22-1057, 22-1061

Carpenter v. Allen

United States Court of Appeals

for the Second Circuit _____________________________________

August Term 2022

(Argued: June 28, 2023 Decided: December 11, 2023)

Nos. 22-1057, 22-1061

_____________________________________

LYNN ALLEN, CHERI GARCIA, TIMOTHY CORSI,

 Defendants-Appellants-Cross-Appellees,

— v. —

GRIST MILL CAPITAL LLC,

 Plaintiff-Appellee-Cross-Appellant,

DANIEL E. CARPENTER,

 Plaintiff.∗

_____________________________________

Before: LYNCH, LOHIER, and BIANCO, Circuit Judges.

The government, through defendant-appellant-cross-appellee Lynn Allen, 

an agent of the United States Department of Labor (“DOL”), appeals from an order 

of the United States District Court for the District of Connecticut (Underhill, J.) 

∗ The Clerk of the Court is respectfully instructed to amend the caption to conform with 

the above.
2

granting, in part, plaintiff-appellee-cross-appellant Grist Mill Capital LLC’s 

(“GMC”) motion for return of property under Federal Rule of Criminal Procedure 

41(g). 

At issue is the government’s retention of financial documents, which the 

DOL obtained pursuant to court-authorized search warrants and a grand jury 

subpoena in connection with a federal criminal investigation and prosecution of 

Daniel E. Carpenter in the United States District Court for the District of 

Connecticut. In May 2022, the district court granted, in part, GMC’s motion under 

Rule 41(g), holding that the government failed to demonstrate a legitimate need 

justifying the continued retention of the seized materials given that this Court 

affirmed Carpenter’s criminal conviction and the Supreme Court denied his 

petition for certiorari. 

We VACATE the district court’s order and REMAND for further 

proceedings consistent with this opinion, and we DISMISS GMC’s cross-appeal 

as moot.

NEERAJ N. PATEL (Sandra S. Glover, on 

the brief), Assistant United States 

Attorneys, for Vanessa Roberts Avery, 

United States Attorney for the District 

of Connecticut, New Haven, CT, for 

Defendants-Appellants-Cross-Appellees.

JONATHAN J. EINHORN, Jonathan J. 

Einhorn Law Offices, New Haven, CT 

(Jeffrey R. Sandberg, Palmer Lehman 

Sandberg, PLCC, Dallas TX, on the 

brief), for Plaintiff-Appellee-CrossAppellant.

JOSEPH F. BIANCO, Circuit Judge:

In this case, the government appeals from an order of the United States 

District Court for the District of Connecticut (Underhill, J.) granting, in part, 
3

plaintiff-appellee-cross-appellant Grist Mill Capital LLC’s (“GMC”) motion for 

return of property under Federal Rule of Criminal Procedure 41(g). This case 

comes to us after a complex procedural history. GMC filed the Rule 41(g) motion 

on the docket of a Bivens action that GMC filed, along with Daniel E. Carpenter 

(collectively, “plaintiffs”), against defendants Lynn Allen, Cheri Garcia, and 

Timothy Corsi in their individual capacities, who were law enforcement agents 

employed by the United States Department of Labor (“DOL”) (collectively, the

“DOL agents”).1 That action was filed shortly after plaintiff Carpenter had been

indicted on criminal charges, and was stayed pending the criminal action, in which 

Carpenter was eventually convicted.

At issue is the government’s retention of financial documents, which the 

DOL obtained pursuant to court-authorized search warrants and a grand jury 

subpoena in connection with the federal criminal investigation and prosecution of 

Carpenter. In that prosecution, also in the United States District Court for the 

District of Connecticut, the government alleged that Carpenter used various 

business entities, including GMC, to facilitate a fraudulent life insurance scheme,

causing over $50 million in losses. In 2016, Carpenter was convicted of multiple 

1 We further explain this complex procedural history infra.
4

fraud and money laundering offenses and was subsequently sentenced to 30 

months’ imprisonment. In the Bivens action, plaintiffs asserted constitutional 

claims against the DOL agents who, in 2011, executed the search warrant at the 

office building where GMC was located and seized evidence in connection with 

the DOL’s investigation. The complaint also asserted a claim for the return of the 

seized materials pursuant to Rule 41(g).

Following completion of the criminal case, the district court turned to the 

Bivens action. In the course of the renewed proceedings, plaintiffs moved under 

Rule 41(g) for the return of certain of the seized records. In March 2022, the district 

court granted that motion in part, holding that the government failed to 

demonstrate a legitimate need justifying the continued retention of the seized 

materials given the final resolution of the criminal case upon the Supreme Court’s 

denial of Carpenter’s petition for certiorari. However, because copies of the seized 

materials were already in plaintiffs’ possession and the documents contained third 

parties’ personal identifying information that Carpenter had previously used to 

perpetrate the fraudulent scheme, the district court ordered the government to 

destroy the seized materials still in its possession, rather than to return them to 

plaintiffs.
5

The government contends on appeal that the district court abused its 

discretion in ordering the destruction of the seized materials, rather than allowing 

the government to retain them given, among other things, Carpenter’s pending 

collateral attack on his criminal convictions in a pro se motion he filed pursuant to 

28 U.S.C. § 2255 (“Section 2255”). GMC cross-appeals the district court’s order, 

arguing that the seized documents should be returned to it, rather than destroyed.

We hold that the district court exceeded its discretion in granting the Rule 

41(g) motion because the government has demonstrated a legitimate need to retain 

the property at issue to defend against Carpenter’s pending Section 2255 motion 

collaterally attacking his convictions and to preserve evidence for use at a potential 

retrial should that motion succeed. 

Accordingly, we VACATE the district court’s order and REMAND for 

further proceedings consistent with this opinion, and we DISMISS GMC’s crossappeal as moot.

I. BACKGROUND

Carpenter’s various fraudulent financial schemes have spawned litigation 

across multiple jurisdictions for over a decade. See Iantosca v. Benistar Admin. 

Servs., Inc., 567 F. App’x 1, 2 (1st Cir. 2014) (Souter, J.) (describing the then-“latest 
6

chapter [of] protracted litigation arising out of financial misconduct by Daniel 

Carpenter and entities controlled by him”).2 Indeed, the procedural history giving 

rise to this appeal is complex. We begin by explaining the background of 

Carpenter’s criminal convictions in the District of Connecticut. We then turn to 

the two Bivens actions that Carpenter and GMC initially filed while Carpenter’s 

criminal case was still pending and the Rule 41(g) motion that is the subject of this 

appeal. 

