Shortly after voters made him mayor of Miami Beach, Philip Levine gave his campaign strategist a garish poster with the strategist's comically smiling face mounted atop the rippled body of warrior Spartan King Leonidas.
Standing before a bloody battlefield, political consultant David Custin carried in his hands two severed heads. One belonged to a vanquished mayoral opponent, and the other to Levine’s predecessor, a 74-year-old woman.
It was supposed to be funny — a gag gift. But all jokes have a little truth to them, and Levine didn’t spend $2 million of his own money on his inaugural political campaign just to go-along-to-get-along at City Hall.
Instead, Levine stormed his way into City Hall five years ago pushing a big-picture agenda that several campaign insiders say was always intended to promote plans for higher office. He paradoxically slayed the political establishment with an assist from Bill Clinton, and steered Miami Beach's cumbersome government in directions that won international acclaim but at times also favored his political aspirations and financial assets.
In slogging his way to Democratic front-runner in the race for governor, Levine has campaigned heavily on his tenure as mayor. And everyone seems to agree: What Miami Beach got during four years of Levine is what Florida will get if he ends up winning four years as governor.
“He was a force of nature,” said Frank Del Vecchio, a prominent gadfly. “He was the best mayor and the worst mayor, simultaneously.”
In commercials and campaign stops around the state, Levine speaks about climate change by discussing his aggressive strategy and construction schedule to raise roads and drain the island with electric pumps. When asked about race relations, he mentions that he brought body cameras to a police department that a few years prior had killed a black man — during a party weekend for a largely African-American crowd — by shooting more than 100 bullets into his car as onlookers recorded.
"As the mayor of Miami Beach we did many things, from reforming a police department, from raising the minimum wage to fighting back sea-level rise, to decriminalizing marijuana, to banning assault rifles (even though unfortunately it was not enforceable), to doing everything a progressive mayor would do," Levine said during a recent debate in Pinellas County. "So, when people say what are you going to do in the future, I say take a look at what we've done."
But what voters won’t hear from Levine is that his tenure has an underbelly peppered with moments where the 56-year-old cruise industry entrepreneur displayed a thin skin, clumsy leadership and venom for anyone who challenged him. He jump-started more than $1 billion in newly planned, legacy-setting projects but also governed impulsively, appointed his business partners to important positions, and burned through supporters and critics alike in pursuit of his ambitions.
“I want him to win,” says former Mayor Matti Bower, whose severed head adorns the poster on Custin’s office wall in Miami. “I want to make sure he stays away from here.”
For someone who’s been quietly called brash and smug by his gubernatorial opponents, the Levine now touring the state is the toned-down, reserved version of the multimillionaire who transitioned from cruise-line marketing mogul to big city chief. Calling himself the "impatient mayor," that Philip Levine took over the city with a swagger and disproved everyone who said he'd struggle to adapt to government life.
It helped that Levine came into power with enough support from commissioners to give him a crucial super-majority that he used repeatedly to bypass red tape. He was elected during an economic upswing, with a green, newly hired city administrator. He brought in basketball legend Pat Riley to pep-talk city employees, and made drink coasters that said, "Just get it done!"
And his first priority as mayor was an issue that affected him directly: flooding.
For years, slowly elevating sea levels and an outdated, gravity-based drainage system had roiled politics in the island city. When Levine took office, the city was in the beginning of a new 20-year, $200 million sea-rise plan that called for more pumps, wells to store storm runoff, higher sea walls and “back-flow” preventers for drain pipes flowing into Biscayne Bay. Two years in the making, the plan was hailed as a bold road map for tackling rising sea levels.
But it wasn’t bold enough for Levine, a World War II buff who liked to compare the threat of climate change to a looming blitzkrieg.
The new mayor appointed friend and business partner Scott Robins as his “flooding czar,” and asked him to team with two retired engineers to review the city’s long-term plans, which were under way but still in their infancy. After just two meetings, Robins reported that the city needed to completely overhaul the plan and double spending in order to keep streets and businesses dry decades down the road. Then, in a pattern that would repeat itself, commissioners declared the city in a state of emergency and waived competitive bidding requirements in order to sign an $11 million contract to build three storm pumps along flood-prone Alton Road — where Levine owns real estate.
Later, they fast-tracked an existing plan to raise roads in Sunset Harbour, a low-lying bayside neighborhood. Levine owned property there, too. In the financial disclosure he filed with the city weeks before he became mayor, he voluntarily explained that Scott Robins Companies was his partner on roughly $20 million in real estate in the neighborhood.
"The fact of the matter was that Sunset Harbour was ground zero," Robins, one of the pioneering developers to perform renovations in the city's historic Art Deco district, told the Miami Herald. "Where do you start with this program? You start with areas with the worst flooding."
Miami Beach would go on to issue close to $40 million in no-bid engineering contracts, extensions and change orders over Levine's two terms, all based on the premise that climate change had put the city in a state of crisis that had jeopardized investment. The projects were a microcosm of Levine's time as mayor: Because of the shredding of government norms, they quickly turned South Beach into an international success story — and kept his own real estate dry.
