Why Is Jeanine Pirro Smiling?

As district attorney, she took on America’s most notorious bad guys. Now the Fox News host believes she can convince you Trump will keep you safe.

by Rebecca Nelson
Originally Published: 

Jeanine Pirro says she’s not trying to scare you. Hear her out: Yes, she regularly shows footage on her Fox News show, Justice with Judge Jeanine, of cities like Seattle and Portland and Chicago in what looks like total anarchy. Yes, she’s warned that “they are coming for your gun” and that “babies are being massacred.” And OK, she has acknowledged that “people are afraid. You too need to be afraid. Afraid for yourself, your family, and your country.”

But scare people? Clearly, I’m missing her point. “My intent is not to create any kind of fear,” she tells me. She’s just gotten back from the White House, where she scored an exclusive interview with President Donald Trump. (In the interview, which aired last month, the president pondered whether Democratic nominee Joe Biden was on performance-enhancing drugs. Pirro nodded along vigorously.) Her spokeswoman patches me into Pirro’s hotel room in Washington, where, between bites of a chicken and tomato sandwich, Pirro tells me she simply wants to show people what’s out there. Is it her fault the world is so scary? “My job is to talk about what’s going on in America the way I see it,” she says. “I give you my opinion.” In Pirro’s opinion, we are in the fight of our lives — and the only person who can save us is Trump.

The one-time judge and former Westchester district attorney is one of Trump’s most vociferous defenders and closest allies. Their friendship, forged in the brash tabloid circles of New York, goes back decades. In the 1990s, she was a Republican Party fixture in the suburbs that are home to a Trump golf course, a would-be Trump golf course-turned-state park, and a Trump family mansion (once also intended to be a golf course). Trump and Pirro both pivoted to television in the 2000s and, now, her show is one of the president’s favorites among the hours of Fox News he binges every day. (He has given her at least six interviews.) She has been an informal adviser to the president, in his ear on everything from criminal justice to administration staffing, and he reportedly considered her for a job in the Justice Department.

From her home studio in Rye, New York, Pirro, who’s 69, has cast this election as America’s last stand — the eleventh hour for law and order, for decency, for the nation as we know it. “I believe in America,” she tells me. “We can’t let her go.” It’s Trump, and only Trump, she tells her 2.8M viewers, that’s standing between you and the apocalypse. It’s also Trump, who, for now, oversees a revolving door between the right-wing channel and the halls of power.

Growing up in Elmira, a small town in upstate New York, Pirro didn’t dream of her wedding day like other little girls in the 1950s. Instead, she pictured herself standing in the well of a courtroom. Her Lebanese-American parents raised her Catholic, and she grew up comfortably middle-class. Her father, Leo, owned a real estate business, and her mother, Esther, was a stay-at-home mom who worked for a time as a model. “I learned to fight from my mother,” Pirro wrote in a 2003 memoir. “She impressed upon me throughout my childhood that I had to fight for myself, and I had to help those who were not strong enough to fight for themselves.”’

She told her family she was going to be a lawyer at age 6, and began volunteering at her local district attorney’s office when she was 15. After graduating high school in three years, she became the first person in her family to go to college, at the University of Buffalo. Then it was on to Albany Law School, where she met her future husband, Al Pirro, in a dining hall. They married a year and a half later.

After law school, the couple moved to Harrison, New York, where Pirro went to work as an assistant district attorney in Westchester County. In 1978, the office received a grant from a new federal program for pilot domestic violence prosecution units. Domestic violence had long been seen as a family issue, something to be handled behind closed doors. The women’s liberation movement in the 1960s and 1970s had begun to change that, and the criminal justice system slowly started catching up. Pirro led the new office, which was one of the first domestic violence units in the nation. “No one was talking about it,” she recalls. “Everybody said, ‘Hey, if you beat your wife, she probably deserved it.’” She constantly battled that attitude in the district attorney’s office, where many of her colleagues treated her work as a joke.

Her political career began in earnest a few years later. In 1986, she announced a run for lieutenant governor of New York, then dropped out two days later after news outlets reported on Al’s investment in a garbage hauling company that allegedly had mob ties. For her next run, she aimed for a more attainable office. Bolstered by her reputation as someone who fought for women and families, she ran for a seat on the Westchester County Court in 1990, becoming the first female judge to sit on the county court bench there. (“Some people might consider that special,” she tells me in answer to a question about something else entirely.) When she became a judge, one of her first cases involved a man who refused to pay child support. She sent him to jail and gave him a day to come up with the money he owed his ex-wife.

