By Jason Horowitz
Washington Post Staff Writer
Friday, June 25, 2010; C01
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."'He came out of nowhere'
On a Thursday morning at the Wynmoor Democratic Club breakfast in Coconut Creek, Fla., more than a hundred senior citizens sat around tables loaded with plates of scrambled eggs and Greene's sleek campaign literature.
"Without all this advertising, we would have never heard of him," said Sara Feinstein, 81. "He came out of nowhere."
Greene walked in and received kisses on the cheek from the bubbes in the room. Wearing a dark suit and striped blue tie, he stepped behind a lectern bearing a green "Jeff Greene: Jobs, Results, Florida" sign and unfolded a white paper to "share with you some jokes I got off the Internet." The gag posited things Jewish mothers might have said about famous people ("Christopher Columbus: You didn't call, you didn't write"; "Bill Clinton: Well at least she was a nice Jewish girl"), and the point was to identify him as Member of the Tribe. Greene then launched into a meandering stump speech.
He insisted that he had the real business experience of creating jobs, a word that is crammed seven times into a 30-second spot flooding the state's airwaves. He brazenly blamed Washington politicians and Crist for Florida having "the third-worst foreclosure rate in the country." He called for a moratorium on donations from oil companies.
"I'm jumping all over the place," Greene said.
A woman wearing a T-shirt with an eagle flying in front of an American flag asked Greene about the threat posed by radical Muslims.
"I'm not an expert on Muslims," Greene said. But he added that anyone who knows anything about the Koran knows that it contains "all kinds of this crazy stuff. And unfortunately that's motivating a lot of these extremists."
"If everyone hates me in Washington," he added in response to another question, "that's the way it is."
After the formal question-and-answer session, Greene showed some admiring seniors pictures of his 8-month-old son ("Malcolm Chandler Greene, nice Jewish name!" Greene said).
Bill Bromberg, 87, approached to chastise him for criticizing career politicians. Bromberg said he and his wife used to push their child in a stroller next to the parents of Sen. Charles E. Schumer (D-N.Y.). "He's a career politician," Bromberg said.
"I like lots of career politicians; I'm not against all career politicians," Greene said. "I am against the career politicians I'm running against."
At moments like this, enthusiastic voters firmly correct his stumbling ways.
At a luncheon at Bageland in nearby Tamarac, Jessie Guido, a retired Democratic activist from Pompano Beach, approached Greene's press secretary Luis Vizcaino. "How did you put him on 'Chris Matthews' last night?" she asked sharply, referring to an excruciating appearance Greene made on the MSNBC show the night before, during which the candidate could not remember whether he voted for Ronald Reagan.
"They invited us and we went," Vizcaino said.
"What were the conditions?" she said.
"There were no conditions," he said.
"Next time, there should be conditions!" she said. "He looked flustered. Apologetic. He didn't remember if he voted?!"
Greene walked up to introduce himself.
"I thought it went well, considering it was Chris Matthews," Greene said, with a bashful smile.
"With all due respect, Mr. Greene," Guido said, "it did not go well at all."
Greene fared better at Bageland. Many of the seniors gathered, nodded approvingly and applauded during his speech. He fielded some questions, including whether his candidacy meant that anyone with extraordinary wealth could run for office.
"I know that I have an unfair advantage in that way," Greene said. A sympathetic voter in the front row leaned forward and suggested that he not phrase it quite like that.
Greene tried again and explained that the "unfair advantage" was that he wasn't beholden to special interests.Businessman and politician
On his way to the airport, Greene stopped off in Fort Lauderdale to meet with the mayor. Paul Blank, one of Greene's chief advisers, was on the phone making sure a press release had been sent alerting reporters to a new spot calling on the U.S. House ethics committee to investigate Meek. The ad was set to air only in Washington.
In the confines of his eight-seater Gulfstream, Green shed the halting delivery that marred his campaign speeches ("If, if, if, if") and barked orders related to his real estate affairs at his campaign scheduler. "I still run a business," he said.
He jumped impressively from issue to issue at lightning speed. He boasted that he had bought the plane at a cut-rate price of $23 million in December 2008, after the economic crash, and said it had essentially paid for itself as a charter. The Democratic Senatorial Campaign Committee, which prefers Meek, had inquired about its availability for a fundraising trip to Texas by its chairman, Sen. Bob Menendez (N.J.), just before Greene announced his candidacy for the Senate seat.
As the jet touched down in Sarasota, Greene assessed the competition: Rubio was "an opportunist taking advantage of the dissatisfaction of these tea party people." Meek was a career politician who didn't understand how finance worked. Crist had stewarded the state into economic ruin.
He handed Blank a stack of business cards that he had collected at the morning events. "I want to call every one of those people," he said, sounding like a politician. Then he added that one of the cards was that of an 87-year-old magician. "His trick is that he's going to be able to live through the show."Working his way up
Greene's passion has always been for business.
