>I almost think Trump keeps winning elections out of a sense of schadenfreude.

I definitely think a lot of his appeal has to do with his ability to rile up the left then demonstrate their ineptitude at stopping him. He's also doesn't seem to have much in the way of strong principles on subjects, instead, he does pretty much exactly what he thinks his supporters will like.

His corruption is the trade-off one makes for electing a politician like him. He'll do whatever it takes to make his constituents happy, and in return they give him a blank check.