A Supreme Court lawyer’s double life
Thomas Goldstein made a career out of a high-risk approach. Then he was called out.
The New York Times Magazine
December 28, 2025

By his early 30s, Thomas Goldstein has already established himself as a unique whisperer to the halls of power. “No one knew more about the Supreme Court than he did,” said the celebrated lawyer David Boies.

His swaggering, risk-friendly approach to litigation had won him enormous influence both as an advocate and through his authoritative blog as a leading public commentator on the justices. Then, in 2023, Goldstein stunned the world of Supreme Court insiders by announcing that he would no longer represent clients before the justices. In public, he attributed the decision to the rightward drift of the court. In fact, over the previous decade-plus, Goldstein had been leading a secret life of ultra-high-stakes gambling and “sugar daddy” relationships with multiple young women — a life so sheltered from those around him that no one knew the full extent of it.

The writer Jeffrey Toobin follows Goldstein’s meteoric rise and precipitous fall in his feature this week.

A high-contrast black-and-white portrait of a balding bearded man sitting a table, his chin resting on one fist and looking directly into the camera.

Jonno Rattman for The New York Times

He Was a Supreme Court Lawyer. Then His Double Life Caught Up With Him.

Thomas Goldstein was a superstar in the legal world. He was also a secret high-stakes gambler, whose wild 10-year run may now land him in prison.

By Jeffrey Toobin

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