The Justice Department is running not one but several criminal investigations into President Donald Trump’s political enemies, according to a court filing by former CIA director John Brennan’s attorney.
That includes a federal grand jury run out of a tiny satellite federal courthouse in Fort Pierce, Florida, where Brennan is being required to testify next month. But a new declaration filed by Brennan defense attorney Kenneth Wainstein says a Trump administration official told him there were “multiple ‘viable’ grand jury investigations.”
Wainstein’s filing noted that Kurt Olsen is taking a leading role in the investigation — meaning Olsen, a MAGA loyalist who helped Trump challenge 2020 election results by presenting conspiracy theories, is likely preparing to relitigate that election.
“Mr. Olsen fielded our inquiries and indicated there are multiple ‘viable’ grand jury investigations, including a ‘far-reaching’ investigation in Fort Pierce that includes ‘issues at Mar-a-Lago and beyond’ into whether President Trump had his civil rights violated,” Wainstein wrote.
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The declaration was filed as part of Brennan’s lawsuit in D.C., where he’s asking a federal judge to order that the DOJ keep every shred of paper or email documenting the ongoing prosecution — with the expectation that the former CIA director will need it to defend himself in court.
Wainstein’s declaration says that Olsen’s comments about the nature of the investigation came up during a Sept. 11 conference call, with Brennan’s two defense lawyers on one end of the call and Olsen and three other members of the prosecution team on the other.
Olsen’s description of investigators’ interest in Mar-a-Lago, Trump’s Palm Beach resort, indicates two things: that the government is using its location to launch the investigation in South Florida, and that former special counsel Jack Smith’s decision to have the FBI raid the house is part of the case.
The only sitting judge in the Fort Pierce courthouse is U.S. District Judge Aileen Cannon, who was appointed by Trump during his first term and later dismissed the criminal indictment against him filed by Smith months before the 2024 election that sent Trump back to the White House.
Prosecutors also appeared to tell Brennan’s lawyers that the former CIA director is a “target” of a narrower inquiry, but that he’s merely a “subject” of the “more wide-ranging conspiracy,” Wainstein’s filing states. However, the smaller investigation was portrayed as potentially a part of the larger one, creating a confusing distinction.
The revelations from Wainstein, who once oversaw the creation of the DOJ’s National Security Division, shed light on parts of what portends to be a wide-ranging effort by the Trump administration to exact vengeance on former government leaders. Trump has long held those leaders personally responsible for tainting his first term with politically motivated investigations into his alleged criminal ties to Russia’s Vladimir Putin.
Wainstein also provided a window into the chaos in the ongoing DOJ criminal probes, noting that the investigations continue despite the sudden departure last week of Joseph diGenova, a Trump loyalist who had been overseeing the effort.
According to Wainstein’s filing, diGenova signed the subpoena for Brennan’s testimony on Wednesday, and the government emailed it to Brennan’s lawyer on Thursday. But when Wainstein texted diGenova about it that same morning, diGenova responded that he would “arrange counsel” to speak to Brennan’s lawyer.
Within hours, news broke that diGenova had quit — telling the New York Post that “if you want indictments where there’s no evidence, you have an ethical problem.”
Several sources have told The Washington Sun that the ongoing probes involved an FBI unit known colloquially as the “payback squad” but carries the formal designation “Director’s Advisory Team.” According to these sources, the team includes John Charles Eckenrode, who once worked on special counsel John Durham’s probe into the origins of the Trump-Russia investigation, and FBI special agent Rosemaria Vasiliki Marketos, who was passed up for Jack Smith’s special counsel team and has repeated Trump’s oft-disproven conspiracy theories about the 2020 election being stolen.
In the D.C. case, Brennan’s lawyers made clear when they sued on July 1 that they will fight any criminal charges by pointing to evidence that he “is being vindictively singled out for investigation and prosecution.”
“Given these strong indicia of vindictiveness, Director Brennan expects that he will forcefully challenge any eventual indictment as the product of an unconstitutionally vindictive and selective prosecution,” they wrote in their complaint.
In court papers, the DOJ has called Brennan’s attempt an “unprecedented step of managing potential discovery” in what it called “a hypothetical future criminal case in Florida.” Prosecutors also dodged any discussion of Brennan’s concerns that the Trump administration deliberately chose to pursue criminal charges in Cannon’s courthouse — far from where most of the actions in question took place in Washington, D.C.
“The government declines to engage with speculative allegations of judge-shopping regarding a hypothetical indictment,” Jeremy Newman, the chief litigation counsel at the DOJ’s civil division, responded July 28.
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