A. The Searches of the Simsbury Offices

Carpenter worked for major corporations in the life insurance industry for 

more than two decades. During his career, he developed considerable expertise 

with welfare benefit plans, which are mechanisms employers use to provide 

various types of benefits, including life insurance, to employees. Carpenter

ultimately started his own businesses and became the trustee for several of the 

largest welfare benefit plans in the United States. 

2 Separate from the Iantosca appeal, Carpenter was also convicted in the United States 

District Court for the District of Massachusetts of mail and wire fraud and sentenced to 

36 months’ imprisonment. See United States v. Carpenter, 781 F.3d 599 (1st Cir.), cert. denied, 

577 U.S. 871 (2015). Neither of these First Circuit appeals is related in substance to the 

instant appeal. 
7

A number of entities Carpenter controlled, including GMC, had offices 

located in a building, allegedly owned by Carpenter, at 100 Grist Mill Road in 

Simsbury, Connecticut (the “Simsbury offices”). As relevant to this appeal, 

Carpenter was the subject of two federal criminal investigations that involved 

searches of the Simsbury offices.

 

The first investigation was conducted by the Internal Revenue Service 

(“IRS”) under the supervision of the United States Attorney’s Office for the Eastern 

District of Wisconsin. In April 2010, the IRS executed a search warrant authorizing 

the seizure of documents located at the Simsbury offices that were related to the 

alleged promotion and administration of unlawful welfare benefit plans. The 

agents seized hundreds of boxes of documents and imaged several computers and 

servers. After the search, while the investigation was still ongoing, fifteen of the 

business entities based in the Simsbury offices and two individuals moved in the 

United States District Court for the District of Connecticut for the return of their 

property under Federal Rule of Criminal Procedure 41(g). See Benistar Admin. 

Servs., Inc. v. IRS, No. 10-mc-60 (AVC) (D. Conn); Pettibone Tavern, LLC v. IRS, No. 

10-mc-64 (AVC) (D. Conn.). As part of a settlement agreement and court orders 

resolving those motions, the government agreed to return the original documents 
8

after it had a reasonable opportunity to copy them. Documents an IRS filter team 

determined to be potentially relevant to its investigation were returned to and 

maintained in the custody of Halloran and Sage LLP, a Connecticut-based law firm 

that represented many of the entities. Boxes containing documents that the team 

determined were not potentially relevant were directly returned to the Simsbury 

offices. The IRS also continued to hold some amount of material in Wisconsin. 

The second investigation was conducted by the DOL under the supervision 

of the United States Attorney’s Office for the District of Connecticut. That

investigation concerned a separate alleged fraudulent scheme to induce life 

insurance companies to issue certain plans that they otherwise would not have 

issued. Specifically, the alleged fraud involved stranger-originated life insurance 

(“STOLI”) policies, which are policies that are obtained for transfer on the 

secondary market rather than for estate-planning purposes. 

In May 2011, as part of that investigation, the DOL executed a search 

warrant at the Simsbury offices and seized various documents and imaged several 

computers and servers. In addition, because some of the evidence the IRS had 

seized in 2010 was relevant to the DOL’s investigation, the DOL obtained search 

warrants to copy the images of the computers or servers seized by the IRS and to 
9

search original material still being held by the IRS. The DOL also obtained and 

served a grand jury subpoena for certain boxes of documents that were still being 

held by the Halloran and Sage law firm.

B. Carpenter’s Criminal Convictions

In May 2014, a federal grand jury in the District of Connecticut returned a 

superseding indictment, charging Carpenter with 57 counts of mail- and wirefraud and money-laundering offenses arising from his alleged participation in the 

STOLI scheme investigated by the DOL. The government provided Carpenter’s 

defense counsel comprehensive discovery of all seized materials in the form of a 

scanned and searchable database. Before trial, Carpenter unsuccessfully moved 

to suppress evidence seized from both the 2010 IRS and the 2011 DOL searches of 

the Simsbury offices on Fourth Amendment and other grounds. 

Following a bench trial, the district court found Carpenter guilty on each of 

the 57 counts and subsequently sentenced him to 30 months’ imprisonment.3 The 

district court further ordered Carpenter to pay restitution of over $12.8 million, 

based on a loss amount of nearly $54 million. This Court subsequently affirmed 

3 After Carpenter was convicted in the District of Connecticut, the United States 

Attorney’s Office for the Eastern District of Wisconsin informed Carpenter that the 

government had declined the prosecution of the IRS case. 
10

Carpenter’s convictions, United States v. Bursey, 801 F. App’x 1 (2d Cir.) (summary 

order), and the United States Supreme Court denied certiorari on November 9, 

2020, 141 S. Ct. 820 (2020).

Carpenter filed a separate appeal to challenge the restitution order. See 

United States v. Carpenter, No. 19-674 (2d Cir.). We ordered that appeal to be held 

in abeyance until the district court ruled on the government’s motion to amend 

the restitution order. 

Carpenter also continues to challenge his convictions in the district court. 

In February 2021, Carpenter filed a pro se motion for the release of grand jury 

transcripts, asserting that the materials that the government seized during the IRS 

and DOL searches contained exculpatory evidence that the government withheld 

from the grand jury. Also in February 2021, Carpenter filed a pro se motion to 

dismiss the superseding indictment for lack of jurisdiction. 

In November 2021, Carpenter filed a pro se Section 2255 motion to set aside 

his convictions, claiming that the federal agents exceeded the scope of their 

warrants and that the government improperly withheld material to which he was 

entitled under Brady v. Maryland, 373 U.S. 83 (1963), and the Jencks Act, 18 U.S.C. 

§ 3500. Carpenter later supplemented his Section 2255 motion to argue that his 
11

convictions are invalid pursuant to the U.S. Supreme Court’s recent decision in 

Ciminelli v. United States, 598 U.S. 306 (2022). 

All three of these post-conviction motions—for release of the grand jury 

transcripts, to dismiss the superseding indictment, and to vacate the convictions 

under Section 2255—remain pending before the district court.

