Analysis of Richman v. United States: Federal Court Orders Return of Unlawfully Retained Digital Files

Assistance from Claude AI.

Document Type and Context

This is a Memorandum Opinion issued by U.S. District Court Judge Colleen Kollar-Kotelly on December 12, 2025. A memorandum opinion is a written decision from a judge explaining the reasoning behind their ruling on a legal motion. This particular ruling addresses a motion filed under Federal Rule of Criminal Procedure 41(g), which allows people to request the return of property seized by the government.

The case is styled as a civil miscellaneous action, meaning it’s a standalone civil proceeding rather than part of a criminal case, though it relates to criminal investigations.

The Parties

Petitioner: Daniel Richman

• Attorney and law professor at Columbia Law School
• Longtime friend and confidant of former FBI Director James Comey
• Has also served as Comey’s attorney
• The person seeking return of his electronic files from the government

Respondent: United States of America

• Represented by the Department of Justice
• Opposing the return of Richman’s files
• Investigating and potentially prosecuting James Comey

Timeline of Key Events

May 2017: A newspaper published details from a Comey memo about a meeting with President Trump regarding the Michael Flynn investigation.

June 2017: Comey testified before the Senate Intelligence Committee, revealing he had given a Columbia law professor friend (Richman) a copy of his memo and asked him to share its content with a reporter.

After June 2017: Richman allowed the FBI to create a complete electronic copy (“image”) of his personal computer, hard drive, cell phone backup, and tablet backup for a limited purpose (details redacted).

April 2017: A newspaper published an article allegedly containing classified information about factors influencing Comey’s decision regarding the Hillary Clinton email investigation. The article quoted Richman by name.

2019-2020: During the “Arctic Haze” investigation into potential classified information leaks, the government obtained four search warrants:

• August 2019: Warrant to search the image of Richman’s computer
• September 2019: Warrant to search two Columbia University email accounts
• January 2020: Warrant to search Richman’s Apple iCloud account
• June 2020: Second warrant to search the computer image

2021: The Arctic Haze investigation closed without filing charges.

September 2025: The government conducted a warrantless search of Richman’s files in connection with a new investigation of Comey in the Eastern District of Virginia.

November 2025: Magistrate Judge William E. Fitzpatrick issued findings in the Comey prosecution raising concerns about the government’s handling of Richman’s files.

November 26, 2025: Richman filed this motion for return of property.

December 6, 2025: Judge Kollar-Kotelly issued a temporary restraining order.

December 12, 2025: This memorandum opinion issued.

The Legal Issues

1. Fourth Amendment Violations

The Fourth Amendment protects against “unreasonable searches and seizures.” The court found the government violated this right in multiple ways:

Issue A: Did the 2019-2020 seizures exceed warrant scope?

• The warrants authorized seizure only of information constituting evidence of violations of specific criminal statutes (18 U.S.C. §§ 641, 793)
• Magistrate Judge Fitzpatrick found a “reasonable basis” to question whether the government seized more than authorized
• Evidence suggests the government may have failed to separate responsive from non-responsive materials
• Court’s finding: Richman established a reasonable basis for this claim, but the court declined to make a conclusive determination on the present record

Issue B: Was continued retention after 2021 unreasonable?

• The government retained the files for approximately 4 years after closing the Arctic Haze investigation
• Court’s finding: Retention was reasonable SO LONG AS the government maintained appropriate safeguards and didn’t search without a warrant
• The court explained that people retain “possessory interests” in copies of their electronic files, including the “right to exclude” others from accessing them

Issue C: Was the September 2025 warrantless search unconstitutional?

• An FBI agent reviewed a “full Cellebrite extraction” of Richman’s phone and tablet without obtaining a warrant
• The agent searched for conversations between Richman and Comey
• Court’s finding: This was “manifestly unconstitutional”
• The Supreme Court has held that officers must “secure a warrant before conducting” searches of cell phone data (citing Riley v. California)

2. Rule 41(g) Motion for Return of Property

Federal Rule of Criminal Procedure 41(g) allows “a person aggrieved by an unlawful search and seizure” to move for return of property. The court must consider whether the seizure is “reasonable under all the circumstances.”

