury).

Under the version of Rule 41(e) in effect prior to the 1989 amendment, if "the motion [for the return of property] is granted the property shall be restored and it shall not be admissible in evidence at any hearing or trial."

In 1989, Rule 41 was amended and the provision that "if the motion [for the return of property] is granted the property shall be restored and it shall not be admissible in evidence at any hearing or trial" was replaced with the language "[i]f the motion is granted, the property shall be returned to the movant, although reasonable conditions may be imposed to protect access and use of the property in subsequent proceedings." See Fed.R.Civ.P. 41(e) (1989). The Advisory Committee Note explained that this change was intended to (1) keep pace with new developments in the exclusionary rule allowing the Government to retain and utilize unlawfully seized evidence in certain circumstances (i.e. grand jury proceedings) and (2) achieve a more equitable balance between the Government's law enforcement interest and the property rights of owners.

The version of Rule 41(e) in effect from 1989 through 2002 provided:

A person aggrieved by an unlawful search and seizure or by the deprivation of property may move the district court for the district in which the property was seized for the return of the property on the ground that such person is entitled to lawful possession of the property. . . . If the motion is granted, the property shall be returned to the movant, although reasonable conditions may be imposed to protect access and use of the property in subsequent proceedings. If a motion for return of property is made or comes on for hearing in the district of trial after an indictment or information is filed, it shall be treated also as a motion to suppress under Rule 12.

Rule 41 was amended again in 2002, without substantive change, such that the former version of Rule 41(e) was divided into subsections (g) and (h), as reproduced above. See De Almeida v. United States, 459 F.3d 377, 380 n. 2 (2d Cir. 2006) (the case law concerning former rule 41(e) may be applied to the current Rule 41(g)).

Rule 41(e) is not intended to deny the United States the use of evidence permitted by the Fourth Amendment and federal statutes, even if the evidence might have been unlawfully seized. See e.g. United States v. Calandra, 414 U.S. 338, 349 n. 6 (1978); United States v. Roberts, 852 F.2d 671 (2d Cir. 1988) (exceptions to exclusionary rule applicable to Rule 41(e)).
* * *
As amended, Rule 41(e) avoids an all or nothing approach whereby the government must either return records and make no copies or keep originals notwithstanding the hardship to their owner. The amended rule recognizes that reasonable accommodations might protect both the law enforcement interests of the United States and the property rights of property owners and holders. In many instances documents and records that are rele-vant to ongoing or contemplated investigations and prosecutions may be returned to their owner as long as the government preserves a copy for future use.

Advisory Committee Notes to the 1989 Amendments to Rule 41. As a result of the new language of Rule 41, granting a motion for the return of property does not inevitably result in the suppression of that property in subsequent proceedings. See 3A Charles A. Wright, Nancy J. King, Susan R. Klein, Sarah N. Welling, Federal Practice and Procedure § 673 at 753 n. 10 (3d ed. 2009).

Despite this change, some courts still consider a pre-indictment 41(e) motion "as the functional equivalent of a motion to suppress, and, absent a showing of irreparable harm" continue the practice of deferring consideration of Rule 41(e) motions until after indictment so as to avoid interfering with the grand jury's investigation. Matter of Premises Known as 26 West 76th Street, M9-150 (JFK), 1990 WL 197845 at *1 (S.D.N.Y. Nov. 28, 1990); United States v. Douleh, 220 F.R.D. 391, 397 (W.D.N.Y. 2003); In the Matter of Searches of Semtex Indus. Corp., 876 F. Supp. 426, 431 (E.D.N.Y. 1995); In re Search Warrant Executed February 1, 1995, M 18-65 (RJW), 1995 WL 406276 (S.D.N.Y. July 7, 1995) ("The Court is loathe to interfere with an ongoing grand jury investigation and, therefore, is of the view that, unless irreparable injury can be established, petitioner's claims are better resolved in the form of a motion to suppress if and when an indictment is filed."); but cf. United States v. Premises known as 25 Coligni Ave., 120 F.R.D. 465, 468 (S.D.N.Y. 1988) (since the exclusionary rule does not extend to grand jury proceedings, United States v. Calandra, 414 U.S. 338, 349-352 (1974), the grand jury is free to subpoena and consider seized material even after a moving party may have prevailed on a Rule 41(e) motion.").