C. The Bivens Lawsuits and Rule 41(g) Motions

While the criminal investigation and prosecution was pending, Carpenter

and GMC together filed two separate civil actions in the United States District 

Court for the District of Connecticut, asserting claims under Bivens v. Six Unknown 

Fed. Narcotics Agents, 403 U.S. 388 (1971), in connection with the 2010 and 2011 

searches at the Simsbury offices and, among other things, seeking the return of the 

property seized during those searches. 

1. The IRS Bivens Lawsuit

In 2013, prior to the indictment in the criminal case, Carpenter and GMC

filed a Bivens action against the IRS officials that were allegedly involved in the 

2010 search of the Simsbury offices. In a second amended complaint, plaintiffs

alleged that the search was unconstitutional and also sought a return of the seized 
12

property under Rule 41(g). The district court stayed the request for return of 

property pending resolution of the criminal case. 

In 2015, the district court denied, in substantial part, the government’s 

motion to dismiss. The government ultimately appealed that order, and this Court 

remanded the matter to the district court, noting that the Court had since vacated 

a decision that the district court had relied on in its order and that the scope of the 

parties’ dispute appeared to have narrowed at oral argument. See Carpenter v. 

Koskinen, 692 F. App’x 666 (2d Cir. 2017) (summary order). After plaintiffs filed a 

third amended complaint, the district court dismissed the underlying claims 

against certain defendants, and that partial judgment was affirmed on appeal. See 

Carpenter v. Shulman, 790 F. App’x 285 (2d Cir. 2019) (summary order). 

2. The DOL Bivens Lawsuit

In 2014, shortly after the filing of the criminal indictment, Carpenter and 

GMC filed another Bivens action against DOL agents allegedly involved in the 2011 

search of the Simsbury offices. Similar to the Bivens action against the IRS agents, 

the complaint asserted various constitutional claims and also included a demand

for return of property pursuant to Rule 41(g). In October 2015, the district court

stayed the action pending the resolution of Carpenter’s criminal case. 
13

In 2020, after the Supreme Court denied Carpenter’s petition for certiorari in 

his criminal case, the district court lifted the stay and the case was ultimately 

reassigned to then-Chief Judge Stefan R. Underhill. The district court later 

dismissed most of plaintiffs’ claims, but allowed “the claims regarding the 

destruction of property, Carpenter’s detention during the search, and whether the 

search exceeded the scope of the warrant” to proceed. Joint App’x at 10. 

Following limited discovery, the parties filed motions for summary judgment on 

the remaining issues, which have been fully briefed and are now pending in the 

district court. 

3. The Rule 41(g) Motions

Following the lifting of the stays in both Bivens lawsuits, the district court

ordered the DOL in the instant case and the IRS (in the other then-pending Bivens 

action) to show cause as to “why all items seized or re-seized by the government 

entities in connection with its investigation of Daniel Carpenter and [GMC]—with 

the exception of Items 28 and 29 as defined in the joint status report . . . —shall not 

be immediately returned to Carpenter and [GMC] by the government entity that 
14

currently possesses them.” Id. at 26.4 In addition, at the district court’s direction,

Carpenter and GMC filed a Rule 41(g) motion for return of property, which they 

had previously filed in the IRS action, in the DOL action. In that motion, Carpenter 

and GMC informed the district court that the parties had narrowed the scope of 

the dispute to 29 boxes of the documents, nearly all of which were in the DOL’s

custody. Moreover, unlike the Rule 41(g) demand that had been contained in the 

original complaint, which was based on the constitutional violations allegedly 

committed by the defendant DOL agents in the course of the searches and seizures, 

the motion now was premised, as permitted by Rule 41(g), solely on the claim that 

the seized materials should be returned to their owners because the criminal 

proceedings have been completed and the government no longer has an 

evidentiary need for them.

With respect to the Rule 41(g) motion in the IRS Bivens action, the district 

court ordered that the government destroy, rather than return, Items 28 and 29. 

[SA6] Additionally, because the IRS represented that it no longer had possession 

4 Items 28 and 29 were a hard drive containing scanned copies of documents and mirror 

images of servers and drives that the IRS had obtained in its 2010 search of the Simsbury 

offices. In the above-referenced joint status report to the district court, the government 

stated that it intended to destroy items 28 and 29 while GMC and Carpenter argued that 

items 28 and 29 should be returned to them. 
15

of the other materials sought by plaintiffs, the district court denied the motion as 

moot with respect to the remaining items and entered judgment in favor of 

Carpenter and GMC.5 Neither party appealed any aspect of the district court’s 

order on the Rule 41(g) motion in the IRS Bivens action.

In the DOL Bivens action, the government opposed the Rule 41(g) motion. 

Specifically, the government offered six distinct grounds in support of its need to 

retain the documents: (1) to use as evidence at a retrial, if Carpenter was successful 

in vacating his convictions; (2) to defend against Carpenter’s Section 2255 petition; 

(3) to defend against Carpenter’s motion for release of grand jury minutes; (4) to 

defend against Carpenter’s appeal of the district court’s restitution order in his 

criminal case; (5) to respond to then-anticipated discovery in the DOL Bivens 

action; and (6) to defend against anticipated future litigation that could implicate 

the seized documents. 

On March 15, 2022, the district court granted, in part, the Rule 41(g) motion

in the instant action. The district court held that the government was not entitled 

5 After the district court entered judgment, the government filed a notice certifying that 

the IRS had no paper documents in its possession from the 2010 Simsbury offices search 

and that it had destroyed all electronic hardware related to that search. 
16

to retain the property, but ordered the DOL to destroy 26 boxes of documents in 

its custody, rather than returning them to plaintiffs.6

At the outset, the district court determined that the return of property is a 

permissible remedy in a Bivens action and that claim preclusion was not a bar to 

the Rule 41(g) motion. The district court also rejected the government’s argument 

that the plaintiffs lacked standing to bring the Rule 41(g) motion and concluded 

that, because the criminal proceedings had ended, the government had the burden 

of demonstrating its need to retain the seized documents. The district court then 

found that the government’s articulated interests in retaining the documents were

insufficient to satisfy its burden. The district court rejected the government’s 

position that it was necessary to retain evidence not introduced at trial because the 

Section 2255 motion would be decided on the trial record. The district court also 

concluded that, “[a]s for the Bivens proceedings or any speculative proposition of 

a retrial, the government may not piggyback off a decade-old warrant to withhold 

documents indefinitely without specifying a legitimate need for them, which it 

fails to do here.” Special App’x at 18. The district court further noted that the 

6 By the time of the district court’s order, the parties had narrowed their dispute from 29 

boxes to 26 boxes. 
17

government could obtain any documents necessary to respond to the pending

Bivens claims against the DOL through civil discovery. 