The Ramsden/Richey Four-Factor Test:

Courts evaluate four factors when deciding whether to exercise equitable jurisdiction:

1. Callous disregard for constitutional rights: Did the government show callous disregard for the petitioner’s rights?
   • Finding: YES. The warrantless 2025 search was “a remarkable breach of protocol” done with knowledge of federal prosecutors.
2. Individual interest in property: Does the petitioner have a compelling interest in the property?
   • Finding: YES. The files contain privileged attorney-client communications, sensitive correspondence about students and faculty, personal medical information, and personal photographs—”a complete record of Petitioner Richman’s electronic life.”
3. Irreparable injury: Would the petitioner suffer irreparable harm without return?
   • Finding: YES. Ongoing Fourth Amendment violations constitute irreparable injury. Additionally, the intrusions risk irreparably burdening Richman’s privacy and professional reputation.
4. Adequate remedy at law: Does the petitioner have another adequate legal remedy?
   • Finding: NO. While the government argued Richman could bring a Bivens damages action, monetary damages cannot fully redress privacy invasions and burdens on professional confidentiality.

The Arguments

Richman’s Arguments (Successful)

1. Over-seizure: The government exceeded the scope of the 2019-2020 warrants by seizing both responsive and non-responsive materials
2. Unreasonable retention: Continuing to hold files for years after closing the investigation is unreasonable
3. Warrantless search: The 2025 search without a warrant violated the Fourth Amendment
4. No adequate safeguards: The government failed to protect the files from unlawful access

Strength: These arguments are well-supported by binding Supreme Court precedent (Riley v. California) and recent D.C. Circuit law (Asinor v. District of Columbia). The warrantless 2025 search is particularly damning—there’s essentially no valid defense for searching cell phone data without a warrant absent exigent circumstances.

Government’s Arguments (Unsuccessful)

1. Collateral attack: Richman’s motion is really an improper attempt to suppress evidence in a potential Comey prosecution
2. No genuine property interest: Since Richman still has his original files, he doesn’t “genuinely want any property back”
3. Adequate legal remedy: Richman could sue for damages under Bivens
4. Government property: Copies made by the government are government property

Weaknesses:

• The court found these arguments “unavailing” and “misses the mark”
• The distinction between Rule 41(g) motions and suppression motions applies primarily to appellate jurisdiction issues
• Bivens damages don’t adequately address privacy invasions
• The “government property” argument has been rejected by multiple courts
• The collateral attack argument fails because the court’s remedy doesn’t actually suppress evidence in the Comey case

Evidence Evaluation

The court relied on several sources:

1. Magistrate Judge Fitzpatrick’s November 17, 2025 opinion in United States v. Comey: This provided critical factual findings after reviewing sealed records and grand jury transcripts
2. Government agent affidavits: The Nero Affidavit and Warren Affidavit described the September 2025 warrantless search
3. The four 2019-2020 search warrants: These established the authorized scope of earlier searches
4. April 2020 letter from Richman’s counsel: This informed the government that it had obtained data outside the temporal scope of warrants
5. Government’s failure to supplement the record: The court invited the government to provide additional evidence but it declined, which the court took as supporting Richman’s claims

Strength of evidence: The evidence strongly supports Richman’s Fourth Amendment claims, particularly regarding the warrantless 2025 search, which is essentially undisputed.

Legal Precedents Cited

Key Supreme Court Cases

1. Riley v. California, 573 U.S. 373 (2014): Officers must secure a warrant before searching cell phone data except in exigent circumstances
   • Application: Directly supports finding the 2025 warrantless search unconstitutional
2. Katz v. United States, 389 U.S. 347 (1967): Warrantless searches are “per se unreasonable” subject to specific exceptions
   • Application: Establishes the baseline warrant requirement
3. United States v. Jacobsen, 466 U.S. 109 (1984): Fourth Amendment governs both initial seizures and continued retention
   • Application: Supports the court’s analysis of ongoing seizure

D.C. Circuit Cases

1. Asinor v. District of Columbia, 111 F.4th 1249 (D.C. Cir. 2024): Fourth Amendment requires “continuing retention of seized property to be reasonable”
   • Application: This recent precedent is crucial—it establishes that in the D.C. Circuit, the Fourth Amendment regulates not just the initial seizure but also continued retention
2. United States v. Kember, 648 F.2d 1354 (D.C. Cir. 1980): Fourth Amendment doesn’t entitle a person to block evidence use against another person
   • Application: Limits the scope of Richman’s remedy—he can’t suppress evidence in Comey’s case

District Court Cases from D.C.

