Searching Old Digital Haystacks: Some Thoughts on the Richman v. United States Litigation

Interesting Fourth Amendment issues, with a novel remedy.

In federal district court in Washington, DC, Judge Colleen Kollar-Kotelly handed down two opinions in the last two weeks in a case involving Daniel Richman, a friend and occasional advisor to former FBI Director James Comey. In the first opinion, dated December 12, the Judge ordered the government to return to Richman digital copies of the contents of his computers.  In the second opinion, released yesterday, Judge Kollar-Kotelly clarified her first order and addressed government objections.

There's a lot going on in these cases.  But the opinions happen to raise important questions of how the Fourth Amendment and the Federal Rules of Criminal Procedure apply to searching and seizing computers. Given my academic focus on those legal issues, I thought I would blog about them and offer some thoughts for the law nerds hoping to learn more about those legal issues and how this new set of opinions deals with them.

Here's the basic problem.  When the government gets a warrant to search a computer, it generally seizes the physical device, copies all the data, and then searches the government's copy of the data for the evidence sought.  Put another way, investigators make a copy of the digital haystack and then search the copy for the needle that the warrant described as the evidence to be sought.

All of this has an important implication: When the case is over, either charged or uncharged, the government still has a copy of that digital haystack.  And if you're the government, you might want to keep that digital haystack.  Storage is cheap, so it's not like you need to free the space. And having that haystack might come in handy some day.  Maybe someday, maybe even in an unrelated case, you'll have an investigative need that can be met by going back to that digital haystack and looking for a whole new set of needles.

The key question now is, what are the rules for dealing with that haystack years later?  Can the government search that already-previously-seized data again, this time for new evidence, either without a warrant—or even with one?  And if the owner of the haystack wants the haystack back, can he get it back—and what does getting it back mean?

(1) Introducing the Richman Case 

Daniel Richman is a lawyer and law professor who is a close friend of James Comey.  Richman has sometimes acted as Comey's counsel, both informally and in the legal sense.  During the first Trump Administration, DOJ obtained warrants to search Richman's computers and online accounts for evidence of unlawful disclosure of classified information that had been obtained through Comey.  No charges were brought, and the case was closed in 2021.  But the  government retained copies of Richman's digital files.

Now fast forward to the second Trump Administration. A lot of people have followed this way more closely than I have, and my apologies if I get some of the details wrong here.  But as you know from following the news, there has been great deal of interest in the current executive branch in prosecuting James Comey.  As I understand things, whereas the Trump 1.0 DOJ investigated Comey for allegedly leaking classified information, the Trump 2.0 DOJ is targeting Comey for allegedly lying to Congress about whether he had authorized Richman to act as a source for news stories.

Here's where the computers come in.

What happened, apparently, is that investigators in Trump 2.0 realized that they still had copies of Richman's digital files held over from the investigation during Trump 1.0.  So they searched Richman's files again, this time searching for what Comey had authorized Richman to do.  At least some of that information was then used as a basis to get an indictment against Comey.  Investigators did not get a second warrant to do this new round of search.  They had a copy of the files, so they searched it for what they wanted without new warrants.

Richman has now come into court, seeking a return of his property under Rule 41 of the Federal Rules of Criminal Procedure.  Rule 41 gives people a limited right to return of property unlawfully seized from them.  As I understand Richman's argument, he's saying that the government never had a right to get copies of all of his data, and that the continued retention of his files violated his Fourth Amendment rights, and that the remedy is to return to him all the copies of his data.

If I'm following this all correctly, there are really three issues in play here.  First, were Richman's Fourth Amendment rights violated?  Second, does Richman have a remedy of returning the digital data under Rule 41?  And third, what exactly does a remedy of returning the digital data look like?

I break out that last point because I assume that's part of what's going on here.  If the right to the return of data means a right to the deletion of data, that could operate as, in effect, a motion to suppress made by Richman on Comey's behalf. If the government can't get its own files, after all, it can't  use them to prosecute Comey.  (Although the charges against Comey have been dismissed, the Justice Department has indicated it will appeal.  Who knows what might happen in the future, either on appeal or in some subsequent set of attempted charges.)

(2) Previous Cases on Searching Digital Files From A Previous Investigation

This question of how the Fourth Amendment appplies to re-searching previously seized computer files has come up in a few cases over the years, and it's getting more important over time.  I want to give you a flavor of the cases to provide some context.  I'll cover two cases in particular: First, the Second Circuit's litigation in the Ganias case; and second, a district court opinion, Nasher-Alneam.