The impartiality of the bench, however, went against her crusading nature. In her memoir, she painted her cases in the DA’s office as battles between good and evil (one chapter is entitled “Cage the Bastards”). “I wanted to fight,” she wrote, “not preside.” When her old boss, the district attorney, announced his retirement, she ran for the office. During the campaign, the press questioned her about who would take care of her two young kids, while her male opponent, also a parent, was never asked the same questions. “I was not the first woman, nor unfortunately the last, to have faced these stereotypes and double standards,” she wrote. Still, she won the race, becoming the first female district attorney in Westchester county.

Pirro with her standard poodles, Lancelot and Stella.

She was the kind of DA, she says, “who believed in women, who prosecuted child abusers. When I started, they weren’t prosecuting child abusers in the family. They said that the purpose of family court is to make sure that the family stays together, and to mediate a problem. Bullshit!” We’re talking over Zoom, in August, and she smacks a hand on her desk, then pauses to compose herself. “We had to change the thinking.”

As DA, Pirro worked around the clock. “Every single morning I would come in and there would be anywhere from half a dozen to 15 or 20 telephone messages from Jeanine,” says David Hebert, her longtime aide. “It was brilliant and it was crazy.”

From the very beginning of her tenure, she was thrown into the fire. The night before she took office, in 1994, a deranged man in Westchester murdered his wife, Anne Scripps Douglas, an heiress to a newspaper fortune. The case made national headlines, and as an advocate for victims of domestic violence and the DA of the county, Pirro was articulate, savvy, and armed with a megawatt smile of gleaming teeth. It was her coming out party to the national media, an entree to recognition outside the region. (Just a few years later, she was named one of People’s 50 Most Beautiful.) When O.J. Simpson was put on trial for allegedly killing his wife, she parlayed her domestic violence expertise and newfound fame into more TV bookings.

Throughout her time as DA, Pirro was dogged by criticism that she too frequently sought out media attention. She was constantly aware of how her messaging played in the press, and after news conferences, she would often retreat into a back room with aides to watch video of how she did. “She always wanted to get her face in the news and on camera,” says Bennett Gershman, a former Manhattan prosecutor and frequent critic of Pirro’s. “She was out for herself.”

In 1996, a man killed a police officer and then took his grandmother hostage. During the standoff with police, Pirro went on the news and said she might seek the death penalty for the man — even though he still had his grandmother held hostage. Critics said she risked escalating the situation. (As it turned out, the man had already killed his grandmother, along with his dog and eventually himself.) Pirro has said her comments at the time were taken out of context.

She also wrote herself into the story of Robert Durst, the accused serial killer featured in HBO’s The Jinx. Durst’s first wife, Kathie, went missing from their Westchester home in 1982, and the case had been cold until Pirro decided to reopen it in 2000. Pirro maintained that Durst had killed her, telling the Associated Press that “every ounce of my prosecutorial being says this guy is an evil person.” During Durst’s 2003 trial for his involvement in the death of his neighbor in Galveston, Texas — a crime which occurred 1,600 miles from her jurisdiction — Pirro made several appearances in the courtroom. The judge eventually gave her a gag order because she spoke so much about it on TV. (Pirro’s 2015 account of the saga, He Killed Them All, has been disputed by many parties in the case.)

During this period, she wasn’t seen as holding particularly right-wing views. “As the DA in Westchester, she wasn’t known to be as politically conservative as she is now,” says Joanne Naughton, a retired New York City police detective who ran against Pirro for DA in 1997. Sure, she was a Republican, but she was socially moderate. As DA, she fought for a more diverse office, hiring more women and minorities, and lobbied for the passage of state and federal hate crimes legislation. She also brought in a former white supremacist to educate law enforcement on the dangers of extremism.

(Over Zoom, I try to nail down whether her views on specific issues have moved rightward — she once supported abortion rights and gun control, for example. She leans into the camera, squints at me, and asks, “Do you do your own eyebrows?”

Well, right now I do, I say, because I don’t want to risk going to my eyebrow lady during a pandemic.

“They look great,” she says. “Hang on to them. As you get older, you lose them. Trust me.”)

