Top Judge

Standing in the conference room of a white-shoe law firm high above Park Avenue in Manhattan, Janet DiFiore nervously waited for what would be one of the toughest job interviews in a standout career that has spanned nearly 35 years.

That was a little under a year ago, and the feeling was uncommon for DiFiore. As someone who’d logged serious time as a judge in Westchester County Court and New York State Supreme Court, and served for more than a decade as Westchester’s top crime-fighter, DiFiore is not known for getting rattled. But angst had crept in as DiFiore was about to meet with members of the Commission on Judicial Nomination, the panel of lawyers, judges, and legal minds who would surely interrogate her in true prosecutorial fashion before recommending for or against her nomination to Governor Andrew M. Cuomo, who would ultimately appoint her to the highest judicial bench in the state.

Before the meeting started, DiFiore remembered an old stone stoop at her childhood home in Mount Vernon, one that her grandfather had built with his own sweat and labor. It’s where she spent many of her early years palling around with aunts, uncles, and cousins from her large Italian American family. In an instant, a calm came over DiFiore when she realized that whether she landed the job or not, her journey had been an amazing one.

“Take a deep breath and enjoy this,” DiFiore remembers saying to herself. “It was one of those moments.”

Even though she only lives a half-mile from where she grew up, DiFiore has come a “loooong way,” as she puts it while sitting on a sofa in her Bronxville home, from her modest early years on Mount Vernon’s North Terrace Avenue to being the chief judge of the New York State Court of Appeals. Only a privileged few have held the post, and past chief judges have gone on to the US Supreme Court, run the US Treasury and campaigned for the presidency. Two even have New York City colleges named after them—Benjamin Cardozo and Westchester’s Founding Father, John Jay.

But such grandiose aspirations do not cross this jurist’s mind. “In my family, we have a saying: You keep your eye on the ball, and everything takes care of itself,” DiFiore says. “You have to focus on what’s in front of you.” It’s a philosophy that has served her well since her early days as a legal eagle, which go back to interning under respected Westchester District Attorney Carl Vergari, who later hired her, in 1981, as an assistant district attorney. She remained in the DA’s office until 1987—worked part-time in private practice and as deputy attorney for the village of Bronxville when her three children were little—and returned in 1994 as chief of the office’s Narcotics Bureau, under then-District Attorney Jeanine Pirro.

Approaching the Bench

Today, as chief judge appointed to a 14-year term, DiFiore, 61, sits in the hot seat on a seven-person bench, where she not only adjudicates a wide range of important legal cases but must build consensus among peers who are sharp and atop their games. The signature black-silk robe she wears now is the same one worn by former judge Judith Kaye, the New York Court of Appeals’ first female chief judge (DiFiore is the second), who gifted it to DiFiore before Kaye died earlier this year. Out of respect, DiFiore also wears a pin, a replica of the red shoes that Kaye wore during her tenure on the bench.

There’s clearly a lot on DiFiore’s docket these days. In addition to the broad scope of legal decisions, she is also responsible for managing the day-to-day administration of a complicated court system that has four million case filings a year and encompasses all of New York State’s 55,000 square miles. In all, she oversees 15,000 employees, 3,500 judges and 350 courthouses and has her own chambers in Albany, Westchester, and Manhattan. On her investiture, or swearing in, DiFiore announced her “Excellence Initiative,” which was part-pledge, part-policy, on making the courts, top-to-bottom, work efficiently for the people who at some point in their lives need the state judicial system. She aims to bring the same philosophy, energy, compassion, and diligence to every job in front of her.

“Work ethic is very important to me,” she says, “and when you have a good work ethic, things usually take care of themselves.”

DiFiore replaced Chief Judge Jonathan Lippman, a former Rye Brook resident who led the appeals court until 2015, when he reached the mandatory retirement age of 70. The two have known each other for two decades, working together on task forces and traveling alongside each other when they were running for their respective offices. “We had such a fun time on the campaign trail,” says Lippman. “Janet is great fun to be with.”

In addition to her sense of humor, DiFiore has a rare combination of intelligence, leadership, strength of character, and street smarts, Lippman says, as well as a unique ability to relate to people of all types. He adds that the concept of justice won’t be a vague textbook notion or high-minded platitude under her direction but that the public can actually place its trust and confidence in the judiciary.

“She is made for this job,” Lippman says. “She will pursue justice each and every day.”

DiFiore, who was a Republican before she switched parties in 2007, was picked by Gov. Cuomo from a pool of seven candidates. In announcing DiFiore, the sitting governor—whose father, Gov. Mario Cuomo, had picked Judith Kaye when he was in office—said DiFiore was “tremendously qualified” and had spent her career working to “ensure fairness and justice for New Yorkers.” She had worked with Andrew Cuomo—himself a former attorney general—for many years, even leading the governor’s Joint Commission on Public Ethics, or JCOPE, for 16 months.

