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Dear Reader,

I can name only two professions where, at the end of every skirmish, some neutral arbiter formally declares one side the winner and the other the loser: combat sports and criminal prosecution. Like boxing or mixed martial arts, the law is often a zero-sum game. Almost by definition, one side’s gain is the other’s loss. 

Yet, somehow, the Special Master’s review of documents seized by the FBI at Mar-a-Lago has become a lose-lose scenario. It’s going dreadfully for Donald Trump – who fought to have a Special Master appointed in the first place, then got his own guy named to the role, and now is paying for it (financially and tactically). But it’s also been a drag for Justice Department prosecutors, as valuable time ticks away while they struggle just to get their heads back above water.

Trump and his legal team won the first round, it seemed, when Judge Aileen Cannon granted their initial request – over DOJ’s furious objection – to appoint a Special Master to review the Mar-a-Lago documents. Trump’s win seemed twofold: he’d have an outsider who could put a check on DOJ’s ability to make unilateral determinations about attorney-client and executive privileges, and he’d generally muck up and slow down the entire document review process. (Looking back at Trump’s recent legal history, he hasn’t actually won often in the courts, but he has succeeded in creating and exploiting delay; what ever happened to that congressional investigation that followed the Mueller report and was supposed to get Trump impeached, anyway?) Trump then scored an apparent followup win of sorts when DOJ agreed to one of his proposed Special Master candidates, Senior U.S. District Court Judge Raymond Dearie, a 1986 judicial nominee of Ronald Reagan. 

Ever since then, however, Trump has been getting his ass kicked by the Special Master. Unsurprisingly, Judge Dearie has developed strong courtroom instincts during his 36 years on the bench in Brooklyn. He immediately homed in on two of Trump’s more untenable public claims: that he had declassified the documents and that the FBI had planted evidence. 

Both of those purported defenses started off strange and then got worse. At least 18 former administration officials have called Trump’s claims that he issued some blanket declassification order “a complete fiction,” “nonsense,” “ridiculous,” “laughable,” and “bullshit.” Trump most recently asserted that he could have declassified documents by “thinking about it.” Apparently, Trump is an adherent to the “magical thinking” principle: wish it and you can make it be. Even the most ardent “unitary executive” doctrinaire must concede that, while the president holds expansive constitutional powers, he has to actually exercise those powers while in office to make them effective, and he can’t just fantasize them into being after the fact. 

On the claim that the FBI planted evidence, which Trump first raised just hours after the search, the tell was right there from the start: how would Trump even have known that the FBI planted anything at that point, not having any information about what they actually did or did not seize?

Trump’s public claims have put his own legal team in a tight spot. Under core ethics rules, an attorney simply cannot make a knowingly false representation to a court. So we’ve seen the Trump legal team tap dance around these issues, notably without ever fully endorsing Trump’s claims: we need more time, we’re still investigating, we’ll address them later, and the like. 

But Judge Dearie was having none of these hedges, ordering Trump’s legal team to take a firm position on the declassification and planting issues, and to back up those claims with some morsel of proof. For the moment, however, Judge Cannon has bailed out Team Trump, ruling that Dearie exceeded his mandate in requiring concrete responses from Trump at this stage. But one feature of our legal system is you can only fake it for so long. Eventually – usually sooner than later – a judge or a jury will put you to your proof. 

While prosecutors surely are having a chuckle as Trump’s own chosen Special Master rakes him over the coals, the Justice Department is losing precious time. It has now been nearly eight weeks since the Mar-a-Lago search, and the Special Master is only just beginning his work. This process is certain to drag on through October and likely into November; Judge Cannon has set a November 30th target deadline, and Trump’s team, true to form, seems dead-set on stretching it out as far as possible. There’s a good reason why DOJ fought so furiously against the appointment of a Special Master in the first place. Prosecutors plainly surmised that the review process would complicate and extend their own investigation. They were right. 

Ultimately, when the Special Master completes his review and hands over non-privileged documents to prosecutors, the DOJ team will just return to where this all started: the very same documents that the FBI seized on August 8th will, finally, be back in their hands (minus any privileged documents, to which DOJ should not have had access in the first place). So even as Trump takes a beating in court, the end result for the Justice Department will be getting right back to square one.

DOJ can point to two silver linings. First, every time Trump articulates some defense and then gets called on it by the judge, that tips Trump’s strategic hand; as Trump’s own lawyers have conceded, they don’t want to take any positions now that might undermine future motions or defenses at trial. It’s a general rule of defense lawyering that you want to say as little as possible for as long as possible, to preserve your ability to raise defenses as needed later in the proceedings. But Trump is now being forced to take positions well before any litigant normally would. 

Second, while arguing the Special Master issue, DOJ has revealed to the public key details about the search, including that memorable photograph of the brightly-colored yellow and red classified document envelopes recovered at Trump’s beach resort. Through the Special Master litigation, the Justice Department has established to the American public that their search was both well-justified and legally proper. 

Maybe we got lulled a bit by the Special Master processes in the Michael Cohen and Rudy Giuliani cases. Both of those reviews were carried out efficiently and quietly. I suspect that has much to do with retired federal judge Barbara Jones, who served as Special Master in both cases. I appeared in front of Judge Jones many times at the SDNY, and she is among the absolute best in the business, brilliant at controlling her docket and her courtroom. Also worth noting: Donald J. Trump was not a party to either of those prior proceedings, and he has a unique knack for knocking the judicial process off its rails.  

The Mar-a-Lago Special Master process so far has been costly, confusing, and cumbersome. Trump’s best-case scenario now is to get through this without sustaining further damage to his own potential defenses, while DOJ’s optimal outcome is to get this thing over with and get on with their investigation. Sometimes in litigation, it turns out, neither side wins.

Stay Informed,

Elie