Other courts, however, have held that the plain language of Rule 41(e) does not permit a court to defer its decision or to engraft an irreparable harm requirement that is not set forth in the text of Rule 41. As the Honorable James C. Francis, IV, United States Magistrate Judge, has noted, "the decisions that require the movant to demonstrate irreparable harm before considering a preindictment Rule 41(e) motion have erected an unjustified barrier." United States v. Premises known as 25 Coligni Ave., supra, 120 F.R.D. at 468; United States v. E. Side Ophthalmology, 95 Mag. 2424 (JCF), 95 Mag. 2425 (JCF), 95 Mag. 2431 (JCF), 1996 WL 384891 at *3-*4 (S.D.N.Y. July 9, 1996);Music Deli Groceries, Inc. v. I.R.S., 781 F. Supp. 992, 998 (S.D.N.Y. 1991); Roberts v. United States, 656 F. Supp. 929 (S.D.N.Y. 1987) rev'd on other grounds United States v. Roberts, 852 F.2d 671 (2d Cir. 1988) (overturning the district court's holding that exceptions to the exclusionary rule did not apply to Rule 41(e) motions without addressing whether the district court properly considered petitioner's motion pre-indictment);Application of First United Fin. Corp. for Return of Seized Prop., 620 F. Supp. 1450, 1452 (E.D.N.Y. 1985).

In this case, the Government has not argued that suppression of these documents would interfere with a grand jury investigation and, accordingly, I conclude that Doane is not required to show irreparable harm in order to bring this motion for the return of his property under Rule 41(g). See e.g. United States v. Roberts, supra, 852 F.2d at 673 (Rule 41(e) was "intended . . . to provide a pre-indictment procedure for the return of property"); United States v. E. Side Ophthalmology, supra, 1996 WL 384891 at *4 ("there is no justification for providing unindicted persons with less procedural protection than accorded those under indictment").

As a fall-back position, Doane argues that he has shown irreparable harm. Specifically, Doane argues that the Government's use of pre-2002 documents to identify and contact clients whose business relationship with Doane predated 2002 has caused and will continue to cause him irreparable harm (Reply Memorandum of Law in Further Support of Petitioner Thomas Doane's Motion for the Return of Property and the Suppression of Evidence, dated September 11, 2005, at 5). Fox, however, testified that she did not obtain the names of any of the people that she interviewed from pre-2002 documents (Tr. 75-76) and Doane has not offered any evidence indicating otherwise. In addition, all of the documents presently at issue identify individuals whose involvement with Doane's business would have been apparent from post-2002 documents. Accordingly, I conclude that Doane's fall back argument fails.

With regard to Doane's motion to suppress those documents which were not within the scope of the warrant, I reach a different conclusion because I do not believe that this issue is currently ripe for adjudication. No criminal charges have been brought against Doane and therefore, it appears premature to address the issue of suppression without knowing how the Government intends to use these documents. Moreover, while I have jurisdiction to hear a Rule 41(g) motion on consent of the parties, the parties can not consent to my jurisdiction in a felony criminal case and it is presently unclear what charges, if any, will be filed against Doane. 28 U.S.C.A. § 636(c)(1); 18 U.S.C. § 3401; see also United States v. Douleh, supra, 220 F.R.D. at 395.

Accordingly, I shall address plaintiff's motion for the return of property at this time, but I do not address his motion to suppress.

B. Plaintiff's Motion for The Return of Documents

There are two categories of documents presently at issue: (1) the pre-2002 documents contained in Government Exhibits Al — A6, and (2) the undated documents contained in Government Exhibit B. As discussed above, I agree with those courts that have held that to prevail on a Rule 41(g) motion asserting an unlawful seizure, the movant must show that (1) he is entitled to lawful possession of the item seized, (2) that the item seized is not contraband and (3) that the seizure was unlawful. United States v. Van Cauwenberghe, 827 F.2d 424, 433 (9th Cir. 1987); 3A Charles A. Wright, Nancy J. King, Susan R. Klein, and Sarah N. Welling, Federal Practice Procedure § 673 at 753-54 (3d ed. 2009). Only the third element is in dispute here.

