We finished lunch and moved to a cabana by the pool, joining her stepdaughter, Nicole, and Nicole’s son, Alexei, who were visiting from Westchester and killing time before massages. Nicole sat barefoot with a fresh pedicure, her aviators and watch glinting in the sun; Alexei, dressed head to toe in athletic wear, towered over all of us, even while sitting. Nicole told me about the first time she met Sheindlin, when she was 8: She came home from school to a car she had never seen before in her driveway. Her father and Judy had recently gotten together; at the time, Jerry was a defense attorney, and Judy handled juvenile-​delinquency and child-support cases for New York City. Jerry explained: “You know how I’m a lawyer, and I try to get people out of jail? You see her? She puts them in jail.” That was that. Judy was in.

Three of Judy and Jerry’s five children are lawyers, as is one of their 13 grandchildren. At least another three are considering careers in the law. Disputes are the family’s love language. At one point, Sheindlin and Alexei disagreed about whether men are capable of prioritizing others’ needs. Alexei told her that there are men in the family — like his dad and brother — who can do just that. Sheindlin grew animated; now she could do what she did best. She started to cross-examine her grandchild, repeating each of his sentences back to him slowly and sharply, punctuating them with phrases like “Is that a fair statement?” in order to, in her own way, tear them to pieces. Alexei sputtered a defense, but then the Judge presented her argument: Jerry and Judy know that Alexei needs to be taken out for breakfast when he wakes up. Judy takes him as soon as he’s hungry; Jerry fits it into his own schedule — because he’s a guy, she said, and that’s what guys do! Alexei was resigned: He knew he was right, but this wasn’t the hill to die on. (He’s one of the prelaw grandchildren.) Judy, satisfied, doubled over with laughter.

During lunch, I asked Sheindlin, a former crime-and-crack-era New York judge, about broken systems: I wanted to know, after so many years on the bench, if she thought systemic failings or individual ones were what put people in front of her. “I don’t know how you deal with systemic irresponsibility,” she answered. “It’s beyond my pay grade. I think it’s much easier to deal with the individual.” After watching them argue, I wanted to know whether Alexei, a millennial like me, was comfortable considering ethical behavior on a grand scale. He said it was easy to be idealistic about people’s intentions but hard to rebut a lived experience, especially when it was his grandmother’s.

Alexei’s youthful optimism had floundered against Sheindlin’s staunch realism. There’s no way she could know every nook and cranny of a case — she considers only the facts right in front of her. It was too easy to get lost in the minute details of an emotion. This is why she went into law in the first place: You know only what you know.

Like most confident and successful women she knows, Sheindlin adored her father, and her father adored her. She was born to a German-Russian Jewish family in Brooklyn in 1942. Though she finished high school a semester early, she claims not to have been particularly academically gifted, not doing well in “touchy-feely” classes like philosophy. “I was smart enough,” she said. “I came from Brooklyn, so I knew how to cross the street in traffic.” She attended the school of government and public administration at American University in Washington, which had a program that allowed undergraduates to enroll in the law school upon completing a bachelor’s degree. She was one of only a handful of women in her graduating class. She understood the law and excelled in her courses — but then she met the man who would become her first husband in 1964, a time when most women followed their husbands, even if the woman was at the top of her law-school class and the man only had a job with Legal Aid in New York that, she says, paid $75 a week. Sheindlin married and finished her degree at New York Law School.

At first, she worked as a corporate lawyer, but she didn’t find any pleasure in it, so she quit and became a stay-at-home mother. Then she divorced. A law-school acquaintance encouraged her to apply to an opening in the New York Family Court system. She prosecuted juvenile-​delinquency and child-support cases around the city — “lots of beaten children, lots of starved children, lots of children who were sexually molested” — and sharpened her obsession with personal responsibility and strong family structure. (Indeed, talking to Sheindlin sometimes felt like talking to a Bernhard Goetz-era copy of The New York Post come to life.) Unlike some of her contemporaries, Sheindlin didn’t believe in putting the blame on the state or the system. “While you can blame the system for not being more vigilant about taking care of these children and hiring people who are less qualified or capable of being overwhelmed, I’m always a big believer in ‘the buck stops right there,’ ” she said. “The person that abuses that child is responsible.”