Zen and the Art of Infrastructure Maintenance

IF YOU WANTED to see Jay Cashman this summer, you needed an invitation to his island. As he has for the past three years, Cashman was using the 200-acre Strong Island, just off the coast of Chatham, as a retreat for himself and his family. One day each week he’d make the four-hour roundtrip drive to his office in Cambridge—he had sworn off helicopters in June after nearly crashing in bad weather—and he’d occasionally agree to important off-site meetings, but that was it. As the season wore on, one of Boston’s most prominent construction moguls pretty much dropped out of sight.

Cashman has long been known as much for his personal life as his huge civil works projects. He lives in what he says is the largest single-family residence in Boston, a six-floor, 16,000-square-foot home with two kitchens, a mini movie theater, and an authentic pub shipped piece by piece from New York. He spent much of the ’80s and ’90s tearing through Boston’s singles scene, cruising the streets in a blue Rolls-Royce, a millionaire Casanova whose tomcatting became a staple of the gossip pages. His role in some of the city’s most controversial construction projects, meanwhile, caused less of a stir. Cashman does the dirty work, the digging and drilling and dredging, yet he’s always managed to keep his hands clean. The work he did on the Big Dig achieved the rare distinction of having no one complain about it. The diffuser tunnels he dug in 100 feet of water for the Deer Island sewage treatment plant were an unqualified success. And while half the South Shore howled in opposition to the Greenbush commuter rail line, Cashman efficiently went about the business of laying track.

Now, however, everything’s turned on its head. Cashman’s private life has settled down since he remarried in 1999, while his business dealings have become the subject of intense scrutiny. First came the news that he’d agreed to sell 73 acres he owns in Fall River to a group proposing to build a liquefied-natural-gas terminal, a project that city’s mayor called “stupid.” Then, at around the same time Cashman went into semi-seclusion on his island, he announced plans for a spectacularly audacious development venture all his own. No longer satisfied doing the contract work on someone else’s deals, Cashman wants to erect a $750 million cluster of massive windmills in Buzzards Bay. He believes the wind farm could supply half of Cape Cod with electricity—but he’ll have to build it first. A flurry of resistance has so far stalled a similar proposal in Nantucket Sound, and already Cashman has heard from outraged citizens who want to know what business a guy who digs tunnels has constructing 400-foot windmills that are certain to jeopardize narrow shipping lanes, a fragile ecosystem, and, by the way, the view.