1. In re Search of Twenty-Six Digital Devices (“Digital Devices I”), 2021 WL 5822583 (D.D.C. 2021) (Magistrate Judge Harvey): Subjects have possessory interests in cell phone data including the “right to exclude”
   • Application: Supports Richman’s property interest claim
2. In re Search of Twenty-Six Digital Devices (“Digital Devices II”), 2022 WL 998896 (D.D.C. 2022) (then-Chief Judge Howell): Government may retain digital extracts but must obtain new warrants for subsequent searches
   • Application: Provides the framework—retention after investigation is permissible IF proper safeguards (especially warrant requirement) are maintained

Validity of Precedents

All precedents cited remain valid. The court carefully navigates one tension: Judge Howell’s statement in Digital Devices II that “the Fourth Amendment does not operate as an arbiter of law enforcement retention policies” appears inconsistent with the D.C. Circuit’s later holding in Asinor that the Fourth Amendment DOES regulate retention. The court resolves this by reading Asinor as the controlling circuit precedent.

Weaknesses and Potential Counterarguments

Gaps in Richman’s Arguments

1. Limited evidence on over-seizure: The court declined to make a conclusive finding on whether the 2019-2020 seizures were overbroad, noting the parties hadn’t supplemented the record sufficiently
2. Consent in 2017: Richman consented to the initial imaging of his computer, though for a limited purpose

Government Could Argue (in future proceedings)

1. Good faith exception: Even if the 2025 search was warrantless, agents may have relied in good faith on AUSA advice
   • Problem: This doesn’t help with the reasonableness of continued retention
2. Inevitable discovery: Evidence would have been discovered through lawful means
   • Problem: Doesn’t address Richman’s own Fourth Amendment rights
3. Standing: Richman lacks standing to challenge searches related to Comey
   • Problem: The court found clear Article III standing based on Richman’s own injuries

The Court’s Decision and Remedy

Holdings

1. GRANTED: Motion for Return of Property
2. DENIED in part: Request to bar government from “using or relying on” the materials in other proceedings
3. DENIED AS MOOT: Remaining TRO requests and government’s motion to dissolve TRO

The Remedy

The court crafted a carefully balanced remedy:

What the Government Must Do:

1. Return ALL copies of covered materials to Richman (computer image, email accounts, iCloud files, and anything derived from them)
2. Certify by December 15, 2025 at 4:00 PM that they have:
   • Returned the materials
   • Not retained additional copies (except the one authorized copy)
   • Not provided copies to anyone else
   • Not shared, disseminated, or disclosed the materials

What the Government May Do:

1. Create ONE complete electronic copy before returning the materials
2. Deposit that copy UNDER SEAL with the U.S. District Court for the Eastern District of Virginia
3. Access that copy in the future ONLY pursuant to a lawful search warrant and judicial order

Why This Balance:

• Protects Richman: Ends the unreasonable seizure, restores his possessory interest and right to exclude
• Protects Government Interests: Preserves evidence for potential future lawful use
• Uses Neutral Custodian: The E.D. Va. court (not the government) controls access, ensuring warrant requirement is respected
• Addresses Privilege: The E.D. Va. court can decide whether to allow Richman to move to quash any future warrant

What the Court Did NOT Order

The court refused to bar the government from “using or relying on” information from the files because:

1. Such an order would be broader than necessary to redress Richman’s specific injuries
2. Binding precedent (Kember, Payner) prevents courts from excluding evidence in prosecutions of third parties based on Fourth Amendment violations against non-defendants
3. Rule 41(g) is not intended to suppress evidence permitted by the Fourth Amendment

Next Steps for the Parties

For the Government (Immediate)

1. By December 15, 2025 at 4:00 PM ET:
   • Prepare one complete electronic copy of all covered materials
   • Deposit that copy under seal with the U.S. District Court for the Eastern District of Virginia
   • Return all other copies to Richman
   • File certification with the court confirming compliance
2. If they want to access the materials again:
   • Apply to the E.D. Va. court for a search warrant
   • Demonstrate probable cause
   • Describe the search with particularity
   • The E.D. Va. court may allow Richman to move to quash the warrant

For Richman

1. Receive returned materials by December 15, 2025
2. Monitor compliance with the court’s order
3. Potential future actions:
   • If the government seeks a warrant from E.D. Va., he may have an opportunity to move to quash
   • Could potentially file a Bivens action for damages (though the court didn’t decide if this is viable)
   • Could raise privilege objections if future warrant applications threaten attorney-client communications

