Executive Branch

Everything Wrong With Judge Cannon’s Ruling

Quinta Jurecic, Natalie K. Orpett, Benjamin Wittes
Thursday, September 8, 2022, 4:32 PM

Judge Aileen Cannon’s opinion in the Mar-a-Lago matter actually defies defense.

U.S. Courthouse for the Southern District of Florida, and Federal Court of Appeals for the Eleventh Circuit, Miami, Florida. (https://commons.wikimedia.org/wiki/File:James_Lawrence_King_Federal_Justice_Building.jpg)

Published by The Lawfare Institute
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The Justice Department has now filed a notice of appeal and a motion to partially stay U.S. District Judge Aileen Cannon’s Monday opinion granting former President Trump’s request for a special master to review material seized at Mar-a-Lago and enjoining the use of the material the FBI took in the meantime for investigative purposes.

Judge Cannon has been taking a bit of a beating all week for her decision. The criticism, some of it vituperative, has contained a lot of falsehoods and a considerable dollop of conspiracy theorizing, and it has often ascribed partisan motive for the ruling. 

All of which might under normal circumstances tempt our contrarian hearts to try to defend the opinion. 

But Cannon’s opinion actually defies defense. It is an epic mess, one that manages to do violence to a remarkable number of distinct areas of law in an admirable economy of only 24 pages. 

The opinion is likely to be short lived—and, as such, might normally not be worth significant comment. As the constitutional scholar Charles Black once wrote, while “the insignificant error, however palpable, can stand, because the convenience of settlement outweighs the discomfort of error[,] the hugely consequential error cannot stand and does not stand.” Whether this opinion will be gone in a week or will take a little longer, it will very likely not stand.

That said, the decision is worth critiquing in depth not just because of its importance to one of the central news stories of the day but also because of the number of its errors, their magnitude, and their capacity for disruption of perhaps the highest-profile national security investigation in American history. 

What follows is a brief summary of the four major errors in Cannon’s opinion.

Error #1: The court has no jurisdiction over this matter.

Judge Cannon describes her jurisdiction in the case as rooted both in the court’s “equitable jurisdiction” and in Rule 41(g) of the Federal Rules of Criminal Procedure. The court’s jurisdictional assertion is a bit odd given Trump’s statement that he has “not yet filed a Rule 41(g) motion, and the standard for relief under that rule is not relevant to the issue of whether the Court should appoint a Special Master.”

Cannon acknowledges that the court should exercise such jurisdiction only in “‘exceptional’ circumstances.” And she purports to be following guidance from the U.S. Court of Appeals for the Fifth Circuit from a case called Richey v. Smith. Here is how the court in Richey described the factors that should determine whether a district court should entertain such a motion:

First, and perhaps foremost, is the question whether the motion for return of property accurately alleges that government agents ... in seizing the property displayed “a callous disregard for the constitutional rights of the taxpayer.” ... Other factors to be considered are: whether the plaintiff has an individual interest in and need for the material whose return he seeks; whether the plaintiff would be irreparably injured by denial of the return of the property; and whether the plaintiff has an adequate remedy at law for the redress of his grievance.

Cannon acknowledges that the first factor does not favor her assertion of jurisdiction concerning a motion Trump denies having filed: “With respect to the first factor, the Court agrees with the Government that, at least based on the record to date, there has not been a compelling showing of callous disregard for Plaintiff’s constitutional rights. This factor cuts against the exercise of equitable jurisdiction.”

It actually does a bit more than that. The Fifth Circuit called this the “perhaps foremost” factor for a reason. Rule 41(g) states 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” (emphasis added). It also states that the “court must receive evidence on any factual issue necessary to decide the motion.” The rule is not a general authority for a district court to supervise an ongoing criminal investigation pre-indictment. It presupposes that there has been or could be some compelling showing of a Fourth Amendment violation—the remedy for which is the return of property seized. 

Leave aside for a moment that most of the property seized at Mar-a-Lago does not even belong to Trump. Cannon nowhere in her opinion even alleges, let alone finds, anything that would remotely satisfy the terms of Rule 41(g).