Nevertheless, Pirro’s media recognition and impressive resume made her a rising star in Republican political circles, and after more than a decade as DA, she decided to forego running for a fourth term, instead challenging Hillary Clinton in a run for the U.S. Senate in 2005. But she botched her announcement when a page of her speech went missing from her lectern, and her campaign never recovered. (She stopped mid-sentence, shuffling pages awkwardly before asking an aide, “Do I have page 10?”) She dropped out of the race a few months later to run for attorney general, eventually losing to now-Governor Andrew Cuomo.

Pirro's high-profile cases, political campaigns, and divorce made her a regular in New York City tabloids. New York Daily News Archive, Getty Images

Her husband, Al, a powerful real estate attorney in the county, didn’t help her political aspirations. In 1999, prosecutors alleged he had written off personal expenses — such as a $1,800 wrought-iron fence for the family’s Vietnamese pot-bellied pigs — as business costs. The couple and their two children lived in an elaborate, custom-built mansion, blanketed in terra-cotta-colored marble they handpicked in Italy. (In addition to the pigs, which lived in their own house in the backyard, there were dogs, birds, and a gerbil.) He eventually went to prison for tax evasion. Pirro herself wasn’t charged, and has maintained that she knew nothing of her husband’s alleged crimes, though she signed the tax return that was at issue in the case. After Al was released from prison, she was investigated based on claims that she had planned to bug the Cristine, his 26-foot motor boat, when she suspected him of cheating. (She was never charged.) The two have since divorced.

“We have been good friends since we separated,” Pirro says now. “I don’t believe in denying that you loved someone throughout the most important years of your life. We still share holidays.”

Though Al’s schemes proved distracting, he did connect her with someone who would come to be an asset to her career down the line. Al served as Donald Trump’s lawyer in his Westchester real estate deals, and Pirro and Trump, whose children were around the same age, became close. Their families often flew down to Florida together on Trump’s jet, where Pirro would make popcorn for everyone while they watched movies. “When I’d bring it out,” Pirro wrote in her 2018 book, Liars, Leakers, and Liberals: The Case Against The Anti-Trump Conspiracy, “Donald would say, ‘Jeanine, did you see any meatloaf in the kitchen back there? Could you heat some up for me?’” In a 1999 New York magazine story, the future president weighed in on her attributes, calling her “sexy as hell.”

When I started, they weren’t prosecuting child abusers in the family. They said that the purpose of family court is to make sure that the family stays together, and to mediate a problem. Bullshit!

When I first meet Pirro in August, she tells me to call her Jeanine. “I’ve been judge, I’ve been boss, I’ve been witch, I’ve been worse.” We’re meeting virtually, out of concerns about COVID-19. On air in March, she likened the virus to the flu, and, by the fall, she’d travel to promote her new book, Don’t Lie To Me and Stop Trying to Steal Our Freedom. But, for now, she’s holed up at home like the rest of us, cooking more for herself — eggplant casserole, pineapple upside down cake — and also for her two standard poodles, Lancelot and Stella. “My dogs love sweet potatoes,” she tells me. Every week, she goes to Costco and gets a big bag of them, then mixes it with hamburger meat and a little dry dog food. It’s their favorite dish.

She’s been doing her show every Saturday night from her home studio. On her first home broadcast in March, viewers speculated that she was plastered on-air after she missed her first segment and made incoherent observations, such as when she remarked to a doctor fighting COVID-19, “I mean, this is worse than the Civil War. In the Civil War, as bad as it was, and you didn’t have everything you needed, you couldn’t catch something from the patient.” (Cecily Strong later satirized the evening on Saturday Night Live: “Oh, this? It’s called a piña cloroxa. It’s pineapple juice, coconut milk, and a half cup of bleach.”) Pirro, who tells me she's not a regular drinker, denies she’d been drinking that night and blamed technical snafus. “You think I’d take a drink before a show?”

Disinhibition is simply Pirro’s natural state, which is partly why she seemed destined for television. Two days after she lost her attorney general race in 2006, she met with a TV executive about possible opportunities. Judge Jeanine Pirro, a daytime court show in the Judge Judy mold, debuted on The CW in 2008. It was an opportunity for Pirro, who had sat on an actual bench for all of three years, to hone her public image as an esteemed arbiter of justice — much like how The Apprentice burnished Trump’s persona as a successful businessman. The show ran for four seasons until it was canceled in 2011. The same year, Fox News debuted Justice with Judge Jeanine. Pirro had been a legal analyst for the channel for five years, and the show was a platform for her to bring her screwball cracks and audacious observations to the biggest legal cases of the week. Fox News was an obvious home for the way she views criminal justice: as a battle between light and dark, where there are good people and evil people, victims and criminals, and no room for shades of gray. These days, though, the show focuses mostly on politics.

