The Apprentice


Nicole Sheindlin remembers the first time she met Judge Judy. She was eight years old when her then-divorced father sat her down, along with her two older brothers, and introduced the new woman in his life…by highlighting Judy’s career. “We do the exact opposite,” she recalls her father saying. “I get people out of jail and Judy puts them in.” At the time, Judy was prosecuting juvenile offenders as an attorney with the Corporation Council in New York County, while Jerry Sheindlin was a criminal defense attorney in private practice; both would soon be appointed judges in New York City.

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“It sounds strange to say, especially since I was so young, but we had an instant connection,” says Sheindlin of meeting her stepmother-to-be that day. “I liked the way she spoke to me so honestly. What you see is what you get with her. She not only became my stepmother but my biggest cheerleader and mentor.”

It’s that connection, sealed at a Nanuet kitchen table 33 years ago, that helped shape the 41-year-old Larchmont resident into who she is today: the founder and executive director of Her Honor Mentoring, a women’s leadership and diversity initiative that she and Judy formed three years ago. The premise of the 25-week program, which starts each September, is to pair high school seniors with female leaders in the community and show these young girls, most of whom come from economically and socially challenging situations, that they, too, have what it takes to be successful. Mentees are paid for their apprenticeships and given monthly “life skills” workshops beginning with how to manage money and ending with how to negotiate and advocate persuasively.

“Her Honor Mentoring is really about supporting the underdog,” says Judge Judy—something her stepdaughter was drawn to at a young age.

Growing up, Sheindlin split her time between her Nanuet residence with her mom (a retired financial planner) and Judy and Jerry’s residence in Riverdale. She has two biological brothers and gained a brother and sister from her stepmom’s previous marriage. They became a blended family when Jerry and Judy married in 1978. The family has been integrated for so long that they don’t refer to each other as “step” anything. In fact, the siblings all have such similar mannerisms that it’s hard to tell who “officially” belongs to whom. And though Sheindlin says there was never any pressure to join what she dubs “the family business” (“I remember sitting in my parents’ courtrooms watching the drama play out,” says Nicole Sheindlin. “A lot of our dinnertime conversations revolved around what happened in the courtroom that day”), the idea of public service was always in the back of her mind. “It seemed like a natural transition,” she says. As the youngest in the family, she watched as sibling after sibling went into “law and order;” one of her brothers is the Putnam County DA, and the other, a former assistant district attorney in Manhattan, is now in private practice. (Her sister is a stay-at-home mom.)

If anything, Sheindlin jokes that she was the “black sheep” of the family as she went to the other side—criminal defense—though it took her a while. She started off studying art at the University of Arizona but soon realized public interest was really her calling. (She also realized that, after seeing the creative students she was up against, she should stick to art as a hobby.) She transferred to the State University of New York at Buffalo University, got her B.A., then applied to law school at New York Law—her stepmom’s alma mater. “I really started to rely on Judy as a mentor while in law school,” says Sheindlin, who, at that time, had moved to Manhattan. “Since the school was three blocks from the Family Court where she was the supervising judge, I would walk over to the courthouse to watch her rule and have her help me do my homework…not a bad tutor.”

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During law school, Sheindlin interned with the district attorney’s office and subsequently with the public defender’s office. “I graduated at twenty-four and immediately joined The Legal Aid Society. It was my ideal job—defending the indigent.” She worked at Legal Aid for 15 years, during which she married an attorney (now a criminal defense lawyer in private practice), had three children (ages nine, seven, and five), and moved from the Upper West Side to Westchester County. (One of her brothers, Jonathan, who is teased by the family for not being an attorney, is a well-known ophthalmologist. He lives a block away and introduced her to the neighborhood.) “Though I loved working at Legal Aid, I was looking to do something more proactive,” she says. “I was feeling burned out.”

And so, the petite brunette, who is almost as small as Judge Judy (both wear heels a lot), looked for a way to directly help women in her community. She says the idea for a mentoring program came as a reflection of her relationship with her stepmom and their ongoing discussions about women’s rights and opportunities, ranging from domestic violence to public education. “It wasn’t very difficult to convince Judy that the program was a good idea,” she says. “I approached her like any good lawyer would: with a clear strategy and a strong argument.”

Her Honor Mentoring officially launched in 2007. Judge Judy agreed to provide the seed money for the program and Sheindlin forged an administrative partnership with the Westchester County Office for Women and the Women’s Research and Education Fund.

In the first year (during which she still worked at Legal Aid), Her Honor supported eight mentees from Mamaroneck High School with mentors from around Westchester County. By the second year, she had partnered with the Eastchester-based Lanza Family Foundation, a local philanthropic organization headed by Patricia Lanza, which enabled the program to expand to 18 mentees, adding Mount Vernon High School. Today, the program serves 30 mentees and mentors and includes White Plains High School.

Current mentors include such community leaders as Donna Fishman, CEO of Gilda’s Club; Guillermina Vidales, office administrator at Hispanic Resource Center; Judy Myers, County Legislator with the Westchester County Board of Legislators; Jennifer Christman, executive director of Pelham Picture House; and Meryl Lefkowitz, manager of public relations at Bloomingdale’s.

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Karem Cayetano, a recent graduate of Mount Vernon High School, today a freshman at John Jay College, is one of Her Honor’s graduates. She says the work she did with her mentor, Martha Anderson, an attorney at the Office for Women in White Plains, “made me much more aware about the world out there and how influential and helpful public service can be.” Semarley Jarrett, a senior at Mount Vernon High School and a current mentee working with Karen Cheeks-Lomax, executive director at My Sister’s Place, concurs that the program was beneficial. “I have a lot more confidence in my abilities and I credit it to the program. It feels good to have powerful and smart women tell me, a seventeen-year-old kid, how successful I can be.”

Tell It to the Judge

Nicole Sheindlin says she’s asked all the time if Judge Judy is as tough at home as she is on the set, and the truth is, yes. “She’s always direct, which to some can seem off-putting, like when you’re a kid and she tells you that what you’re wearing looks horrible. But I’ve always appreciated her way with words and the fact that I have someone so straight-forward in my life.” She admits her stepmom can be softer with the grandkids, though she’s known to announce to everyone, ‘We’re full. Put your forks down.’

“That’s just who she is, and that’s one of the reasons she’s so successful. She’s genuine, authentic, and though she can be abrupt, she uses her quick wit and wisdom in whatever she does.”

Jeanne Muchnick, a regular contributor to Westchester Magazine, says it was nice to talk to Judge Judy, and learn that, despite her oversized personality, at the end of the day, she’s a proud mother like many of us.


Her Honor founder Nicole Sheindlin (right) with her own mentor, Judge Judy Sheindlin

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