However, the court ordered the government to destroy the documents

because the government had represented that plaintiffs had copies of the 

documents and because “the documents contain third parties’ personally 

identifying information used by [p]laintiffs to perpetrate a fraud, and prudence 

counsels in favor of not returning them.” Id. Plaintiffs subsequently filed a motion 

for reconsideration as to the portion of the district court order directing the 

government to destroy the documents and sought to stay the destruction order. 

The district court denied the reconsideration motion, including the request to stay 

destruction of the documents. 

The government appealed. GMC then cross-appealed. 7 The parties also 

filed a joint stipulation with the district court in which they agreed that the 

destruction of the materials would be stayed pending resolution of this appeal, but 

7 The government contends that, although both Carpenter and GMC filed the notice of 

appeal, Carpenter has waived his arguments on appeal because he did not file a brief on 

his own behalf either in response to the government’s appeal or in support of his crossappeal, and GMC’s briefs do not indicate that they were filed on behalf of Carpenter. We 

agree. In any event, even if we were to attribute GMC’s arguments to Carpenter, such 

arguments would fail for the same reasons explained infra.
18

the district court has not “so ordered” or taken any other action with respect to the 

joint stipulation. 

II. JURISDICTION

Prior to oral argument, this Court ordered the parties to brief the issue of 

this Court’s appellate jurisdiction. Having reviewed those submissions, we 

determine that we have jurisdiction over the district court’s order under 28 U.S.C. 

§ 1291.

Before explaining why we have jurisdiction under 28 U.S.C. § 1291, we 

briefly review certain aspects of the complicated procedural history that bear 

directly on the question of appellate jurisdiction. In May 2014, while a criminal 

action was pending against Carpenter, Carpenter and GMC initiated a Bivens 

action against the defendant DOL agents. In the same complaint, they included a 

Rule 41(g) demand for return of property from the United States, based on the 

same alleged constitutional violations committed by the agents. Although the 

United States was not named as a defendant, the plaintiffs sued Allen in both her 

individual and official capacities, the latter of which effectively brings in the 

United States as a party. See Robinson v. Overseas Mil. Sales Corp., 21 F.3d 502, 510 

(2d Cir. 1994) (“[A]n action against a federal agency or federal officers in their 
19

official capacities is essentially a suit against the United States . . . .”); Silver v. 

Smith, 70 F. App’x 17, 19 (2d Cir. 2003) (summary order) (“[B]ecause [plaintiff] 

sued [IRS employees] only in their official, not their individual, capacities, the 

district court properly substituted the United States for its employees as the 

defendant in this action.”). Moreover, the Rule 41(g) allegations in the complaint 

do not mention any of the individual defendants, referencing only “the 

government.” Joint App’x at 23. The defendants were at all times represented by 

the United States Attorney, and in all proceedings regarding Rule 41(g), the parties 

proceeded without objection to litigate the interests of the United States, not the 

individual DOL agents, in retaining the property at issue. We therefore do the 

same.

All aspects of the civil case were stayed, however, pending the resolution of 

the criminal proceedings against Carpenter, during which the district court denied 

a motion to suppress the seized documents on Fourth Amendment grounds. 

When the district court, upon the final resolution of the criminal case, turned its 

attention to the Bivens action, the substance of the motion changed. Rather than 

renew their claims that the documents had been illegally seized, the plaintiffs 

based the Rule 41(g) motion on the simpler theory that, whether or not the 
20

property had been lawfully seized, the plaintiffs as owners of the property were 

entitled to its return, because, with the criminal case resolved, the government no 

longer had a legitimate reason to retain it.8

Because that motion appears on the docket of the Bivens action, which has 

not yet reached a final judgment, the district court’s resolution of that motion may 

look like the type of interlocutory order that we lack jurisdiction to review. But 

that appearance is misleading. 

First, the motion has no bearing on the Bivens action itself. The demand for 

the return of seized property, based on the termination of the criminal case, seeks 

relief from the government, not from the individual defendants from whom 

damages are sought for violating the plaintiffs’ constitutional rights. The motion’s 

resolution is not a step on the way to resolving the agents’ civil liability; rather, it 

seeks relief independent of the liability of the agents for damages for their alleged 

constitutional violations.

8 Rule 41(g) (then numbered 41(e)) had been amended to make clear that “a person whose 

property has been lawfully seized may seek return of property when aggrieved by the 

government’s continued possession of it.” Fed. R. Crim. P. 41 advisory committee’s note 

to 1989 Amendment.
21

Second, there is an extensive body of law relating to the proper 

characterization of Rule 41(g) motions. It bears emphasis that Rule 41(g) is a rule 

of criminal procedure; it is not a rule that relates to the processing of civil cases. 

When the motion is made on the docket of a pending criminal case, on the ground 

that the property in question was illegally seized, the motion has typically been 

treated as an interlocutory suppression motion, and it has long been the rule that 

an adverse decision on the motion is not appealable. See Grant v. United States, 282 

F.2d 165, 169 (2d Cir. 1960).9

But while Rule 41(g) is a rule of criminal procedure, we have also long held 

that where, as here, a motion under that rule is filed “[a]fter a criminal proceeding 

has ended,” the district court should construe such a motion “as initiating a civil 

action in equity.” Lavin v. United States, 299 F.3d 123, 127 (2d Cir. 2002); see also 

Viola v. United States, 203 F. App’x 366, 366 (2d Cir. 2006) (summary order) (“[A] 

motion pursuant to Federal Rule of Criminal Procedure 41([g]) made after the 

conclusion of the movant’s criminal proceedings is treated as a new civil action for 

equitable relief.” (citations omitted)). In other words, we often treat Rule 41(g) 

