The Liberation of Jeanine Pirro

Westchester’s ex-D.A. strives to eschew the confines and controversies of her former life by recasting herself as a media personality. But some things never change.

It is Friday evening when Jeanine Pirro’s publicist finally emails to inform me that the interview he promised me, which was to take place the following Monday at a White Plains diner, then in New York City, then at another possible Westchester location, would not take place after all. This comes after several weeks of back-and-forth, which is not uncommon when dealing with the likes of, say, an Emmy-winning actress or the “it girl” du jour. But for a former Westchester district attorney launching a new career as a daytime television personality? It seems more than a bit excessive. When I tell Pirro’s beleaguered flack that this story is proceeding with or without her cooperation, a last-minute deal is struck for a phone interview. I’m told, “She’ll give you all the time you need.”

On Monday morning, when the interview finally takes place, Pirro actually calls early and sounds downright chipper—although she confesses to having spent a late night in a veterinary emergency room near her home in Harrison with her two standard Poodles. (“I won’t bore you with the details, but they’ll be okay,” she assures. “They’re on antibiotics.”) The woman at the other end of the phone is in full-court press mode to talk about her new show, Judge Jeanine Pirro, airing weekdays at 3 pm on The CW. When I ask why television’s already crowded docket needs one more judge, she doesn’t hesitate to respond: “Judge Judy is the gold standard,” Pirro begins, before employing her signature phrase: “Make no mistake about it, all these shows are personality-driven. It’s not just my personality that will distinguish me but my experience.” Pirro then proceeds to give me her well-rehearsed press pitch, reeling off her familiar résumé. After graduating from Albany Law School, she became an assistant district attorney in Westchester in 1975. In 1990, she went on to become the first female judge to sit on the county court bench. Her three terms as district attorney—she handily won elections in 1993, 1997, and 2001—made her a highly visible figure in New York politics and resulted in some valuable face time as a talking head during the O.J. Simpson murder trial. Pirro says she was one of the first to call for allowing cameras in the courtroom during the trial. “I said it was about time the American public got a look at a criminal trial from the inside.” When describing her career path, the Elmira, New York, native of Lebanese descent emphasizes her work as an outspoken advocate for children and victims of domestic violence—the real link to the role of counselor and victims’ advocate, she says, that carries over to her new gig as a television judge. Afterward, she lets out a whoop of laughter. “I’m sorry,” she says. “That was a pretty long answer to a simple question.”

The truth is there’s nothing simple about Jeanine Pirro. Her reputation as a telegenic, tough-as-nails prosecutor whose ambitions propelled her to seek higher office has always been at odds with her other persona as wronged wife who chose to stand by her philandering husband despite his admission of having fathered a child with another woman, convictions of tax fraud, and reputed mob ties. “Even to some of her friends she’s a bit of a mystery in that regard,” says one former colleague. “But she has this steely determination. She’s like Hillary Clinton in that way. I think she’s using this new chapter in her professional life to turn away from her old life—the DA’s office, politics, the marriage. She’s free now.”

- Advertisement -

Pirro’s move to television is a second act for the 57-year-old that, she says, finally closes the book on a once promising political career. “For everything there is a season, and that season has passed,” she concedes. “Television has always been an option for me. There have been contracts that have been offered to me over the years, but I always said no.”

However, when Telepictures came calling last year, it must have been a relief to Pirro, who once was considered to be among the Republican Party’s most formidable women. All that changed after an aborted run for the Senate against Hillary Clinton and a resounding loss in 2006 to Andrew Cuomo for State Attorney General. The final humiliation that sealed her fate involved yet another scandal surrounding her tumultuous marriage to Westchester businessman Al Pirro. Just weeks before the election, Pirro was caught on tape talking to former NYPD Commissioner Bernard Kerik about possibly investigating and allegedly wiretapping her husband, who she suspected of cheating. Unbeknownst to Pirro, Kerik was himself being wiretapped by federal investigators (and subsequently was convicted of misdemeanor corruption charges). Her conversation set off talk of a possible criminal investigation into whether there was any wrongdoing on Pirro’s part involving illegal eavesdropping. During an emotional press conference at the time, she said, “There is no way, when I have the opportunity to be the first woman attorney general in the history of this state, that I am going to be pushed out of this race because somebody wants to delve into the personal lives of my husband and myself. I’m standing up for myself and I’m standing up for women.” Pirro also said that she ultimately decided against surreptitiously taping her husband. “I was a very angry woman, and I said a lot of things, but what matters is what I did and didn’t do. I didn’t do anything here other than vent.”

