Billionaire Bill Ackman Has the Best Arrogance Money Can Buy
One problem with ultrarich people like Bill Ackman is that their riches often spill over beyond the economic realm into other realms — like, in his case, the kind of delusional self-confidence that led him to buy his way into a professional tennis match.

Bill Ackman speaks about higher education and Harvard University at the twenty-eighth annual Milken Institute Global Conference at the Beverly Hilton in Beverly Hills, California, on May 6, 2025. (Patrick T. Fallon / AFP via Getty Images)
I’m not a fan of Billy Ackman for several reasons, but nothing has roused my ire more than than this: because of Ackman, I now have to write about sports, which is something I never talk about unless it’s to make fun of it.
For those of you who don’t follow such things, Ackman bought his way into some sort of big tennis match with a lot of big tennis pros. He sucked and lost, prompting Martina Navratilova to mockingly tweet of him, “Oh to have the confidence . . . ” She might have added: “ . . . of a very rich white man.”
I can’t understand all the ins and outs of this story, except that his buying his way into this match took away a spot from many other deserving players. Which is ironic for Ackman, an infamous opponent of diversity, equity, and inclusion (DEI), since this is a much more flagrant version of what he and his cronies are always complaining about with affirmative action and DEI. Except that of course students of color are not buying their way into anything; nor are the spots that used to go to white men being taken by undeserving candidates.