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 the 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, readily spouting all-too-quotable quotes, such as a statement that everyone knows the Koran contains "all kinds of this crazy stuff," as well as the instant classic, "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. Most of what Floridians know about Greene so far comes from a massive television and direct mail campaign, a relatively generic offensive that in one case featured his 83-year-old West Palm Beach mother, and highlights his criticisms of "career politicians" like his Democratic rival. With the help of the ad onslaught, he finished in a statistical tie in the Quinnipiac poll released in June.
As for Meek, he began trying to define Greene to Democratic primary voters during their first debate of the political season last week in West Palm. He charged him with being the "king of the undercover credit default swap that brought about the destruction of our economy that we have right now."
That complicated Wall Street financial transaction ultimately led Greene to an $800 million payoff, the base for Meek's charges that he profited directly from the subprime mortgage crisis that has devastated hundreds of thousands in Florida.
But before we get to that intriguing story, what else do we know about the mysterious Mr. Greene?
For one thing, he's lived most of his life outside the Sunshine State. When I ask him how long he's actually lived in Florida, Greene reacts with slight exasperation. He points out that he got his driver's license in Florida and bused tables at the Breakers, the oceanfront luxury hotel in Palm Beach.
But he grew up in Worcester, Massachusetts. Unquestionably intelligent, he graduated from Johns Hopkins College in Maryland after just two and a half years. Then, after saving $100,000 from a telemarketing gig while in college, he attended Harvard Business School in the fall of 1977.
It was at Harvard that he began his real estate career, and his life as a Republican. After graduating, he moved to Los Angeles and in 1982 ran as a Reagan Republican in an unsuccessful bid for the GOP nomination for Congress.
Of course, that was then. When asked by MSNBC's Chris Matthews on Hardball if he voted for Reagan for president in either 1980 or 1984, Greene was suddenly hit with a case of amnesia, saying he simply couldn't recall.
Since he was described in a Forbes 2008 profile as having "an active social life," perhaps the '80s are a blur to Greene. Or maybe he did vote for the Gipper. On this question, it was probably wiser for Greene to act dumb than confess his support for a man who ranks alongside George W. Bush and Richard Nixon as Democrats' Least Favorite Presidents Ever.
His lack of connection to the Democratic Party in Florida was exacerbated when he told a Sarasota media forum earlier this month, "Whether I was a Republican or Democrat, who cares?"
Actually, a lot of Democrats in Florida do. The comment provoked a letter from a group of local party heads chastising him, ending with the comment, "Since you are seeking the Democratic nomination in this race, we urge you not to be dismissive of our Democratic Party."