1. The Pre-2002 Documents

a. Wholesale Seizure

The Government has conceded that the pre-2002 documents fall outside the scope of the warrant (Letter of Assistant United States Attorney Telemachus P. Kasulis, dated September 10, 2008 at 2). The Government first claimed at oral argument that it need not justify the seizure of documents outside the scope of the warrant because on-site sorting of documents would be impractical and unduly time-consuming.

Several courts have upheld the reasonableness of the wholesale seizure of folders or boxes of documents without an on-site examination of every individual document to determine if it fits within the scope of the warrant. These courts, however, were only addressing the limited issue of whether the seizure of a group of documents so flagrantly exceeded the authority granted in the warrant such that all of the evidence seized, including evidence clearly within the scope of the warrant, should be suppressed. See United States v. Hargus, 128 F.3d 1358, 1363 (10th Cir. 1997) ("although we are given pause by the wholesale seizure of file cabinets and miscellaneous papers and property not specified in the search warrant, the officers' conduct did not grossly exceed the scope of the warrant" such that suppression was warranted, in part because the Government did not offer at trial any item not specified in the warrant); United States v. Kimbrough, 69 F.3d 723, 728 (5th Cir. 1995); United States v. Santarelli, 778 F.2d 609, 615-16 (11th Cir. 1985) ("we believe that the agents acted reasonably when they removed the documents to another location for subsequent examination. . . . [W]e cannot see how Santarelli's privacy interest was adversely affected by the agents' examination of the documents off the premises, so long as any items found not to be relevant were promptly returned."); 2 Wayne R. LaFave, Search Seizure, § 4.11(a) at 776 (4th ed. 2004); see also United States v. Shi Yan Liu, 239 F.3d 138, 140 (2d Cir. 2000) (holding that blanket suppression of all of the items seized during a search is warranted when the Government agents "(1) effect a `widespread seizure of items that were not within the scope of the warrant,'United States v. Matias, 836 F.2d 744, 748 (2d Cir. 1988), and (2) do not act in good faith."); see generally U.S. Postal Serv. v. C.E.C. Servs., 869 F.2d 184, 187 (2d Cir. 1989); United States v. Wapnick, CR-92-419 (CBA), 1993 WL 86480 at *6 (E.D.N.Y. 1993) (upholding a broad warrant which authorized the seizure of all books and records without limitation as to date or transaction type because the alleged tax scheme was complex and requiring the agents to sort the documents based on relevance on-site was impractical).

Moreover, these cases do not contemplate the indefinite retention of all materials contained within intermingled files. The rationale for these decisions is that where a large number of files contain a mix of documents some of which fit a search warrant's criteria and some of which do not, it is impractical for the executing agents to analyze each document at the site of the search to determine whether it is within the scope of the warrant or not. United States v. Hargus, supra, 128 F.3d at 1363;United States v. Santarelli, supra, 778 F.2d at 615-16; United States v. Regan, 706 F. Supp. 1102, 1114 (S.D.N.Y. 1989) (upholding a broad warrant because if the agents had been required to analyze each of the hundreds of thousands of documents "they would probably still be on the premises now"); 2 Wayne R. LaFave, supra, Search Seizure, § 4.11(a) at 776 n. 9 (collecting cases). Accordingly, a number of cases in this Circuit have held that "when items outside the scope of a valid warrant are seized, the normal remedy is suppression and return of those items. . . ." United States v. Matias, supra, 836 F.2d at 747; accord United States v. George, 975 F.2d 72, 79 (2d Cir. 1992); United States v. Dunloy, 584 F.2d 6, 11 n. 4 (2d Cir. 1978); United States v. Artieri, 491 F.2d 440, 445-46 (2d Cir. 1974); United States v. Argentina, 01 Cr. 245 (JSM), 2002 WL 54602 at *1 n.l (S.D.N.Y. Jan. 14, 2002); United States v. Longo, 70 F. Supp.2d 225, 252 (W.D.N.Y. 1999); United States v. Corcoran, 855 F. Supp. 1359, 1367 (E.D.N.Y. 1994). Thus, even where practical considerations permit the Government to seize items that are beyond the scope of the warrant, once the fruits of the search are segregated into responsive and non-responsive groups, the "normal" practice is to return the non-responsive items.

