EL PASO, Texas—Beto O’Rourke was running for the El Paso City Council in 2005 when he asked to meet with the illustrious real estate investor William Sanders.

Sanders had earned a fortune and a reputation as a brilliant businessman in Chicago before returning to his remote hometown on the West Texas-Mexico border. He thought the aspiring politician was there to solicit a donation. But O’Rourke was seeking permission to marry Sanders’ daughter Amy, whom he’d met less than three months before.

“I sat down with him in his office and he was kind of an imposing figure and I was very nervous,” O’Rourke said in a phone interview. After he asked for Sanders’s blessing, it got worse: His future father-in-law spent “a lot of time talking about her previous boyfriend, whom he liked a lot.”

“It was a very awkward — very, very awkward — conversation.”

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