The second Richey factor is doing a lot of work in Cannon’s analysis. She writes that the government has conceded that “the seized materials include medical documents, correspondence related to taxes, and accounting information. ... The Government also has acknowledged that it seized some ‘[p]ersonal effects without evidentiary value’ and, by its own estimation, upwards of 500 pages of material potentially subject to attorney-client privilege.” She thus concludes that “[p]laintiff has an interest in and need for at least a portion of it.” 

Well, no. Not exactly. These numbers certainly show that Trump has a property interest in some portion of the seized material—though the ratio is fairly low, the government having seized a number of documents in the neighborhood of 13,000 pages. But it doesn’t remotely establish “need.” The government conducts court-authorized searches all the time, in which it seizes people’s property. The mere fact that Trump has a cognizable interest in some of the seized material is not, absent some suggestion of impropriety in the conduct of the search, a basis for court intervention. 

Cannon’s reasoning with respect to the third Richey factor is similarly flawed. She finds that the third factor, irreparable injury, “likewise supports the exercise of jurisdiction” because Trump is being “deprived of potentially significant personal documents.” This is because, she reasons, he “faces an unquantifiable potential harm by way of improper disclosure of sensitive information to the public,” as a result of the “Government’s retention and potential use of privileged materials in the course of a process that that, thus far, has been closed off to Plaintiff and that has raised at least some concerns as to its efficacy,” and from the “threat of future prosecution and the serious, often indelible stigma associated therewith.” Cannon adds: “As a function of Plaintiff’s former position as President of the United States, the stigma associated with the subject seizure is in a league of its own.”

Note that with the exception of the last sentence, all of these factors apply to a great many subjects of search warrants in perfectly ordinary cases in which the government seizes documents. Equitable jurisdiction is supposed to be exercised in extraordinary circumstances, but it is true in the perfectly ordinary case that the suspect is deprived of potentially significant personal documents, faces some risk of disparaging leaks, is kept blind to the process of privilege review, and faces the stigma of possible future prosecution (though, notably, both the Eighth and the Tenth Circuits have found that a threat of imminent indictment is not sufficient to establish irreparable injury). 

Cannon here is describing the run-of-the-mill federal criminal investigation’s impact on the individual, not anything extraordinary. Which is why that last sentence is doing all the work. The only thing different about this case is that Trump is a former president. The judge might as well say that Trump’s status alone is her basis for jurisdiction.

“As to the fourth Richey factor,” writes Cannon, “[p]laintiff has persuasively argued that there is no alternative adequate remedy at law.” Trump has actually done no such thing—nor is he differently situated in this regard than anyone else whose house, office, car, or golf resort has been the subject of a federal search warrant. In such matters, the normal course of business, absent some reason to believe the search illegal, is to wait until the investigation is done. At that point, either the material gets returned and that is the remedy, or the subject gets indicted and the remedy is a motion to exclude the evidence. Cannon complains that “[w]ithout Rule 41(g) Plaintiff would have no legal means of seeking the return of his property for the time being” (emphasis added). But why is it so urgent for Trump to get the documents back right now that, alone among criminal suspects, it warrants interrupting an ongoing criminal investigation to speed up his access to material he mostly doesn’t own at all but stole from the federal government? The judge does not answer this question. 

Cannon’s Rule 41(g) analysis is particularly objectionable because Trump didn’t file a motion under Rule 41(g) at all—in fact, he repeatedly argued that a special master was warranted because the special master’s oversight would allow him to assess whether to file a Rule 41(g) motion. Trump’s complaint, rather, is styled as a “motion for judicial oversight and additional relief.”

To put the matter simply, Cannon’s analysis here has turned a rule designed to offer a pre-indictment remedy for Fourth Amendment violations into a vehicle for people who have not yet even been indicted to file collateral challenges that have the capacity to prohibit the government from conducting the very investigation that would otherwise properly result in their indictment.

This brings us to …

Error #2: A district court has no authority to block a criminal investigation. 

In the wake of the ruling, Fourth Amendment scholar and Lawfare contributing editor Orin Kerr posed the following question: “[D]oes a federal court have authority to enjoin executive branch ‘use’ of seized materials for ‘investigative purposes’”?