Neither the Government's research nor my own has disclosed any authorities holding that the Government may seize folders containing documents outside the scope of a warrant and then retain and utilize these documents without demonstrating that they fit within one of the recognized exceptions to the search-warrant requirement. See e.g. United States v. Slocum, 708 F.2d 587, 606 (11th Cir. 1983) (Since each of "the individual documents contained in the file could be legitimately seized under the plain-view exception, [the officer] acted reasonably in ordering the seizure of the entire file."); United States v. Tamura, 694 F.2d 591, 595-96 (9th Cir. 1982). Indeed, permitting the Government to retain items outside the scope of the warrant without such a showing would dramatically dilute the right to privacy in one's personal papers. See Andresen v. Maryland, 427 U.S. 463, 482 (1976).

Accordingly, I conclude that where voluminous items responsive to a search warrant are intermingled with non-responsive items, the Government may seize all containers holding responsive items without rendering the entire search unlawful. However, the retention of items outside the scope of the warrant can be justified only if the Government meets its burden of demonstrating that those items fall within an exception to the warrant requirement.

b. Plain View

The Government's second argument is that the pre-2002 documents were lawfully seized under the plain-view exception. For a seizure to pass muster under the plain-view exception, the following requirements must be satisfied: (1) "the officer did not violate the Fourth Amendment in arriving at the place from which the evidence could be plainly viewed," (2) the seized item's "incriminating character must be `immediately apparent,'" and (3) "not only must the officer be lawfully located in a place from which the object can be plainly seen, but he or she must also have a lawful right of access to the object itself." Horton v. California, 496 U.S. 128, 136-37 (1990); Arizona v. Hicks, 480 U.S. 321, 326-27 (1987). The Government has the burden of demonstrating each of these elements of the plain-view exception.United States v. Kiyuyung, 171 F.3d 78, 83 (2d Cir. 1999); United States v. Perea, 986 F.2d 633, 639 (2d Cir. 1993).

Only the second element of the plain-view doctrine is in dispute here. In evaluating whether this requirement has been met, courts assess whether the officers "have probable cause to believe that an object in plain view is [evidence of a crime] without conducting some further search of the object." Minnesota v. Dickerson, 508 U.S. 366, 375 (1993); United States v. Moreno, 897 F.2d 26, 32 (2d Cir. 1990); United States v. Davis, 06 Cr. 911 (LBS), 2009 WL 637164 at *10 (S.D.N.Y. Mar. 11, 2009); United States v. Padilla, 986 F. Supp. 163, 170 (S.D.N.Y. 1997). "Probable cause exists where "the facts and circumstances within [the officers'] knowledge and of which they had reasonably trustworthy information [are] sufficient in themselves to warrant a man of reasonable caution in the belief" that the object is evidence of a crime. Brinegar v. United States, 338 U.S. 160, 175-176 (1949); Texas v. Brown, 460 U.S. 730, 742 (1983). In determining whether probable cause exists, a Court may consider the agent's special experience and knowledge at the time of the search. See e.g. United States v. Barrios-Moriera, 872 F.2d 12, 17 (2d Cir. 1989); United States v. Garcia, 496 F.3d 495 (6th Cir. 2007).

i. The Incriminating Character Of the Seized Documents

As discussed in Section III(B)(1)(a) above, I have concluded that it was appropriate for the Government to seize file folders of documents without conducting an on-site examination of every document within each folder to ascertain whether that document fell within the scope of the warrant.

The manner in which the plain view doctrine is applied to off-site reviews of voluminous, intermingled documents is not well established. See United States v. Stierhoff, 477 F. Supp.2d 423, 444 (D.R.I. 2007) (describing the task as a voyage into "uncharted waters"). First, the law is not clear whether the plain-view doctrine even applies to the results of a search that are reviewed in an agent's office after the search warrant has been executed. The solution most compatible with the concerns underlying the particularity requirement of the Fourth Amendment may be to require that officers obtain a second warrant authorizing the seizure of documents outside of the warrant, see United States v. Tamura, supra, 694 F.2d at 595-96, because the policy considerations underlying the plain-view doctrine are diminished in the context of off-site sorting. See Arizona v. Hicks, 480 U.S. 321, 327 (1987) (the plain-view doctrine is justified by "the desirability of sparing police, whose viewing of the object in the course of a lawful search is as legitimate as it would have been in a public place, the inconvenience and the risk — to themselves or to preservation of the evidence — of going to obtain a warrant").

