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‘Special Master’ to Trump: “You Can’t Have Your Cake and Eat It”

The investigation of the classified documents found at Mar-a-Lago is in a messy legal phase—here’s what to watch for.
September 21, 2022
‘Special Master’ to Trump: “You Can’t Have Your Cake and Eat It”
In this aerial view, former U.S. President Donald Trump's Mar-a-Lago estate is seen on September 14, 2022 in Palm Beach, Florida. (Photo by Joe Raedle/Getty Images)

A flurry of filings in several different courts has created a wad of legal confusion around exactly what is happening to the boxes of material seized by the FBI from Mar-a-Lago on August 8. To help sort through the perplexing details, here’s an explainer in three parts.

1. Who are the various judges involved?

So far, there are three judges and four different courts involved in this case.

The judge who signed the Mar-a-Lago search warrant relating to a variety of potential criminal offenses is Bruce E. Reinhart, who has been a magistrate judge for the Southern District of Florida since 2018. Federal magistrate judges are not appointed by presidents or confirmed by the U.S. Senate under Article III of the Constitution. They are appointed instead by majority vote of the active district, or trial-level, judges of the particular court involved, and can handle all matters authorized by the court except for felony cases. Magistrates serve not for life but for eight-year terms, and they often function as “helper” judges to the Article III district court judges for the purpose of things like fact discovery and settlement negotiations.

Judge Aileen M. Cannon, by contrast, is an Article III judge confirmed by the Senate and sitting for life. However, the matter before her was not filed under the criminal docket number. It is a civil action filed by Donald Trump seeking injunctive relief under civil standards—essentially, Trump used a back-door remedy to muck with the criminal matter pending before Judge Reinhart. It worked.

Like Cannon, Judge Raymond J. Dearie is a U.S. district judge. But instead of sitting in Florida, he serves on the United States District Court for the Eastern District of New York. He is on what’s called “senior status,” meaning he does not have a full docket of cases, unlike his more junior counterparts.

At Trump’s request, Cannon agreed to appoint a “special master” to review the documents seized at Mar-a-Lago. Special masters are even less constitutionally grounded than magistrate judges, and are often appointed to help with complex cases, such as class actions involving lots of mini-trials on damages. Cannon agreed to appoint a special master, Trump suggested Dearie, and the Department of Justice (DOJ) agreed with the suggestion, so Dearie was appointed. It is coincidental that he is also a federal judge—he could have been a lawyer or law professor, for example, and still served as a special master. As a result, Dearie’s orders are not filed under his Eastern District of New York designation. Instead, they are filed under the civil docket number governing the case before Cannon. Because he is a well-respected sitting federal judge, however, Dearie’s actions in this matter already strike legal observers as more authoritative than those of Cannon, a poorly qualified Trump appointee whose sloppy legal reasoning in this case thus far has already elicited intense backlash.

Although DOJ agreed to the suggestion of Dearie, it has also appealed Cannon’s order approving a special master to the 11th Circuit, and Cannon denied DOJ’s request to stay the special master process pending the appeal. So although Dearie has already begun his work in the role, the 11th Circuit could put a halt to the entire endeavor if DOJ wins its appeal.

2. Is the special master ruling a “win” for Trump?

Not really.

When Cannon first granted Trump’s motion, much of Twitter howled with outrage and anxiety over what it could mean for the investigation, particularly given the grave national security implications of Trump illegally removing boxes of top-secret information from the White House, transporting it to Florida, leaving it unsecured for months in a working private resort, stonewalling the National Archives and the FBI when asked for its return, and promising through counsel that everything was turned over when it wasn’t. By the time Trump filed his motion, two weeks had passed, and the FBI had already reviewed the recovered materials. Although Cannon enjoined “the Government from reviewing and using the seized materials for investigative purposes pending completion of the special master’s review,” she simultaneously allowed the Office of the Director of National Intelligence (ODNI) to continue its use of the materials for the purpose of “classification review and/or intelligence assessment.” Both entities are within the executive branch and ultimately answer to Joe Biden, which makes Cannon’s ruling a strange one. It creates an important practical problem: ODNI does not have the same investigative powers as the FBI, and would need to rely on the latter’s capacities to properly complete the national security investigation sanctioned in Cannon’s ruling. (It should go without saying that this lapse reveals a disturbing lack of understanding on Cannon’s part of how these government agencies function.)

Enter Judge Dearie, a lauded judge who once served on the Foreign Intelligence Surveillance Court. There is no doubt that he understands the need for an urgent resolution to his work as special master. While Cannon set a completion deadline of November 30, Dearie reportedly instructed the parties to disclose details about any materials Trump claims to have cavalierly “declassified” by October 7. (The transcript or order setting forth this directive does not appear to be public.) In a September 19 letter to the Court, Trump’s lawyers balked at this timeline, and also complained that “the Special Master process will have forced the Plaintiff to fully and specifically disclose a defense on the merits of any subsequent indictment without such a requirement being evident in the District Court’s [i.e., Cannon’s] order.”

Let’s unpack this.

Normally, if the government executes a search warrant and a defendant is later indicted, he or she can argue in defense that the search was conducted illegally and in violation of, say, the Fourth Amendment to the U.S. Constitution. Trump didn’t wait for this, instead sort of initiating a civil action under Rule 41(g) of the Federal Rules of Criminal Procedure, which allows a person subjected to a search to file a motion to get an order directing the government to return their property. The bulk of the unlawfully taken White House records are not Trump’s, of course, and Trump didn’t actually file that motion, instead merely hinting at it in his motion for a special master. In the September 19 letter, his lawyers claim that Dearie should not take up issues like declassification now; he should wait until Trump actually files the Rule 41 motion. And, they add, if Trump were to show his declassification hand now, it could come back to unfairly bite him later, if he is indicted.

