Donald Trump had been in the race for six weeks, and he had already stumbled into another controversy. It was August 2015, after the first Republican primary debate, and Fox News's Megyn Kelly had called out Trump's demeaning comments about women. The next day, Trump accused Kelly of having blood coming out of her "wherever."
Trump adviser Roger Stone, for decades a Republican operative, believed Trump was hurting his own cause. The day after the attack on Kelly, Stone crafted his resignation letter.
“Provocative media fights . . . overwhelmed your core message,” he wrote. “I can no longer remain involved in your campaign.” Stone was due to appear that night on one of Trump’s favorite Fox News shows, “Justice With Judge Jeanine.”
But when Pirro learned of Stone’s plans, she got word back to Trump, according to then-campaign manager Corey Lewandowski and two people familiar with the exchange. Now Trump could say he fired Stone before the strategist could go on the air.
Pirro’s heads-up allowed Trump to save face. He narrowly avoided one of his least favorite activities — looking like a loser.
‘All the best people’
How President Trump’s inner circle has changed the way Washington works.
For Jeanine Pirro, the decision to put her bond with Trump ahead of staging a dramatic moment on her TV show was not hard. “At this point in time, he’d been a candidate for six weeks, and she had been a friend for 25 years,” said a Trump adviser, one of several who declined to be named because they were not authorized to speak about Pirro.
It was one episode in a decades-long friendship marked by transactional loyalty. Showy New Yorkers living tabloid-ready lives, prodigious generators of media attention, Trump and Pirro have fed off each other’s fiery pronouncements for decades.
But when Trump moved to the White House, Pirro was no longer just a fellow performer. She became a lifeline back to the brash, street-savvy New York crowd Trump favored. When official Washington gave Trump a cold welcome, the new president reached out to longtime loyalists, people who got his humor and spoke his language, New Yorkers who could face down the barrage of criticism. The president turned to Judge Jeanine.
Trump has told aides that in the White House, he has at times felt surrounded by people he cannot trust, people who are aligned with him for their own political purposes. He doesn’t worry about that with Pirro.
“She is one of the few people who is loyal to him because of their history, not because she wants something from him,” said a former senior White House official.
The Stone moment — his version of his departure is different, ending with him quitting rather than being sacked — was not an isolated one. Scarcely a month before the election, at their first debate, Hillary Clinton confronted Trump with his comments calling Alicia Machado “Miss Piggy” for gaining weight after she won the title of Miss Universe in the pageant he owned.
To win, Trump needed women to look past such behavior. But he kept digging himself deeper.
The morning after the debate, on “Fox & Friends,” Trump described Machado as “the worst, the absolute worst. And she gained a massive amount of weight, and it was a real problem.”
“She is one of the few people who is loyal to him because of their history, not because she wants something from him.”
Former senior White House official
Not long after, Trump spoke to Pirro, according to two people familiar with the call. They had known each other since her then-husband Al served as one of Trump’s real estate lawyers and she was district attorney of Westchester County, just north of New York City.
“Donald, you don’t need to talk about this,” Pirro told him, according to a person who heard the conversation. “We’ll take care of it.” (Pirro denies saying this.)
Days later, Pirro leaned in to the camera and did her best to take care of it. “Although he may be impolitic, and while I am not a fan of things he said 20 years ago about a woman under a contractual obligation to maintain her appearance,” she paused, shifting to address Hillary Clinton directly, “your history with women is all about destroying them.”
Pirro’s connection to Trump is one of his most enduring friendships. She has spent Thanksgiving with him at Mar-a-Lago. She and Al used to travel with Trump on his jet for weekends in Palm Beach, Fla. She has described how they’d watch movies on the plane and Pirro would make the popcorn, even heating up meatloaf for Trump at his request.
“They both are New Yorkers, and both speak in a very common-sense conservative way to the American people,” said David Bossie, an early Trump campaign adviser. “Having come from the same world and same generation, they understand each other completely.”
In each other’s corner
The loyalty between Pirro and Trump runs both ways.
In March, Pirro asked on air if Rep. Ilhan Omar’s hijab signaled that the Democratic freshman from Minnesota was loyal to sharia law, “which is in itself antithetical to the United States Constitution.”
Fox suspended Pirro from her show for two weeks. She went straight to Trump to discuss the punishment, according to two people close to Fox Chairman Rupert Murdoch. The president called Murdoch to urge that Pirro be put back on air, these people said, a development first reported by Vanity Fair.
Murdoch takes Trump’s calls with a grain of salt — Pirro’s show was never going to be canceled, the Murdoch associates said. Fox News denied any plans to discipline Pirro further, but people close to the president said Pirro feared she might be fired.
Keeping Pirro’s supportive, combative voice on Fox was vital to Trump, as it’s been since before his campaign began.
