Jeff Greene touts business savvy, outsider status in run for U.S. Senate seat

By Jason Horowitz
Washington Post Staff Writer
Friday, June 25, 2010

PALM BEACH, FLA. -- After a morning of stumping and schmoozing, U.S. Senate candidate Jeff Greene kicked off his loafers and fastened a gold-plated seat-belt buckle over his belly. In midair, he looked out the window of his Gulfstream V private jet and pointed at one of the mansions by the turquoise waters of Palm Beach.

"We're flying right over our house!" Greene said excitedly. "See the one with the swimming pool right on the water, with the tennis court behind it? That's our house!"

In any other year, Florida voters might have written off the frenetic, unpolished candidacy of the 55-year-old billionaire as yet another footnote in the list of fabulously rich businessmen who self-fund a run for higher office in midlife. Voters may still do just that.

But Greene's campaign for the Democratic nomination is looking less quixotic by the day. For the August primary, he has spent more than $4 million on advertising, including in media markets outside of Florida, and has caught up in the polls with four-term congressman Kendrick Meek, a political scion with the party's backing. Greene has hired the political consultants behind John Edwards's 2008 presidential campaign and the pollster behind New York Mayor Michael R. Bloomberg, an independent. The plane -- replete with polished wood paneling, bed, sofa and kitchenette -- served a political point: Greene's wealth meant he was beyond the establishment and couldn't be bought.

Floridians, he hopes, will see him as a credible insurgent and jobs creator with a compelling story. He also hopes that they overlook a few milestones in his unusual biography:

-- He's now in his third year as a Florida resident. Greene is a Massachusetts native and lived his adult life in Southern California. (The recent Celtics vs. Lakers NBA Finals, he said, were a contest between his "two home teams.") In 1982, he ran unsuccessfully for a Southern California congressional seat as a Republican.

-- A few years ago, he placed an enormously profitable bet against the crumbling housing market, a win he unabashedly peddles as evidence of his business savvy. ("Took on Wall Street and boldly predicted the collapse of the housing market," reads his campaign literature.) That windfall from the foreclosure crisis earned him a front-page 2008 Wall Street Journal headline, "In Beverly Hills, a Meltdown Mogul Is Living Large," a story from which he has publicly distanced himself -- but one that he had framed and displays in a bathroom in his mansion.

-- Greene speaks freely of his close relationship with Mike Tyson, who was best man at his $1 million wedding in 2007 to real estate executive Mei Sze Chan, now 35, at the Beverly Hills mansion once dubbed Palazzo di Amore. He doesn't hide from his friendship with "Hollywood Madam" Heidi Fleiss ("She's a businesswoman") or his feud with film director Ron Howard ("He screwed me"). He denies the anecdotes about his extravagant life as a bachelor detailed in "The Greatest Trade Ever," a book by Wall Street Journal columnist Gregory Zuckerman, two copies of which are in a bookcase in Greene's billiards room. ("I've never even been into strippers or had a hooker," he said. "It's not my thing.")

To distract from his own problematic past, Greene has attacked Meek at every opportunity.

"He's gone super-negative because he doesn't want anyone to focus on his past, and his past is a very murky one," Meek said in a phone interview. The congressman argued that Greene has no real connection to Florida or to the Democratic Party, as evidenced, Meek said, by a $5,000 check Greene wrote in 2009 to California's Republican gubernatorial candidate, Meg Whitman. Meek slammed Greene for housing Fleiss, a woman who "ran a prostitution ring," and for paying for ads with money made off of the misery of Americans who lost their homes. "Floridians are going to learn about those facts," Meek said.

Florida Gov. Charlie Crist, who has lost the support of the Republican Party and may prefer Greene as the Democratic nominee in a three-way Senate race with "tea party" Republican Marco Rubio, was more reserved.

"I don't really have an opinion," Crist said. "Everybody has a right to run."

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