Originally Posted by benjamin

I'm the worst gambler in the history of the universe, and I think I would actually win this bet. =)

I would be very very surprised to see Bloomberg run for President, mostly because I can't imagine a guy who was Mayor of a city -- even New York -- being elected President immediately after. Not Bloomberg, and not even Giuliani at his peak. I agree that he aspires to higher office, though. I think Bloomberg would be more likely to run for Governor, but not until after Eliott Spitzer is done with the post. Bloomberg simply couldn't compete with Spitzer for the post.