08/02/2010 04:05 pm ET | Updated May 25, 2011

Profile Of Jeff Greene, Democratic Florida Sen. Candidate, Details A Ruthlessly Successful Businessman With Quirky Past

Billionaires rarely rise to monetary greatness without ruffling a couple feathers -- just ask Florida Democratic Senate candidate Jeff Greene. In a St. Petersburg Times profile of the real estate tycoon and political novice, it quickly becomes clear that this newcomer covers a vast expanse of life experiences that will likely play a large part in his electability.

Whether its the struggle of paying your own way through school, the pain of losing a father, the inspiration of becoming a self-made billionaire, Greene's been through it. Or, if its the animosity felt toward an uncompassionate landlord or the suppressed feelings of envy or shock directed at a "playboy bachelor" whose past is spotted with descriptions of "Moroccan 'love dens'" and vomit-caked multi-million dollar yachts, Greene's received it.

Coming from less-than-middle-class roots, Greene grew up as "a studious and accomplished band geek" in Worcester, Massachusetts. After graduating high school, Greene went to Johns Hopkins University with the help of scholarships and supplemental income from side jobs. Having successfully saved a nice chunk of money during college, Greene enrolled at Harvard business school, where he started getting involved in the real estate business. His father, Marshall Greene, died at 51, leaving behind bills and expenses that had accumulated over a lifetime of business struggles.

From the Times profile:

Investing heavily in low-end apartment buildings, Greene was a millionaire by his mid 20s and a multimillionaire by his mid 30s. He ran unsuccessfully for Congress as a Republican in 1982, a detail more than a little at odds with Greene's campaign rhetoric about Democratic ideals deeply ingrained in him.

After amassing an empire of more than 8,000 properties, at least one account of Greene's occasional attendance to landlord duties show the real estate mogul being seemingly unconcerned with the public relations side of his ownership duties.

One tenant complaining about heat and water problems in 2002 wound up on the phone with Greene. She said he threatened to get a city council aide who was advocating for her fired and scoffed when the woman said she was complaining to then-Los Angeles City Attorney Rocky Delgadillo.

Skip to the 21st century, during the first 10 years of which Greene saw his wealth skyrocket from $800 million to $1.4 billion after successful betting on credit default swaps -- effectively placing investments in the impending failure of the subprime mortgage market.

More from the Times:

As Greene's wealth grew, so did his reputation as a playboy bachelor. Vanity Fair in 2003 ran a spread about Greene's 12,000-square-foot mansion in the Hollywood Hills -- complete with disco and a Moroccan "love den" -- being a go-to spot for debauchery at late-night parties.

Despite his riches, however, numerous low-level acquaintances told the Times that Greene was an absolute nightmare to work for. Here's what Adam Lambert, one of his former yacht captains, had to say:

"I don't think I ever once had an actual conversation with him. It was always, 'I should just get rid of you, what f------ good are you? You're just a f------ boat driver. You're the third-highest paid employee in my corporation and I should just get rid of you,' '' Lambert, 43, recalled by phone from a yacht in Croatia. "It didn't bother me. I just felt sorry for the man. He doesn't seem very happy."

Harlan Hoffman, a former Greene deckhand recounted similar neglect to the Times:

"This guy Jeff Greene threw tons of money into new diving gear, but the crew's basic equipment -- food and supplies -- he didn't want to spend any money on. Summerwind has a terrible reputation,'' Hoffman said. "Mr. Greene's yacht is known to be a party yacht. When it went to Cuba, everybody talked about the vomit caked all over the sides from all the partying going on."

Greene has since claimed that he wasn't on the Cuba-bound yacht in question.

Closer friends of Greene, now married and with a 9-month old son, say that the Senate candidate's life is no longer one of legendary lavish and excess.

"Everybody talks about how Jeff has changed and how marriage matured his life's outlook, but he was moving in that direction for a long time. He was always an intellectual,'' Rabbi David Baron, who performed Greene's marriage, told the Times.