Jeff Greene is staring at me with a somewhat bemused grin. I’m reading to him a quote from an article published earlier that day in Politico, the online political website, that references the fact that Mike Tyson was the best man at his wedding, and former madam Heidi Fleiss was a housemate. The story goes on to say that because he’s surging and might possibly become the Democratic nominee for U.S. Senate in late August, some Florida Democrats are now looking even more longingly at Charlie Crist as their choice in November.

“Look, Charlie Crist is a Republican governor, he’s always been a Republican,” Greene replies in his Massachusetts accent, as he sits a few feet away from me. “His nickname, if I’m not mistaken, used to be ‘Chain-gang Charlie.’ I think that Democrats, when they get to know me, will get to know I’m the real deal.”

Greene’s candidacy is drawing national attention, and his connections with Tyson and Fleiss have become de rigueur set pieces in every political profile written about him. A much-discussed piece in Friday's Washington Post explained the connections (he met Tyson at a Malibu barbecue and met his future wife at a party Tyson hosted; he let Fleiss stay in one of his houses as she recovered from an abusive relationship). The story also shows that he's still, well, green, spouting all-too-quotable quotes, such as a statement that the Koran contains "all kinds of this crazy stuff," as well as the instant classic line, "I've never even been into strippers or had a hooker, it's not my thing.” The latter was tweeted en masse by Florida political junkies throughout the day.

Greene's newness to the Florida (or any) political scene will be both a curse and a blessing for the 55-year-old billionaire over the next two months, leading up to the August 24 Democratic Senate primary election against Kendrick Meek.

This article appears in Jun 24-30, 2010.