If this can become the "politicians we think are total losers", I'd like to add Jim Matheson
I would have never guessed...
What can I say, he's a local politician, and I really, really don't like him (even though I've resigned to the fact that I'll vote for him in the end, just to avoid Mia Love taking office). I talk about him and other Utah politicians so much because no one else does.
Plus, Casey and Matheson have striking similarities; both are politicians in their 50s who owe their initial success in politics at least partially to their fathers good reputation as moderate Democrats of their time (if I read Casey Senior's Wiki page correctly), both are absolutely hated by most of the other party while only lukewarmly supported by their own party and independents/moderates. Both are also moderate-to-conservative Democrats (depending on the issue), and both seem to disdain entire wings of their party.