It appears that the appointment of Judge Raymond Dearie, made special master for the classified documents investigation, might already be causing headaches for former President Donald Trump.
Despite picking Dearie, who will investigate any privilege violations among documents seized by the FBI from Trump's Mar-a-Lago residence, the former president's legal team are already resisting some of the special master's requests.
In a court filing on Monday, the team argued they shouldn't be expected to disclose additional details around the purported declassification of documents taken by FBI agents from Mar-a-Lago, a move derided by some legal experts.
However, according to some commentators, Dearie might yet face difficulties of his own, associated with his involvement in previous investigations surrounding the former president.
Some have suggested that Dearie's approval in a 2016 investigation of Carter Page, former Trump campaign foreign policy adviser, could present a conflict of interest and prematurely end his review of the Mar-a-Lago documents.
Dearie approved federal investigators' request to investigate Page as part of the inquiry into Russia interference in the 2016 presidential election.
Investigative journalist Scott Stedman, in a tweet posted on September 16, suggested that "there's going to be a huge problem if the Trump docs include the Page FISA. Dearie then has a big conflict of interest and likely can't continue."
Similar comments were repeated elsewhere on the social media platform.
I see possible perceived conflict if Dearie reviews a doc containing intel from a FISA he approved. It won’t be readily apparent from the doc but he could recognize the subject matter. Unsure if risk assessment would flag this yet, if at all. Neutral/objective challenge by Trump?
— Frank Figliuzzi (@FrankFigliuzzi1) September 17, 2022
So, could the Foreign Intelligence Surveillance Act (FISA) investigation of Page derail Dearie's involvement as special master?
First, we don't know if the Page FISA records are at Mar-a-Lago. This is entirely speculative and appears to be spurred simply by Dearie's appointment.
While the FBI Mar-a-Lago affidavit revealed that documents found at Mar-a-Lago included FISA papers, that isn't a smoking gun for documents related to the Page investigation.
To provide some context, the investigation into Page's Russia connections took place while Trump was still president, in the midst of an ongoing FBI investigation into Trump's connections with Russia.
The Mueller report, published in 2019, concluded that the investigation had not established "that Page coordinated with the Russian government in its efforts to interfere with the 2016 presidential election."
Though the Justice Department in 2019 determined the last two of four FISA warrants to surveil Page were invalid, Page's resulting lawsuit against the Justice Department was dismissed by a federal judge in September.
On the face of it, it seems that even if there were Page FISA records among the documents at Mar-a-Lago, Dearie is simply being asked to judge whether the documents recovered from it attract certain privileges.
Dearie is set to wade through thousands of pages, then report back to Judge Aileen Cannon, and state whether any of the documents violated privileges that Trump's defense has inquired about.
So, not only do we not know whether there are even any documents related to the Page FISA warrant, it does not appear that Dearie would, as special master, even have to face the possibility of a conflict of interest.
Jimmy Gurulé, professor of law at the Notre Dame Law School and a former federal prosecutor, told Newsweek: "Any claim of a conflict of interest is highly speculative and overstated at this point.
"Unless I am missing something, I don't know why Judge Dearie's approval of the Page FISA warrant would create a conflict of interest or even an appearance of a conflict of interest that he could not impartially determine whether documents seized at Mar-a-Lago fall within the attorney-client or executive privilege."
Robert Fisher, a partner at law firm Nixon Peabody with about 16 years of experience in federal and state prosecution, told Newsweek that although the Page FISA warrant was classified, there didn't appear to be a link between that and the purported privilege that Dearie is investigating.
"If you're asking the judge to weigh on whether the Carter Page FISA warrant was justified and met the standards then, OK, that may be a conflict issue," Fisher said.
"But here, he's only deciding whether there's an attorney client privilege on any of the documents, and therefore the DOJ can't see them, or whether there's some type of executive privilege, basically, whether there are government materials, personal materials.
"Now, he [Dearie] may be aware of the Carter Page investigation, that he signed off on the FISA warrant, but if he sees one of those documents that may be relevant to the Carter Page investigation I don't see how his having allowed the FISA warrant is going to impact his decision on whether they're government documents or personal documents or what privileges apply. I just don't see the connection."
Fisher, who has expertise in government investigations and white collar defense practice, added that while there could be certain privileges attached to documents related to the FISA warrant in some way, Dearie would conclude on those matters only, "not the underlying facts of the Carter Page investigation (and) whether that was meritorious or not."
Any risk to Judge Dearie's appointment, Fisher argued, "may be less of an absolute legal issue and more of an optics issue.
"You want the public to be assured that a special master involved in this was completely objective and neutral, and in the eyes of the public, particularly people who are defenders of President Trump, will they be confident that this special master was neutral?
"From an optics perspective, maybe not? Maybe they won't, they'll say, 'Well, you know what, he was involved in that. We don't think that was legitimate, and therefore he cannot be objective and neutral in this matter.'"
Of course, opponents would counter that it was Trump's representatives that picked Dearie as special master, despite his involvement with the Page case.
Gene Rossi, a former federal prosecutor with almost 30 years of experience, echoed this and added what he saw as Dearie's capability.
"The Trump people have asked for Judge Dearie and I cannot think of a better person to be a special master in this case than Judge Dearie," Rossi said.
"He's a former federal prosecutor, he's a former U.S. Attorney, he's been a judge for decades, he has incredible judicial temperament and no one can question his moral compass and his integrity. So for the Department of Justice, Judge Dearie is the perfect choice to be a special master."
While the possibility cannot be ruled out that Trump's legal team might raise the FISA case as a potential conflict of interest and demand the judge's removal in the future, there is no evidence at the moment to suggest this is the direction they will take.
Instead, the defense has signaled Tuesday that it might already be preparing for a potential indictment.
Trump's attorneys have argued that submitting a draft plan about the declassification of documents to the special master would force them to disclose their defense against any indictments that could be issued at a later point, an implicit acknowledgement that the investigation could result in an indictment.
"The Special Master process will have forced the Plaintiff to fully and specifically disclose a defense to the merits of any subsequent indictment without such a requirement being evident in the District Court's order," the letter read.
Newsweek reached out to Trump for comment.
