Jeannine Pirro, the former Fox News personality turned federal prosecutor in Washington, is now seen as a main figure in a Justice Department issue of losing in court even more than Pam Bondi’s DOJ.
A New York Times report placed Pirro at the center of an investigation into how prosecutors and Trump appointees in U.S. attorney offices have struggled to convince grand juries to approve indictments. Some cases have failed to progress even after charges were filed.
NYT labeled this situation as an “unusually high rate of failure” for prosecutors trying to secure indictments and convictions on cases that match the president’s priorities. The report stated that this pattern is not confined to one office or one lawyer, but it pointed out Pirro’s Washington, D.C., office as particularly noteworthy.
The report mentioned Lindsey Halligan, a former real estate lawyer turned prosecutor, who has gained attention for mishandling cases involving former FBI Director James Comey and New York Attorney General Letitia James. However, the Times noted that Pirro “may have the poorest track record overall.”
Pirro’s background has always been part of her public persona. Before she became a conservative media figure, she worked as a prosecutor. Now, as the head of the U.S. attorney’s office in Washington, she oversees cases in a city where juries can be doubtful of politically charged prosecutions, especially those involving Trump, his critics, or his administration.
NYT highlighted problems that have become ongoing issues for the department, noting that jurors are not convinced by what prosecutors present.
Trump-appointed D.C. Attorney Jeanine Pirro is losing case after case amid the president’s federal takeover—the judge calling her latest attempt to jail a local attorney and West Point graduate “one of the weakest requests for detention” he’d ever seen.https://t.co/UwWiU0JGEz pic.twitter.com/xlAlAVZ0gN
— The New Republic (@newrepublic) August 29, 2025
As Glenn Thrush and Alan Feuer from the Times reported, “In recent months, grand jurors in Washington rejected efforts to indict or convict anti-Trump activists: a woman who posted a threat against Mr. Trump on Instagram and, most famously, a Justice Department employee who threw a sandwich at federal officers.”
The sandwich case stands out in the report. Pirro’s office prosecuted Sean Dunn after he was accused of throwing a sandwich at a U.S. Customs and Border Protection officer in Washington, D.C. This case did not end with a conviction, contributing to the Times’ broader point about repeated failures.
The report then suggested that Pirro’s office has often fallen short even when prosecutors tried various approaches. “That distinction appears to belong to Jeanine Pirro, the U.S. attorney in Washington, whose office failed three times to secure an indictment against a woman who pushed an F.B.I. agent against a wall during a protest over the summer,” they wrote. “Even when Ms. Pirro’s subordinates changed strategy and pursued misdemeanor charges that did not require an indictment, a trial jury acquitted the woman completely.”
Overall, these details paint a troubling picture for Pirro and Trump’s Justice Department. Grand juries are refusing to indict in certain cases, and even when prosecutors shift strategies to avoid the grand jury step, juries are still not cooperating. This is not just an internal problem; it is a public issue as well. In a system that relies on persuading citizens, repeated losses can become a significant story in themselves.
The Times report does not claim that prosecutors should win every case, but it outlines a series of outcomes that, in the context of Trump’s agenda, seem more like a pattern than mere coincidences.
