There’s a reason his biography doesn’t feature much in the campaign. For O’Rourke, the phenomenon on display in that race—failure without negative effects, and with perhaps even some kind of personal boost—is a feature of his life and career. That biography is marked as much by meandering, missteps and moments of melancholic searching as by résumé-boosting victories and honors. A graduate of an eastern prep school and an Ivy League rower and English major, the only son of a gregarious attorney and glad-handing pol and the proprietor of an upscale furniture store, the beneficiary of his family’s expansive social, business and political contacts, O’Rourke has ambled past a pair of arrests, designed websites for El Paso’s who’s who, launched short-lived publishing projects, self-term-limited his largely unremarkable tenure on Capitol Hill, shunned the advice of pollsters and consultants and penned overwrought, solipsistic Medium missives, enjoying the latitude afforded by the cushion of an upper-middle-class upbringing that is only amplified by his marriage to the daughter of one of the region’s richest men…

It’s not just Republicans who think this. “He’s a rich, straight, white dude who, you know, married into what should politely be called ‘fuck you money,’” Sonia Van Meter, an Austin-based Democratic consultant and self-described “raging feminist,” told me. “His biggest success is by definition a failure,” she added. “He’s absolutely failed up.”

Even by the experience-light standards of the most recent occupants of the White House—a first-term senator followed by a real estate scion and reality TV star—the notion of O’Rourke’s uneven résumé blazing a path to the presidency is new and remarkable. For the moment, he is trailing and slipping in the polls, but it’s early, and he is still attracting besotted fans. The support O’Rourke built that even allowed this run in the first place did not depend on traditional concepts of meritocracy and diligent preparation. To look deeper into his past, to talk to his friends from his teens and his 20s, to read distant clips from money-losing media ventures, and to talk to voters, too, is to see a different kind of claim to excellence. In the end, O’Rourke’s best recommendation that he can win might be that he knows how to fail big—and then aim even higher.