By David Smiley, Joey Flechas and Danny Rivero, Miami Herald and wlrnnews.orgPhilip Levine has told the story so many times that it sounds like a fable.With $500 in the bank, a young man opened a small office on South Beach, launched a cruise-line media company and created a tourism marketing empire that sold a decade later for a small fortune. The tale is the backbone of a campaign promoting a self-made, blue-collar businessman who as governor would change Tallahassee to make it work for its 21 million "customers."But how Levine made the money that's opened doors to City Hall, Air Force One and perhaps the governor's mansion is far more complex. So too are the details behind his $133 million net worth.A Miami Herald review of hundreds of pages of court and corporate filings and interviews with current and former Levine business partners reveal a complicated portrait of a businessman who through impeccable execution and timing built several successful companies from scratch. He also received steady support from a well-heeled family, had acrimonious splits with former partners and dealt with a controversy in Alaska involving allegations of strong-arm tactics by cruise-line shopping guides.Through it all, the Democrat and former Miami Beach mayor accumulated admirers, political allies and enough wealth to become his own top campaign donor in his run for governor — a key advantage that could help him win the Democratic nomination next month as he competes with Jeff Greene, Andrew Gillum, Gwen Graham and Chris King."I like the idea of someone (running for governor) who's done big things in business," said John Morgan, a wealthy personal injury attorney who flirted with his own campaign for governor as a Democrat. "I don't really understand his business. But I know he was successful."As Levine tells it, his story begins when he was a young boy growing up in Massachusetts, where he shoveled snow and swept the floor at an auto body shop for cash. When his family moved to Hollywood, he scooped ice cream at a Sheridan Street Baskin-Robbins and worked as a legal courier for law firms before graduating from Hollywood Hills High School.Levine went away to the University of Michigan and roomed with future Design District developer Craig Robins, whose father would later become a crucial investor in Levine's companies. After graduation, holding a political science degree but unsure of his career path, Levine responded on a whim to an ad in the Miami Herald for a port lecturer with Royal Caribbean.Levine, in his early 20s, lied to get the job, claiming he had experience in public speaking. He was placed on the Song of America, docked at San Juan, Puerto Rico."I'm out in the middle of the ocean and they give me a cabin that's, like, below the porthole, the waterline. No port hole, no bathroom, no anything. And I'm thinking this is the worst decision I have ever made in my entire life. I was thinking of calling the Coast Guard to get me off," Levine said in a recent interview.But the next morning, he walked up on stage: "I tell a couple of jokes and I think, 'Oh my God, they're actually responding.' And to me that was the beginning of the rest of my life."Levine worked that job for only a short time. He went on to dabble in investment banking and then spent about a year in the late 1980s developing and expanding the in-house port lecturing program for Carnival Cruise Lines. But he wanted to get into business for himself.So in 1990, with $500 saved up, Levine created OnBoard Media and negotiated a lease with late-Miami developer Tony Goldman — at the time involved in South Beach real estate with the Robins family — for a small office on the second floor of the News Cafe building, where he says termite wings littered the floor. This was before Ocean Drive was a world-famous tourist attraction, so rent was only a couple of hundred bucks. But Levine says he had to find a contract before he could actually pay.Philip Levine opened his first office for OnBoard Media above the News Cafe on Ocean Drive in 1990. (Miami Herald)His first deal was with a Greek company called Chandris Fantasy Cruises.The company, which would later become Celebrity Cruise Lines, was seeking a contractor to publish programs and magazines. Levine cold-called the chief operating officer, mispronouncing his name badly and getting an earful for it — and an invitation to New York. He nailed down a contract with shipping tycoon John Chandris to produce promotional materials for the Amerikanis, a converted, 40-year-old ocean liner."I used to fly to Puerto Rico every Monday myself because that was where it was docked. And every time I got here there would be two officers out front smoking cigarettes, like 'Who are you?' Every week it was like starting over again," Levine said. "But when you make it with the Greeks, you can make it anywhere."Levine, whose reputation as a relationship-building businessman runs counter to his brash political persona, says he is still close