Judge’s Snub Could Give DOJ Second Thoughts about Appeal in Trump Case

Former president Donald Trump takes the stage at the Conservative Political Action Conference in Dallas, Texas, August 6, 2022. (Brian Snyder/Reuters)

The latest directive, for all its flaws, gives prosecutors a path to prompt access to the classified files they need for their investigation.

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The latest directive, for all its flaws, gives prosecutors a path to prompt access to the classified files they need for their investigation.

J udge Aileen Cannon has rejected the Justice Department’s proposal of a compromise that would have avoided an appeal of her order appointing a special master to review documents seized from former president Donald Trump’s Mar-a-Lago resort by the FBI.

Judge Cannon’s ten-page order was issued on Thursday evening. That’s because prosecutors had vowed to seek redress in the Eleventh Circuit Court of Appeals if she had not partially reversed herself by today. Nevertheless, I suspect the Justice Department is having second thoughts about appealing. Cannon’s latest directive, for all its flaws, gives prosecutors a path to prompt access to the seized classified documents they need to proceed with their investigation — whereas even a successful appeal could entail weeks or months of delay.

In her original September 5 ruling, Cannon (a) ordered that all seizures (reportedly, over 11,000 documents and items) be reviewed by a special master to determine whether they are privileged; and (b) barred the government from using any of the seizures in its criminal investigation until this special-master review was completed. Last Thursday, the Justice Department countered that, while it believes Cannon’s ruling was entirely wrong, it might be willing to forego an appeal and live with the special-master review if Cannon modified her directive by excluding the small subset of approximately 100 documents bearing classified markings from both the special-master review and the order suspending the government’s use of seized documents in its ongoing criminal probe.

In last night’s order, Cannon declined to take either of those steps. But she offered an enticing compromise solution of her own — one in which DOJ would accept the special master and potentially get a quick resolution on the classified documents. Directly addressing the government’s concerns about damage to its investigation, Cannon wrote:

The Court will direct the Special Master to prioritize review of the approximately 100 documents marked classified (and papers physically attached thereto), and thereafter consider prompt adjustments to the Court’s Orders as necessary.

In tandem with this directive, Cannon has appointed senior district judge Raymond J. Dearie, of the U.S. District Court for the Eastern District of New York (EDNY), to serve as special master. (Judge Dearie, 78, is not retired, as one of my priors posts suggested; he took senior status and its more limited docket over a decade ago, and some reporting has indicated that he plans to retire at the end of this year.)

Though Judge Dearie was initially proposed by former president Trump’s lawyers, the Justice Department quickly agreed that he was well qualified for the assignment. No surprise there: Prior to his appointment to the EDNY bench by President Reagan, Judge Dearie was the U.S. attorney — the Justice Department’s chief prosecutor in the district. Moreover, one of Dearie’s most recent assignments, after serving as the EDNY’s chief judge for four years, was his appointment by Chief Justice John Roberts to a seven-year stint on the Foreign Intelligence Surveillance Court — a term that ended in 2019. In that capacity, Dearie was not only steeped in highly classified intelligence; he was schooled in and had to abide by the government’s exacting rules on the handling and storage of national-defense secrets.

To put it mildly, I would not expect Judge Dearie to be sympathetic to Trump’s cavalier treatment of classified documents, nor to his unsubstantiated claims that he de-classified top-secret intelligence en masse (which was, if it took place, condemnably irresponsible). I would expect Dearie to be alarmed by the possibility that classified information may still be missing, and sympathetic to the government’s claim that it is imperative to get the seized classified documents in the hands of the criminal investigators who are trying to track down any such missing documents. That is, Dearie is likely to see the urgency of reviewing the documents marked classified, to prioritize that task (as Cannon has directed), to conclude in short order that those documents are not covered by any plausible claim of executive privilege, and to recommend to Cannon that those documents be released forthwith to the prosecutors for the criminal investigation.