This is the world according to Pirro: America’s cities are on fire, desecrated by looting and riots. People are terrified to go outside because police have been rendered feckless — and that’s why we need to reelect the president. (Her warnings conveniently ignore the growing threat of white supremacist violence, which according to the Department of Homeland Security is the deadliest domestic terror threat.) It will only get worse, she says, under a Biden presidency. “Do you want to live in Joe Biden’s America, or President Donald Trump’s America?” she asked on a recent show. “Think hard. Your life may depend on it.”

In August, the day after Kamala Harris was announced as Biden’s vice presidential pick, Pirro said, “For some reason, I just have this feeling that Joe Biden isn’t going to be on the ticket… I have a sense that something’s going to happen before the election and he’s not even going to be on the ticket, so don’t even ask me if he's going to make the four years.” It was an outrageous theory that her fellow Fox hosts backed away from.

As soon as I bring this up during our interview, she interrupts me. Shaking her head, she says, “Did everybody go crazy or what?” She explains what she meant: “There’s an article. I forget… Well, I have the quote here.” She starts reading from a piece of scrap paper: “‘It's not out of the question that the Democratic Party, worried about Biden’s failing verbal skills and growing confusion, will find a way to ease him out just before the election.’”

Wait, where was this published?

“It was an article in… I’m not sure where the article came from,” she says. (A Google search suggests it was an un-bylined editorial on a conservative opinion site called Issues and Insights.)

In March 2019, Pirro went on a tirade about Minnesota Rep. Ilhan Omar, questioning the congresswoman’s loyalty to the United States given her Muslim beliefs. “Think about it: Omar wears a hijab,” Pirro said. “Is her adherence to this Islamic doctrine indicative of her adherence to Sharia law, which in itself is antithetical to the United States Constitution?” Apparently, the statement was too offensive even for Fox News brass. The network released a rare public statement rebuking her, and Justice subsequently went off the air. (There is nothing, Pirro tells me, that she regrets saying. “I’m sure I’ve said things that I wish I said differently,” she says. “But I’m not going to be an apologist for things that I think are worth saying and worth talking about.”)

But she had the ultimate ally. “Bring back @JudgeJeanine Pirro,” Trump tweeted when her show missed its regular time slot. Behind the scenes, according to Vanity Fair, he called News Corp Chair Rupert Murdoch to levy his complaints. She was back on the air after two weeks. (The network says her job was never on the line.)

On Justice, Pirro is one of the most ardent supporters of the president, praising him and his administration at every turn. She has called him “almost superhuman” and “a force of nature.” In our Zoom interview, she regularly breaks into generous flattery, at one point repeating three times in the span of 26 seconds that Trump is “such a kind man.” The flattery goes both ways. She recounts in Liars, Leakers, and Liberals that, during her tenure as DA, when the two walked down the street in Manhattan, Trump would promote her to passersby. “You know who this is?” he’d say. “It’s Jeanine Pirro! She’s the DA from Westchester!”

“He was a big supporter of hers and a champion of hers,” says Hebert. “There is certainly a longstanding history of loyalty. He was there supporting her even through very difficult times and she has, I think, never forgotten that.” He added: “Win, lose, or draw, Jeanine was going to be able to count on Mr. Trump’s support and his friendship.”

Pirro with Lara and Eric Trump at the President's one-year anniversary party in Mar-a-Lago, January 2018.

One of her favorite stories from the White House is the time she met Conan, the military service dog that helped U.S. special forces kill ISIS leader Abu Bakr al-Baghdadi, and was injured in the mission. When Pirro heard about the Belgian Malinois, she called Trump. “Mr. President, you have to bring the dog,” she recalls telling him. She wanted Conan to receive a hero’s welcome at the White House. After three more calls to inquire about the dog, she says she convinced the president to include Conan in a ceremony in the Rose Garden. She came down to Washington for the festivities. At this point in her story, she leaves my computer frame, returning a few moments later with a framed photo of her posing with Trump and Conan in the Oval Office.