9 With respect to suppression motions that have been granted, the government has since

been given, by statute, a right to file an interlocutory appeal. 18 U.S.C. § 3731.
22

motions after the completion of criminal proceedings as stand-alone civil actions

in equity that are conceptually and procedurally distinct from the actions in which 

the motions were docketed.10

“Finality is determined on the basis of pragmatic, not needlessly rigid pro 

forma, analysis.” Mead v. Reliastar Life Ins. Co., 768 F.3d 102, 109 (2d Cir. 2014) 

(internal quotation marks and citation omitted); see Nelson v. Unum Life Ins. Co. of 

Am., 468 F.3d 117, 119 (2d Cir. 2006) (“We are instructed to give Section 1291 a 

practical, as opposed to technical, construction.”). Moreover, the rationale 

underlying the finality requirement is “to provide the parties with an opportunity 

10 The Supreme Court announced in DiBella v. United States that decisions on even preindictment motions under then-Rule 41(e) can be final under 28 U.S.C. § 1291, but only if 

the motion is “[1] solely for return of property and is [2] in no way tied to a criminal 

prosecution in esse against the movant.” 369 U.S. 121, 131–32 (1962). In other words, “[i]f 

a motion for the return of property is made independently of a criminal prosecution—in

that it is not intended to gain some strategic advantage for a criminal defendant—the 

order denying relief is final.” United States v. Nocito, 64 F.4th 76, 81 (3d Cir. 2023) 

(explaining that “an order denying a Rule 41(g) motion can be final because such a 

motion, unlike a motion to suppress, could be premised entirely on property rights and 

not intertwined with a criminal prosecution in any way” (citation omitted)). We have 

read DiBella as announcing a test for when a preindictment Rule 41(g) appeal is “final for 

purposes of [§ 1291].” Standard Drywall, Inc. v. United States, 668 F.2d 156, 157–58 & n.3

(2d Cir. 1982). Although the Rule 41(g) motion at issue here is not a pre-indictment 

motion, it nonetheless sufficiently meets the requirements set out in DiBella to the extent 

that those requirements apply to post-indictment or post-proceeding Rule 41(g) motions. 

See, e.g., Nocito, 64 F.4th at 83 (applying DiBella to both pre- and post-indictment Rule 

41(g) motions). 
23

for a single review of all the questions raised at the trial level . . . and thereby to 

avoid the waste of time and the delay in reaching trial finality which ensue when 

piecemeal appeals are permitted.” Nelson, 468 F.3d at 119 (internal quotation 

marks and citation omitted). The district court’s order here finally resolves the 

single dispute between the parties to the Rule 41(g) motion—that is, GMC and the 

United States—as opposed to the ongoing Bivens action which, although 

appearing on the same docket, is between plaintiffs and the individual-capacity 

defendants and remains unaffected by the district court’s order. Accordingly, 

there is nothing “piecemeal” about the appellate review here. That is why 

although the district court’s order on Rule 41(g) may not look like a “final 

decision” in form, it is a “final decision” in function that “conclusively determine[d] 

the pending claims of all the parties” in the separate action-within-an-action 

“leaving nothing for the court to do but execute its decision” with respect to the 

Rule 41(g) action. Mead, 768 F.3d at 109 (internal quotation marks and citations 

omitted). 

Accordingly, we conclude that we have appellate jurisdiction to review the 

district court’s resolution of the Rule 41(g) motion.
24

III. MERITS DISCUSSION

The government argues that Carpenter’s pending Section 2255 motion 

challenging his convictions constitutes a legitimate need under Rule 41(g) for it to 

retain the seized materials at issue at this juncture. As set forth below, we agree. 

After the completion of a criminal proceeding, a district court’s order granting the 

return of property is a civil equitable remedy. See United States v. Zaleski, 686 F.3d 

90, 92 (2d Cir. 2012); Diaz v. United States, 517 F.3d 608, 610 (2d Cir. 2008). “We 

review a district court's grant or denial of equitable relief for abuse of discretion, 

but we review de novo any legal conclusion underlying such a decision.” Zaleski, 

686 F.3d at 92.

Rule 41(g) provides that “[a] person aggrieved by an unlawful search and 

seizure of property or by the deprivation of property may move for the property’s 

return.” Fed. R. Crim P. 41(g). As originally adopted, the Rule 41 provision 

governing the return of property, then codified as Rule 41(e),11 “provided a 

method for enforcing the protection against unreasonable search and seizure 

11 In 2002, Rule 41 was reorganized, and subsection (e) was redesignated as subsection 

(g) without substantive change. See De Almeida v. United States, 459 F.3d 377, 380 n.2 (2d 

Cir. 2006). “Accordingly, courts have applied the case law concerning former Rule 41(e) 

to the current Rule 41(g).” Id.
25

guaranteed by the Fourth Amendment.” 3A Charles Alan Wright & Arthur R. 

Miller, Federal Practice & Procedure § 690 (4th ed. 2023). That changed with a 

1989 amendment that expanded then-Rule 41(e)’s scope to allow “a person whose 

property has been lawfully seized [to] seek return of property when aggrieved by 

the government's continued possession of it.” Fed. R. Crim. P. 41 advisory 

committee’s note to 1989 amendment (emphasis added). The 1989 amendment 

reflected the well-established understanding that “goods not in the nature of 

contraband, which were legally seized, should be returned when their evidentiary 

utility is exhausted.” Bova v. United States, 460 F.2d 404, 406 n.5 (2d Cir. 1972) 

(Friendly, C.J.).12 In sum, as the advisory committee for the 1989 amendment

explained, “[t]he amended rule contemplates judicial action that will respect both 

possessory and law enforcement interests.” Fed. R. Crim. P. 41 advisory 

committee’s note to 1989 amendment.

Several district courts within this Circuit have noted that we have never 

directly addressed the questions of whether the movant or the government bears 

the evidentiary burden in the context of a Rule 41(g) motion and when, if ever, that 

12 The advisory committee’s note to 1989 amendment referenced United States v. Wilson, 

540 F.2d 1100 (D.C. Cir. 1976), a case that cited our decision in Bova with approval. See id. 

at 1103 & n.4.
26

burden shifts. See, e.g., United States v. Morgan, 443 F. Supp. 3d 405, 407 (W.D.N.Y. 

2020); Awan v. United States, No. 12-cv-3844 (JS), 2014 WL 1343129, at *3 (E.D.N.Y. 