Born in the 1950s in Worcester, Mass., to a middle-class family, Greene shoveled walks before other kids woke up. He had a paper route with 80 customers. When he was in high school, his father lost his textile mill machinery business and his parents moved to Florida, where his mother waited tables and his father stocked vending machines.
Greene, a band nerd, stayed in school in Massachusetts, studied a semester in Israel and worked as a busboy at the Breakers hotel in Palm Beach during breaks. When tips dwindled in the off-season, he answered a classified ad and started selling circus tickets as a telemarketer, helping to pay his way through Johns Hopkins, from which he graduated in 2 1/2 years.
He then drove a Datsun around the country, overseeing telemarketing centers, and saved $100,000, which he used to enroll at Harvard Business School in 1977. Three months after his graduation, his father died unexpectedly.
"I had to unwind his whole life," Greene said. "I went to his office and what's there? Piles of bills. You see, that was the source of the stress, no question."
Greene had started dabbling in real estate at Harvard. He had great instincts. He moved to Los Angeles in 1980, where he bought and sold real estate -- making and losing and remaking a fortune.
Along the way, he made famous friends and foes. At a barbecue in Malibu, he met Tyson, the former heavyweight champion, and was impressed with his "photographic memory." Given all that Tyson had gone through in his life, Greene said the boxer was remarkably stable. Greene met his wife at one of Tyson's birthday parties, and he picked the boxer as best man for his 2007 wedding. Tyson had just emerged from rehab, Greene said, and "I felt it was the right thing to do."
Greene also became friendly with Fleiss, the onetime Hollywood Madam, whom he let stay rent-free for a year in one of his houses when she was escaping an abusive relationship.
"Look, she's a Jewish girl; her dad's a pediatrician," he said. "Look at who her best friends are today: She's friends with [financier and Clinton ally] Steve Bing. Heidi Fleiss knew everybody; that was the business she was in."
Director Ron Howard was a less appreciative tenant.
In the '90s, Greene rented a luxury house in Brentwood to the Howard family for $28,500 a month. Diana Ross had rented the house before them without problems, Greene said, but the roof soon started leaking under heavy rains, and a rodent made an unwelcome appearance. Howard, who was making the movie "EDtv," ("It was a big flop," Greene said. "I was happy to see that.") moved out a month into the lease and sued Greene.
At trial, the prosecutor announced the existence of a video of the damage. "I'm thinking, 'Oh, God. Ron Howard. The kids are going to be crying, "Help, help, help, Dad! I'm drowning!" ' " Greene said. "It turns out it's a towel in front of the door, and it's the wife Cheryl saying, 'Ron! Over here. Ron, Ron, Ron, over here.' . . . He's like, 'Okay, honey.' "
Greene lost the case and paid Howard $616,000 during a tough stretch for his business.
"If you look at the record and the outcome," Howard said, "he committed fraud and that's why it was so expensive for him. With what I know about Jeff Greene as a tenant, I certainly wouldn't vote for him, and I wouldn't relish the idea of him being in the Senate."
By 2006, Greene had built his portfolio back up to around $700 million. To protect his investments, he said, he bought credit default swaps that skyrocketed in value as subprime mortgages fell. By 2008, he had cracked the Forbes 400 with a net worth of $1.4 billion.
Greene said he has no regrets about how he made the money that "put me over the top."
"I was glad I was able to do it," he said. "I wish I could have been able to do it for the country."A new phase
Crist was making the case that he is the true independent because he is "without a party," when Greene arrived at the Sarasota Ritz-Carlton. The Florida governor stepped off the stage and bumped into Greene, who was watching from the back of the room. Crist, tanner than the tan Greene, offered a bright smile and a hearty handshake.
Greene then gave his best performance of the day onstage. As he left the hotel, he eagerly sought reviews from Blank.
"How do you think I did? I was more relaxed. That was like being the White House press secretary," Greene said. "I didn't hit Rubio and Crist on the corruption thing. I gave it to Kendrick Meek."
The plane returned to Palm Beach, and Greene crammed in a quick visit to his wife and infant son before heading back out. Sze Chan, a tall and elegant woman with an Australian accent, waited for him at the door holding their son, who wore "Surf's Up" pajamas. Greene bounced the baby in his arms, had some family time on the veranda and then rushed into the house to attend to some real estate business.
"What a day, honey!" he exclaimed as he walked from the marble foyer into his office, decorated with oil paintings, classical statues and candelabra. The ocean lapped a few yards away. He told his wife how he had survived the barrage of questions from Florida reporters at the forum. "Wow," she said. "Drama."
Greene furiously organized stacks of papers and called for a time-check till the next event. His wife paused from tending to Malcolm and considered this new political phase in her husband's life.
"What's he going to do?" she said. "Is he going to make more money, or is he going to make a difference?"