“When I joined the team, we called her on a lot of issues to get her ideas,” Lewandowski said. “She was very open to having someone from the team on her show, which is exceptionally helpful — and, to be clear, not every show was as willing.”
For decades, Pirro, who declined to be interviewed for this article, had been on the receiving end of the full Trump charm offensive.
“Long before I was on television, Donald was promoting me” on the streets of Manhattan, Jeanine wrote in her book “Liars, Leakers and Liberals: The Case Against the Anti-Trump Conspiracy.” “Every time we’d pass a cop, a hard-hat, or someone gawking at him, he’d point to me and say, ‘You know who this is? It’s Jeanine Pirro! She’s the D.A. from Westchester!’”
Late in the campaign, after The Washington Post revealed the “Access Hollywood” tape featuring Trump’s vulgar language about women, Pirro was one of the few women to stand by the candidate: Trump’s “words are disgusting, devastating, and embarrassing,” she said on her show. “It’s the kind of locker-room and frat-house talk that personally infuriates me. But guess what? I still, without a doubt, support Donald Trump. . . . He has always been a gentleman.”
Defending a man accused was nothing new for Pirro. She had just come off a summer of standing by her media patron Roger Ailes, the Fox News boss who had been sued by former host Gretchen Carlson for sexual harassment and retaliation.
Pirro supported Ailes and tried to get other women at Fox to do so, too. She called the allegations against him “absurdities.”
Ailes was forced to resign, and Fox settled with Carlson for $20 million.
Pirro’s loyalty to Trump has occasionally caused her problems inside Fox. Alongside fellow host Sean Hannity, she appeared at a Trump rally before the 2018 midterm elections. Fox management warned her against participating in campaign events.
But her pro-Trump monologues got only more fervently supportive. Like her friend, she responded to criticism by hitting back harder than ever.
“She’s fearless in a way that is unique to cable TV commentary, and she is aligned perfectly with the era of Trump,” said White House counselor Kellyanne Conway.
A champion for women
Before she was one of Trump's most ardent defenders, before she was a rising star in New York politics, before she was a legal commentator on everything from O.J. Simpson to Robert Durst, Jeanine Pirro was a crusader for crime victims, and especially for women.
Jeanine Ferris, born in Elmira, N.Y., to Lebanese American parents, graduated in three years from Notre Dame High School and found time to intern for the local district attorney.
“I didn’t dream of my wedding day,” Pirro wrote. “I dreamed of standing in the well of a courtroom.”
She achieved her dream and picked up a husband along the way. At Union University’s Albany Law School, she met Albert Pirro, and in 1975, they married and moved to Westchester, where she became an assistant district attorney. Two years later, she was overseeing a bureau specializing in domestic violence.
Pirro took to visiting battered women and their families. “She’d ask the names of all who were there . . . and what the circumstances were, and she’d commit that to memory,” said Marianne Walsh, then an administrator for Victims Assistance Services, a nonprofit agency. “Years later, she’d still remember them.”
Before Pirro came along, prosecutors in Westchester were tight-lipped about their cases, Walsh said. For Pirro, talking up her cases before the cameras was part of prosecuting them.
“She couldn’t resist a camera or a microphone,” said Bennett Gershman, a former Manhattan prosecutor and frequent Pirro critic. “She’d go on camera and speak in the most inflammatory and incendiary way she could think of to destroy the character of the defendant she was accusing.”
Making her mark
In 1993, Pirro was elected Westchester's first female district attorney.
“It was a really big deal,” said former New York governor George E. Pataki (R), who was close to the Pirros and a beneficiary of Al’s donations. “The Republican Party in Westchester was very much of an old-boy network, and she didn’t care and was willing to fight through it all.”
She appointed her office’s first media handler and set about staying in the public eye.
Hours before her inauguration, a Westchester man, Scott Douglas, bludgeoned his estranged wife, Scripps newspaper heiress Anne Scripps Douglas, in her bed. Pirro kept the press updated at every step in the hunt for the killer, appearing almost daily on “Nightline,” “Larry King Live” and “Geraldo.”
Then came another crime made for the cameras. In 1994, when O.J. Simpson’s wife, Nicole Brown Simpson, was murdered, the killing took place clear across the country, but Pirro found a way in.
She became more famous than any Westchester district attorney had ever been. On TV, she talked about O.J. Simpson and about Robert Durst, the Westchester millionaire suspected of murdering his wife.
Sometimes she said too much. In 2005, a registered sex offender kidnapped a 12-year-old girl and raped her repeatedly. In interviews, Pirro hinted strongly that the alleged perpetrator was HIV positive, a move that drew a prosecutorial misconduct complaint from the New York State Association of Criminal Defense Lawyers.
Pirro’s office responded to that complaint by saying that she “will continue to protect the people of Westchester County despite the rantings of these critics, who should be embarrassed by their callous indifference to innocent crime victims.”
