Long before she was a Fox News host who pushed pro-Trump election conspiracy theories, Jeanine Pirro was an ambitious New York politician whose career stalled after she was recorded plotting to bug her then-husband’s boat to catch him in an affair.
The revelation rocked Pirro’s campaign for New York attorney general nearly 20 years ago, resulting in days of front-page headlines in the city’s tabloids (“BUG THIS LOVE BOAT!” blared the Daily News cover).
The conversation took place in 2005 between Pirro and the former commissioner of the New York Police Department, Bernard Kerik, a close ally of Rudy Giuliani’s.
“What am I supposed to do, Bernie? Watch him f— her every night?” Pirro said, according to a transcript obtained by WNBC-TV’s Jonathan Dienst in 2006. “What am I supposed to do? I can go on the boat. I’ll put the f—–g thing on myself.”
The incident is likely to receive renewed attention now that Pirro is President Donald Trump’s pick to be the interim U.S. attorney for Washington, D.C. Her selection came after the president withdrew the nomination of conservative activist Ed Martin, whose defense of Jan. 6 rioters was criticized by some Republican senators.
In announcing Pirro as his choice for Martin’s replacement, Trump described her as “in a class by herself.”
He’s right in one sense: No other U.S. attorney nominee is known to have come under federal investigation after being caught on tape scheming to catch a cheating spouse in the act.
The U.S. attorney for the Southern District of New York confirmed the existence of an investigation into Pirro at the time, but no charges were brought.
Pirro was the district attorney of Westchester County when she was caught on tape talking to Kerik, who was under investigation by the Bronx District Attorney’s Office. At the time, she was gearing up for a run against then-New York Sen. Hillary Clinton.
Suspicions of an affair
According to WNBC, Pirro believed her then-husband, Albert Pirro, was using the family’s 26-foot boat — the Christie, named after the couple’s daughter — for sexual trysts with his then-mistress. Pirro appeared to grow frustrated that an employee of Kerik’s security firm was reluctant to plant a recording device on the vessel.
“We can just simply say, if there is an issue, that I am redecorating it for our anniversary,” Pirro said, according to WNBC.
“But Jeanine, I’m having the same problem with everybody,” Kerik allegedly replied. “Everybody is panic-stricken because it’s you. I’ve gone out on a limb. I had two other people looking at this. It’s a problem.”
At a press conference after the WNBC report came out, an emotional Pirro blasted the federal probe as a “waste of taxpayer money” but didn’t deny the substance of the conversations.
“I said a lot of things, but what matters is what I did and didn’t do — and what I did was vent,” Pirro said.
FILE — Jeanine Pirro in Harrison, New York, in 2006. (Enid Alvarez/NY Daily News Archive via Getty Images)
Pirro ultimately dropped out of the race after polls showed she had little chance of defeating Clinton in the heavily Democratic state of New York.
Her subsequent campaign for New York attorney general was also seen as an uphill battle despite her name recognition. And two months after the revelation of the tapes, she lost the race to future Gov. Andrew Cuomo in a landslide, marking the end of her political career.
What happened over the next two decades is well known. Pirro became a TV star and one of Trump’s most ardent defenders.
In 2020, she repeatedly pushed conspiracy theories on her Fox News show about Trump’s election loss. In the course of litigation filed by Dominion Voting Systems, it was revealed that Pirro’s executive producers sent a blunt assessment of one of her monologues to higher-ups: “This is completely crazy.”
Pirro’s evolution from a once-lauded district attorney to an election-denying Trump booster mirrors the trajectory of other MAGA figures, most notably Giuliani.
Douglas Muzzio, a retired Baruch College political science professor with extensive knowledge of New York politics, said he finds it “unfathomable” that Pirro is now on a path to helm one of the country’s most important federal prosecutor’s offices.
“If you would have told me 20 years ago, or even 15 years ago, that she would be in the position she’s being put in now, I wouldn’t believe it,” Muzzio said. “There were many more people who I was familiar with by reputation who deserved the job more in terms of qualifications than Pirro.”
Efforts to reach Pirro through the Justice Department and the White House were not successful. (A Fox News spokesperson said she was no longer employed there.)
Kerik did not respond to a request for comment.
Rising GOP star
In the 1990s, Pirro was seen as a rising star in the Republican Party.
She was the first woman to be elected as a judge and district attorney in Westchester County. Her telegenic appearance and distinctive speaking voice made her a natural on TV.
She developed a reputation as an aggressive prosecutor, but over the years she was also dogged by reports of mob ties and forced to deal with a stream of scandals involving her former husband.
Albert Pirro, a wealthy businessman and GOP fundraiser, was convicted of conspiracy and tax evasion charges in 2000 and sentenced to 29 months in federal prison. The trial shed light on the couple’s lavish lifestyle, the Daily News reported at the time, in which Albert Pirro “wrote off vacation home repairs, country club dues, paintings, luxury cars” — including two Ferraris — “and a fence for the family’s pet pot-bellied pigs.”
Five years later, the Daily News published a report that a top lieutenant in the Gambino crime family was caught on an FBI wiretap claiming Albert Pirro had discussed one of his wife’s pending cases with a mob associate.
Federal prosecutors in Manhattan investigated the claim, but no charges were brought.
Albert Pirro denied that such a conversation ever took place, and Jeanine Pirro told the Daily News in 2005: “I was surprised. It seemed incredible.”
Later that same year, Jeanine Pirro’s Senate campaign was dealt another blow when the Daily News reported that six donors with ties to organized crime had written nearly $12,000 in campaign checks to her since 2003.
“We will take a look at the facts and make the appropriate decisions on a case-by-case basis,” her campaign spokesperson said at the time.
But those scandals paled in comparison to the Kerik conversation tapes.
Kerik’s phone was bugged as part of an investigation into accepting free renovations to his apartment from a contractor with alleged mob links while he was the commissioner of the New York City Corrections Department. He ultimately pleaded guilty to two misdemeanors.
After the transcript of his phone call with Pirro was leaked, Kerik’s lawyer, Joseph Tacopina, told the Daily News: “Bernie spoke to a friend in distress regarding a domestic conflict. Nothing illegal was discussed and nothing illegal was done.”
At the time, Pirro’s husband issued a statement through his attorney: “Al Pirro is outraged at the conduct of the U.S. attorney in launching a federal investigation into a private marital dispute.”
Pirro separated from her husband in 2007. He was pardoned by Trump in 2021.
Trump also pardoned Kerik after the former commissioner served three years in prison on federal charges of tax fraud and making false statements.
In her conversation with Kerik, Pirro lamented how her then-husband was impacting her political career.
Without him, she said, “I move into the governor’s mansion.”
Jeanine Pirro, also known as “Judge Jeanine,” is a former Westchester County judge and successful media personality. Here’s what you need to know.
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