It’s a sweltering Tuesday afternoon and a man who could be just about anywhere in the world is sweating outdoors in a suit at the Florida State Fairgrounds, weathering insults from drivers headed to a Donald Trump rally in Tampa.
“Jeff Greene sucks!” someone yells from an open window.
Greene, a billionaire developer running for Florida governor, isn’t fazed. He’s played the villain before, and the Democrat didn’t exactly come here to this MAGA event to make friends.
Nope. Greene ventured to hostile territory in late July for the TV cameras and the optics of his mug outside the president’s own party alongside a tour bus emblazoned with the words “Trump’s Worst Nightmare.”
In a year where few things rile Democratic voters more than the mention of the president of the United States, Greene has gone all-in trying to position himself as the anti-Trump candidate in the five-way Democratic primary for governor. Spending millions on his campaign, he’s produced commercials and mailers that show him jawing with the president at his Trump Palm Beach golf course and looming outside Trump’s winter White House in Palm Beach.
But look a little deeper, and Greene’s insurgent candidacy begins to feel less like a rejection of Trump’s politics than a counter-punch. While Greene ardently rejects the president’s rhetoric, he is running as a party outsider trying to convince Florida’s Democrats to fight fire with fire by embracing a brash-talking Mar-a-Lago member with deep pockets, zero government experience and a record pocked with media fights and tabloid fodder.
“I know I’m known as this billionaire and it’s a terrible thing to be known as in the Democratic Party,” Greene said last week at a leadership meeting of the Miami-Dade Democratic Party in Doral. “I’m prepared to use what I’ve accrued in my lifetime to flip Florida blue once and for all.”
Since jumping into the race in early June, Greene has spent more than $29 million on his campaign for governor, blanketing the state with mailers and commercials promoting his plans to bring the fight to Trump. He’s antagonized the NRA with images of bull’s-eyes emblazoned over the silhouettes of schoolchildren, paradoxically promoted public education policies based around a private school he founded for his three sons in West Palm Beach, and promised to throw about $5 million of his money into competitive state races this election cycle.
For all his millions, polls show Greene running in the middle of the pack. But he’s also running what is by far the most aggressive campaign, going after his rivals’ environmental records on TV and in mailers that have changed the dynamic of the Democratic primary.
“He’s come in this race and basically been the bull in the china shop,” said Tom Eldon, a Democratic pollster who recently found Greene trailing in fourth place, ahead of Chris King but behind Philip Levine, Gwen Graham and Andrew Gillum. “He’s been the disruptor.”
Greene’s unapologetic campaign is reminiscent of his 2010 U.S. Senate run, when he and former congressman Kendrick Meek savaged each other for months before Meek won out in August. This year, Greene and Levine — whom Greene has blasted for taking money from a Ukrainian-born billionaire who contributed to Trump’s inaugural campaign — have spent the last two weeks barking about who is the Trumpiest.
“We’re not going to take on Trump by passing the Grey Poupon across the table at his country club at Mar-a-Lago, OK?” Levine said Sunday morning during a forum the two men attended in Delray Beach, according to the Palm Beach Post.
The previous day, Graham, who’s been battered relentlessly by Greene ads, told the Miami Herald during a Miami Lakes campaign stop that “everywhere I go people tell me how disgusted they are at what he’s doing.”
“All we have in our lives is our record, who we are and were,” Greene countered Monday. “And I’m proud of what I’ve done.”
Before unleashing a torrent of attacks at Graham and Levine, Greene had seemed interested in shedding the sharp elbows that marked his Senate campaign.
Appearing at events with his wife, Mei Sze, and their sons, Greene came out of the gate in June focusing on education and fighting Trump, not his Democratic opponents. He talked about his work at The Greene School, a private institution the Greenes founded when they were underwhelmed with the options for their children, spouting off statistics about Florida’s woeful schools.
The “Rs” were still missing from his accent — a reflection of his hard Boston upbringing — but the edges were softer.
A few days after absorbing insults from Trump voters, Greene appeared inside a cramped community center in a black neighborhood in Coral Gables where he lifted bookbags out of boxes and handed them to elementary school kids. His wife and two of their sons watched as boys and girls picked over Moda West bags and strapped them to their backs, with Greene standing over it all in khakis and a blue dress shirt and tie, smiling.
“I love your hair, it’s very cute,” Greene, standing later outside his tour bus, told Precious Forbes, a rising fifth-grader. “Do you like your backpack? Are you going to get all A’s this year?”
That’s the softer side of Greene, the same guy who grew up poor in Worcester as the son of a textile machinery salesman who lost his job and moved to West Palm Beach. Greene, who’s made sure to communicate his self-made story to voters, stayed behind for school after his family left, eventually skipping his senior year in high school to attend Johns Hopkins University.
With his degree in hand at 19, he took a job as a sales rep hawking circus tickets and traveled the country in a Pontiac Grand Am with his clothes in the back seat for more than two years. He says he’d saved $100,000 by the time he attended Harvard to obtain his master’s degree, and purchased a three-story apartment building for $37,000, living in one unit and renting out the other two to stretch his income.
By the time he finished business school, he says he had 18 properties. Greene says he sold his first building just a few years later for $180,000.
Greene moved to California in 1980, where he made millions as a developer, went cash-broke in the 1990s and then again built up a fortune in the residential housing market. He ran an unsuccessful campaign for Congress in 1982 — as a Republican.
His move onto the Forbes list of billionaires didn’t come until the late 2000s, when the real estate market collapsed. Greene, having already lost his fortune once, began shorting mortgage-backed securities, essentially betting against the mortgage bonds financing thousands of home loans. When borrowers defaulted en masse, Greene made an estimated $800 million.