A number of courts have held that when the Government searches a computer, which often contains relevant documents intermingled with "documents that the government has no probable cause to seize," In the Matter of the Search of: 3817 W. West End, First Floor Chicago, Illinois 60621, 321 F. Supp.2d 953, 958 (N.D. Ill. 2004), the warrant must state with particularity the files to be seized from the computer. See e.g. United States v. Vilar, S305-cr-621 (KMK), 2007 WL 1075041 at *36 (S.D.N.Y. Apr. 7, 2007); United States v. Riccardi, 405 F.3d 852, 862-63 (10th Cir. 2005). If a law enforcement officer conducting an off-site search of a computer discovers evidence of other crimes, "that officer is required to procure a second warrant to continue searching the computer for additional evidence of that other crime." United States v. Vilar, supra, 2007 WL 1075041 at *37, citing United States v. Carey, 172 F.3d 1268, 1276 (10th Cir. 1999).

The second issue in assessing the second element of the plain-view doctrine, is whether the incriminating nature of the document must be apparent from the face of the document at the time the agent first views the document at her office to determine whether it falls within the scope of the warrant. In some cases, such as child pornography investigations, the incriminating nature of a document may be readily apparent, even when the document is viewed in isolation. The applicability of the plain view doctrine to such cases presents no substantial obstacles. In other cases, including this one, a document viewed in isolation may appear innocuous. Its relevance may, however, only become clear to an agent after reviewing all of the other documents in the file to determine whether they are within the scope of the warrant. For example, if the agents in this case came across a receipt, bearing a 2001 date, made out to Doane for the purchase of household fixture such as a chandelier or a washing machine, the significance of the receipt would not be readily apparent; Doane may have been buying the items for himself. If, however, a subsequent document in the same file suggests that the fixture was installed in a client's building in 2002 and that the amount charged to the client exceeded the price paid by Doane, the 2001 document would have value as evidence of income earned in 2002. Under these circumstances, it is unclear whether the evidentiary value of the 2001 document can fairly be said to be readily apparent. Compare United States v. $557,933.89, More or Less, in U.S. Funds, 287 F.3d 66, 83 (2d Cir. 2002) (explaining that the "immediately apparent" requirement of the plain-view exception requires an inquiry into what information was readily apparent without subjecting the object to a "more searching scrutiny" and whether that information gave "rise to a sufficient probability that the [items] represented evidence of criminal activity to justify their" seizure) and United States v. Garcia, supra, 496 F.3d at 510-11 ("an object's incriminating nature is not immediately apparent if it appears suspicious to an officer but further investigation is required to establish probable cause as to its association with criminal activity. . . . The officer must recognize the incriminating nature of an object as a result of his immediate or instantaneous sensory perception.") (internal quotations omitted); and United States v. Miles, 05-CR-59A, 2006 WL 2403464 at *5 (W.D.N.Y. Aug. 18, 2006) ("To meet the `immedi-ately apparent' standard, police officers must have probable cause to believe that an object in plain view is contraband without conducting some further search of the object.") with United States v. Barrios-Moriera, 872 F.2d 12, 17 (2d Cir. 1989) (the probable cause determination is based on the agent's special experience and knowledge at the time of the search). See also United States v. Menon, 24 F.3d 550, 563 (3d Cir. 1994) (the Government agent did not exceed the scope of the warrant by seizing two documents, outside the scope of the warrant, because he had probable cause to believe that those documents were "interrelated" with an incriminating document which had already been discovered); see generally Coolidge v. New Hampshire, 403 U.S. 443, 466 (1971) ("[T]he `plain view' doctrine may not be used to extend a general exploratory search from one object to another until something incriminating at last emerges.").

