During the 2012 campaign, Mitt Romney was repeatedly dogged by negative stories about his personal wealth. There was the car elevator. There was Cookiegate. Four years earlier, John McCain—hardly anyone’s idea of a typical plutocrat—got hammered for not being able to remember how many houses he owned. It was an issue for Steve Forbes before him and for George H. W. Bush before him. Republicans are already trying to use the many millions accumulated during Bill Clinton’s post-presidency as a cudgel against Hillary. Although it’s true that great wealth confers considerable advantages in politics, in terms of optics, it can also prove a meaningful handicap.
Except when it doesn’t. Donald Trump is richer than any of the aforementioned candidates, and his wealth, far from being a handicap, is a central rationale for his campaign. It’s what proves (in theory) that he knows what he’s doing. It’s what proves that he’s not a “loser,” like—well, pretty much anyone Trump is inclined to put down. (Can you imagine if Romney had slung that word around so recklessly?)
There’s a reason that Trump’s wealth is not an issue for him, and that reason can be summed up in a single word—as it happens, the title of a single Harold Ramis comedy: Caddyshack.