with Chandris. He also remains tight with Jerry Robins, the father of his college roommate.The elder Robins hatched an agreement to become a silent OnBoard Media partner in his Miami Beach office on 41st Street during the mid '90s after a nervous Levine spilled coffee all over his conference table."He said, 'Don't worry. Don't worry. The first time Jay Pritzker invested in my company I did the same thing,'" Levine says, using a playful New York accent. "We made a deal on the back of a napkin."Jerry Chafetz was Levine’s first business partner in the cruise line marketing business. He ran operations for OnBoard while Levine focused on business relationships and contracts. (Ronna Gradus/Miami Herald Staff)By the time Robins and his two sons invested, Levine was president of three cruise line marketing and retail companies, managing relationships, seeking out deals and negotiating contracts while long-time business partner and former jeweler Jerry Chafetz oversaw operations. They'd invested at a boom time for cruising, with annual passengers jumping from 1.4 million in 1980 to 5.4 million in 1998, and expanded their business into cruise lecturing, in-cabin programming, magazines, books and art auctions."He told me how the Caribbean was really the jewelry Mecca of our area. I couldn't believe it," said Chafetz, who met Levine through Levine's mother, at the time one of Chafetz's employees. "They were delivering so many passengers to each port every day and directing them toward the right jewelry stores. It was incredible. I sold my jewelry store and went to work with him."They were successful enough to sell a majority stake in the late '90s to Berkshire Partners, an equity firm out of Boston. Berkshire quickly acquired duty-free retailers Greyhound Leisure Services and Nuance Global, and rolled them into the Starboard Cruise Services, today one of the largest luxury cruise line retailers in the world. The merger took an old model of cruise line retail and put it on steroids by placing the marketers, art auctioneers, duty-free shops and port retailers all into the same hands.Filings with the Securities and Exchange Commission from an early, aborted 1999 Starboard deal show that Levine's three companies were valued together at $47 million. Levine, who writes on his website that he partnered with Berkshire after turning OnBoard into an $85 million company, says LVMH Louis Vuitton Moet Hennessy swooped in just a few months later with a better, undisclosed offer."His business ended up being a game-changer," said Royal Caribbean CEO Richard Fain, whose company has a business agreement with Royal Media Partners, a marketing and media company Levine founded in 2011. "Not so much because the concept was extraordinary, but because his execution was extraordinary."A photo of Philip Levine taken during the mid-90s, when he was president and CEO of OnBoard Media.Levine's career wasn't all smooth sailing.He faced lawsuits from business partners like Mohammad Saeme, a Swiss physician who claimed in court that Levine used Saeme's expertise to snare a license agreement with a spa and wellness center and then cut him out of the deal. Levine also had an ugly falling-out with Albert Scaglione, a Michigan businessman who partnered with him in 1996 to launch art auctions.Levine, though, quashed the allegations in court with little trouble. Today, he counts Scaglione as one of his gubernatorial campaign supporters and donors.Later, in Alaska, OnBoard Media and Royal Media Partners ran into accusations that port lecturers bad-mouthed local retailers and misled customers into believing the shops they recommended were of higher quality or better value, when in truth the shops were paying commissions and fees to earn recommendations. The companies signed consent judgments with the Alaska Department of Law after they were sued in 2013.OnBoard Media paid $75,000. Royal Media Partners paid $45,000. But it remains unclear what role, if any, Levine's leadership played in the controversy.Chafetz and Levine, who stepped away from OnBoard around 2004, say their employees weren't involved in bullying, and neither company admitted to breaking the law or committing any wrongdoing while working with the state. Christian Ulvert, a top campaign strategist for Levine, also says the Alaskan government began its enforcement and investigations before Royal Media Partners entered the market around the mid-point of 2012.Ulvert told the Miami Herald that Levine's company willingly worked with the state without having any knowledge about ever being the subject of a consumer complaint related to the investigation at the time."Once this issue was brought to the attention of Royal Media Partners, they joined the State of Alaska in their consent decree as willing partners to make sure that the updated standards were put in place to protect consumers," Ulvert said.Levine defended himself aggressively against Alaska-themed attacks by his opponents during his 2013 campaign for