Yesterday, at his first hearing as special master, Judge Dearie told Trump’s lawyers: “You can’t have your cake and eat it.” Trump jumped the gun with his filing instead of waiting for an indictment to raise complaints about the search. He managed to stall the government’s activity, so now he has to fess up to why that injunction, in Trump’s mind, is warranted. Dearie explained that he cannot assess whether any of the 11,000 documents seized were declassified based simply on the markings designating them as highly sensitive national security secrets.

Trump’s lawyers have painted him into a corner. Or, to put it another way, he has to show his cards (meaning: reveal that he has none) now that he’s won his special master ploy. Or he can abandon that effort, let the FBI do its work, wait to see if he’s indicted, and raise his legal defenses then.

Dearie also remarked that, if this were a criminal proceeding, the government would bear the burden of proving it could use the documents. But since Trump filed it as a civil action, it’s up to him to prove that the government cannot proceed. The government doesn’t have to “prove” anything at this point. It’s all on Trump. (Legal “ouch.”)

3. What is the special master actually tasked with deciding?

Nothing of substance, which is why Cannon’s decision has been so widely criticized.

Given that Judge Reinhart found probable cause for the search warrant, the government had the legal power to conduct the search and seize the documents. This is typically how both criminal and civil litigation works—one side has legal power to obtain information (in civil actions it’s called discovery). The other side can object to certain categories of information, but otherwise has to give up anything it has that is responsive to the search or the request, absent a valid objection.

It appears from Trump’s garbled initial filing that he raises four objections: (1) some material is covered by the attorney-client privilege; (2) some material is covered by executive privilege; (3) Trump declassified some material; and (4) some of it doesn’t belong to the government at all but instead amounts to Trump’s personal effects, like “photos, handwritten notes, and even President Trump’s passports” (the latter of which the FBI returned).

On attorney-client privilege, DOJ stated in its opposition to the special master request that “the government’s filter team has already completed its work of segregating any seized materials that are potentially subject to attorney-client privilege.” Keep in mind that Trump would only have a serious claim on these grounds to written communications pertaining to the giving or receipt of legal advice between him and his personal lawyers. Documents involving his communications with White House counsel as president would not be covered by his personal attorney-client privilege after leaving office. So this likely involves a small segment of materials that Dearie could dispense with rapidly and without much dispute between the parties.

Executive privilege belongs to the sitting president—which is to say, not to Donald Trump but his successor, Joe Biden. The law is pretty clear on this, and for common-sense reasons. The point of executive privilege is to enable presidents to seek advice on matters of national concern without worrying that the communications will become public. Once a president leaves office, the job of tending to the public interest—and thus deciding whether to exert executive privilege—passes on to the next president. Right now, Biden through his Justice Department is seeking to use the materials seized to further the public’s interest in national security, among other things. Citing language written by Justice Brett Kavanaugh (taken out of context from another case), Cannon ruled that there is a question mark over whether Trump can exert executive privilege against a sitting head of the executive branch in connection with Trump’s stealing of classified information from the White House. This analysis is nonsensical. There is no question mark. If Cannon were right, DOJ could not legally use classified information to investigate breaches of national security because the classified information would belong to Trump, even though he illegally took it, and not to the U.S. government. Trump will lose this argument in the 11th Circuit.

The third point is precisely the one on which Dearie called Trump’s bluff at yesterday’s hearing. Trump claims he declassified all the materials that were at Mar-a-Lago; Dearie is telling Trump to show the court the record reflecting that declassification process. DOJ correctly argued that this objection is beside the point anyway, as the Espionage Act (one of the legal bases for the search) doesn’t care if information is classified—it only refers to “defense information.” So a declassification determination would not make the documents irrelevant to DOJ’s probe, and even if it did, that wouldn’t mean that Trump gets to keep them. The declassification claim is just another sideshow that Trump put on to avert the public’s gaze from the real story here, which is that he took top secret information illicitly, and some of it is still missing; he dodged and weaved when asked for it; and it remains unclear whether some of it is floating out there still—possibly in the hands of adversaries. That’s what presumably worries Dearie most. Thank the legal heavens that he is squarely on the job.

Which brings us to the fourth and final category of potential objections to the seizure of materials from Mar-a-Lago: the trinkets that may be entirely personal to Trump and thus likely irrelevant to the investigation anyway. Presumably, the FBI would have had no objection to turning those over without the need for a court order, as it already did with Trump’s passports (which may actually be informative, as they were discovered in his Mar-a-Lago office desk drawer alongside classified documents, a detail that arguably bears on his knowledge and intent: Most people keep really important papers like passports—and especially potent classified documents—in a place they can easily and reliably retrieve them).

This is all to say, in short, that the special master saga is not a big deal legally for the FBI. And it is certainly not a win for Trump. It does delay things a bit, which is indeed bad—bad for the American people. After all, the documents that Trump took are unequivocally the American people’s records—not his—under a now-infamous federal law called the Presidential Records Act.

Kimberly Wehle

Kimberly Wehle is a contributor to The Bulwark. She served as an assistant U.S. attorney and an associate independent counsel in the Whitewater investigation. She is currently a professor at the University of Baltimore School of Law. An ABC News legal contributor, she is the author of three books with HarperCollins: How to Read the Constitution—and Why, What You Need to Know About Voting—and Why, and, most recently, How to Think Like a Lawyer and Why—A Common-Sense Guide to Everyday Dilemmas. Her new book, Pardon Power: How the Pardon System Works—and Why, is forthcoming in September 2024 from Woodhall Press. @kimwehle.