Last October, two weeks before the midterm elections, a budding model named Jeff Thomas walked into the Polo Lounge at the Beverly Hills Hotel for lunch with a friend who had been working with a well-connected Democratic political operative named Jack Bury. Thomas, then 35, dabbled in real estate, the art world, and the inchoate realm of social media influencing. But his most relevant avocation was as a former boyfriend of Peter Thiel, the multi-billionaire entrepreneur and Republican mega-donor. Thomas, who first met Thiel at Coachella in 2015, lived near the hotel at a $13 million place in the Hills that Thiel had underwritten. 

Thomas was startled by the stakes of the meeting:  Did he want to participate in Bury’s sprawling opposition-research project against Thiel, one that would pry into Thiel’s private life, apply pressure, and persuade him to leave national politics?

For six years, after all, ever since he appeared on stage during the 2016 Republican National Convention, Thiel had been a fixation in G.O.P. donor circles—a potential bottomless-pocketed heir to Sheldon Adelson or the Koch brothers. Meanwhile, he’d simultaneously developed into a fixation among Democrats, caricatured as a blood-swilling, Gawker-slaying, Trump-fluffing venture capital villain and putative Judas of the gay community, a portion of which could not square his personal orientation with his politics.