Trump wanted a special master. So did a businessman. The judge treated them differently

Four months before U.S. District Judge Aileen Cannon granted Donald Trump’s request to have an independent special master review documents that the FBI seized from his Palm Beach estate, she rejected a similar bid from an indicted healthcare executive seeking the same treatment.

Newly unsealed documents show that, unlike in the former president’s case, Cannon found that a Justice Department “filter” team tasked with separating privileged attorney-client records from other evidence taken from South Florida businessman John Paul Gosney Jr.’s office would be able to do its job — no need for a neutral special master, she ruled in May.

How did Cannon’s decisions in the high-profile and low-profile cases turn out so differently?

Cannon, who was nominated by Trump to the federal bench and is under a microscope as she rules over his case, provided substantially different legal reasoning in the two cases, according to previously sealed court records that Cannon made public this week at the request of the Miami Herald.

Some observers told the Herald that it looks like Trump got favorable treatment and Gosney did not. But that would be looking strictly through the lens of partisan politics and not the legal cases cited in her rulings, according to experts who are familiar with the Justice Department’s use of filter teams as well as the appointment of special masters.

Under the Justice Department’s policy, a filter or “taint” team consists of agents and prosecutors who review records seized in a property search to protect confidential communications between an individual and his lawyer. Filter team members review the records first, consult with the defense and can then return any privileged materials to the defendant — a process that Cannon rejected in Trump’s case but approved in Gosney’s case. However, the filter team members cannot share that privileged information with investigators and cannot join them in the actual prosecution of a case.

The two cases

In September, after federal agents concerned with Trump’s handling of classified and top-secret government materials pulled boxes of documents from Trump’s Mar-a-Lago estate, Judge Cannon appointed an independent “special master” to examine what agents seized from his home to ensure that no privileged information between the former president and his attorneys was mixed in with the core evidence. Cannon’s ruling siding with Trump instead of the Justice Department generated national headlines and widespread commentary in both legal and political circles.

The judge, who has been on the federal bench in Fort Pierce since November 2020, concluded that “the appointment of a special master is not uncommon in the context of attorney-client privilege,” citing cases in New York and Miami.

In support of her decision, Cannon cited at least two instances where investigators saw privileged records belonging to Trump and then had to turn them over to a government “filter” team to set them apart from evidence in the Justice Department’s classified documents probe of the former president.

“Those instances alone, even if entirely inadvertent, yield questions about the adequacy of the filter review process,” Cannon found.

Cannon also focused her ruling on the “unprecedented circumstances” of seizing property from a former president’s residence in a criminal investigation, noting that “the stigma associated with the subject seizure [at Mar-a-Lago] is in a league of its own. ... A future indictment, based to any degree on property that ought to be returned [to him], would result in a reputational harm of a decidedly different order of magnitude.”

Yet just a few months earlier, Cannon took an opposite stand in a Medicare fraud case when a businessman asserted attorney-client protections after federal agents searched his Boca Raton office that he shared with his company’s lawyer. The defendant, Gosney, generally opposed the use of “any filter team” consisting of Justice Department prosecutors or agents, saying a “special master” would be a fairer arbiter to ensure potential attorney-client records didn’t fall into investigators’ hands.

READ MORE: Read for yourself: Here are the items the FBI took from Trump’s Mar-a-Lago office

Gosney’s Miami defense attorney, Howard Srebnick, argued that ideally the privileged records should first be reviewed by the defense — not the government’s filter team — to prevent the possibility of tainted information falling into the hands of investigators.

But Cannon sided with the Justice Department, while modifying the oversight of the filter team agents and criminal investigators so they don’t answer to the same government supervisor. The judge agreed to make her ruling and a handful of Justice Department documents public this week after the Herald’s lawyers with Holland & Knight intervened in the Gosney case and asked her to unseal them.

“Gosney provides no legal authority for the proposition that government filter teams are improper per se, and no such authority appears to exist,” Cannon ruled in Gosney’s case in May. “Rather, numerous courts [including federal appellate judges overseeing Florida, Ohio and Virginia] have approved of the use of filter teams involving independent government personnel.”

Then, earlier this month, the U.S. Supreme Court denied Srebnick’s separate petition on the same issue in an unrelated case involving the FBI’s search of a Miami investor’s office where his lawyer also worked.

Asked for comment, Srebnick pointed the Herald to a legal filing in Gosney’s case, in which he and Michael Dreeben, former U.S. deputy solicitor general, argued that “the attorney-client privilege and work-product protections are sacrosanct, and they are eroded whenever someone outside the privilege circle is permitted to see privileged material. The intrusion is at its apex when the unwanted eyes are those of the government.”