Judge Cannon did not just order that a special master review the seized material. She went a lot further and determined “that a temporary injunction on the Government’s use of the seized material for investigative purposes—but not ODNI’s national security assessment—is appropriate and equitable to uphold the value of the special master review.” This injunction is one of the most striking things about the opinion—particularly as it was not specifically sought by the Trump legal team. (Trump’s complaint did seek a protective order under Rule 26(b)(5) and Rule 26(c)(1), but Cannon did not rule on that.)

Cannon begins by disclaiming the need to even conduct an analysis of whether this measure is appropriate, observing that “a temporary restraint on use naturally furthers and complements the appointment of a special master” and citing two instances in which courts did not discuss Federal Rule of Civil Procedure 65, the rule governing injunctions, when issuing them in similar contexts.

Nonetheless, “for the sake of completeness and prudence,” she chooses to lay out her Rule 65 analysis anyway. She badly bungles this analysis too. The standard here is well-known. To get an injunction, Trump needs to show (1) a substantial likelihood of success on the merits, (2) that he will suffer an irreparable injury in the absence of relief, (3) that this injury outweighs the damage that granting relief will cause the government, and (4) that the public interest is not adverse to an injunction. 

The judge spends exactly one sentence on Trump’s likelihood of success on the merits. It reads as follows: “As discussed above ... the Court is satisfied that Plaintiff has ‘a likelihood of success on the merits of [his] challenge to the [Privilege Review Team] and its [p]rotocol.’” The phrase “as discussed above” refers back to the following passage earlier in the opinion:

[T]he Government’s argument assumes that the Privilege Review Team’s initial screening for potentially privileged material was sufficient, yet there is evidence from which to call that premise into question here. ... As reflected in the Privilege Review Team’s Report, the Investigative Team already has been exposed to potentially privileged material. Without delving into specifics, the Privilege Review Team’s Report references at least two instances in which members of the Investigative Team were exposed to material that was then delivered to the Privilege Review Team and, following another review, designated as potentially privileged material. Those instances alone, even if entirely inadvertent, yield questions about the adequacy of the filter review process.

But Rule 41(g), the supposed jurisdictional basis for Cannon’s opinion, does not authorize a “challenge to the [Privilege Review Team] and its [p]rotocol.” It authorizes a challenge by “a person aggrieved by an unlawful search and seizure of property or by the deprivation of property” in order to effectuate “the property’s return.” And Cannon nowhere even suggests that Trump has a substantial likelihood of success on the merits in establishing that the government has acted improperly in conducting the search or in seizing the material. 

Indeed, Trump’s briefs do not even purport to establish a likelihood of success on the merits of the point on which Cannon credits them with doing so. Rather, Trump claims that the government’s review should be overseen by a special master to “preserve the sanctity of executive communications and other privileged materials.” They argue that the search warrant might be overbroad or improperly executed (while offering no evidence that either is true), the filter team protocol was procedurally deficient, and the government’s team might include “FBI agents involved in the Russia defamation matter” or other biased personnel from a “government that has long treated [Trump] unfairly.” They invoke the need for the appearance of fairness given that “this matter has captured the attention of the American public.” More bizarrely, Trump argues that a special master is necessary to “provid[e] defense counsel with information needed to support any Rule 41(g) filing.” In other words, the judge has found that Trump has established a likelihood of succeeding on the merits of a claim he believes he cannot make until a special master is appointed to help him decide whether such a claim is worth bringing.

Cannon uses “the same reason—chiefly, the risk that the Government’s filter review process will not adequately safeguard Plaintiff’s privileged and personal materials in terms of exposure to either the Investigative Team or the media” to find that “Plaintiff has sufficiently established irreparable injury”—the second factor in the test for granting an injunction. But this is not an irreparable injury. For one thing, if evidence is ever found to be privileged, it can be suppressed at trial—if there ever is a trial. It can be returned. For another thing, a judge does not get to simply announce that there will be leaks and that those leaks will constitute an irreparable injury. There is no record evidence of any material leaking at all. And maybe any leaks, if they do occur, will prove minor and altogether reparable in whatever injury they cause to Trump. 