Mar. 31, 2014); Hallock v. United States, No. 09-cv-1141 (DNH/DEP), 2010 WL 

4025615, at *3 (N.D.N.Y. July 28, 2010), report and recommendation adopted, No. 09-

cv-11411, 2010 WL 4022935 (N.D.N.Y. Oct. 13, 2010); Sash v. United States, No. 09-

cv-450 (DC), 2009 WL 3007379, at *3 & n.4 (S.D.N.Y. Sept. 22, 2009). We now clarify 

that, during the pendency of an ongoing criminal investigation or proceeding, the 

defendant bears the burden of demonstrating that the government’s retention of 

the seized property is unreasonable. See United States v. Chambers, 192 F.3d 374, 

377 (3d Cir. 1999); see also Ramsden v. United States, 2 F.3d 322, 326 (9th Cir. 1993) 

(“The United States’ retention of the property generally is reasonable if it has a 

need for the property in an investigation or prosecution.”). However, once the 

criminal proceeding is completed, there is a presumption that non-contraband 

property should be returned to its owner and, thus, the evidentiary burden under 

Rule 41(g) shifts to the government to demonstrate that it has a “legitimate reason” 

for retaining the seized property. Lavin, 299 F.3d at 128. In other words, “[a]
27

defendant’s [or third party’s] right to the return of lawfully seized property is 

subject to the [g]overnment’s legitimate continuing interest in that property.” Id.13

In articulating this evidentiary framework, we are in agreement with our 

sister circuits that have also determined—consistent with Rule 41(g)’s purpose—

that “[t]he government can rebut the presumption that property ought to be 

returned by proving a ‘legitimate reason’ for retaining the property that is 

‘reasonable under all of the circumstances.’” United States v. Gladding, 775 F.3d 

1149, 1152 (9th Cir. 2014) (alteration adopted) (citation omitted); accord Perez-Colon 

v. Camacho, 206 F. App’x 1, 3 (1st Cir. 2006) (per curiam); United States v. Pitts, 639 

F. App’x 105, 107 (3d Cir. 2016) (per curiam); United States v. Roca, 676 F. App’x 

194, 194–95 (4th Cir. 2017) (per curiam); United States v. Jackson, 771 F.3d 900, 902 

(5th Cir. 2014); United States v. Silva, 26 F. App’x 544, 547 (7th Cir. 2001)

(unpublished order); Jackson v. United States, 526 F.3d 394, 397–98 (8th Cir. 2008); 

United States v. Rodriguez-Aguirre, 264 F.3d 1195, 1213 n.14 (10th Cir. 2001); United 

States v. Potes Ramirez, 260 F.3d 1310, 1314 (11th Cir. 2001).

13 The district court relied on the substantially similar standard we articulated in United 

States v. David, 131 F.3d 55 (2d Cir. 1997); however, that decision was decided in the 

context of a constitutional due process challenge to a government seizure of property, see 

id. at 58–59, and is not directly on point here given that GMC has only invoked Rule 41(g).
28

Here, applying this standard, we conclude that the district court exceeded 

its discretion in determining that the pending Section 2255 motion did not create 

a legitimate need for the government to retain the documents even after the 

completion of Carpenter’s criminal proceedings. In rejecting the government’s 

argument that it needed the seized materials to defend against the Section 2255 

motion, the district court reasoned that the government had “no need to retain 

materials that were not introduced as evidence” at Carpenter’s criminal trial 

because the Section 2255 motion would be decided based on the trial record. 

Special App’x at 18. However, that reasoning failed to take into account the 

specific claims that Carpenter asserts in his Section 2255 motion, which relate 

directly to the seized property at issue. In particular, he contends that the agents 

executing the search exceeded the scope of the warrant. He also asserts that the 

government failed to disclose Brady material that was contained within the seized 

documents. In order to defend against these claims, the government may need to 

utilize the entirety of the documents seized during the search, not just the seized 

documents admitted as exhibits during the trial. 

Moreover, a district court is not limited to the trial record in addressing 

claims for relief under Section 2255. Indeed, Section 2255 requires the district court 
29

to hold a hearing, or to “use methods . . . to expand the record without conducting 

a full-blown testimonial hearing,” Chang v. United States, 250 F.3d 79, 86 (2d Cir. 

2001), “[u]nless the motion and the files and records of the case conclusively show 

that the prisoner is entitled to no relief,” Puglisi v. United States, 586 F.3d 209, 213 

(2d Cir. 2009) (quoting 28 U.S.C. § 2255(b)). Thus, the district court erred in 

concluding that the seized documents could have no bearing on the government’s 

defense against the claims related to the search in the pending Section 2255 motion, 

or in the district court’s resolution of those claims.

Even apart from the government’s articulated need to retain the materials 

to defend against the particular claims in Carpenter’s Section 2255 motion, we 

conclude that the government demonstrated a legitimate need to retain the seized 

materials during the pendency of the Section 2255 motion in order to preserve its 

ability to use the seized materials as evidence in a potential retrial should 

Carpenter prevail in his collateral attack on his criminal convictions. In the context 

of a Rule 41(g) motion made while a defendant’s direct appeal is still pending, 

courts have recognized that the government has a legitimate need to retain seized 

materials because of the possibility of a retrial if an appeal is successful. See, e.g.,

United States v. Saunders, 957 F.2d 1488, 1495 (8th Cir. 1992) (affirming denial of 
30

Rule 41 motion on the basis that “[t]he motion for the return of the [seized] 

paperwork, even papers that were not introduced at trial, was premature because 

defendant’s direct appeal was still pending”). That same logic applies with equal 

force here, where the conviction is being collaterally attacked under Section 2255

and, thus, rebuts the general presumption that the seized materials should be 

returned once the criminal proceeding has ended. See, e.g., United States v. Mendez, 

860 F.3d 1147, 1150 (8th Cir. 2017) (recognizing that “[t]he pendency of a direct 

appeal or a post-conviction proceeding might justify the government’s further 

retention of property as potential evidence in a criminal case”).14

14 GMC argues that a retrial is not possible because the Double Jeopardy Clause of the 

Constitution would bar a second trial in the event that Carpenter’s Section 2255 motion 

is successful. The Double Jeopardy Clause does not categorically bar the retrial of a 

defendant whose convictions are overturned on direct appeal or collateral attack. See, 

e.g., Lockhart v. Nelson, 488 U.S. 33, 38 (1988) (“[T]he Double Jeopardy Clause’s general 

prohibition against successive prosecutions does not prevent the government from 

retrying a defendant who succeeds in getting his first conviction set aside, through direct 

appeal or collateral attack, because of some error in the proceedings leading to 

conviction.”). Having said that, we express no view as to whether, under the particular 

circumstances of this case, the Double Jeopardy Clause could bar any retrial of Carpenter 

should his Section 2255 motion prevail. Instead, we more narrowly conclude that the 

government’s legitimate need to retain seized property as evidence during a pending 

Section 2255 motion challenging a conviction is not weakened at this stage by any 

anticipated legal or practical obstacles to a retrial should the collateral attack on the 

conviction be successful. See generally United States v. Gulledge, 739 F.2d 582, 586 (11th Cir. 

