Why he could run: A well-regarded media executive, Diller helped spur the creation of the FOX Broadcasting Co. as well as USA Broadcasting and has been outspoken critic of media monopolies. A lifelong Democrat, he has been known to open up his checkbook for like-minded candidates in the past and has been described as a bit of a kingmaker in the television industry.
Why he probably won't: While he has been an active donor in Democratic circles, Diller has not spent nearly the same amount of time or money as many of the others on the list rubbing elbows in political circles. It's unclear if he'd have the political clout to make presidential waves, even if he wanted to.
Why he could: A hedge fund manager, Druckenmiller used to manage investments for a well-known Democratic money man: George Soros. But Druckenmiller is not a liberal like Soros. His political contributions have gone almost exclusively to Republicans, including big gifts to the re-election bids of Republican House leaders.
Why he probably won't: Druckenmiller has been a critic of President Barack Obama, but while he has served as a CNBC talking head, he has not spent much time in raising his profile since his retirement in 2010.
Why he could do it: The only person on this list who can rival Oprah's name recognition, Gates' name has for decades been synonymous with technological innovation and philanthropic efforts for years. The Bill and Melinda Gates Foundation is seen as a philanthropic powerhouse and, at 60, he'd still be relatively young come 2016.
Why he probably won't: A Gates-for-POTUS campaign would constitute a pretty big flip flop. Asked about his potential political ambitions in 2012, Gates declared: "I decided the philanthropic role is where my contribution would be more unique, and so that is what I will work on the rest of my life. . . . I actually think, maybe I'm wrong, that I can have as much impact in that role as I could in any political role. In any case, I would never run for political office."