As to the third and fourth prong, which the judge merges in her analysis, Cannon admits that she’s treating Trump differently from any other criminal subject: “As Plaintiff articulated at the hearing, the investigation and treatment of a former president is of unique interest to the general public, and the country is served best by an orderly process that promotes the interest and perception of fairness.” But that reasoning is backward; the standard isn’t that a judge should do whatever she thinks is in the public interest, other considerations be damned. The standard is that where a movant has a likelihood of success on the merits and will suffer an irreparable injury absent an injunction, a judge should nevertheless refrain from imposing an injunction that benefits that movant if the injunction would be contrary to the public interest or if the government’s countervailing interests outweigh the movant’s interest in an injunction. Here, the first two factors are entirely missing. 

The judge here once again grants Trump more than he sought. Trump asked the court for a protective order enjoining the government’s review of the documents until such time as she decides whether to appoint a special master, saying: “[I]t is unreasonable to allow the prosecutorial team to review [the documents] without meaningful safeguards” because, by Trump’s telling, they are “all presumptively privileged.” A protective order, which is governed by Rule 26, is a fundamentally different mechanism from an injunction, which is governed by Rule 65; the former merely regulates discovery produced by the parties in a civil proceeding, whereas the latter is being used here to reach into a separate criminal proceeding and order the government to stop its work. The protective order Trump asked for would have had a more modest impact than the injunction Cannon granted. 

Cannon, as it turns out, grants an injunction against the government’s review and use of the material. As Kerr argues: “Appointing a special master is very odd here. But the bigger deal is enjoining ‘use’ of the seized materials that were already searched, for further ‘investigative purposes’ (whatever that means).” He asks: “Is indicting Trump ‘use’? ... If a federal court lacks power to stop the executive branch from prosecuting a case, can it have power to stop the executive branch from investigating a case to see if a prosecution is appropriate?”

To make matters even weirder, Cannon enjoins the government from using the seized materials “for criminal investigative purposes pending resolution of the special master’s review process” but allows it to “continue to review and use the materials seized for purposes of intelligence classification and national security assessments.” This might seem like a good way of limiting the potential harmful effects on national security of the delays caused by the special master process. But the fact of the matter is that there’s no way to cleanly distinguish between these two different functions.

As former FBI counterintelligence agent Pete Strzok notes on Twitter, “[T]he seized material provides reasonable inference there still may be classified info in the wild,” which would be crucial to the intelligence community’s assessment of the risk posed by the mishandling of the documents—yet now the FBI is enjoined from investigating further. Likewise, before Cannon’s ruling, former CIA attorney Brian Greer pointed out that, “[o]ther than the contents of the documents, the critical element” for the intelligence community review “is who accessed the documents & under what circumstances”—information that the FBI now can’t look into because of the injunction. Cannon’s attempt to draw a bright line between the inherently related streams of criminal and counterintelligence work suggests a lack of understanding of how national security investigations function.

Error #3: The ruling is simply incoherent with respect to executive privilege.

Judge Cannon does not just rule that a special master should review the material in question for information covered by attorney-client privilege. She also rules that the special master should review it for executive privilege. Specifically, she finds that “even if any assertion of executive privilege by [Trump] ultimately fails in this context, that possibility, even if likely, does not negate a former President’s ability to raise the privilege as an initial matter.” 

Her analysis of executive privilege reflects a deep ignorance of the subject. Discussing Cannon’s ruling on Twitter Spaces, Lawfare’s Jonathan Shaub—an expert on executive privilege issues—described the judge’s reasoning on the subject as expressing “a complete misunderstanding of the nature of executive privilege.”

