Jon Manafort is back at work after his first vacation aboard his new yacht, Independence 2.
    The collar on his cotton shirt is open, his sleeves are rolled up, and he has the kind of tan that is doomed to peel, the kind people get when a week in the sunshine is a bonus, not a way of life. He offers me a chair in the conference room at the headquarters of his demolitions company in Plainville, Connecticut, and asks if he can grab me a drink, the way a friend might at a barbecue. He then takes a seat at the head of the table, settling into it rather than assuming it, and asks quietly how I would like to begin. Tell me about your life in boating, I say.
    Many boaters, particularly those from a more affluent background, would have begun by speaking of the lifestyle—the stepping ashore in Monaco, the top-deck hot tubs, the heated Italian marble in each head.
    But then there are the yacht owners who are simply drawn to the boating life, as opposed to the cliched lifestyle. They like sitting barefoot in the breeze, immersed in a book as gulls chase their wake, climbing through the trails of untamed islands, picking, rather than purchasing, the day’s fruit.
    So it is with Manafort, who started his story about his life with ``the boating disease'' by telling me not about his new motoryacht, but about a 6-foot dinghy.

A Lifelong Love of Boats
He was born into a family that enjoyed a certain level of affluence. Patriarch James Manafort emigrated from Italy to Connecticut, founded a wrecking company in 1919 and taught his four sons the business. After World War II, the sons renamed the company Manafort Brothers Inc. and built it into the large, successful demolitions company it is today.
    The third generation of Manaforts, including Jon, took over in the 1960s after growing up with all the trappings of the family’s success, including summers spent among hordes of cousins at a family cottage near Old Lyme, Connecticut. It was there that Manafort was introduced to life on the water.
    When he was 10, somebody gave him the dinghy. He painted it white, rowed it all around Soundview Beach, and got hooked on boating. Seeing other boats that cruised by, he started saving his allowance.
By the time he was 12 or 13, he had scraped together $150, enough to buy a converted wooden rowboat. It was 16 feet long and had a foredeck and a center deck, all theoretically powered by a 7 ½-horsepower Elgin outboard motor. He was, among the family cousins, The Man.
    "It was a big event," he said, swiveling slightly in his chair and looking down at his hands. "Until you started it up and tried to go somewhere, it looked like a real boat."
    During the next decade, race cars became his passion, but his early boating experiences stayed with him. After serving two years with the Army in Korea, he returned to Plainville in the 1970s to join the family business, get married, and start a family.
    When his first son was born, he and his wife decided that doing 100 mph in modified open-wheel stock cars at Plainville Stadium was no longer the ideal hobby, and they looked to the Connecticut River near Old Saybrook for weekend relaxation. "I had to get out of town on weekends so I wouldn't hear the cars," he said with a chuckle.

Trading Up and Traveling
It was on the river that the Manaforts kept their first boat, a used 23-footer by Formula, essentially a race car built to float. The speedster entertained them on weekends, but as their son grew, so did their aspirations for a family-oriented boat. They moved up to a used 31-foot Chris-Craft sedan with a berth for the couple and a pair of bunks for their son and, soon, his younger brother. They began to make friends who liked to explore and became part of the cruising community, traveling to Block Island, Rhode Island, and beyond in their boat, Cloud Nine.
    After a few years, Manafort traded up again—to a used 40-foot Chris-Craft that had a salon for entertaining. When the boys were in their early teens, he bought a used 48-foot Egg Harbor convertible, a boat designed for serious fishing but with an interior that could accommodate the family (hence the name "convertible"). He named it Wrecker and, for the first time, hired a skipper—not because he wanted to be waited upon, but because the captain could fill in with the boys where Manafort fell short, in enthusiasm for angling.
    In 1996, Manafort bought the first new boat he'd ever owned: a 43-foot Viking Express, a comfortable family boat decked out for fishing that would allow him to take his sons when the urge hit. He installed 10-cylinder, 1,000-horsepower engines. At 40 knots, he felt like the second Wrecker flew.

Discovering Charter
He and his wife, thanks to the boat's speed and their newly empty nest, expanded their cruising distances on long weekends and vacations. They cruised the Intracoastal Waterway all the way to Fort Lauderdale, Florida, learning which areas they liked and returning year after year. All was perfect for four years, until, well, he got restless again, especially after seeing advances in the marketplace. So he impulsively put his 43-footer up for sale and made a deal, but then was unable to get the new model he wanted. It was April, the beginning of the 2000 boating season, when hot ``debuts'' could be tough to come by.   

    "We were boatless," he said, "and we wanted to go boating."   

    Manafort took a friend's advice and went to Newport, Rhode Island, to look at boats he might charter for his family, which now included two grandchildren.
   When he stepped onto the docks of tony Newport, he had never dreamed about using, let alone owning, a 100-foot or larger "megayacht." And he hadn't a clue what he wanted when he started wandering around. He spent a few hours meandering, and then he almost called it a day.
    “I was walking around on the docks and I saw a sign: International Yacht Collection,” he recalled. “It was 8 or 9 at night, and a guy named Mark Elliott was sitting at a computer, still working, and he said, ‘Sit down.’”
    Manafort didn't know it, but he had walked into the office of one of the best-known charter yacht captains-turned-brokers in the world. That night in Newport, Elliott listened for what Manafort remembers as about 15 minutes before booking the family for a week aboard the 100-foot Burger motoryacht Southern Star. The yacht’s weekly base rate was in the $20,000 to $30,000 range, a hefty sum for what might have turned out to be the wrong style of boating for the family.
    “Never having chartered before, I didn't know what to expect,” Manafort said. “It ended up being a tremendous experience. Not having to run the boat yourself, worrying about dockage. It was so relaxing. You say, ‘I want to go to Sag Harbor,’ and the next thing you know, you’re there. You raise your hand, and they give you a martini!”

