In early January 2000, Supreme Court Justice Clarence Thomas was at a five-star beach resort in Sea Island, Georgia, hundreds of thousands of dollars in debt.

After almost a decade on the court, Thomas had grown frustrated with his financial situation, according to friends. He had recently started raising his young grandnephew, and Thomas’ wife was soliciting advice on how to handle the new expenses. The month before, the justice had borrowed $267,000 from a friend to buy a high-end RV.

At the resort, Thomas gave a speech at an off-the-record conservative conference. He found himself seated next to a Republican member of Congress on the flight home. The two men talked, and the lawmaker left the conversation worried that Thomas might resign.

Congress should give Supreme Court justices a pay raise, Thomas told him. If lawmakers didn’t act, “one or more justices will leave soon” — maybe in the next year.

At the time, Thomas’ salary was $173,600, equivalent to over $300,000 today. But he was one of the least wealthy members of the court, and on multiple occasions in that period, he pushed for ways to make more money. In other private conversations, Thomas repeatedly talked about removing a ban on justices giving paid speeches.

Thomas’ efforts were described in records from the time obtained by ProPublica, including a confidential memo to Chief Justice William Rehnquist from a top judiciary official seeking guidance on what he termed a “delicate matter.”

The documents, as well as interviews, offer insight into how Thomas was talking about his finances in a crucial period in his tenure, just as he was developing his relationships with a set of wealthy benefactors.

Congress never lifted the ban on speaking fees or gave the justices a major raise. But in the years that followed, as ProPublica has reported, Thomas accepted a stream of gifts from friends and acquaintances that appears to be unparalleled in the modern history of the Supreme Court. Some defrayed living expenses large and small — private school tuition, vehicle batteries, tires. Other gifts from a coterie of ultrarich men supplemented his lifestyle, such as free international vacations on the private jet and superyacht of Dallas real estate billionaire Harlan Crow.

Precisely what led so many people to offer Thomas money and other gifts remains an open question. There’s no evidence the justice ever raised the specter of resigning with Crow or his other wealthy benefactors.

George Priest, a Yale Law School professor who has vacationed with Thomas and Crow, told ProPublica he believes Crow’s generosity was not intended to influence Thomas’ views but rather to make his life more comfortable. “He views Thomas as a Supreme Court justice as having a limited salary,” Priest said. “So he provides benefits for him.”

Thomas and Crow didn’t respond to questions for this story. Crow, a major Republican donor, has not had cases at the Supreme Court since Thomas joined it and has previously said Thomas is a dear friend. David Sokol, a conservative financier who has taken Thomas on vacation on a private jet, said in a statement that he and Thomas had never discussed the justice’s finances or when he might retire.

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