"Everyone owns property all over the place in different areas," Levine said Thursday during a sit-down in his Wynwood headquarters, dismissing any perception of conflicts. "Scott was uniquely qualified to do this. ... I couldn't think of anyone better."
Levine ran into other situations where his newly elected position collided with his personal finances and relationships.
After tapping Robins to advise the city on climate change, Levine appointed Brian Elias — a close friend and former business partner who now chairs his gubernatorial political committee — to head a quasi-judicial planning board that vets real estate projects in need of special approvals.
Shortly after his reelection, Levine tried to do an end run around the local ethics commission in order to vote on an up-zoning for a developer building a residential tower next to one of his Sunset Harbour properties before conflicting out. And Custin says it was Levine's visit to Cuba in 2016 with Tufts University graduate students that led to their political divorce, after the consultant accused Levine of trying to ingratiate his cruise line marketing business with the Communist government as it finally opened its ports to sea-bound tourists.
"He knew he was going to take that trip. He kept it hidden from me and misled the Hispanic voters" during his 2015 reelection campaign, said Custin, who is Cuban American. "It was also disappointing that he'd put his personal profits ahead of the public."
Custin, who now helps Florida's Republican leadership strategize their legislative campaigns, says Levine openly talked during his 2013 campaign about treating his time on the third floor of City Hall as a springboard to better things, like becoming governor or president. Two other sources familiar with Levine's aspirations confirmed this. But longtime Levine consultant and friend Christian Ulvert says that's false,and argued that Custin is simply acting as a Republican operative inventing dirt on the Democratic front-runner. The former mayor called his one-time campaign strategist a disgruntled liar "who was fired and jealous and would love to be part of this campaign."
The trip to Cuba "wasn't for business reasons," Levine told the Miami Herald, arguing that Custin became angry when the city passed a law during his final year as mayor banning campaign consultants from lobbying commissioners. "David Custin was very unhappy with that because we cut off part of his income. I thought it was ethically incorrect for people who handle campaigns to be lobbying the city. It was wrong."
The businessman, who sold a cruise line media and retailing company to LVMH Moët Hennessy Louis Vuitton SE in 2000 for a reported nine-figure sum, had never been involved in politics on the relatively small barrier island. But he’d caught ambitions from his time traveling with former President Clinton and working with the Clinton Global Initiative.
He had almost filed to run for mayor of Miami-Dade County twice in the past, deciding against it each time. Then over lunch in the early summer of 2013, Robins suggested that his friend challenge two sitting Miami Beach commissioners for the open mayor's seat.
Levine called his friend at 5 a.m. the following morning to say he'd decided to run after an all-nighter thinking about it — but under one condition. "You're helping me," he told Robins.
Despite previously keeping a relatively low profile, Levine became the city’s ubiquitous mayor-as-emcee once elected, reprising his job as a young man working as a cruise line lecturer.
Between fundraisers and interviews around the country as a Hillary Clinton surrogate, he promoted the city’s climate-change projects on National Geographic and in a Leonardo DiCaprio movie. He held his first state-of-the-city address in the city’s convention center and bused in hundreds of people in order to record it and broadcast it in other parts of the state. He hosted an XM radio show called "The Mayor." And he promoted a centennial celebration that included a beachfront concert featuring singer Gloria Estefan, actor Andy Garcia, tenor Andrea Bocelli, and a little Philip Levine. To fund it, the city gave its contractor the green light to accept $1.7 million in sponsor donations from entities including the Seminole Hard Rock Casino — not exactly a welcome player in a virulently anti-gaming city.
After having built a marketing empire, Levine was using those same skills to build a political one. But it worked only because he had something to promote.
“Philip is a doer,” said Norman Braman, a Republican billionaire who credits Levine for guaranteeing Art Basel’s long-term future in the city by dismantling and reinventing the previous administration’s long-delayed plan to renovate the city’s convention center. “They just talked about it. He’s the one who did it.”
Levine’s philosophy of treating impatience as a virtue was a result of a career spent running things his way. The closest thing he knew to the Miami Beach City Commission was probably a corporate board, and he developed a reputation among lobbyists and high-ranking city officials for wielding an outsized amount of power in a mostly ceremonial position.
"He's impatient, and when he decides something is the right path to take, he executes pretty aggressively,” said Elias, who was a partner of Levine's in Lucky Strike bowling alleys until, the former mayor says, Levine divested years before he became mayor. "His biggest strength is his biggest weakness: His impatience.”
The restlessness rippled through City Hall. Elizabeth Wheaton, a sea-rise projects professional whom Levine tapped for eight months to work as his final chief of staff, says Levine’s corporate sector mentality and media background made him a demanding boss. Other office staffers told her not to post an "away" email message when she went on vacation, because Levine always expected her to check her messages.
And Levine seemed to practice what he preached. He was always "on" as mayor, and once posted video of himself berating a FedEx driver for parking illegally in a lane of traffic. Fans saw an enforcer, and critics a hothead. Levine's opponents sometimes dealt with a man who treated politics like war, and who joked with Custin about lopping off the heads of their opponents.