That became a problem for his Senate campaign in 2010. With the economy still in the depths of a recession — and Florida arguably the epicenter of the real estate collapse — Greene was dogged by the Wall Street Journal’s “Meltdown Mogul” moniker. Meek toured the state talking about Greene’s “ill-gotten gains.”
This time around, those barbs still exist but are subdued. Time has helped, as has the rebounded economy. Plus, it wasn’t so long ago that the Academy Awards bestowed an Oscar upon “The Big Short,” a movie about investors who made fortunes by betting against the housing market.
“The [home mortgage] loans were already out there. They were already in default. I was basically betting against the bond in the bank. I wasn’t betting against homeowners,” Greene said recently in an interview with the editorial boards of the Miami Herald, South Florida Sun Sentinel and Palm Beach Post. “I wasn’t hoping people would lose their homes.”
Also less in-your-face in this campaign are the stories about Greene’s friendships with celebrities like boxer Mike Tyson and wild parties aboard his yacht, Summerwind. Those tales were among the stories written by the Tampa Bay Times — at the time the St. Petersburg Times — and also published in the Miami Herald. Greene sued in 2010 claiming he had been libeled, and the two newspapers settled separately out of court with Greene two years ago for an undisclosed sum.
Greene said the two stories over which he sued — one related to a real estate deal in California and another about Mike Tyson’s time spent aboard his yacht — cost him the 2010 U.S. Senate primary against Meek. The Times and Herald appended notes at the end of their stories explaining that they shouldn’t be read as accusing Greene of committing any crimes, but the Times’ publisher said at the time of the settlement the paper did not retract or regret their coverage of Greene and that the settlement “represents our insurance company’s calculation of acceptable legal expenses.”
Some of Greene’s opponents have privately groused that he’s received little vetting in the press since he jumped in the race on June 1. But even if that’s true, they haven’t forgotten about his baggage.
Following Greene’s release of a commercial blasting Levine’s environmental record when he was mayor of Miami Beach, Levine began running commercials featuring a quote Greene gave on Fox Business following the 2016 presidential election about Trump being a “great guy.” Greene calls the ad “misleading.” Levine also tweeted out (and later deleted) a link to a Broward Palm Beach New Times post written by Sharyn Peach, a musician who said she worked as an attendant aboard the Summerwind for two months and quit after tiring of 24-hour-a-day debauchery that became too much when she had to serve boxer Mike Tyson a vodka and Red Bull while he received oral sex from a “hired entertainer.”
Greene has adamantly said his yacht, which he no longer owns, was frequently chartered and noted that he had a strict no-drug-use policy on board. Peach signed an affidavit in 2012 saying that she “in no way intended to convey that Jeff Greene participated in illegal drug use, sexual acts, or other inappropriate behavior on Summerwind.”
“She was in a band that wanted to get publicity. She figured that was her 15 minutes of fame. I don’t even remember meeting her,” Greene said.
Peach couldn’t be reached for comment.
Greene also sued gossip columnist Jose Lambiet this year over a story that questioned whether the billionaire was using dirty tactics to fight a Related Group project in West Palm Beach. The case was settled in March.
Last week, POLITICO reported on a series of lawsuits and liens that Greene has dealt with since running for Senate, including a lawsuit filed by then-media consultant Devine Mulvey that alleged Greene owed the firm nearly $400.000 (The case was dismissed, but Greene paid $140,000, according to his federal campaign reports).
Greene told the Miami Herald that, as a businessman with hundreds of millions in real estate holdings, the lawsuits are an inevitability considering the number of workers and contracts wrapped into his empire.
Greene’s history hasn’t changed, although Greene says he has.
Once the subject of tabloid news and stories about all-nighters, he’s now a married father of three who campaigns with his children. He and his wife created The Greene School in West Palm Beach, run a philanthropic foundation and agreed to donate a bulk of his net worth to charity when he dies by signing onto the Giving Pledge in 2011.
“When you have three kids it changes everything,” Greene said. “You realize how vulnerable children are and the needs for kids. Children in Florida have been short-changed for a generation.”
Greene is also consciously courting the press this time around. Following a strange entry into the race — during which he opened a campaign account without granting so much as a single interview — he’s been giving free-range interviews to reporters and answering just about any question thrown his way, even telling POLITICO that he tried cocaine years ago (and “didn’t like it”).
On a recent helicopter ride over Lake Okeechobee, he told the Miami Herald that he tried to buy the Palm Beach Post this year but was outbid by GateHouse Media. He said this time around he’s received a “completely different reception.” In the past, he said, enemies “tried to make a cartoon character out of me.”
If elected, Greene would be by far the wealthiest governor in Florida’s history, rendering Rick Scott’s roughly $255 million net worth (or more) laughably modest. Greene lists his net worth at $3.3 billion, including his $85 million estate on Palm Beach, located a short walk down the beach from Mar-a-Lago.
With his money, Greene says he’ll flush down-ballot races with cash, perhaps pushing the party into control in the state Senate for the first time since 1998. That promise was met with a heavy dose of skepticism, considering that the $195,000 he’d personally given to Democratic candidates and committees over the last eight years was, while far from paltry, hardly enough to sway an entire election cycle. Then this week, Greene announced that he’d placed $5 million into a political committee that he intended to use to help other Florida Democrats.
Greene’s money is his biggest weapon. With the president endorsing likely Republican gubernatorial nominee Ron DeSantis, Greene is playing up his Trump card, hoping voters will tap him to be the guy who takes on the president’s surrogate. To reach voters, he’s blanketing the airwaves with commercials promising to fight the president.
And he’s doing it unabashedly.
“I’m not consciously trying to portray anything,” Greene told the Miami Herald. “I’m just being me.”
Tampa Bay Times reporter Langston Taylor contributed to this report.