DiFiore was introduced to the justice system at an early age. When she was 12, her cousin was tried and convicted of an armed robbery. While court was in session, she and her large Italian family filed into the gallery, to be supportive, and DiFiore was captivated by what she saw: the courtroom… the prosecutor… the judge.

Suddenly, her calling was clear: She would devote her life to the fair administration of justice.

“Even though I was crushed that my cousin went to jail, it was about accountability,” she says. “His action had a consequence, an appropriate consequence. When it’s fair and right, who can argue with it?”

A graduate of Mount Vernon High School, DiFiore went on to study sociology at Long Island University’s C.W. Post College. Campus living lasted all but 24 hours for her. “I couldn’t stand being away from home,” she says.

Unlike most freshmen, she didn’t think she was missing out on college life. “I lived in a crazy house that my grandfather built. There was family everywhere,” she says. “Every night was like a party.”

From then on, she commuted an hour each way, as she did when she went on to St. John’s University School of Law. While studying in Queens, she met her future husband, Dennis Glazer, during a study session in the library. As the story goes, Glazer left his books unattended on a table there, taking up valuable real estate. DiFiore wasn’t having any of it: Thinking it rude, she simply brushed his pile aside and got to work. Realizing he had met his match, the two wed at Westchester Country Club in 1981, after graduation.

Soon after, Davis Polk & Wardwell—the New York law firm where Glazer worked—wanted to relocate him to Paris. DiFiore wasn’t swayed by the allure of a foreign assignment, so her response was quick and decisive: “Can my mother go?” she asked Glazer, knowing full well the answer.

With that, they stayed put, and DiFiore continued building her own career. “There’s no way I would leave my family,” she says.

It’s clear that family is at the heart of DiFiore’s life and has shaped every aspect of her career.

Her father, Anthony, who didn’t pass the eighth grade, ran his own sheet-metal business, while her mother, Josephine, raised the family. Growing up an only child, but with parents, grandparents and a large extended famiglia buzzing around constantly, DiFiore says she was loved and cared for. She’s particularly grateful for her mother, who, she avers, was “perfect” in every way. “She was good at everything she did,” DiFiore says.

When DiFiore was considering going back to work at the district attorney’s office after raising her children, she was fearful that her mother would be disappointed, as family came first under their roof. But her mother surprised her, saying, “Of course you’re going back. You’ve worked so hard to get where you are.”

With that, Mama DiFiore came over each day to prepare dinner for the family and help with the children. That happened until both of DiFiore’s parents passed away: her father in 1998, at age 71, and her mother in 2002, at age 73, losses she admits remain hard to grasp.

“I still, to this day, go to the phone to call my mother,” she says. “It’s a very powerful connection.”

So, too, is her connection to her husband—a confidant, cheerleader, and confidence booster whose support she says has been invaluable to her through the years. “If you don’t have a supportive spouse, it doesn’t work,” she says.

Glazer’s participation has been a constant; he has run every one of her campaigns (she’s never lost an election) going back to her run for Westchester County Court judge in 1998, when she was a Republican. (When she officially became a Democrat, the first call she received welcoming her to the party was from Hillary Clinton.)

The Power of the Law

Despite having a limited background in family law, it was in family court that DiFiore developed a reputation for applying her unique combination of common sense, fairness, and compassion in rendering her decisions. It was a formative experience, as DiFiore worked at the intersection of complicated matters such as domestic violence, child-custody battles, and juvenile delinquency, among other personal and foundational life issues. “That was the most important and meaningful assignment I had,” DiFiore says of family court. “People come to that court for real help.”

Some minors who came before her bench still stay in touch—even ones she’s been tough on. One young man asked her to officiate his wedding, while another, whom she sentenced for a violent felony when he was 15, later turned his life around, went to school and landed an internship in the DA’s office with DiFiore’s help.

After serving in family court until 2002, DiFiore was elected to New York State Supreme Court. While there, she was appointed supervising judge of Criminal Courts for the judicial district, where she restructured the case-assignment system, eliminated a backlog of criminal cases and established the district’s Mental Health Courts and Sex Offender Courts.

Surprising many judges and colleagues, however, she hung up her robe and resigned from the bench in 2005—leaving a comfortable job and giving up all of the legal prestige that comes with it—to run for Westchester County District Attorney after then-DA Jeanine Pirro ran for US Senate. DiFiore says it was a natural progression and that her years serving in the halls of justice made her a better crime-fighter. “I don’t think I would have been as well-rounded a DA if I had not been a judge first,” she says.

In her first term as district attorney, she was approached by the Innocence Project on behalf of Jeffrey Mark Deskovic, who at 19 was convicted of raping and killing a 15-year-old high-school classmate in Peekskill. Deskovic, who was serving a 15-years-to-life sentence, had long maintained his innocence, yet DiFiore’s predecessor refused to reopen the case. A year into her term, DiFiore intuitively felt something wasn’t right and reconsidered the evidence. She approved new DNA testing (an option that was not available years earlier) that eventually showed another man—a drug addict from Peekskill—had murdered the young girl. Deskovic was exonerated and released after serving 16 years in prison. The actual perpetrator was apprehended, prosecuted, and convicted.