‘The bottom line’

The use of filter teams in property searches led by Justice Department investigators has generated some controversy over the past decade.

The Justice Department revised its filter team policy after incurring the wrath of a pair of district court and magistrate judges in Miami for mishandling the 2016 search of a major Medicare fraud suspect’s office where his in-house attorney also worked. The suspect, Philip Esformes, was also represented by Srebnick and his law partner, Roy Black.

Legal experts said it’s clear from her rulings in the Trump and Gosney cases that Judge Cannon viewed the issue of filter teams and the two defendants differently.

“Here’s the bottom line,” Miami attorney Joseph DeMaria said. “In Trump’s case, the question of whether a special master should be appointed is not unprecedented.” He noted examples of special masters being appointed in the New York federal investigations of Trump’s personal lawyers, Michael Cohen and Rudy Giuliani. “The Department of Justice gave her [Cannon] a reason to doubt the effectiveness of the taint team and gave the judge a basis to appoint the special master,” he said, noting the two mistakes cited by Cannon in the filter team’s review of Trump’s privileged correspondence with his lawyers.

“In contrast, Gosney did not give the judge a reason to doubt the taint team and was only asking for a blanket rule against taint teams,” said DeMaria, who worked in the Justice Department’s organized crime task force in Miami. “That’s not a winning argument.”

DeMaria and other legal experts said that, in Trump’s case, where Cannon appeared to have “gone too far” was in granting the Trump legal team’s request for an injunction to stop the Justice Department’s criminal probe of about 100 classified documents recovered from his estate at Mar-a-Lago during the FBI search on Aug. 8. The judge did, however, allow an intelligence agency to continue its assessment of whether disclosure of the classified materials posed any risk to national security.

In Trump’s civil case, the judge rebuffed the government’s insistence on using its filter team and allowed the special master to review everything seized from the former president’s residence, including classified documents, other government records, executive privilege materials and attorney-client privileged information. The day of the raid, the FBI seized roughly 11,000 government documents, 1,800 additional items, including photos, letters and newspaper clippings, and 500 pages of potential attorney-client privileged correspondence, according to court records.

Justice Department prosecutors challenged Judge Cannon’s ruling, focusing on her specific decision to halt their ongoing use of the classified materials found at Mar-a-Lago.

Cannon was partly overturned by the 11th U.S. Circuit Court of Appeals in Atlanta, which ruled that the Justice Department could continue to investigate the seized classified documents — which records show include “top secret” information about defense, national security and nuclear weapons issues. The appeals court also decided that the special master, New York federal Judge Raymond Dearie, could not review the classified materials. Trump’s lawyers asked the U.S. Supreme Court to weigh in, but on Thursday the court rejected their request.

In addition, the appeals court criticized Cannon for finding that Trump would experience “irreparable injury” if the Justice Department retained the classified, government and privileged materials in its documents probe. She cited the “serious, often indelible stigma” of the threat of future prosecution. But this risk, appellate judges said, did not establish irreparable harm. And if it did, they found, every potential defendant could ask a civil judge to exercise jurisdiction over criminal investigations in an effort to “restrain criminal prosecutions.”

Longtime Miami defense attorney Mark Schnapp, a former federal prosecutor in South Florida, concurred that Cannon exceeded her authority in putting the Justice Department’s classified documents investigation on hold during the special master’s review.

At the same time, Schnapp said that while he supports the idea of using a special master to examine seized property involving attorney-client privileged information, he believes Cannon’s justification for appointing one in Trump’s case was faulty. He noted that prosecutors had volunteered to turn over all of the potential attorney-client privileged documents seized at Mar-a-Lago to the former president’s legal team. Yet, the judge rejected the Justice Department’s offer, then found that its filter team made a couple of mistakes before deciding to appoint the special master.

“Instead of just saying ‘return the privileged documents to the president,’ she used that [mistake] as a basis for appointing a special master,” Schnapp said.

He added that in Gosney’s case, Cannon recognized that prosecutors could make the same mistake and approved a protocol allowing a defendant and his attorney to “claw back” privileged documents from the filter team and investigators.

Schnapp also said Cannon unnecessarily expanded Trump’s special master review beyond attorney-client correspondence to include executive-privilege records and classified materials.

Said Schnapp: “This review is much broader than past precedents and highly unusual.”