‘Judge Jeanine’ Is Learning It’s Hard to Be Trump’s Favorite Prosecutor

In that moment and others throughout her nearly yearlong tenure, Pirro has sought to emphasize her willingness to pursue cases Trump cares about. Her ability to manage a mercurial president, combined with their longstanding relationship, has made her a dark-horse candidate in MAGA circles to succeed   Pam Bondi   as the next attorney general.

But, as Bondi’s ouster demonstrated, Trump is looking for not only eagerness but also effectiveness in pursuit of his political adversaries, and that has proven a hurdle for Pirro. Many of her marquee efforts—from pursuing Powell and Democratic lawmakers, to prosecuting protesters—have been rejected by judges and juries. Trump has personally noted to advisers that some of her cases have flopped, and while he has privately praised her tenacity, Pirro isn’t currently a front-runner for the attorney general post, White House officials said.

Still, Pirro and her deputies remain undaunted.

In recent weeks, prosecutors in her office have been reviewing evidence and preparing to question witnesses as part of an   investigation opened last year   into whether former New York Gov.   Andrew Cuomo   lied to Congress about his actions during the Covid-19 outbreak, according to people familiar with the inquiry.

“President Trump has nothing but respect for the great Judge Jeanine Pirro, who is doing a tremendous job cleaning up Washington, D.C., and putting criminals behind bars,” White House press secretary   Karoline Leavitt   said.

Pirro, a former Fox News personality, said at a press conference Wednesday, “I’m doing what I know best, and I’m doing what I love. And that’s why I left a very nice life. That’s what the president has asked me to do.”

The   Cuomo investigation   stems from a referral by House Republicans accusing the former governor of lying in 2024 in   closed-door testimony   related to nursing-home deaths during the Covid pandemic.

A Cuomo spokesman declined to comment. In a previously released   letter to the Justice Department , the former governor’s lawyer characterized the original referral as “meritless” and politically motivated. The letter also said Cuomo testified truthfully when he said he didn’t recall events that occurred years earlier during a public-health crisis.

Pirro, a former district attorney and local judge in New York’s Westchester County, brings a personal history to the Cuomo investigation: In 2006, she lost to him in a bitter campaign for New York attorney general.

Justice Department leaders have sent another new investigation about congressional testimony to an office other than Pirro’s. The Justice Department’s Civil Rights Division is leading an inquiry into   Cassidy Hutchinson, a former Trump White House aide who drew the president’s ire with congressional testimony that implicated him in the Jan. 6, 2021, attack on the Capitol, according to people familiar with the matter. A representative for Hutchinson didn’t respond to a request for comment.

Pirro’s relationship with Trump goes back decades to their time in New York. In Trump’s first term, one of his final acts as president was pardoning Pirro’s ex-husband, lobbyist   Al Pirro, who was convicted of conspiracy and tax evasion in 2000.

After her recent string of high-profile losses, Pirro expressed frustration with the grand juries and judges in Washington to Trump and others in the White House, people familiar with the discussions said.

One federal judge,   James Boasberg, in March threw out her subpoenas to the Federal Reserve, ruling that they appeared designed solely to “harass and pressure” Powell to bend to Trump’s will. The probe sought to scrutinize the Fed’s headquarters renovation and whether Powell lied in congressional testimony about the project. Pirro called Boasberg an “activist judge” and said her office would appeal.

Boasberg’s ruling followed on the heels of Pirro’s office trying and   failing to persuade a grand jury   to indict six Democratic lawmakers who released a video last fall reminding military servicemembers of their obligation to refuse illegal orders. Jurors also have rejected efforts by Pirro’s office to prosecute aggressive cases stemming from Trump’s law-enforcement surge in the nation’s capital, including one against a man who   threw a sandwich at a federal agent .

Last year, Pirro hired two lawyers and conferred upon them the title of special counsel. One of them,   Steven Vandervelden, served as a local prosecutor during Pirro’s days as a district attorney and has also worked as a dance photographer.

Vandervelden supervised joint investigations by state and federal law enforcement and led the organized crime bureau for the district attorney’s office in a tenure that spanned more than 20 years, a spokesman for Pirro’s office said. 

Another special counsel,   Carlton Davis, once briefly worked as a federal prosecutor in eastern Virginia but has otherwise spent his career largely as a staff member for congressional Republicans, including Rep.   James Comer   of Kentucky, the chairman of the House Oversight Committee who   referred Cuomo for prosecution .

Davis and Vandervelden are both involved in the Cuomo investigation, according to people familiar with the inquiry. 

They also have been central in the Powell inquiry.

Davis sent a pair of emails in December to the Fed in hopes of arranging an in-person meeting, including one note that invited staff to “hop on a call”—language that struck some within the central bank as casual from a federal prosecutor, according to recently unsealed court records. 

Vandervelden in court filings argued that overruns in the Fed’s headquarters renovation raised the “specter of fraud” and that “possible discrepancies” in Powell’s congressional testimony raised the “specter of false statements.”

But another lawyer—a longtime federal prosecutor appearing in court on his second day working for Pirro—conceded that her office so far didn’t know whether there was any evidence of misconduct. Boasberg would later rule that prosecutors had “offered no evidence whatsoever that Powell committed any crime other than displeasing the president.”

Absent intervention from a higher court, Pirro’s investigation is all but dead.