Lisa Wexler

Probate Judge, Radio Personality, and Jewish Mother

In June 2011, a beautiful summer evening found me plastered to my couch with a glass of chardonnay, watching season four of Real Housewives of New York.

In this episode, Sonja Morgan was readying herself to watch a dermatologist inject Jill Zarin’s face full of dermal filler when Jill’s sister, Lisa Wexler, appeared and counseled Sonja on bankruptcy because Sonja had just lost a boatload of dough on a bad movie deal. Or something like that. The storyline isn’t my point.

This is my point: Lisa Wexler.

There Lisa sat discussing bankruptcy law, unencumbered by monster diamonds, age-inappropriate clothing or back-stabbing histrionics. What was it about her that made me put down my wine and listen?

Bravo’s goal with the Housewives is not to win a slew of McCarthy genius grants, so we rarely see glimpses of unadulterated intelligence. Was that why Lisa made such an impression? Yes, but there was something else. While speaking with Sonja, Lisa never got annoyed at her sister for constantly interrupting her. Aha! Lisa displayed kindness, Bravo TV’s second most vilified and untelevised trait.

If you recognize her name it’s because you watch RHONY, you know she’s been the Westport-Weston probate judge since 2013, and/or you’re familiar with her award-winning radio talk show, now on WICC-600. (Of personal note, I was thrilled when I learned we lived in the same town.)

Or maybe you read her book, written with Jill and their mother, Gloria Kamen, Secrets of a Jewish Mother. It’s on the pages of this tome I discovered the secret of her appeal: Lisa, like the matriarch illustrated in her book, is guided by the power of kindness and wants others to succeed.

Lisa grew up surrounded by a loving, supportive, loud family in Long Island. After graduating Johns Hopkins University (were she met her husband, Bill) she attended New York University law school and was an award-winning student. Her life was shaped by strong Jewish mothers and, eventually, she became one herself.

In her book, she alludes to the talkative nature of her tribe, “a Jewish mother’s wisdom isn’t reserved for her children… it is spread around to anyone who will listen.” Well, Lisa loves to talk. And talk. And many people, like myself, hang on every word.

So when she heard Rush Limbaugh she thought, “I have something to say that’s better!” Despite a full slate of legal clients and a family of four, she attended the Connecticut School of Broadcasting for a crash course in radio. Then she called the local radio station and brokered an hour of talk time on Saturday morning. Within months her show rocketed to the top and she was promoted to the coveted evening commute time, from 4:00-6:00 p.m. And, of course, won awards.

The beauty of her show is her respect for people, both callers and in news stories. Her tone is straightforward and her opinions are compassionate and thoughtful as she transitions from toilets to the democratic primaries to the administering of Narcan by children of over-dosing parents.

While her empathy and logical assessment of facts make her a great attorney, she claims “As a judge, one of the most important gifts you can give is to really listen to people. Even if you make a decision they don’t agree with they understand why you made it and don’t feel left out of the process - that’s part of justice.”

Lisa brings this process of justice and her cuddly pooch, Shaina, into the probate courtroom (Room 100 in Town Hall) almost every afternoon. While Shaina minimizes stress levels, Lisa carefully untangles sad, sticky knots of lives and problems that most of us never witness.

Children of addiction faced with incompetent parents and caught in guardianship struggles, young adults at St. Vincent’s Medical Center with severe mental afflictions who want to return home, elderly people abandoned by their families, living in squalor and unable to take care of themselves. Lisa advocates for these incapacitated or neglected residents. Law may be reason free of passion but, as a Judge, Lisa gives it humanity, enabling law to elevate and safeguard. “Every single day I feel like I’m helping and protecting people who can’t protect themselves,” she states. She’s their Jewish Fairy Godmother.

During a meeting in her office this March, Lisa asked me if I wanted to hear her favorite song: Westport songwriter David Friedman’s 1994 hit “We Can Be Kind” sung by Nancy Lamott.

I listened to the song while I sat among notebooks Lisa had filled with unintelligible research and opinions. Across from me was a table fluffed with a cloud of tissues Shaina had recently mauled and Lisa had patiently tidied. Lisa herself had run out and returned with packets of cashews, in case I was hungry.

As we munched nuts, Nancy sang “So much pain that won’t ever go away/How do we make it better?/We can be kind.”

Though they didn’t know each other at the time, David could have written it for Lisa. Without artifice or ulterior motive, she is kind. And Westport is incredibly fortunate to have her.

Probate Judge

Room 100, Town Hall

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