‘I wanted to fight’
While Jeanine raised her profile, Al built a real estate law practice and used his deep ties to Westchester's political establishment to draw donors to Jeanine's campaigns.
Al “was a huge fundraiser for the Republicans,” Stone said. Al was effective on zoning and land use issues “because of his role as a fundraiser. That’s what Donald used him for.”
Al’s political savvy boosted his wife’s career. “Do my relationships open doors for her in the GOP? Unquestionably,” Al told New York magazine in 2006.
But Al was also a liability. In 1986, when Jeanine ran for lieutenant governor, news outlets reported on Al’s alleged business ties to the Mafia. Two days later, Jeanine quickly withdrew her candidacy. (Al Pirro did not respond to The Post’s questions about the allegations.)
Four years later, Al took credit for getting his wife nominated for a family court judgeship. She quickly moved up to Westchester’s highest criminal division, County Court.
But after three years on the bench, Pirro wanted something more. “At heart, I was a crusader,” she wrote. “I wanted to fight, not preside.”
“Our relationship was then, and remains today, symbiotic,” Al Pirro said in a statement to The Post. “Jeanine [is] a star and she would have raised to the position she ultimately held without any assistance.”
When they weren’t working, the Pirros held court at their Italianate mansion. What gold is to Trump, marble was to the Pirros. She once described her beloved home as “Loggias, porte-cochères, balustrades, palladium windows, low roof, balcony.”
Jeanine and Al threw $5,000-a-plate fundraisers and became friends with Pataki, then-Sen. Al D’Amato (R-N.Y.) and their wives. At one cookout, the Pirros hosted Trump’s daughters, Ivanka and Tiffany, who were around the same age as the Pirros’ children.
Jeanine loved to cook, and the house was always full, friends said. The guests were often Al’s clients, real estate people who needed a little grease, as one local paper put it, “to save their projects from the mire of bureaucracy or local opposition.”
Trump needed something saved. When he bought the dilapidated Seven Springs mansion in Westchester in 1995 for $7.5 million, he planned to turn it into a luxury golf course. But neighbors pushed back against the traffic such a project might create. Al Pirro represented Trump in the real estate battle.
A year later, Jeanine, looking forward to a second term as D.A., rented the property from Trump for a one-night costume party to raise money toward retiring her campaign debt. The Trump Organization charged the Pirros just $250 in rent. The local news media questioned whether the rental might be considered an undisclosed campaign contribution. Pirro’s spokeswoman defended the price as fair for such a rundown property.
At the fundraiser, the Pirros dressed as Queen Isabella of Spain and King Ferdinand. Trump attended, but wore no costume, according to an attendee. He watched a Yankees game on a large television.
Legal and marital trouble
In 1999, Donald Trump divorced his second wife, Marla Maples. That same year, the Pirros faced a trial of their own: Al was prosecuted for tax evasion.
The press loved the story of a sitting district attorney’s husband being tried for a federal crime. Jeanine became a staple in the courtroom, chatting up reporters.
Prosecutors alleged that Al hid more than $1 million in income by listing his personal expenses as business deductions. He declared as business expenses a $45,000 electronic fence for their Harrison home, $1,800 grillwork for their pet pigs’ pen, a $4,450 portrait of their two children, Al’s $123,000 Ferrari 348 Spider convertible, a Mercedes for Jeanine and another for her mother.
Jeanine was not charged, but one of her former secretaries testified that Jeanine regularly forwarded personal bills to her husband’s business office to be paid. Court documents showed she had co-signed fraudulent personal tax returns.
And documents revealed that Al had hired a private detective to investigate a woman who claimed he was the father of her child. Al deducted the cost of that investigation as a business expense, too. (A DNA test later proved his paternity; the affair took place when he and Jeanine had been married for six years.)
Jeanine tore into the prosecution. “It looks like they’ve investigated every aspect of my personal life,’’ she said. “I think it’s a desperate attempt by them to bring me in this.’’
In 2000, Al Pirro was convicted on 34 counts of conspiracy and tax evasion. He was sentenced to 29 months in prison. (He served 11.)
It was the beginning of the end for Jeanine’s political career. Many of the Pirros’ friends drifted away, but a core group rallied around her, including Trump.
Trump and Jeanine were “very close,” said David Hebert, Pirro’s longtime aide, especially when Al was in prison. “He was very helpful to her when a lot of people were distancing themselves.”
Jeanine won a third term with Al locked up. After his release, they tried to rebuild their previous life. But Al’s legal license had been suspended (it was later reinstated), and the ordeal had hurt his fundraising power, former associates said.
Jeanine announced she would not seek a fourth term, instead aiming higher, challenging Hillary Clinton for Senate. But in August 2005, Jeanine stumbled in her announcement speech: Having lost Page 10 of her remarks, she paused for 32 seconds to try to find it, becoming fodder for late-night comics.
