As a former federal prosecutor and white-collar criminal defense attorney in New York for more than four decades, I have been continually amazed by the inexplicable choices made by so many of the lawyers representing Donald Trump. Tuesday’s hearing before Eastern District of New York Senior Judge Raymond Dearie—who was appointed by Southern District of Florida Judge Aileen Cannon as special master to determine the validity of Trump’s claims of executive and related privileges covering the documents seized at Mar-a-Lago—only reinforces the belief that Trump’s lawyers’ penchant for undermining their client’s position continues unabated.
The Mar-a-Lago madness is, of course, only the most recent example. On the extreme end, we have the astounding degree to which members of his legal team have made public statements and court filings containing specious legal arguments and readily provable lies about the 2020 election. Their willingness to cross ethical boundaries very few lawyers would even approach is beyond comprehension, as such conduct is the antithesis of what lawyers are educated, trained, and required to do. Not surprisingly, some of the Trump lawyers are beginning to face the consequences. Rudy Giuliani has reportedly been a target of more than one grand jury investigation, has had his license to practice law in New York State suspended, and faces potential financial ruin in a civil lawsuit filed by Dominion Voting Systems.* John Eastman, who was told by a White Counsel staff member that he needed to “get a ‘effing great criminal defense lawyer” because of his unlawful attempts to overturn the 2020 election, had his cell phone seized by federal agents. Jeffrey Clark, who Trump tried to install as attorney general as part of his effort to overturn the last election, had his home searched. Election conspiracy advocate Sidney Powell is reportedly both a grand jury target and a co-defendant in the Dominion lawsuit. Most recently, Trump’s Florida counsel Christina Bobb signed and submitted to the FBI what appears to be a false affidavit concerning the presence of classified documents at Mar-a-Lago. Trump’s former, longtime lawyer Michael Cohen went to prison for Trump because of an illegal effort during the 2016 election to coverup an alleged affair with an adult film performer. And this is not even a complete list.
But even many of the Trump lawyers’ actions that do not cross legal or ethical lines cannot be rationally explained, which brings us to Tuesday’s hearing. I and so many others have been unable to figure out why in the world the Trump legal team nominated Judge Dearie to serve as Mar-a-Lago special master in the first place. Yes, Judge Dearie is apparently a Republican, and yes, he was appointed to the bench by President Ronald Reagan. But, really, Judge Dearie? Didn’t Team Trump know that the person they were choosing to uphold their dubious legal position is among the most respected members of the New York federal judiciary, admired for decades by prosecutors and defense counsel alike for his rational, ”by the book” approach?
Given Judge Dearie’s reputation for integrity and objectivity, it is no surprise that the Department of Justice quickly agreed to his appointment. After all, DOJ is appropriately convinced its legal position on the Mar-a-Lago seizure will be upheld by any fair minded, experienced judge, one like, say, Raymond Dearie. But from the Trump perspective, having lucked into the clearly sympathetic Judge Cannon to oversee the Florida seizure litigation, why would they let a model of judicial objectivity serve as special master to make key rulings in a matter in which they are, as a matter of law, flying by the seat of their pants? Why not just nominate another member of the Federalist Society with ties to the Republican right? Had they done so, the Department of Justice would have surely objected to both of their nominees, leaving it to Judge Cannon to make the selection. Given her rulings thus far, it would have been a good bet she would have chosen a Trump nominee, or at least selected a new special counsel of her choice who might have had sympathies consistent with her own.
As evidenced by Tuesday’s proceedings, there can be little doubt that the Trump team will not be pleased with Judge Dearie’s ultimate findings. The judge pressed team Trump to establish by sworn affidavit any declassification of the documents seized as Trump has asserted publicly, but his defense team has refused to say clearly one way or the other in court. When Trump lawyer James Trusty objected to providing such detail, saying to do so would fully disclose the Trump defense to any potential indictment, Judge Dearie responded that Trusty “could not have his cake and eat it too.” Given the pending appeal of Judge Cannon’s earlier rulings, and her ultimate oversight of Judge Dearie, how this ultimately plays out is unclear, but Team Trump did not have a good day.
In the end, both Trump and Judge Cannon will be hard pressed to preclude the inevitable result: the DOJ Mar-a-Lago probe will proceed, classified documents in hand. While this will surely be unwelcome news for Trump, who will find it difficult to attack a judge he himself recommended, it may be a blessing for Judge Cannon. Judge Dearie’s ability to satisfactorily resolve the executive privilege claims at the center of the dispute, the credibility of which will be enhanced by his reputation, gives Judge Cannon the perfect exit vehicle to uphold what is left of hers.
Which brings us back to the mystery of how Trump’s legal team undermined its own litigation strategy with the Dearie recommendation. A recent Axios article offers a possible explanation that if true, only underscores the problematic nature of their selection analysis. According to Axios sources, the Trump lawyers picked Judge Dearie because years ago, in his FISA Court role, he approved search warrants in the Carter Page investigation unaware that the FBI statements he relied upon were both materially false and incomplete. As a result, per this analysis, they believed Judge Dearie became “a deep skeptic of the FBI” and would perform his special master role with that jaundiced perspective. So, if this information is accurate, these lawyers concluded that a judge known for his integrity, objectivity, and career-long determination to follow the law, who served on the FISA Court for seven years and, thus, regularly came face to face with the enormous task our intelligence services have in keeping the country safe, would be influenced by a years-old grudge he very likely never had, to conduct himself in a manner completely antithetical to experience and, most importantly, to his very core.
Whether or not this explanation is true, the decision to nominate Judge Dearie was an easily predictable gift to prosecutors. Expecting Raymond Dearie to blindly uphold their extreme legal position is also evidence that the Trump legal teams’ addiction to self-inflicted wounds continues, as does the hemorrhaging of their client’s ability to avoid criminal prosecution.
Correction, Sept. 20, 2022: This piece originally misspelled Rudy Giuliani’s first name.