Sean "Diddy" Combs and Donald Trump have been running in the same New York new-money rich-celebrity circles for decades, and both of them have plenty of experience being both loved and hated by vast swaths of the country. And while Diddy threw his weight behind President Obama in the last two presidential campaigns, and spearheaded the get-out-the-vote Vote Or Die campaign in 2004, he hasn't brought himself to decry Trump's toxic candidacy. He might even vote for the guy.