1984) (“If [the defendant] believes that the introduction of certain evidence at his second 

trial will constitute double jeopardy or violate any other rights, he may press the claim in 

the district court and on appeal after final judgment has been entered against him.”).
31

During a conference on the Rule 41(g) motion, the district court suggested 

that the government did not need to retain the seized materials because, in a 

potential retrial, the government could rely upon copies of the previously 

admitted trial documents to prove its case. However, “[u]pon . . . reversal of a 

conviction[,] the [g]overnment is not limited at a new trial to the evidence 

presented at the first trial, but is free to strengthen its case in any way it can by the 

introduction of new evidence.” United States v. Shotwell Mfg. Co., 355 U.S. 233, 243

(1957); see also United States v. Gallagher, 602 F.2d 1139, 1143 (3rd Cir. 1979) 

(“[A]part from the requirement that the new evidence conform to the indictment, 

there is no reason to restrict the government’s case at a second trial. By the same 

token, the defense is also free to present testimony at the retrial which it had not 

utilized in the first encounter.”). 

In rejecting the government’s argument, the district court overlooked the 

many scenarios in which the government may need to offer new evidence at a 

retrial, including from the seized materials, even though the evidence was not 

offered at the first trial. For example, if the Section 2255 motion were granted 

based upon the Supreme Court’s rejection in Ciminelli of the “right-to-control” 

theory of wire fraud (under which Carpenter was prosecuted and the jury was 
32

instructed), in a retrial the government might focus on an alternative theory of 

criminal liability against Carpenter, with a potential need to utilize other evidence 

from the seized materials to support the alternative theory. In addition, although 

Carpenter consented to a bench trial at the first trial, he could opt for a jury at any 

retrial, and the government thereby may need to adjust its trial strategy to present 

different evidence to a jury. Moreover, Carpenter would be free to offer new 

defenses and legal arguments at a retrial and, under those circumstances, the 

government may need to rely upon additional evidence from the seized materials 

to respond, including to rebut new evidence offered by the defendant at a retrial. 

In short, when a Section 2255 motion is pending, Rule 41(g) does not operate to 

limit the government’s evidentiary options at a retrial if the motion is successful.15 

Instead, the existence of a pending Section 2255 motion challenging a conviction 

creates a legitimate need for the government to retain any seized materials that 

15 GMC points out that—to the extent it is formally a separate entity from Carpenter—it 

has never been charged with a criminal offense. However, the government may lawfully 

seize evidence from even innocent third parties. See Zurcher v. Stanford Daily, 436 U.S. 

547, 560 (1978) (holding that the Fourth Amendment allows for warrants where “the 

owner or possessor of the place to be searched is not . . . reasonably suspected of criminal 

involvement”). 
33

could be used as evidence at a potential retrial, even if the materials were not 

introduced as evidence in the first trial.16

At oral argument, counsel for GMC also noted that the success rate of 

Section 2255 motions is statistically “negligible” and suggested that a court should 

take that reality into consideration when assessing the government’s claim that it 

needs to retain the evidence for a potential retrial because of a pending collateral 

attack. Oral Arg. at 31:40–57. We disagree. As an initial matter, counsel’s 

suggestion is inconsistent with his recent Rule 28(j) letter to this Court, which 

argued that two recent U.S. Supreme Court decisions, including Ciminelli, “will 

have a major impact on the future of the litigation between the parties [in this 

case].” GMC Rule 28(j) Letter at 1 (2d Cir. June 20, 2023), ECF No. 102. In any 

event, even assuming arguendo that a particular Section 2255 motion has a low 

probability of success, that assessment does not undermine the government’s 

legitimate need to retain the seized materials while the motion is pending. Courts 

16 Critical to this portion of our holding is that the pending Section 2255 motion seeks to 

vacate the convictions and, thus, a grant of Carpenter’s requested relief implicates a 

potential retrial on the charges. We need not decide now whether a pending Section 2255 

motion that does not challenge the underlying conviction but rather seeks a narrower 

form of relief, such as a resentencing, creates a legitimate need to retain the seized 

materials. Nor need we speculate whether the government has a legitimate need to retain 

the seized materials because of the mere possibility of a Section 2255 motion.
34

do not consider the likelihood of success of a pending direct appeal of a 

defendant’s criminal convictions in determining whether the government is 

permitted under Rule 41(g) to retain evidence for a retrial if the appeal is 

successful, and we do not require such a consideration under Rule 41(g) in 

connection with a pending Section 2255 motion. In other words, we conclude the 

presumed right to the return of seized materials following the completion of the 

criminal proceedings is rebutted by the existence of the pending Section 2255 

motion challenging the conviction, due to the government’s legitimate need to 

retain seized materials as evidence at a potential retrial, regardless of the 

likelihood of success of that motion.

For similar reasons, we do not impose a requirement that the government 

demonstrate its need to use the seized materials at a potential retrial on a 

document-by-document basis. See generally Harbor Healthcare Sys., L.P. v. United 

States, 5 F.4th 593, 601 n.4 (5th Cir. 2021) (per curiam) (explaining, in the context of 

a Rule 41(g) motion, that the district court was not required to review “each and 

every document” for claims of privilege but rather could do so “based on 

categories of documents”). As discussed above, given the many variables that 

may affect the relevance of various seized documents at a retrial, such a 
35

requirement would place the government and ultimately the district court (which 

would be required to make any such determination) in an unworkable position

when faced with a large volume of seized materials related to an underlying 

criminal prosecution. Instead, in such situations, the “legitimate need” 

requirement under Rule 41(g) can be satisfied by the government as long as the 

category of documents at issue would be potentially admissible at a retrial. Here, 

although GMC generally argued that a potential retrial was not sufficient 

justification for retaining the seized materials during a pending Section 2255 

motion (which we reject for reasons discussed supra), it did not contend in the 

district court (nor does it argue on appeal) that particular categories of documents 

in the seized materials could not possibly be admitted at a retrial.