The first case, United States v. Ganias, is one I blogged about a bunch of times here at the Volokh Conspiracy back in the day. It involves the seizure of an accountant's computers.  First, in 2003, the government seized the accountant's computers to get evidence of crime of his customers. The accountant himself was not suspected of involvement in crime, but during that investigation, they copied the accountant's computers—and held on to the copies.  Years later, in 2006, investigators came to suspect the accountant himself had committed other crimes, and they realized there was a copy of the accountant's computers already in government custody.  So the investigators obtained a second warrant to research the copy of the accountant's computers, this time for the accountant's crimes—looking for different needles in the held-over copy of the digital haystack.

In the initial ruling in Ganias, the Second Circuit ruled that this violated the Fourth Amendment because the government was required to delete the old haystack after it wasn't needed in the original case.  But the ruling didn't last: In 2016, the en banc court reviewed that ruling, held that the good faith exception to the exclusionary rule applied, and declined to reach whether the Fourth Amendment was violated.

The same basic issue arose in United States v. Nasher-Alneam, a district court case from 2019. In that case, the government obtained a warrant to search the computers of a physician for evidence that he had improperly provided narcotics to patients.  At trial, the jury hung. The government then decided to search the copies of the computers a second time, this time for evidence of billing fraud. Unlike in Ganias, however, the government did not get a second warrant.  The district court ruled that the search for evidence of billing fraud violated the Fourth Amendment, as the government could not just search for evidence outside the warrant just because it had a copy of the suspect's computer.

What to make of these cases? The government doesn't have unlimited authority to hold on to and re-search data leftover from old cases.  But exactly what the limits are remains uncertain.

For what it's worth, in my scholarship and my new book, The Digital Fourth Amendment, I argue for use restrictions on digital warrants. The government is allowed to seize and copy all those files, but whatever it copies that outside the scope of the first warrant can't be used in later case, including if the government has a second warrant.  This is needed, I argue, to ensure that the government doesn't use the switch from physical to digital environments as a way to massively expand government power and turn all digital warrants into general warrants.  But that's just my proposal.

(3) The Court Rules That The Government Violated Richman's Rights

In the major opinion in the Richman case, dated December 12th, Judge Kollar-Kotelly first rules that the government violated Richman's Fourth Amendment rights by re-searching his seized files without getting a new round of warrants:

Although the Government, in a single footnote, broadly "denies that there has been any violation of the Fourth Amendment," it has presented no substantive argument that this warrantless search of Petitioner Richman's files was consistent with—or even cognizant of—his Fourth Amendment rights. See Gov't's Opp'n & Mot., Dkt No. 12, at 16 n.11.

Recognizing the extraordinary scope and sensitivity of data available on personal digital devices, the Supreme Court has commanded that officers must "secure a warrant before conducting" a search of data stored on cell phones, except in the rare case in which exigent circumstances make a warrantless search reasonable. Riley v. California, 573 U.S. 373, 386, 402 (2014). Moreover, it is well established that when the Government seeks to conduct another search after it has finished executing a previous warrant, it generally must secure another warrant. See Digital Devices II, 2022 WL 998896, at *9 (collecting cases).

These requirements reflect familiar, bedrock Fourth Amendment principles. "Searches conducted outside the judicial process, without prior approval by judge or magistrate, are per se unreasonable under the Fourth Amendment—subject only to a few specifically established and well-delineated exceptions." Katz v. United States, 389 U.S. 347, 357 (1967). "When the right of privacy must reasonably yield to the right of search is, as a rule, to be decided by a judicial officer, not by a policeman or Government enforcement agent." Johnson v. United States, 333 U.S. 10, 14 (1948).

In short, the Government's warrantless search of the contents of Petitioner Richman's cell phone and tablet in September 2025 was manifestly unconstitutional.

This holding is a lot like the United States v. Nasher-Alneam case I discussed above. The government was allowed to hold on to the files from the first warrant, but it couldn't go back to that well and draw more water (so to speak) without getting a new set of warrants to look for the new evidence.

As I hinted at above, I would personally have gone beyond that holding, in that I don't think the government should be able to go back and re-search the data even with a new warrant.  I've detailed this argument in this article and in my new book, but the basic idea shouldn't be able to vastly expand its power when we switch from physical to digital searches.  The government only has a copy of the extra information that was non-responsive to the first warrant for practical reasons: Courts allow the government to over-seize that irrelevant data in executing the first warrant to allow for a later forensic search.  I think that part is reasonable.  But, in my view, allowing the government to  double-dip into those files years later with a second warrant is unreasonable; it lets the practical need from the first warrant be the basis for expanded power unrelated to that warrant.

