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.
The reason this story interests me is that it brings me back to an old argument in political theory that doesn’t get much attention anymore.
Back in the early 1980s, Michael Walzer wrote a very interesting book called Spheres of Justice. This was the high tide (or maybe ebb tide) of liberal thinking about inequality. Most liberal and, in fact, a lot of leftist thinking about inequality focused on the simple fact of rich and poor, that some have much and many have little, as the wrong or injustice in question. As a solution, they recommended what Walzer called “simple equality.” The rich should have less, and the poor should have more. Or maybe everyone should have the same amount.
Walzer wasn’t against this solution so much as he was against this way of thinking about the problem. He favored what he called “complex equality.” He thought the real problem with rich people is that their riches spill over, beyond the realm where wealth matters, into other realms, or spheres. It’s the way their wealth dominates throughout society, across the spheres, not the mere fact of their wealth, that should trouble us. In these other spheres, other things matter. In the educational sphere, knowledge and pedagogy matter. In the medical sphere, health matters. In the political sphere, leadership and power matter. In the performing arts, musicality or dramatic skill matters. And in the realm of athletics, the skills of football or baseball or — yes, tennis — matter.
The point of all this sphere talk is that each sphere has its own value or “good,” and the world ought to be structured in such a way as to allow those spheres to promote their internal goods and allocate positions to those who promote those goods, or at least best promote those goods. Again, the problem is when the good of one sphere — in this case, wealth — spills over and begins dominating the distribution of positions in other spheres. Say, politics. Or tennis.
There are many problems with Walzer’s argument, which I won’t rehearse here. But it’s interesting that already in 1983, he managed (as he often does, again despite my misgivings about his theorizing, particularly when it comes to war and peace, and Israel) to see further than many of his contemporaries. For while they were arguing about the more immediate and obvious questions of wealth and poverty, he saw what would become the real problem of our own age: not simply the fact that some have much and others have little, but that those who have much, have so much in, and so much control over, every sphere of social life.
Enter Billy Ackman. After his defeat, he told the New York Times, “I feel like maybe it’s one and done. But I figured one, in my life, that seemed fair.”
How does he figure that “that seemed fair?” How is one fair? And if one is fair, why not two? Why not a rematch? Why not buy the whole tournament and every year he gets to compete like this, until finally, maybe with enough coaching and practice, he can win? This is the kind of thing Walzer was talking about: maybe there are some things, beyond love, that money shouldn’t be able to buy you. Once we acknowledge that, maybe we can see that money shouldn’t buy you health care, education, housing, a decent retirement, the Washington Post, Twitter, a ride to the moon, or the mayoralty of New York City.
In a way, Navratilova’s tweet enhances Walzer’s point. It’s not just that Ackman can buy his way into a tennis match that he doesn’t belong in. It’s that he can buy his way into such confidence and arrogance. That’s the ultimate social point. We think of confidence and psychic states as entirely our own, but we know, from experience, that money and status can buy you those too. Maybe they shouldn’t.
Walzer worried about money being converted into power of all kinds. But Ackman shows what happens when money can be converted into power of all kinds. It ceases to get you power, and it just turns into vanity. Extraordinary, remarkable, unfathomable vanity. Or what Thomas Hobbes called “vainglory,” which, as Hobbes said, is the “supposing of power” where there really is none.
Hobbes thought vainglory was mostly a problem of young men that would be corrected with experience and age. He didn’t reckon on Billy Ackman. Or Donald Trump. Or America.