As others have said this purchase didn't really fuck up his overall lifestyle.
Yet when the topic of raising taxes on these people comes up they all freak out, like if they have to pay an extra 20% on their wealth they will be living on the streets.
There is only one way to hurt him- to humiliate him. To hit his ego. Booing him at the Chapelle show, for instance.
All we can do is keep doing that sort of thing until Real Life Iron Man becomes Real Life Terrence Howard as War Machine and gets replaced with some other asshole billionaire that sycophants will worship instead who hopefully will be mildly less insufferable.