Pirro wasted no time exploring her options once it became clear her political career was over. When Hilary Estey McLoughlin, president of Telepictures Productions, called her the day after her loss to Cuomo, Pirro agreed to meet the very next day. According to McLoughlin, what was supposed to be a quick getting-to-know-you chat at The Palace Hotel in New York City turned into an almost two-hour heart-to-heart in which Pirro opened up about her public and private life. McLoughlin was convinced she had found a fledgling television star. “We did the deal really quickly. I think she always wanted to be in television,” McLoughlin says.

McLoughlin says the very issues that proved insurmountable to Pirro in her political career were assets when assessing her future in television. “I liked that she admitted to whatever problems she had and she was willing to share her life,” says the executive. “She said it had been hard. The best personalities on television are those who have lived, endured drama, and overcome. That’s key to daytime.”

Pirro’s real-life drama certainly fit the bill. During their first meeting, says McLoughlin, Pirro “talked about her husband—she said she still loved him but she felt she was put in a bad position.” It was clear, she says, that Pirro’s first concern was for her children. “She’s really dedicated to them. She said her main objective was trying to protect them.” McLoughlin says she walked away from the meeting duly impressed that Pirro had weathered such a public battering while remaining resolutely optimistic. “She wears it all like a coat of armor, forges ahead, and keeps a positive attitude. Jeanine is able to place what happened in context and push ahead.”

- Partner Content -

While Pirro’s personal and political scandals made for some colorful headlines in the New York tabloids and gave the political pundits on cable something to chew on between breaks covering Hillary Clinton, one close Pirro confidant says none of it stuck and it has no significance in Pirro’s new life as a television judge. “It made for some interesting cocktail-party conversations in Westchester, but the people out there in Middle America that watch these court shows neither know nor care about any of this,” insists this longtime friend.

McLoughlin agrees. “I don’t think viewers are familiar with it,” she says. “It’s a New York story—the New York Post can’t get enough of it.”

But Pirro’s fresh start has been marred by some unpleasant reminders of the past. When her show premiered in September, dozens of picketers descended upon the Manhattan offices of Warner Brothers, distributor of her show, to protest what they allege were Pirro’s misdeeds and ethical violations surrounding two cases whose verdicts have been overturned with admonishments by the judges for the district attorney’s office’s handling of the evidence. The leader of the pickets, Jeffrey Deskovic, told the New York Times that Pirro was guilty of “prosecutorial misconduct.” In 1989, Deskovic was prosecuted by the district attorney’s office (Pirro was not in charge at the time) and wrongly convicted of the rape and murder of a fellow student at Peekskill High School. He spent 16 years in prison until DNA evidence submitted by the Innocence Project to Pirro’s successor, Janet DiFiore, led to another suspect and Deskovic’s release from jail. Deskovic maintains he wrote to Pirro on two occasions asking her to re-examine the DNA sample taken from the victim and match it with the state’s database. Deskovic alleges that his letters went unanswered. Pirro’s attorney, William I. Aronwald, told the Times a search of the files never uncovered any such letters, and that a formal appeal could not have involved a DNA match because at the time, no DNA database existed.

In another case, Anthony DiSimone, who was convicted of killing Louis Balancio in a Yonkers gang fight in 1994, was released in 2007 when a federal district court threw out the conviction on the grounds that there had been withholding of exculpatory evidence—including a tape recording made the day before DiSimone’s indictment in which a federal prosecutor told Pirro that an informant claimed another individual and his brother had confessed to the murder. The judge who overturned the verdict ruled there was an “egregious” witholding of evidence by Pirro’s office. Aronwald told the Times that Pirro believed she was supposed to wait for the federal prosecutor to validate the informant’s credibility, but since he never followed up with her she assumed that the informant’s story didn’t pan out.
Pirro herself won’t talk specifics about anything that’s taken place in her professional or personal life except to say, “I have absolutely no regrets about anything. I’m not that kind of person. I rarely turn my head and look back.”

This is perhaps what is most fascinating about Jeanine Pirro: if there’s a battle- scarred woman behind the extremely confident, downright pragmatic personality on display in front of the cameras—and at the other end of this phone call—she’s the only one who knows it. When she finally allows the conversation to veer off into her personal life, there’s only momentary wariness when I ask about the current state of her marriage. “We’re separated,” Pirro says softly of the couple’s official split last November. Then, she repeats herself as she brightens once again: “We’re separated, but the proud parents of two great kids. My daughter, Kiki, is at Penn Law School in her second year and is doing extremely well. My son, Alex, spent last year at the London School of Economics with New York University.” Having famously said, “I love my family” when asked back in 2006 if she loved her husband in the midst of one of his legal woes, Pirro sounds almost conciliatory when she says, “As crazy as life was, we were both good parents. They were number one.” (Calls to Al Pirro’s White Plains office were unreturned).