The fact that the prosecution ultimately recognizes the evidentiary value of the document is immaterial. The plain view doctrine requires that the objects evidentiary value be apparent at the time of the seizure. United States v. Barrios-Moriera, supra, 872 F.2d at 16 ("[p]ut another way, it must have been immediately apparent to the officer before seizing the item, not after seizing it, that it was of a criminal character"); United States v. O'Brien, 498 F. Supp.2d 520, 537 (N.D.N.Y. 2007) ("[r]eadily apparent also means that the police may not first search or seize an object without some constitutional basis to do so, and then seek to determine whether there is probable cause to believe the object is evidence or contraband"); see also United States v. Szymkowiak, 727 F.2d 95, 99 (6th Cir. 1984) (a weapon's incriminating character was not immediately apparent if it could be discerned only by calling an ATF agent to the scene because from the "facts available to [the search team] . . . at the time . . . of discovery [they did not] have probable cause to believe that the firearm was incriminating.") (internal citations omitted); United States v. Gonzalez, 334 F. Supp.2d 275, 281 (E.D.N.Y. 2004).

The problem here, however, is even more basic because the Government has not offered any evidence concerning when the documents in issue were determined to have evidentiary value, how they were determined to have evidentiary value or how their evidentiary value was "immediately apparent."

Agent Gorra testified that he did not realize, at the time of the search, that he was seizing pre-2002 documents and he was not shown any of the documents at issue during the evidentiary hearing (Tr. 47-48). Accordingly, Agent Gorra's testimony does not establish that the incriminating nature of any of the documents at issue was ever apparent to him. Agent Silva testified that he realized he was seizing pre-2002 documents but he seized those documents because they appeared "related" or "relevant" to post-2002 documents and, therefore, "substantiated what happened in 2002 and thereafter" (Tr. 13, 25). However, when Silva was questioned about how he knew that several of the pre-2002 documents (Government Exhibits 2A-2F), presently at issue, were related to post-2002 documents, he was unable to offer any explanation other than the fact that all of the documents were in the same folder (Tr. 28-30). Finally, on cross-examination, Agent Fox stated that there was nothing "on the face of" Government Exhibits 2D, 2E and 2F that suggested a crime had been committed but that "these documents are part of other documents which together are evidence of future crimes" (Tr. 83). When Agent Fox was given a chance on re-direct to explain how Government Exhibits 2D, 2E and 2F constituted evidence of a crime, she stated:

Agents Gorra and Fox testified regarding the nature of documents contained within the "William Knight" folder (Tr. 53-59, 84-86); see Government Exhibits 2G-2Q). After the evidentiary hearing, however, the Government decided that it would agree to the return and suppression of all of the documents contained within the William Knight folder (Letter of Assistant United States Attorney Telemachus P. Kasulis, dated October 31, 2008 ("Oct. 2008 Ltr."), at 5-8).

I was shown invoices, and I was shown correspondence, I was shown a listing of payments that were made. Those documents in and of themselves don't explain the whole relationship with the other individuals. The documents that I was shown were from 9 Bank Street. 9 Bank Street is owned by Jennifer Curran. She has a business that she's running. It's called Asylum Adventures. The relationship between her and Thomas Doane isn't going to be clearly defined in one document on its face. To understand the scope of all the work that was commissioned prior to 2002 is critical — in my opinion, is important to understand in order to determine the tax liabilities and consequences and understand the entire scope of the work that was being done by Thomas Doane post-2002 and what he's being paid for you. . . .

(Tr. 88-89). Agent Fox did not testify regarding any of the other documents presently at issue.

Agent Fox did testify regarding the incriminating nature of Government Exhibit 2B (Tr. 79-82) and the nature of documents within the "William Knight" folder. The Government has, however, consented to the return and suppression of all of these documents (see Oct. 2008 Ltr. at 5-8).

With the exception of Exhibits 2D, 2E, and 2F, the Government has, therefore, failed to present any testimony explaining how the incriminating nature of the seized documents was immediately apparent. See generally United States v. Jones, 652 F. Supp. 1561, 1578 (S.D.N.Y. 1986), citing United States v. Strand, 761 F.2d 449, 454 (8th Cir. 1985) (the Government must establish the applicability of the plain view doctrine for each individual item seized). With respect to the documents discussed by the agents, it is not evident from the face of Government Exhibits 2D, 2E and 2F why these documents are "evidence of future crimes" or "critical . . . to determine the tax liabilities and consequences" of work performed by Doane post-2002 (Tr. 83, 88-89). While I am willing to credit Agent Fox's testimony that Government Exhibits 2D, 2E and 2F are evidence of pre-2002 jobs performed by Doane for Curran, this fact alone without any further showing of a connection between the pre-2002 documents and the post-2002 jobs is insufficient to meet the Government's burden of demonstrating that the incriminating nature of the documents was immediately apparent so as to justify their seizure under the plain-view doctrine.