She dropped out of the race within four months. Instead, she ran against Andrew M. Cuomo for state attorney general.
But as she traveled the state campaigning, Jeanine began to suspect her husband was again being unfaithful. She sought help from former New York City police commissioner Bernie Kerik, then under investigation himself.
Federal agents looking into Kerik’s business dealings recorded Jeanine asking him to bug Al’s boat. “What am I supposed to do, Bernie? Watch him f--- her every night?” she said on the tape, which leaked to a TV station weeks before Election Day.
Jeanine found herself under investigation for possible illegal wiretapping. She accused federal agents of conducting a “political witch hunt.”
Cuomo won by nearly 20 points. In 2007, Jeanine and Al announced their separation. They divorced in 2013.
In an email to The Post, Al Pirro called reports of their marital troubles “greatly exaggerated” and wrote that “despite an unfortunate conclusion to our marriage . . . our friendship has never been stronger as it is today.”
A TV star is born
In 2006, Pirro started work as a Fox News legal commentator. In 2008, she launched an afternoon show on the CW Network called "Judge Jeanine Pirro," in the genre of CBS's "Judge Judy." It was canceled in 2011 due to low ratings.
The same year, Ailes gave Pirro her own show: “Justice with Judge Jeanine.” Her ties to Trump boosted the show’s ratings, which have doubled since his election, from about 1 million viewers before he entered the race to a current average of around 2 million.
Critics say being on Fox changed her. Joanne Naughton, a retired New York City police officer who ran against Pirro in 1997, said she was not surprised Pirro became a TV star. “What is surprising is that she’s . . . a vociferous advocate of right-wing policies,” Naughton said. “When she was in Westchester, she wasn’t especially conservative at all.”
Pirro’s language had always been frank and tough; like the president, she thrived on seeming to tell it like it is. But now she grew more bombastic, reveling in Trump’s detonation of political traditions.
“Twenty years ago, she demanded and deserved some respect for the way she handled herself as DA,” said Lisa dePaulo, who worked on Pirro’s book about Durst before she and Pirro had a falling-out. “She’s gotten more and more unreasonable on Fox.”
Since the election, the president has dominated Pirro’s show — as object of her praise, subject of her advice and, at pivotal moments, as a guest. In January, he called in to advocate for emergency funds on the southern border. Pirro interviewed Trump and then-Chief of Staff John F. Kelly in the West Wing for her book.
Off screen, she has dined with the president several times at the White House, mostly in the Blue Room, according to former Trump aides. She has, they said, threatened to “go straight to POTUS” if White House press aides rebuffed her requests for interviews or if Trump mentioned media personalities other than her in his speeches.
She remains close with the Trump family, attending a baby shower for Lara Trump, the president’s daughter-in-law, in 2017.
For a while, Trump considered Pirro for a Washington job, interviewing her for a top Justice Department position under Jeff Sessions — a job she lobbied hard to get, according to a senior administration official. But Sessions blocked the appointment, the official said, after which Pirro attacked Sessions on her show for recusing himself from the Russia investigation.
On Nov. 1, 2017, Pirro met privately with Trump in the Oval Office. According to people familiar with the meeting, the president and the TV host discussed appointing a special counsel to investigate Clinton, a move Sessions resisted. Two days later, Trump publicly attacked Sessions.
In the White House and on Fox, Pirro has steadfastly encouraged Trump to press harder on his agenda of disruption and provocation. In one segment, she called for a “cleansing” at the FBI and Justice Department, demanding that purged individuals not simply be fired but “taken out in cuffs.”
Rumors that Trump might bring her inside have mostly cooled. Trump has concluded, associates say, that Pirro, with her full-throated defenses of him on Fox, is of more use there.
“Jeanine has a greater impact on the outside because the issues on which she is most expert rose to the fore of this presidency almost immediately,” Conway said. “And [Sessions], who didn’t make her an offer at Justice, fell out of favor . . . while her stock was rising on the outside.”
Bossie, the Trump campaign adviser, agreed: “She has brought the attention of the American people to the fact that we must investigate the investigators, and I think that’s really been a place where she’s found her voice.”
Being that outside voice for Trump has also benefited Pirro. Since the inauguration, according to campaign filings, she has earned more than $230,000 for paid speeches for Republican groups, such as a March 2018 fundraiser for the Kern County Republican Party in House Minority Leader Kevin McCarthy’s California district.
The day after the speech, McCarthy appeared on Pirro’s Fox show and complimented her on the talk. Pirro and McCarthy spent their time together pushing Trump’s effort to “drain the swamp” because, McCarthy said, “you can’t trust what’s happening.”
Correction: An earlier version of this article incorrectly reported that Jeanine Pirro’s parents were immigrants.
Design and development by Joe Moore. Illustration by Mitch Gee