I take the Court here as adopting only a much more modest position.  Richman retains Fourth Amendment rights in the copy for the files that were not the subject of the first warrant,  and the government searching the computer for those files is a new search that requires a new warrant.  So far, that's not an unexpected holding.

(4) The Court Concludes that Rule 41 Allows an Order to Return Property Here.

Having found a Fourth Amendment violation, the next question is whether there's a remedy.  The right to a return of property under Rule 41 is limited, and usually Rule 41  can't be used while a case is ongoing.  (Basically, you don't want Rule 41 to be used as a sort of suppression remedy, so it's saved as an equitable remedy to get property back, not to stop a case.) This situation is odd, though. There's no pending case against Richman, only against Comey.  Judge Kollar-Kotelly rules that Rule 41 is available here and that Richman has a right to the return of his files.  A brief excerpt:

The Fifth and Ninth Circuits have each adopted four-factor tests for evaluating whether a court should exercise its equitable jurisdiction to order the return of property under Federal Rule of Criminal Procedure 41(g). See Richey v. Smith, 515 F.2d 1239, 1243 (5th Cir. 1975); Ramsden v. United States, 2 F.3d 322, 325 (9th Cir. 1993).3 The four relevant factors are: (1) "whether the Government displayed a callous disregard for the constitutional rights of the movant"; (2) "whether the movant has an individual interest in and need for the property he wants returned"; (3) "whether the movant would be irreparably injured by denying return of the property"; and (4) "whether the movant has an adequate remedy at law for the redress of his grievance." Ramsden, 2 F.3d at 325; accord Richey, 515 F.2d at 1243.

Other courts, including at least one court in this District, have applied the same or similar factors. See, e.g., In re Singh, 892 F. Supp. 1, 3 (D.D.C. 1995) (SSH); Trump v. United States, 54 F.4th 689, 694 (11th Cir. 2022) (per curiam) (following Richey as binding precedent in the Eleventh Circuit); Matter of Search of 4801 Fyler Ave., 879 F.2d 385, 387 (8th Cir. 1989) (concluding that "callous disregard" of Fourth Amendment rights, "irreparable injury if relief is not granted," and "lack of an adequate remedy at law" are each required).

Applying the Fifth and Ninth Circuits' four-factor tests to the facts of this case, this Court concludes that each factor weighs in favor of exercising equitable discretion to order the return of Petitioner Richman's property here.

There's a lot going on in this part of the opinion, but with my apologies I'm going to pass over it to get to the really interesting question: If there's a right to the "return" of digital data, what exactly does that remedy look like?  That's up next.

(5) But What Exactly Is the Rule 41 Remedy for Digital Files?

Now we get to the details of the remedy.  Judge Kollar-Kotelly takes this to be an equitable question in which she can fashion a remedy.  She starts with the order to "return" the files.

As far as I can tell, the Judge does not detail what "returning" the files means.  The files are lots of zeros and ones that were likely copied onto government servers— probably a lot of different servers.  But the language in the opinion suggests that returning means giving Richman a copy and then deleting all remaining government copies.   As she writes, the government has to certify that it has "(1) returned the covered materials to Petitioner Richman" and "(2) not retained any additional copy or copies of the covered materials." In this context, not retaining sounds a lot like deleting.  So I think she's talking about a deletion requirement, rather than, say, just handing Richman an extra copy.

But if that's what returning the files means, does that mean the government can never access Richman's files?  No, the Judge concludes: Rule 41 can't be used to effectively suppress evidence for Mr. Comey. So the Judge fashions a sort of middle ground: the government can make a copy of Richman's files and deposit that with the district court that is overseeing the Comey prosecution, and it can access those files only with a future warrant.  Here's the explanation:

Allowing the Government to preserve a complete copy of the relevant materials in the custody of a neutral third party, in this case the U.S. District Court for the Eastern District of Virginia, permits the Court to redress the specific legal wrong that Petitioner Richman has established without unduly burdening the interests of the Government or the public at large. In other cases, courts have exercised their discretion under Rule 41(g) to allow the Government to create copies of files and preserve those copies in the Government's own records before returning the originals to aggrieved movants. See, e.g., J.B. Manning Corp. v. United States, 86 F.3d 926, 928 (9th Cir. 1996). Here, however, the Court has concluded that the Government has not maintained the files at issue in a manner that adequately protects Petitioner Richman's right to be free from unreasonable searches and seizures. See supra Section III.B.