- Advertisement -

While Pirro still lives in the mansion in Harrison she shared with her husband, her current companions are of the four-legged variety: her two standard poodles and her 18-year-old potbellied pig, Wilbur. These days, though, she spends most of the week in Chicago where Judge Jeanine Pirro is filmed (in the same studio as Jerry Springer’s show), leaving New York on Monday or Tuesday and returning home to her beloved pets on the weekend. “I love going to Chicago and I was dying to take my dogs, but the hotel I’m staying in won’t take them,” she says. “I love coming home. I love gardening, running around, and going to The Westchester.”

When I tell her we first met years ago at an event for Manolo Blahnik at Neiman Marcus—whereupon learning I was a reporter, she implored me not to write that she was at the store trying on $400 shoes—she laughs and says, “That was the old days. Now I can tell you I shop at Neiman Marcus!”

Clearly relieved to have the days of having her shopping habits as well as the cuts and color of her trademark suits deconstructed in the press, Pirro says, “The best part [of my new job] is I can have fun and make a difference. I was always extremely serious about what I was doing. Now I can say some of the things that I wouldn’t necessarily say before.” But Pirro’s newfound chattiness is limited to her exchanges in front of the camera in her television courtroom. While she seems game to talk during our initial interview, which focuses largely on how she’s adjusting to her new career, calls for a follow up chat about more personal issues go nowhere. She also declines to offer up a close friend or family member to speak on her behalf on—or off—the record.

Pirro is even decidedly circumspect when asked to weigh in on the current crop of female candidates who are engaging in the “bloodsport” world of politics. When asked about Hillary Clinton’s failed presidential bid and Sarah Palin’s viability as a vice presidential candidate, Pirro demurs. “Not gonna go there. I’m not going to talk politics. Maybe one day.” She does admit, though, that it’s pretty tough going for any female candidate. “There is no question that women are looked at differently.” As she continues, her comments offer more insight into her own psyche and approach to dealing with the pressures of public life than they do on the experiences of others: “One of the distinctions people don’t talk about is that if a woman isn’t done up to the nines, people don’t think she’s up to the job, so there’s a part of it that requires that your hair be in place and your makeup be impeccable and you not look drawn with dark circles under your eyes.”

When Pirro enters a courtroom now, she’s always camera-ready—which is a good thing since she says she never knows just what she’s going to encounter on any given day. While taping her very first episode of her show last summer, she unwittingly uncovered sexual abuse when two female cousins, who were suing each other over unpaid rent, engaged in a war of words that ended up with both of them tearfully blurting out they had been raped by the same man, the boyfriend of an aunt called as a character witness in the case. “I had no idea this was coming,” says Pirro. “I’m going to follow up, believe me.” In fact, Pirro took the young women into her “chambers”—with the cameras rolling—to offer advice on how to restart the cold case.

While Pirro’s television court’s jurisdiction is set within the framework of small claims court for civil cases with judgments up to $5,000 in a case such as this, the former prosecutor will use her contacts in the DA’s office in the women’s home state and follow up with the victims. “I’ve got several cases like that and that’s what makes me different,” she says. “The fact that I can identify victims and I want to make sure they get justice, not just in my courtroom but wherever they need it.”

Somehow it’s hard to imagine Judge Judy counseling a rape victim, so Pirro may have found a niche that could distinguish her from the pack. Still, she has her work cut out for her slogging her way through train-wreck television territory of family disputes, warring neighbors, and the just plain weird that is the stock and trade of the court show genre. But Pirro has little to lose and everything to gain if she finds television stardom. She has a contract with Telepictures for 150 episodes—a year’s worth of shows—which is an extraordinary order for a first-time television host. “That’s very unusual in this business,” says one former talking head who has worked with Pirro. “Her deal proves just what a tough negotiator she is. I salute what she’s done. She’s using television to reinvent herself as a woman, and as an older woman in her second career. It’s impressive.”

True to form, Pirro may have gone to the mat on getting the deal she wanted, and might feel some pressure to succeed, but you’d never know it listening to her. “There’s a certain peace I have now. I have a total sense of freedom and I laugh a lot more than I used to. I’m in a good place.”

So what makes Pirro run today? Her new television boss offers this insight: “I think she feels like she has to succeed,” says McLoughlin. “There’s no option not to.”

Diane Clehane is a bestselling author and journalist whose work has appeared in Vanity Fair, Variety, Men’s Health, and People. She currently is at work on her first novel.

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.