Our holding is consistent with the conclusions reached by many other courts

under similar circumstances. For example, in United States v. Alford, the Eleventh

Circuit held that, where the defendant had a pending motion to vacate his 

conviction, “[t]he [g]overnment has a legitimate need to retain the evidence until 

[defendant] exhausts his post-conviction remedies because it would need the 

evidence at a new trial if his motion to vacate is successful.” 805 F. App’x 924, 926 

(11th Cir. 2020) (per curiam). In addition, two unpublished decisions from the 
36

Ninth Circuit reached the same outcome. See United States v. Basey, 837 F. App’x 

603, 603 (9th Cir. 2021) (unpublished) (“The government demonstrated a 

reasonable need to retain the property in light of [defendant’s] pending collateral 

attack on his 2017 convictions.”); United States v. Davis, 749 F. App’x 618, 619 n.1 

(9th Cir. 2019) (unpublished) (“The district court properly denied [defendant’s] 

motion to return the remaining items of property in light of the government’s 

explanation that it was retaining the property in connection with [defendant’s] 

pending habeas corpus proceedings under 28 U.S.C. § 2255.”).

Numerous district court decisions have also reached the same conclusion. 

See, e.g., United States v. Kourani, No. 17-cr-417 (AKH), 2022 WL 19762, at *1 

(S.D.N.Y. Jan. 3, 2022); Sosa-Pintor v. United States, No. 19-cv-033 (CAN), 2019 WL 

2273758, at *2 (E.D. Tex. Apr. 22, 2019), report and recommendation adopted, No. 19-

cv-33 (MAC), 2019 WL 2267293 (E.D. Tex. May 24, 2019); United States v. Cobb, No. 

14-cr-123 (CEH), 2017 WL 3499257, at *3 (M.D. Fla. Aug. 16, 2017); Mendoza v. 

United States, 10-cv-9002 (HB), 2011 WL 1345712, at *2 (S.D.N.Y. Apr. 4, 2011); 
37

United States v. Reyes, No. 06-cr-5005 (FDB), 2010 WL 996416, at *2 (W.D. Wash. 

Mar. 15, 2010).17

Here, the district court expressed its concern that “[t]he government 

shouldn’t be allowed to take documents pursuant to a warrant and hold them 

indefinitely . . . for whatever purpose it wants.” Joint App’x at 56. Along similar 

lines, GMC emphasizes a government attorney’s statement at oral argument to 

another panel of this Court, in the first appeal in the IRS Bivens action, that once 

the criminal case is over, all materials would be returned. To be sure, we recognize 

that “the government may not by exercising its power to seize, effect a de facto 

forfeiture by retaining the property seized indefinitely.” Rodriguez-Aguirre, 264 

F.3d at 1212 (alteration adopted) (internal quotation marks and citation omitted). 

However, we find that legitimate concern not to be implicated in the current 

posture of this case. First, we note that, although the documents were seized by 

the government over a decade ago, only relatively recently did Carpenter’s 

conviction become final on direct appeal when the United States Supreme Court 

denied his petition for certiorari in 2020. Moreover, our narrow holding today is 

17 Counsel for GMC acknowledged at oral argument that he was unaware of any court 

reaching a contrary holding. Our own research has not uncovered any such conflicting 

authority.
38

tied to the uncertainty surrounding the criminal convictions created by the 

pending Section 2255 motion and by no means allows for the government’s 

indefinite retention of the seized property. If the pending Section 2255 motion is 

denied, the legitimate need that we have found sufficient to satisfy Rule 41(g) will 

cease to exist and, if the government wishes to continue to retain the property, it 

will be required to meet its burden of demonstrating another legitimate need for 

such retention.18 

In sum, we conclude that the district court exceeded its discretion in 

granting the Rule 41(g) motion and holding that the government failed to 

18 We recognize that the government has articulated other alternative grounds to support 

its legitimate need to retain the documents under the Rule 41(g) standard, including the 

pending litigation over the restitution order, the ongoing Bivens action which contains a 

claim related to the legality of the 2011 search, and the pro se motions to dismiss the 

indictment and for grand jury materials filed by Carpenter. We need not (and do not) 

address these alternative grounds raised by the government. Instead, if the current 

ground for retention based upon the pending Section 2255 motion and a potential retrial 

were to fade away, plaintiffs can renew their Rule 41(g) motion in the district court, and 

any remaining arguments for retention of the materials articulated by the government at 

that juncture would be reassessed by the district court in the first instance. Additionally, 

to the extent that GMC alleges that the seized documents should be returned on the 

grounds that they were illegally seized, “because the district court did not reach this 

question below, we decline to address it for the first time on appeal.” Holland v. Goord, 

758 F.3d 215, 223 (2d Cir. 2014). We nonetheless note that the district court in Carpenter’s 

criminal case rejected similar arguments in its order denying Carpenter’s suppression 

motion, which this Court subsequently affirmed. 
39

demonstrate a legitimate need to retain the property at issue to defend against 

Carpenter’s pending Section 2255 motion collaterally attacking his convictions and 

also to preserve evidence for use at a potential retrial should his collateral attack 

succeed.19

IV. CONCLUSION

We VACATE the district court’s order and REMAND to the district court 

for further proceedings consistent with this opinion, and we DISMISS GMC’s

cross-appeal as moot.

19 Given our determination that the government at a minimum is entitled to retain the 

seized materials during the pendency of the Section 2255 motion, plaintiffs’ cross-appeal 

challenging the district court’s decision ordering the government to destroy the seized 

materials (rather than to return such materials to plaintiffs) is moot for present purposes, 

but plaintiffs may reassert such a challenge in the future if the same relief is ordered by 

the district court in connection with any renewed Rule 41(g) motion.