Cannon writes that, even as a former president, Trump may still be able to invoke executive privilege under Nixon v. Administrator of General Services, and she points to the Supreme Court’s recent ruling in Trump v. Thompson, concerning Trump’s efforts to block the Jan. 6 committee from obtaining records despite President Biden’s determination not to invoke privilege. Ruling that Trump could not withhold the records, the Court focused its analysis on the nature of Jan. 6, 2021, rather than resolving the question of whether a former president’s assertion of the privilege might ever overcome an incumbent president’s determination. Cannon, however, points to the Court’s statement that “[t]he questions whether and in what circumstances a former President may obtain a court order preventing disclosure of privileged records from his tenure in office, in the face of a determination by the incumbent President to waive the privilege, are unprecedented and raise serious and substantial concerns.”

The first and most fundamental problem here is the judge’s apparent belief that executive privilege can ever be invoked to prevent documents from being shared within the executive branch itself, given that the privilege is meant to protect internal executive branch conversations from being disclosed outside the branch. 

Indeed, the Supreme Court in Nixon v. Administrator of General Services rejected former President Nixon’s efforts to block documents from being shared with the National Archives in part because Nixon’s was an “assertion of a privilege against the very Executive Branch in whose name the privilege is invoked.” Cannon herself notes that Trump v. Thompson, which she cites, concerned information that Trump sought to shield from a different branch of government—which is to say, Congress. As Shaub stated on Lawfare’s Twitter Spaces conversation, the incumbent president does have the authority to direct how information is or is not shared within the executive branch—but that is the informational management role of the presidency, not the privilege. And, in any event, it’s the authority of the incumbent president, not a former chief executive.

Second, even if a former president may assert executive privilege over documents notwithstanding an incumbent’s determination not to do so, and even if he can do so against review by the executive branch itself, it would not follow from this that Trump would be entitled to the return of classified documents illegally held at Mar-a-Lago. Only the incumbent president has the authority to determine what documents are classified and to ensure they are protected accordingly. By contrast, a former president does not even have the right to view such documents—let alone possess them—unless the incumbent president chooses to allow it. Remember that this ruling is predicated on Rule 41(g), the remedy for which is the return of material. How could it be the case that a former president’s assertion of executive privilege could not only defeat the incumbent president’s judgment as to executive privilege but also nullify his classification authority and the federal government’s ownership of the material and thus require that classified documents be returned to an insecure facility? 

A third problem is that executive privilege functions differently when it comes to criminal investigations than in other circumstances. Cannon’s ruling doesn’t address the other Nixon case—U.S. v. Nixon, concerning the Watergate tapes. There, the Supreme Court found that Nixon’s invocation of executive privilege, while constitutionally grounded, could not overcome Special Prosecutor Leon Jaworski’s interest in obtaining the tapes as evidence in a criminal trial. The case concerned a criminal prosecution, rather than the earlier stages of a criminal investigation, but it nevertheless strongly suggests that any invocation of executive privilege by Trump—if one were even possible—would not be enough to shield materials from an ongoing criminal probe by the Justice Department. Indeed, the Justice Department pointed to U.S. v. Nixon on exactly this point in its response motion to Trump’s initial filing, quoting Nixon to argue that “the Executive Branch has a ‘demonstrated, specific need’ for the records at issue,” because “the records—and particularly any records marked as classified—are central to the investigation.”

Perhaps Cannon disagrees with the department’s reasoning. But given how directly U.S. v. Nixon speaks to the question of evaluating executive privilege claims in the context of a criminal probe, it’s strange that she doesn’t mention the case at all. 

Fourth, given how uncertain the law is on matters of executive privilege, it’s not clear at all how a special master would make the necessary determinations about which documents are privileged or what should happen to them if they are. Special masters in settings like this are typically used to determine issues of attorney-client privilege—an area of law in which the rules of the road are pretty well known. A special master confronted with the Mar-a-Lago documents would be hard-pressed to come to a definitive conclusion about which material is privileged under which doctrine and what outcome should flow from what sort of finding. And, as Greer points out, it’s not even clear that the special master would, as a practical matter, even be able to conduct the inquiries necessary to make a proper determination.  

There is, finally, an important factual issue on which Cannon is simply incorrect. She states that Biden has not weighed in on the matter of the Mar-a-Lago records being privileged. The judge writes in a footnote that “Plaintiff has not formally asserted executive privilege as to any specific materials, nor has the incumbent President upheld or withdrawn such an assertion.” This is wrong. It’s true that Trump made only a “protective” assertion of executive privilege, a means of preserving the ability to formally invoke the privilege in the future. But Cannon is wrong about President Biden. 