"That was truly just something fun. For us it was just kind of a fun victory thing," Levine told the Miami Herald Thursday about his victory poster. "We were able to conquer the remnants of the old administration that was holding the city back."
Levine's bravado energized some of his earliest supporters, who saw a self-funded millionaire who donated his mayoral salary and benefits to a city charity and cut through stereotypes of the lazy bureaucrat and stuck-up politician.
“He put his money where his mouth was,” said Margueritte Ramos, a businesswoman from Miami Beach’s northern, sleepier part of town, where Levine supported a push to redesign and revitalize a struggling commercial market. Ramos, a registered Republican, says Levine will be the first Democrat to ever get her vote for governor:
“He did more than any other mayor has done for North Beach.”
Levine undoubtedly kept his campaign promise to end a political culture in the city that would agonize on even simple decisions, like whether to install clay or hard tennis courts in its biggest park. Like Ramos, some of his earliest supporters saw him as a great disruptor — the multimillionaire who would rewrite a political system greased for decades by contracts and campaign donations.
Instead, Levine appeared to perfect it.
Two years after campaigning against cronyism and special interests, Levine would spend spring afternoons on his 70-foot boat, named The Baron, and at Fisher Island making phone calls to developers and city contractors for campaign cash. With the help of city commissioner Jonah Wolfson, the two raised $1.4 million into a political committee called Relentless for Progress, whose RFP acronym was conspicuously the same as the acronym the city used for competitive contract solicitations.
Levine says he got involved at Wolfson's behest. But sources with knowledge of the political committee say they were equal partners trying to drum up the money to help elect a new slate of commissioners and promote Levine's brand. With the mayor doing the heavy lifting, they solicited six-figure deposits from wealthy scions seeking approvals for their privates manses, and donations from contractors who received no-bid deals to perform sea-rise work around Levine's properties.
In terms of public relations, it may have been the worst blunder of Levine's tenure.
Though hitting up special interests for money is a tried and true political practice, Levine and Wolfson drew quick attention from activists and the press when they raised $500,000 in a single month. When veteran WPLG-Local 10 political reporter Michael Putney criticized the fundraising as "sleazy," Wolfson took out a full-page ad in the Miami Herald attacking him. Wolfson, the PAC chairman, ultimately shut down the political committee, returned the remaining money and proposed legislation banning the very contributions he and Levine solicited — but not before Levine defended the solicitations as standard South Florida politicking.
"Right now, this is the world we live in," Levine told Putney during an appearance on his live Sunday morning show. "It's appropriate. It's legal. If we want to change the laws, I'd be the first to do it. I think we should. Remember something, Michael, I self-finance my campaigns."
Meanwhile, the committee ran ads featuring Levine during commercial breaks.
In some ways, Levine's defiance came to define him as mayor.
He temporarily stopped talking to the Miami Herald during his initial run for office, later declaring the newspaper a "fakakta" company — Yiddish for screwed up. He ostracized an FIU hydrologist who reported findings that Levine’s vaunted flood pumps were sending water into Biscayne Bay that tested positive for concentrated levels of human waste. He refused to turn over to radio show host and activist Grant Stern a list of people he blocked on social media , prompting a lawsuit that the city continues to defend today.
He pushed $20,000 fines for short-term renting and waged war on Airbnb. He guaranteed a still ongoing lawsuit by passing an ordinance raising the minimum wage despite a law that says only the state can do that. And he convinced the city to pull out of a countywide effort to pursue a comprehensive light-rail plan in order to push a no-bid contract for a French operator that he met with while on a trade mission to Bordeaux.
The idea was widely derided, and became known as the "train to nowhere."
But even as the $244 million light-rail loop derailed, Levine's ambitions continued to grow. Having discussed whether he should run for governor or the U.S. Senate with his close friends in 2016, Levine was already airing commercials around the state and country, preparing for his next big campaign. He published a video at the end of the year declaring that he wouldn't seek a third, final term as mayor and that he'd done most of what he set out to accomplish.
Levine spent his final year as mayor elevating his profile and raising money for his gubernatorial run. He lobbied to host the U.S. Conference of Mayors. And under new political guidance, he seemed to strike a less recalcitrant tone, though he still feuded openly with club owners on Ocean Drive, where Levine fought unsuccessfully to stop liquor sales at 2 a.m. amid complaints about drunken revelry.
Though he started advertising his speeches and accomplishments outside South Florida before finishing his first year in office, Levine says he only made up his mind to run for governor a few months before announcing last November when, just weeks after chartering a plane packed with supplies to hurricane-ravaged Puerto Rico, he made official what everyone else already knew.
So far, his long-term plans are going swimmingly. This month, an independent poll showed him with a double-digit lead over his opponents in the Democratic primary. That has a lot to do with the millions of dollars he's spent on campaign commercials. But Levine the candidate will sink or swim come the Aug. 28 primary at least in part because of what Levine the mayor did over the last few years.
"There's a lot of things that we did. And we did them in a pretty short time," Levine said. "Overall, I think we brought the government back to the people."