Buying a Yacht for Charter
It was the first time during our conversation that Manafort raised his voice in excitement, but the enthusiasm wasn’t for the experience alone. The businessman’s tone grew even more passionate as he explained the two lessons that week had taught him about yacht charter.
    First, he sure liked it.
    Second, it had been hard to find a boat that fit his needs, which he saw as rather general.
    “The machinery started turning,” he said, pointing to his head. “I thought, ‘If there aren’t a lot of boats in this range, maybe there’s room for one more.’ It was like a labor of love. I couldn’t afford and I couldn’t justify having a boat like that just for myself and how I use it.”
    And so, with the idea that he could create enough charter business to offset the cost of buying and running the boat, Manafort set out to buy his first megayacht.
    This approach to yacht ownership is fairly common, as smaller-boat owners look for ways to get into bigger yachts. A lot of times, though, the endeavors fail. Owners tend to want to use their new yachts, and men in Manafort’s position can easily forget that their newest purchase needs to be run like a business, not a weekend cottage. For instance, they often choose to use their boats during the high seasons and holidays, when charter bookings soar. That sends charter clients to other boats, which quickly develop better reputations. By the time the owner realizes his bottom line isn’t adding up, it’s often too late and he’s forced to sell.
    Manafort, though, did it like a businessman. He set his price range, which put him in the market for a 15-year-old yacht of no more than 100 feet in length, and ended up making what he called “a stupid offer” on a 90-foot Broward, just to see if the owner would take it. He closed on the deal in January 2001 and found himself with an older but well-kept three-stateroom yacht that had a full-beam saloon and a fighting chair for fishing. He named her Independence (he didn't think Wrecker would bring in business), signed her into the charter fleet of The Sacks Group Yachting Professionals, a well-respected charter company, and set about finding clients.
    That summer, under the command of Capt. Joshua Simcox, Independence got five weeks of charter–an impressive amount, about half of what established yachts hope to get each season. Manafort made himself scarce when charter clients wanted the boat, and he earned his crew’s respect by treating them well, another necessity first-time owners often overlook.
    “He’s a very easygoing guy,” Simcox said. “They come aboard and he puts on NASCAR or the stock market, watches Speed Vision. We make this punch, with pineapples, and we let it ferment for about five days. That’s the grog of the boat. They love to have friends and share their boat with as many people as they meet. It’s a business, too. The more people you introduce to the boat, the more business you'll get.”

Making Market Adjustments

Manafort was optimistic until that fall. On September 11, 2001, the worldwide travel industry collapsed along with New York City’s Twin Towers. A lot of yacht owners pressured their charter companies to get more bookings as business tumbled, but Manafort wasn’t one of them. He moved Independence to Liberty Landing, New Jersey, across the Hudson River from downtown Manhattan, and lived aboard for four months while he and his team from Manafort Brothers Inc. took down damaged World Trade Center Buildings 4 and 5. Independence didn’t return to the charter business until the summer of 2002, when it was docked near the Manaforts’ Connecticut home at Island Cove Marina, which they also own.
    “Being that it was right there, I’m a tinkerer, and we upgraded,” Manafort said. Charter business came back, and Manafort again stayed off his yacht to let her reputation and bookings grow. “A couple of times, I thought about signing on as a mate just so I could go along,” he joked.
    Then, during the winter of 2002-03, Manafort traded up again, in part because of business. “The bigger boats seem to work more” in the charter market, he said. “The huge boats are busy all the time. And this opportunity came up.”
    The “opportunity” was a 1993-built, recently refit, 105-foot Broward. It has four staterooms—including a master with a king-size berth and his-and-her heads separated by a hot tub (in addition to the hot tub on the top deck. The saloon is nearly as long as some of the boats Manafort used to own, and dining options include private outdoor seating, a country kitchen-style galley for guests who want to chat with the chef, and a small dinette in the pilothouse for anyone who wants to snack and talk with the captain while under way.
    Independence 2 is a far cry from the 23-foot Formula the Manaforts used to cruise up and down the river near Old Saybrook, Connecticut, but she does bring back memories of the speedster. And Independence 2 hits 22 knots, Manafort is quick to point out, compared with the first Independence’s 11 knots.
    Still, the businessman has no plans to overindulge in the high life. While Independence 2 set off to earn her keep (as of 2009 in the fleet at Robert J. Cury and Associates) at a weekly base rate of $36,000—which includes Manafort’s older son’s 34-footer as a tender—Manafort himself traveled back and forth to Bridgeport, Connecticut, monitoring the progress on a 30-foot aluminum workboat he was building to share with his wife on the river in and around their home.
    “There are a lot of nice days in January and December when all the other boats are gone,” he said. “You can watch sailboat races, and we get a lot of eagles.”
    He’s also still happy wandering around in the 15-foot skiffs he keeps at his marina. They’re a lot like the one he bought as a kid for $150, only with seven times the horsepower. Manafort told me he’s also happy with Independence 2, but has thoughts about five-stateroom models in the back of his mind.
    “I like this boat. I think I’m settled for the foreseeable future,” Manafort said, looking fondly at a photo of Independence 2 on his conference room table.
    He chuckled and shook his head.
    “Well, both of my daughters-in-law are pregnant. We might have outgrown this thing already.”—Kim Kavin

Original date of interview: 2003. Updated in October 2009.