Can billionaire Jeff Greene become a serious candidate in Florida?

Alex Pappas Political Reporter
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Billionaire Jeff Greene announced his candidacy for Florida’s open Senate seat on Friday — and much of the press has mentioned his friendships with heavyweight champ Mike Tyson and former madam Heidi Fleiss and that he made his fortune by betting against the housing market before its downfall led to America’s economic crisis.

With a background like that, even with dough to bankroll a fierce campaign fight, how do you become a boring candidate that voters take seriously?

Reached on his cell phone Friday, Greene declined to comment, claiming to be in the middle of making a series of phone calls on his first official day as a candidate. But a Democratic strategist involved in the campaign said voters will be focused on how Greene is the only one in the race who hasn’t been in the political arena all his life.

“This is not a guy who lived his life looking in the rearview mirror, like career politicians do, thinking about whether he was going to run for office. This campaign is not going to be about the past, it’s going to be about the future,” adviser Paul Blank said.

Cook Political Report editor of Senate races, Jennifer Duffy, said several factors play a role in whether a candidate like Greene can become a serious contender, but one of the most important includes how he transitions from self-made million or billionaire to the world of the candidate.

“It’s really unlike anything they’ve done before. Do they listen to advice?” Duffy asked, pointing out that some candidates from self-made men discount vital counsel from political professionals out of hubris.

Little is known about Greene’s campaign style at this point, but there’s another candidate for the Senate this year with the same sort of unorthodox background. “You’ve got somebody like Linda McMahon who has really made the transition well,” Duffy said.

McMahon, running as a Republican for the Senate seat in Connecticut, made her fortune by forming a professional wrestling league that once hosted a soap opera match — now a heavily trafficked YouTube video — where she kicked her husband in the area most men hope to never be kicked.

One of her primary rivals, former congressman Rob Simmons, had the early momentum in the race, but his campaign coffers appear to be drained as polls show McMahon, buoyed by a self-fueled war chest, leading.

“She’s a good retail campaigner,” Duffy said. “She does listen and takes advice.”

Greene, reportedly worth $1.4 billion, is said to be open to spending whatever it takes to win. McMahon is willing to spend $50 million of her own money on the race.

Such wealth allows the candidates to spend freely, and put in place campaign gimmicks — as Greene did — like refusing to take campaign contributions of more than $100 from individuals or from special interests at all. McMahon has also restricted donors from giving the same amount.

But can candidates, running on their wealth, win? History has mixed examples: Self-funded candidates such as former Gov. Jon Corzine and New York Mayor Bloomberg have cruised to victory. But millionaire presidential candidates like Steve Forbes and Ross Perot have shown it takes more than personal fortune to be able to win a seat.

Despite Greene’s ability to self-fund what would absolutely be a tough race presumably against Republican Marco Rubio and independent Charlie Crist, Duffy said she’s “not getting the sense that Democrats are too happy about it,” considering the baggage he brings to the race.

It’s been reported that Greene once ran in the Republican primary for a California congressional seat. He was once forced to pay more than $600,000 in damages to Ron Howard over property he rented to the movie director. Tyson was the best man in Greene’s $1 million wedding, and Fleiss once lived in his house after the former madam got out of jail. The Tampa Tribune said Greene “was a pioneer in credit-default swaps and got out before the financial implosion,” making more than $800,000 by betting against the housing market while many Americans couldn’t pay their mortgages.

Blanks downplayed some of the criticism leveled at Greene, saying opponents have mischaracterized his past. Asked about Greene making money on the housing market, Blank said Greene watched economic loss his entire life — from watching his dad lose his job when the textiles mills closed to almost losing everything during the recession in the 1990s — and wanted to insure himself against loss. It was not about playing both sides of the market like some on Wall Street, Blank said.

“This time around, when it became clear to Jeff that there was an increasing risk in the real estate market, what happened was, he learned from his life experiences that he had to protect the business he created and the jobs he created,” Blanks said.

“Jeff would’ve been just as happy, being very successful, which he was, never having this crisis happen.”

Asked about Fleiss, Blank said she was merely Greene’s friend who needed a place to live after being subjected to domestic abuse. “If someone’s being abused, of course you’d say yes.”

Democraict Rep. Kendrick Meek, running for the Florida seat, has enjoyed some vocal support from the Democratic Senatorial Campaign Committee, whose chairman Robert Menendez released a statement on Thursday night saying, “Kendrick has run a very strong campaign and will likely emerge as the candidate of choice for Democrats, Independents and even moderate Republicans.”

Blank said “what Washington thinks doesn’t matter,” and that the campaign is taking their “message directly to the voters of Florida.”

Duffy said candidates are, of course, “judged by the company you keep,” and pointed out another successful Washingtonian with a connection to Tyson: RNC chair Michael Steele was once the brother-in-law of the heavy-weight champ, who was married to Steele’s sister.

“Now Heidi Fleiss, I don’t know how that plays,” Duffy said.

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