“That was a seminal moment for sure,” DiFiore says. “It was life-changing. It drove home the power of the office and its ability to change people’s lives.”

Acting Westchester County District Attorney James A. McCarty started with DiFiore under DA Vergari and years later appeared before her when she was a judge. Through it all, she’s shown herself to be authentic and honest, someone who does the “right thing for the right reasons,” he says.

On the Deskovic matter, McCarty said it would  have been safe and easy to stand pat and not reopen the case. “In fairness, it was investigated and prosecuted, and no one did anything wrong,” he says. “She had the strength and courage to reopen the case, which led to the release of an innocent man.”

On The Defense

Serving in such positions doesn’t leave one without critics, however. Some have faulted DiFiore for not getting convictions in other high-profile cases, including three fatal shootings of black men involving police officers. Among them are: off-duty Mount Vernon police officer Christopher Ridley, who was shot by police in 2008 while wrestling with a mugging suspect; Pace University football player Danroy Henry, who was shot by police in 2010 in a parking lot during a chaotic melee; and the 2011 shooting of a retired corrections officer, Kenneth Chamberlain Sr., who locked himself in his apartment with a weapon when police arrived at his home for a medical emergency.

Though she wouldn’t discuss particulars of any case (judges are prohibited from doing so), DiFiore believes that the only true way to measure your work as a prosecutor is to base it on the authenticity and strength of the investigation. For that, she says, she’ll defend every action taken by her office.

Her most vocal critic has been Selim “Sam” Zherka, a strip-club owner, real estate investor, and controversial publisher of The Westchester Guardian. He went so far as to offer a $100,000 reward for anyone who had verifiable information of misconduct that would lead to DiFiore’s arrest, conviction, or disbarment. But nothing ever materialized. In 2015, meanwhile, Zherka pled guilty to filing false tax returns and fraud charges relating to a multimillion-dollar loan he’d sought; he is now serving a 37-month sentence in federal prison.

Another matter covered extensively by local press was when a social-services employee—also a member of the Independence Party, which had long opposed DiFiore and been a political foe—in 2012 claimed that a live-in nanny of the district attorney may have improperly received social-service benefits. DiFiore maintained all along that she did nothing wrong, and social services eventually cleared her and her nanny of any wrongdoing.

As DA, DiFiore took a markedly different approach than her media-savvy predecessor, opting for fewer press releases, press conferences, and television appearances. Instead, she focused on education and prevention and let the work speak for itself. “It was never my style to showcase in a flashy media way,” she says. “We spoke through our work in the courtroom.”

DiFiore also worked closely with former New York City Police Commissioner Ray Kelly on several commissions, including one on wrongful convictions that Lippman appointed her to chair. While serving together, Kelly was impressed with the way DiFiore skillfully managed a number of large personalities and built consensus. “Everybody liked her, which is not easy in a charged environment,” Kelly says. “She struck me as a doer, someone who gets things done.”

Kelly credits DiFiore with convincing him to green-light the installation of cameras in all interrogation rooms of New York City police precincts. A hot-button issue that could have easily been squashed, DiFiore implored Kelly and others that the NYPD and New York State must lead the way. “I must say, for me, she was the prime mover in this regard,” Kelly says. “It turned out to be the right thing.”

Throughout it all, DiFiore has learned to balance the rigors and stresses of her job with a regimen of yoga, healthy eating, and rising most days by 5 a.m.—all while prioritizing her family. She also credits her Italian grandparents for having good genes.

Also passed down to her was a love of cooking and entertaining. Her table is always full with family and friends, particularly on weekends. “We eat at home all the time,” she says.

Her daughter, Alexandra, 32, who is a lawyer “paving her own way” in the Manhattan District Attorney’s office, says her mom has boundless energy. “She has 48 hours in her day when we mere mortals have 24,” she jokes. Alexandra is married to Matthew Murphy (a wedding that DiFiore officiated), has two children—Charlotte, 2, and James, 5 months old (whom DiFiore, known to them as “Gi-Gi,” adores)—and lives nearby. Of DiFiore’s sons, 30-year-old Joseph runs a technology company, and Michael, 27, works in wealth management.

Although DiFiore and Glazer are both lawyers, they never pushed law careers on their children. Rather, they instilled the importance of finding careers their children loved. “We all took very different paths that are suited to our strengths,” Alexandra says. “They never wanted us to dread our jobs.”

Together, the family bond remains tight. They have traveled the globe, visiting places like Africa, the Galapagos Islands and, most recently, for DiFiore’s 60th birthday, took a family trip to Italy. Much like DiFiore’s own upbringing, they dine together often in their Bronxville home and enjoy time together in their Southampton beach getaway.

In the final analysis, Janet DiFiore’s life is one of compassion, justice, and family. And she’s enjoying the moment.