Accordingly, I conclude that the Government has failed to meet its burden of persuasion because the evidence did not establish that the incriminating nature of the documents was immediately apparent.

ii. Hours Billed to La Loca

The second page of group A3, entitled "Hours Billed to La Loca" indicates hours billed by three individuals, "Domingo," "Rodolfo," and "Refugio" in 2001 and 2002 for repairs to several apartments, presumably within 9 Bank Street. This document falls within the scope of the warrant because it appears to be a record relating to the businesses run by Doane, for the years 2002 to the present (Attachment A to the Search Warrant, dated January 4, 2008, at ¶ 1). Where part of a document is within the scope of a search warrant, the Government is under no obligation to separate physically any non-responsive potions. See United States v. Beusch, 596 F.2d 871, 876 (9th Cir. 1979) (holding that the Government may properly seize an entire ledger and was not required to remove those pages which contain the incriminating evidence); accord United States v. Christine, 687 F.2d 749, 760 (3rd Cir. 1982).

Accordingly, this document was lawfully seized within the scope of the warrant.

2. The Undated Documents

Doane also seeks the return of the undated documents (Government's Exhibit B) "because they are outside the scope of the limitations of the search warrant [] and their incriminating nature is not apparent on their face" (Pet. Mem. at 6). Doane has not, however, produced any evidence that these undated documents fall outside the scope of the warrant; Doane has not established any reason to believe that these records are from prior to 2002.See United States v. Arboleda, 633 F.2d 985, 993 (2d Cir. 1980) (the "general rule [is] that the moving party in a suppression hearing has the burden of production and persuasion," but when the defendant has produced evidence that he was searched without a warrant the burden of justifying the search shifts to the Government); 6 Wayne R. LaFave, Search and Seizure, § 11.2(b) at 41 (4th ed. 2004). In this case, Doane's apartment was searched pursuant to a warrant and, therefore, Doane "bear[s] the burden to prove that the challenged items were seized outside the scope of the warrant [and, accordingly,] any ambiguities in the descriptions of the seized items will be resolved against [Doane]." United States v. Kaufman, CRIM. A.04-40141, 2005 WL 2304345 at *6 (D. Kan. Sept. 21, 2005);United States v. Evanson, 05-CR-805 (TC), 2007 WL 4299191 at *15 (D. Utah Dec. 5, 2007); United States v. Platt, 06-cr-214 (MEF), 2007 WL 1034958 at *8 (M.D. Ala. March 29, 2007) (defendant was unable to demonstrate that the officers had exceeded the scope of a warrant authorizing the seizure of "recently deleted" images from defendant's computer because it was impossible for defendant to demonstrate the date on which a deletion had occurred); United States v. Gawrysiak, 972 F. Supp. 853, 864 (D.N.J. 1997).

Therefore, Doane has not presented any evidence that the documents contained within Government Exhibit B are pre-2002 documents and, accordingly, I conclude that the agents did not exceed the scope of the warrant in seizing these documents.

IV. Conclusion

For the aforementioned reasons, I conclude that the pre-2002 documents seized by the Government do not fall within the plain-view exception to the warrant requirement and the originals and all copies must be returned to Doane. Doane is hereby ordered to maintain all of the originals should the Government desire to use these documents in a future proceeding. See Fed.Crim.P. 41(g).

There appears to be no legal obstacle to the Government's subpoenaing any of the documents in issue for use before the Grand Jury. United States v. Calandra, 414 U.S. 338 (1978); Lawn v. United States, 355 U.S. 339 (1958); Costello v. United States, 350 U.S. 359 (1956); Wagman v. Arnold, 257 F.2d 272, 276 (2d Cir. 1958) (independent source doctrine). I express no opinion concerning the ability of the Government to subpoena or use the documents in any other proceeding.

I further conclude that Doane has failed to produce any evidence that the remaining documents — including the "Hours Billed to La Loca" document and the undated documents — were illegally seized. Accordingly, Doane's motion for the return of these documents is denied.

For the aforementioned reasons, I conclude that Doane's motion to suppress under Rule 41(h) is not ripe for adjudication at this time and, accordingly, it is denied.