Because his friend that brought him children to rape got arrested, and the friend whose dick he sucked was stuck married to Hillary Clinton.

Honestly don't know what his beef with Hillary was; I'm still pretty convinced he was supposed to be a fake candidate for her to trample. Considering her main concern with all the women Bill slept with, harassed, and/or raped was to discredit or silence them in the press, I don't see a world where Dumbass didn't want her to win, so much as maybe she didn't want to win all that badly, because naked fascism is less work than pretending.

Who?

Because he never learned to count.

Counting money goes fast nowadays since it's a bank account number. So he needed more money to count.

Because he also craved power and women.
Harry Harrison gave a description of the despot, from his immortal character James Bolivar 'Slippery Jim' DiGriz in 'The Stainless Steel Rat For President':
"I want all the money, all the power and all the women, and I want them right now".

Not as fun i imagine