In a May 10 letter from the National Archives to Trump lawyer Evan Corcoran, Acting Archivist of the United States Debra Steidel Wall informed Corcoran that, according to the White House counsel, “President Biden defers to my determination, in consultation with the Assistant Attorney General for the Office of Legal Counsel, regarding whether or not I should uphold” Trump’s assertion. And Wall says that she has “decided not to honor the former President’s ‘protective’ claim of privilege,” on the grounds that “the Executive Branch here is seeking access to records belonging to, and in the custody of, the Federal Government itself.” She also notes that, according to the Office of Legal Counsel, protective assertions of privilege have only been made in response to requests for information by Congress, not by the executive itself. The Justice Department entered Wall’s May 10 letter into the record as an attachment to its lengthy opposition to Trump’s request for a special master.

The fact that the incumbent president has in fact determined not to honor Trump’s invocation of privilege seems highly relevant to Cannon’s analysis. It may be that Cannon would not view Biden’s decision as dispositive: She quotes Justice Brett Kavanaugh’s concurrence in Trump v. Thompson reasoning that “[a] former President must be able to successfully invoke the Presidential communications privilege for communications that occurred during his Presidency, even if the current President does not support the privilege claim.” But because of her factual error, she relieved herself of the burden of laying out her reasoning on this front.

Error #4: Normal people don’t get special masters when the FBI executes search warrants against them.

The idea of having a special master review seized material for attorney-client privilege is less controversial than either having one review for executive privilege or having a judge enjoin use of seized documents. It has some precedent, after all, and the standards are at least manageable, meaning that one can infer with reasonable accuracy what the special master would actually do. 

Yet it’s still wrong, though it may be an error with which the government can live. Normal people don’t get special masters to review for attorney-client privilege when the FBI executes search warrants against them and seizes their documents. The practice, as the government explained in its brief, is used almost exclusively in cases of searches of lawyer offices—where one might expect to find documents implicating lots of different clients’ privileges. Trump cited no contrary case in which a special master had been appointed to review for attorney-client privilege in a search targeted at a non-lawyer. He was asking for special treatment, and, again, he got it.

The error on this point may be harmless. Recall that this seems to be a small universe of pages—around 500—that are potentially subject to attorney-client privilege. To be privileged, a document must reflect communications or work product of Trump’s private attorneys or their agents; Trump has no privilege before a federal criminal investigation with White House counsel or other government lawyers. So this work, for a competent special master, would be brief if Judge Cannon’s order were limited to the attorney-client privilege. 

But harmless or not, it is an error for a judge to grant a special master in a case over which she has no jurisdiction in circumstances in which no normal criminal suspect could expect to get an additional layer of review. The action contributes to the growing sense that Trump demands and receives different treatment from the legal system than anyone else gets. And it’s corrosive for that reason. 

To put the matter simply, Judge Cannon’s opinion is wrong in almost every way it is possible for it to be wrong. How exactly the Justice Department handles the matter involves tactical and strategic considerations related to venue, the specific needs of the investigation, and the broader interests of the federal government. One way or another, however, expect the government to move decisively to erase this opinion from the books—and from the path of the FBI.

Quinta Jurecic is a fellow in Governance Studies at the Brookings Institution and a senior editor at Lawfare. She previously served as Lawfare's managing editor and as an editorial writer for the Washington Post.
Natalie Orpett is the executive editor of Lawfare and deputy general counsel of the Lawfare Institute. She was previously an attorney at the law firm Jenner & Block, where she focused on investigations and government controversies, and also maintained an active pro bono practice. She served as civilian counsel to a defendant in the Guantanamo Military Commissions for more than eight years. She also served as counsel to the National Security and Foreign Policy Legal Team of the Biden-Harris Transition Team.
Benjamin Wittes is editor in chief of Lawfare and a Senior Fellow in Governance Studies at the Brookings Institution. He is the author of several books.

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