In the summer of 2023, Jack Dorsey was deathly bored, stupendously rich, and spending way too much time listening to podcasts featuring fringe presidential aspirant Robert F. Kennedy Jr. Dorsey, who had recently opted to keep his $1 billion stake in Elon Musk’s Twitter, was nominally the C.E.O. of Block, his payments company that he had renamed from Square as a way to explore his passion for Bitcoin. But his emerging enthusiasm was presidential politics—in particular, supporting a pro-crypto candidate like R.F.K. At one point, he planned to make a donation to Kennedy’s super PAC on the order of $5 million… in Bitcoin.

Jack’s support for such a controversial figure, after years of disinterest in campaigns, has alarmed people who have worked for him and ostensibly oversee him. “He’s very interested in politics, but he stays an arms length away from it,” said a person who has done political stuff alongside him. Historically, his personal interests have leaned more toward “wellness”—from intermittent fasts to the Myanmar silent meditation retreats to the morning cold plunges. People who know him don’t think he is anti-vax, per se, but Kennedy’s cultivation of the wellness community appeals to him.