She also uses her influence to sway the White House on matters related to humans. According to the Washington Post, Trump wanted her for a top Justice Department position, but then-Attorney General Jeff Sessions blocked her appointment. (Pirro denies that she interviewed for any job in the Trump administration. “I’d like to know who interviewed me,” she says.) She later waged a successful campaign against Sessions for recusing himself from the Russia investigation. She denounced the attorney general in a November 2017 meeting in the Oval Office, whipping up the president against him. Days later, Trump fired him.

The president trusts her opinion, she explains, because of their decades-long friendship. “I’ve known the president a long time,” she tells me. “I don’t want anything. I don’t need anything.”

Trump rewards her loyalty with sit-down interviews, regular trips to the White House, frequent phone calls, and Twitter exhortations to watch her show. “That sort of constant endorsement by the president has been really, really good for her career,” says Nicole Hemmer, a historian at Columbia University and author of Messengers of the Right: Conservative Media and the Transformation of American Politics. “It’s protected her. She’s not going to get fired as long as Donald Trump is in the White House and supporting her, it seems.” At the height of the coronavirus crisis earlier this year, when PPE was in perilously short supply, Pirro reportedly demanded that the administration’s COVID task force ship masks to a hospital she liked. She was, according to a whistleblower on the team who was told to prioritize PPE requests from Trump’s allies, “particularly aggressive” in her appeals.

When I ask Pirro if there’s anything she disagrees with the president on, she says sure — but she won’t divulge what. Can you just give me one example? “No, no, no, no,” she says, shaking her head. “It’s between him and I.”

Pirro’s latest book, Don’t Lie to Me, is dedicated to “one person: The one person who has stood fast against an incredible onslaught of attacks, insults, and lies; a man with the uncommon stamina, energy and perseverance to fight the dark forces that seek to tear down mankind’s greatest experiment in freedom; a man who brings truth, light and transparency to a nation clouded in darkness and chaos; a man who never wavers in his determination to Make America Proud, Strong, and Yes, Great Again, President of the United States Donald J. Trump.”

Win, lose, or draw, Jeanine was going to be able to count on Mr. Trump’s support and his friendship.

Perhaps the most jarring dissonance between District Attorney Pirro and Fox News host Pirro is her longstanding battle to avenge female victims of domestic violence and sexual assault. Now, she fervently supports a man who has been accused of sexual misconduct by two dozen women, and whose inner circle contains several men who have been accused of domestic violence. Pirro says those two positions are not in conflict — after all, she knows Trump is innocent. “I’ve seen him at all hours,” she says. “I mean, at parties, New Year’s Eve parties at Mar-a-Lago, at the end of the night. I just know him too well. I don’t know him to be that man.”

She also maintains that her political views haven’t changed. “If someone says, ‘Oh, she’s a little different now, she’s a little more hardcore,’” Pirro says, well, that’s just the nature of her business. “Yeah, maybe I am hardcore. Maybe that just comes with being on television where you got three minutes to say what you really think.”

The hyperbole contributes to the impression that Fox News talent aims to create programming Trump likes, not just for the free publicity and insider exclusives, but because it leaves open the possibility of working in his administration, as more than a dozen former Fox employees have. For Pirro, who is unusually entwined with Trump, the effect is even more pronounced. A dire outlook on a potential Biden presidency stands to push her audience toward the outcome that is most fruitful for her professionally — though she says she’s not looking for a job. “I ran for office five times,” she says. “It’s a blood sport. I’ve done my time in the political trenches.”

While the latest polls show Trump trailing Biden by 10 points nationally, she is confident the president will win reelection. Given that polls indicated Hillary Clinton would win in 2016, Pirro doesn’t put any stock in them this time around. “In 2016, people didn’t say they were going to vote for him,” she says. “In 2020, people are definitely not saying they’re voting for him because they’re scared to death. You wear a MAGA hat, you get beat up, you get spit on, you get harassed. I mean, you think people are ready to tell a stranger, ‘Yeah, I’m voting for Donald Trump’?”

Whether in a few months or four years, Pirro’s direct line to the White House will eventually be severed. What does Justice look like without Trump to defend? Pirro says it will look exactly the same. “This is what people want. This is what America needs,” she tells me. “It’s about what I think is right and what I think is wrong.”

Recently, Pirro has taken to giving an ominous election countdown in the opening monologue of her show. “You have 100 days,” she’ll say gravely. “100 days to save this country.” This election, she says, the choice is ours: We can reelect Trump, or “descend into the depths of despair and darkness.” She has a lot to lose.

Photographer: Nicholas Calcott

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