For the E.D. Va. Court

1. Accept the sealed materials into its custody
2. Maintain security of the sealed materials
3. Evaluate any future warrant applications using normal Fourth Amendment standards
4. Exercise discretion on whether to give Richman advance notice and opportunity to move to quash

For Any Comey Prosecution

1. The government is not barred from prosecuting Comey
2. The government is not barred from using information from Richman’s files, but ONLY if:
   • They obtain a valid search warrant from E.D. Va.
   • The warrant is based on probable cause
   • The warrant describes with particularity what they’re searching for
3. Richman may challenge any such warrant, raising privilege and other objections

Broader Implications

For Constitutional Law

1. Digital Privacy Rights: Reinforces that Fourth Amendment protections apply robustly to digital devices and that cell phone searches require warrants
2. Ongoing Seizures: Strengthens the principle (from Asinor) that the Fourth Amendment regulates not just initial seizures but continued retention
3. Government Retention Policies: Establishes that the government cannot indefinitely retain digital files without maintaining proper warrant-based safeguards

For Politics and Society

1. High-Profile Investigations: This case involves investigations of a former FBI Director related to communications with a sitting President—it touches on politically sensitive territory regarding Trump-era controversies
2. Press Freedom Implications: The underlying investigations concern potential leaks to the press, raising questions about source protection and whistleblowing
3. Attorney-Client Privilege: The case highlights tensions between law enforcement investigations and attorney-client confidentiality
4. Separation of Powers: While not directly addressed, the case involves investigations of executive branch officials and presidential communications

For Legal Practice

1. Defense attorneys should be aware they could seek return of improperly retained client files under Rule 41(g)
2. Prosecutors must maintain proper safeguards for retained digital evidence and cannot search previously-seized materials without new warrants
3. Magistrate judges should carefully scrutinize warrant applications for searches of previously-seized materials
4. Law enforcement must implement better systems to prevent warrantless searches of retained digital files

Notable Legal Reasoning

The “Right to Exclude” Analysis

The court’s discussion of possessory interests in digital copies is particularly sophisticated. It recognizes that even though Richman still has his original files, he has a cognizable interest in controlling who can access copies. This “right to exclude” is an inherent part of property ownership, and each copy the government makes diminishes this right.

Balancing Framework

The court expertly balances competing interests:

• Richman’s Fourth Amendment rights and privacy interests
• The government’s legitimate law enforcement needs
• The public interest in both constitutional compliance and effective prosecution

The solution—a neutral judicial custodian—is creative and well-justified.

Treatment of Digital Evidence

The court shows strong understanding of digital forensics, noting that:

• Complete images are often necessary for forensic soundness
• Separating responsive from non-responsive data can be impractical
• Digital devices contain “immense trove[s] of information”
• Special care is needed for privileged materials

Potential Vulnerabilities in the Ruling

While the opinion is well-reasoned, potential issues for appeal include:

1. Scope of relief: The government might argue the remedy is too broad since it requires return of ALL copies, not just improperly accessed ones
2. Third-party effects: Despite the court’s assurances, this ruling could impact the Comey prosecution, potentially giving grounds for mandamus
3. Equitable jurisdiction: The government might challenge whether Rule 41(g) authorizes this remedy given the ongoing criminal investigation
4. Precedent interpretation: The government might argue Digital Devices II should control over Asinor on different grounds

However, none of these vulnerabilities appear strong enough to undermine the core Fourth Amendment holding regarding the warrantless 2025 search.

Conclusion

This is a significant Fourth Amendment decision that:

1. Vindicates digital privacy rights by requiring the government to return improperly retained electronic files
2. Reinforces warrant requirements for searches of digital devices
3. Establishes that retention must be reasonable and properly safeguarded
4. Creates a workable framework balancing privacy and law enforcement through judicial oversight

The opinion is thorough, well-reasoned, and grounded in binding precedent. Judge Kollar-Kotelly crafted a remedy that protects Richman’s constitutional rights while preserving the government’s ability to pursue legitimate investigations through proper legal channels.

For readers interested in privacy, government surveillance, or the intersection of law and technology, this case provides an important example of courts enforcing constitutional limits on digital searches and seizures.