Allowing the Government to retain a copy in its own possession therefore would not provide adequate redress to Petitioner Richman. Meanwhile, requiring the Government to return all copies of the files to Petitioner Richman could unduly impede the Government's interests in pursuing future investigations and prosecutions if—as the Government strongly suggests in its briefing—it intends to pursue further prosecution of Mr. Comey. See supra Section III.C. The appropriate way to balance these interests, and to provide redress to Petitioner Richman without transforming his motion into a "collateral (and premature) motion to suppress evidence in another criminal proceeding," see Gov't's Opp'n & Mot. at 7, is to allow a copy of the files to be retained for safekeeping in the custody of a court in the Eastern District of Virginia as a neutral third party. Because the Government has represented that the evidence at issue may be relevant to an investigation and potential prosecution in the Eastern District of Virginia, depositing the evidence under seal with the District Court for that District is the appropriate course of action

(6) The Clarifying Order: Richman II

Yesterday, December 23rd, the Judge entered an opinion clarifying the first opinion in response to the government's objections. In particular, she states the following about what she is ordering:

[T]he Court is not ordering the Government to "delete or destroy" anything. The Court is ordering the Government to return the materials initially seized from Petitioner Richman and any copies thereof to Petitioner Richman and to deposit a single copy of those materials with a neutral third party: the District Court for the Eastern District of Virginia. Although the Government originally obtained these materials pursuant to Petitioner Richman's 2017 consent and the lawful 2019 and 2020 warrants, it was prohibited from conducting warrantless searches on these materials—which included material that was not responsive to the 2019 and 2020 warrants— after the 2019 and 2020 warrants had been executed. The Court's Order does not require the Government to return any material that it had deemed responsive and segregated from the materials it originally seized in 2019 and 2020 because the Government has not identified any such material. Nor does the Court's Order prohibit the Government from accessing these materials in the future, so long as that access is obtained through a valid search warrant. Accordingly, the Court's order to the Government to return to Petitioner Richman the covered materials and any copies thereof and, if the Government so chooses, to deposit a copy with a neutral third-party remains unchanged.

(6) My Own Reaction to the Judge's Opinions

For the reasons offered above, I'm on board with Judge Kollar-Kotelly's ruling that Richman's Fourth Amendment rights were violated.  That seems sound.  My main questions are about the remedy.

Whether and how a Rule 41 motion to return property can apply to data without a physical device associated with the data is, as far as I know, new ground.  Off the top of my head, I haven't seen this before.  Does it even make sense to have a Rule 41 motion for the return of intangible data?  With tangible things, the remedy is clear. When a motion to return property is granted, the government gives back the tangible thing it is wrongly possessing.  I want my stuff back, the owner says.  Give back the stuff, the court directs. Simple enough.  But I'm not sure how that maps on to a world of zeros and ones.

This reminds me of the Ganias litigation from 2014 that I discussed above.  The initial panel ruling in Ganias talked about a right to the deletion of non-responsive files.  But it was never entirely clear what that meant in practice, and the en banc court's resolution of the case without reaching the merits left that unclear. Maybe Rule 41 motions to return property make sense for intangible data, but I'd need to think more about it.

Beyond the conceptual question, I'm not entirely sure how this works in practice, even after the clarifying order yesterday.  My apologies if I missed this, but I don't see where in the opinions there is discussion of what to do with what the government previously learned.   A search through the copies of Richman's computers already happened.  For the sake of simplicity, call those searches the 2025 search.  Imagine a future prosecution of Comey in which the government wants to use the fruits of the 2025 search made in violation of Richman's rights. At least under traditional views of Fourth Amendment standing, Comey would lack standing to object to that search in a motion to suppress.  But at a future trial against Comey, if there is one, can the government use the fruits of the 2025 search?

For example, can agents testify at trial as to their recollections of what they saw in Richman's files in the 2025 search?  If an agent cut and pasted an excerpt from the Richman files into a separate file— even just a few words—do they need to delete the new file?  If they quoted from the files in their notes, do they have to destroy the notes, or at least delete the quote?  And outside of trial, can agents use their recollection or notes to get a warrant to search the computers yet again, either just to find what they already found or to look for something new? Maybe these aren't real issues under the facts of this case; the opinions don't tell us enough to say.  But I'm not sure what the answers would be.

As always, stay tuned.