DOJ investigation into Trump's enemies suffers a massive leadership blow

A major Justice Department investigation into an alleged "grand conspiracy" against President Donald Trump has suffered another high-profile blow following the abrupt resignation of a second senior prosecutor in less than a month. Kurt Olsen, a prominent attorney who previously backed Trump’s legal challenges regarding the 2020 election, stepped down from the closely watched inquiry on Monday, September 28, 2026, amid issues involving his security clearance.

Olsen’s unexpected departure marks the latest sign of significant upheaval for the yearlong investigation, which is headquartered in Florida. His exit follows just three weeks after the team's lead prosecutor, Joseph diGenova, also resigned. DiGenova, an 81-year-old former U.S. attorney during the Reagan administration and a long-time Trump ally, reportedly stepped down after superiors grew impatient with the prolonged timeline required to bring formal charges. The dual departures leave the future of the federal probe in a state of deep uncertainty.

The Justice Department's inquiry focuses on whether previous government officials illegally conspired to deprive Trump of his rights while investigating his 2016 campaign and his retention of classified documents at Mar-a-Lago. Investigators have demanded extensive testimony and records from individuals involved in those initial Trump-related inquiries, seeking evidence of institutional bias or coordinated misconduct. However, critics have increasingly described the federal probe as a meandering, fits-and-starts operation built on unsubstantiated theories.

Olsen’s prominent role within the case had only recently come to light. Earlier in September, an attorney representing former CIA Director John Brennan disclosed that Olsen had been coordinating a subpoena to compel Brennan's testimony before a federal grand jury in Fort Pierce, Florida. According to Brennan’s legal team, Olsen indicated that the former CIA chief remains a central target of a narrower false statements investigation connected to the overarching probe.

Internal friction has plagued the prosecution team for months. In April 2026, a lead national security prosecutor assigned to the Brennan aspect of the case was reassigned after raising serious internal concerns regarding the actual legal strength and viability of the charges. Days later, diGenova was officially sworn in to take command of the unit before his own recent resignation.

Olsen’s background made him a highly unconventional pick for a complex Department of Justice probe, given his complete lack of prior experience as a federal prosecutor. Before joining the Justice Department to work on election security and integrity, Olsen served in a White House advisory post. He previously assisted Texas Attorney General Ken Paxton in a Supreme Court challenge regarding the 2020 election results and subsequently represented Kari Lake during her legal challenge of the 2022 Arizona gubernatorial election.

As the "grand conspiracy" investigation faces a leadership vacuum, it remains entirely unclear whether any formal criminal indictments will ever be brought, or what substantive evidence prosecutors have compiled to validate the premise of a government-wide plot.