On Twitter, the New York Times’ Maggie Haberman, who reported on the EDNY beat back when Dearie was an active judge, observes that “he is known as exceptionally slow in his pace.” This is true enough. But the appellate process can be exceptionally slow, too — and Dearie could be expected to get through the 100 documents as to which privilege claims are likely implausible much more quickly than the other 11,000-plus items seized, which are less important in the grand scheme of things.

To be sure, the Justice Department will be tempted to appeal. In last night’s order, Judge Cannon essentially doubled down on all the flaws of her initial ruling (which I’ve outlined here and here). In particular, she attempted no explanation of how the former president could plausibly claim executive privilege against the incumbent executive branch. And mind you, the case before her involves an ongoing criminal investigation of potential national-security breaches; that is, it implicates executive interests that are much more significant than others that the courts have nevertheless relied on in rejecting a former president’s privilege claim in the past. (As we’ve previously discussed, in Nixon v. Administrator (1977), the case that dubiously recognized a former president’s highly qualified retention of executive privilege, the Supreme Court reasoned that such a claim would have to give way to an executive agency’s need to archive government records — a trivial interest compared to stakes in the Mar-a-Lago probe.)

Moreover, Cannon indulged Trump’s claim that the documents marked classified might no longer be classified — even though he provided no affidavit attesting that he declassified them, his lawyers have taken pains to avoid claiming that he did, and the known facts indicate that Trump made no such claim when it would have made sense to do so if he had, in fact, declassified the documents. Cannon did not grapple with the lack of declassification proof; she just peremptorily said that it would be fairer to let a special master sort things out.

Cannon also engaged in factitious parsing of the Justice Department’s objection to her suspension of its use of the classified documents in the criminal investigation. Prosecutors contend, in reliance on a testimonial statement from a top FBI counterintelligence agent, that the criminal investigation is “inextricably intertwined” with the risk assessment that Cannon has permitted the FBI and other intelligence agencies to conduct (to determine the potential national-security implications of the documents’ mishandling). Cannon first mined from the agent’s statement his commonsense assertion that it would be “exceeding difficult” to bifurcate the criminal investigation and the risk assessment; then she concluded that mere exceeding difficulty does not mean the two tasks are so inextricably intertwined that they can’t be compartmentalized.

Notably, the judge’s stated rationale for these verbal gymnastics is that the court “cannot abdicate its control over questions of privilege.” If you’re keeping score, these would be the same “questions of privilege” that Judge Cannon has avoided addressing, much less deciding, despite the Justice Department’s pointed contention that Trump lacks the executive privilege he is claiming.

In sum, Judge Cannon’s reasoning gives the Justice Department plenty of rich grounds for appeal. But while success on appeal may be likely, it is not certain, and the appeals process might take a long time. By contrast, Judge Dearie should be able to get through the classified documents in just a few days, even if he is deliberate. He is highly likely to rule in the Justice Department’s favor on the classified documents. And now that Cannon has planted her feet on the reliability of Dearie’s review, she would be hard-pressed not to accede to any recommendation he makes — particularly considering that he has ample experience in national-security matters and she doesn’t.

The Justice Department could immediately seek an expedited appeal, but it would be better off swallowing hard and accepting the special master, at least for now. It is reasonable to expect that Judge Dearie’s review, at least as to the seizures with classified markings, would be expeditious. That would place them in the prosecutors’ hands for full use in the criminal investigation more quickly — maybe much more quickly — than a successful appeal would.

By rule, the Justice Department has 30 days to file a notice of appeal. Even if that clock is deemed to have started on September 5 (when Judge Cannon issued her first ruling), rather than yesterday (when she rejected the government’s motion to reconsider), the government will still have nearly three weeks from now to decide whether an appeal is warranted. That should be enough time to assess whether Judge Dearie is moving efficiently through the special-master review, starting with the classified documents. If the early returns show Dearie to be unduly slow or erratic, prosecutors can appeal in early October. Until then, it is in their interests to hold off in the expectation that the experienced special master will see things their way, obviating any need for an appeal.

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