Miami Beach mayor. At one point, he threatened to sue a Miami Beach blogger, J.P. Morgan, who unsuccessfully sued Alaska's Department of Law to try to open its investigative files and better defend himself.Alaska's attorney general's office has repeatedly declined to release its documents on the case, and would not discuss their investigation with the Miami Herald, citing a state law they say makes the details of their enforcement efforts confidential. But lawmakers in Juneau, one of Alaska's port cities, said shortly after the consent judgments were announced that the city's problems with port lecturers extended back decades."For more than three decades that cover the terms of seven Alaska governors, there have been several attorney general investigations into the improper practices of the port lecture system," State Sen. Dennis Egan and two state representatives wrote to Alaska's attorney general in 2013. "The pattern is one where the state gets tough, there is a promise of better conduct, port lecturers improve their behavior, and then, after a while, they go back to their old ways."The cruising industry remains one of Levine's best sources of campaign cash. It's also his biggest source of personal income, bringing him more than $3.6 million last year, according to his financial disclosures.Following the sale of Starboard, Levine took his new-found wealth and became a regular donor for the Democratic party, contributing at least $1.7 million over the last 25 years to campaigns other than his own, according to a Herald review of state and federal campaign finance databases. He bought a home on tony Sunset Islands, where he began hosting fundraisers that helped him host and meet major party players, including Bill Clinton, with whom he quickly established a close friendship after they were introduced by former Miami-Dade Mayor Alex Penelas.He's the rare politician who shows up on the gift disclosures of other politicians, like the time Royal Media Partners spent $2,500 on air fare and room for Miami Commissioner Keon Hardemon in 2016. It was one of Levine's businesses, Lucky Strike bowling alley on South Beach, that was home to the now-infamous 2008 fundraiser where former University of Miami president Donna Shalala posed with a $50,000 check cut by ponzi schemer Nevin Shapiro.Donna Shalala accepted a $50,000 check from Nevin Shapiro in Lucky Strike bowling alley on Miami Beach in 2008. Levine was a bowling alley co-owner at the time. Shapiro is now a convicted ponzi schemer. (Miami Herald)Levine is also a philanthropist. He is heavily involved in Best Buddies, a special-needs charity, and used his money to charter a plane to Puerto Rico after Hurricane Maria to deliver supplies. Chafetz said Levine, whose business has kept him invested in the Caribbean for decades, has delivered supplies to storm-ravaged islands for years, long before anyone cared to notice.Though cruising remains the biggest source of Levine's income, he is also invested in an array of mutual funds. And under the brand "Baron," Levine also began investing his money into yachts and start-ups after he sold OnBoard Media. He plunged millions into gentrifying Miami neighborhoods with Scott Robins, which brought him more than $1.4 million in income last year, his biggest source of income outside of leisure.Today Levine owns more than $100 million in real estate from South Beach to Manhattan, with Robins a partners in as much as $42 million in property. Robins, who speaks almost daily with Levine, described the former mayor as a high-energy businessman who has little patience for analysis and rumination. He said Levine places great trust in his inner circle, and will quickly dismiss anyone or any idea that he feels will slow progress unnecessarily."We have 100 percent trust of each other, so, he and I just have very frank conversations", Robins said. "He's not a micro-manager at all, and he's an excellent guy to bounce things off of."One source of income Levine is no longer tapped into, according to his campaign: fossil fuels. Ulvert says Levine sold his nearly $600,000 in oil and gas-based stock since disclosing his finances last month with the state.How Levine made his money, and where his investments are, have real implications on his candidacy and on his potential tenure. The former Miami Beach mayor is and has always been his biggest campaign donor, having spent more than $12 million so far on his two mayoral campaigns and his current bid for governor. His assets are potentially affected by whether he takes office in Tallahassee this November, though he told the Miami Herald he'll stay hands-off with the cruising industry and place his assets in a blind trust."I think when you're the CEO of an $89 billion organization," Levine said last month, referring to the state budget, as he filed his financial disclosure, "I'm not so sure you have time to run anything else."Miami Herald Tallahassee Bureau reporter Mary Ellen Klas contributed to this report.