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.

The controversy didn’t seem to particularly disturb Cashman. He kept busy with his plans, enjoying his time on the island. Then, on the night of July 10, a 38-year-old Jamaica Plain woman was crushed to death by several tons of plummeting Big Dig ceiling tiles. The demise of Milena Del Valle, unlucky enough to have been traveling with her husband through the I-90 connector at the precise moment 24,000 pounds of tiles came loose, precipitated a public firestorm in Boston. No longer merely an embarrassing boondoggle, the costliest construction project in U.S. history was now a deathtrap, and somebody was damn well going to be held responsible.

Jay Cashman Inc. had done several hundred million dollars’ worth of Big Dig work—but that wasn’t the source of his problems. It turned out that the ceiling tiles at the center of the unfolding tragedy had been installed in 1999 by Modern Continental, the construction behemoth that had made itself the perfect symbol for the entire Central Artery debacle by somehow managing to parlay a few billion dollars of Big Dig contracts into impending bankruptcy. To head off that looming financial disaster, the insurance firm that was on the hook for Modern’s failures hired Cashman in 2004 to provide management oversight of the company. That meant media inquiries about Modern Continental’s role in the tunnel accident were directed to Jay Cashman Inc. Cashman, ensconced on his island, was uncharacteristically silent. He wasn’t returning my messages, either, even though he’d invited me to his island weeks earlier. Just as I started to think he was going to cancel on me, I got a call: It was Cashman, wondering when I was coming down.

Cashman can seem a little distracted at times. You’re never quite sure if he’s heard what you’ve said, or remembered what he’s told you. Which is why it crossed my mind, when I called him from Route 6 on Cape Cod, exactly as he’d instructed me to do just two days earlier, that he might have forgotten about me. “Oh, you’re at Exit 11,” he said, sounding surprised. “Do you swim?”

Upon arriving at the Strong Island landing, I walked down a gently sloping beach, past several overturned dinghies, and approached the water. Cashman sat in a Boston Whaler bobbing five feet offshore, talking into a cell phone and puffing on a cigar, an empty Coors Light can at his feet. He looked tanned and healthy in a black rugby shirt, nylon cargo pants, and sunglasses, still possessing, at 53, a splash of the charm that had made the bedroom conquests of his bachelor days the topic of so much conversation. So engrossed was he in his phone conversation that I assumed it involved the Big Dig accident. Gradually I realized he was discussing the 16-foot gazebo he was building outside his island home. He’d been authorized to build only a 12-footer. He told his lawyer he’d make it right, and then he hung up.

For a man who routinely deals with some of the toughest characters in Boston, this seemed a strangely accommodating way to negotiate. “I don’t like the hard-line approach—it takes too much time,” he explained as a handyman named Mark steered us out into the bay. We were heading for Nauset Spit, a long strip of sand a couple of miles from his island, where Cashman’s wife and her visiting family were swimming. “I always worry that if I get too greedy about something I’ll blow the deal, I’ll have nothing.” He narrowed his eyes, the way he often does during conversations, as though searching for a sign that his point is getting across. “Some people have to milk every deal. My father was that way. He hated to think he’d left a nickel on the table. I often know I could have gotten more out of a deal.”

This approach should not be mistaken for passivity. After all, you can’t compete in Boston’s tooth-and-claw construction industry by playing nice. Peter White, president of J. F. White Contracting, describes Cashman as an extremely aggressive rival. “Until you’ve banged heads with Jay,” he said, “you can’t know him or respect him.”

Cashman’s certainly willing to roll up his sleeves when the need arises. In 1994, while separating their interests after 20 years in business together, he and his brother Jamie got into a fistfight in their lawyer’s office. Jamie had accused Cashman of stealing money from the company. (Friends of both men say there was nothing to the claim. Jamie Cashman did not respond to requests for comment.)

Then there’s the feud with Boston’s mayor. “The problem with Tom Menino,” Cashman told me, “is when everyone is kissing your ass, you start to believe your ass is beautiful. But it’s really just a big, fat ass.” He went on like this for a while. “Tom Menino works that job like no other mayor. Every little bakery that opens up, he’s there.” Cashman and Menino were good friends going back 25 years. They used to meet for beers during the summer at the Red Coach Grill in Braintree. Cashman traces their falling-out to an incident five years ago, when one of his employees “ripped Menino a new asshole” after Jay Cashman Inc. failed to land a particular contract for the new convention center. “I tried to explain the story to him, that the guy was nuts,” Cashman said, “but it didn’t seem to do the job. Ever since then, it’s been weird.” The frostiness, he said, didn’t inhibit Menino from requesting a $30,000 contribution for the 2004 Democratic National Convention.

A Menino spokesperson was a little more circumspect: “Mayor Menino is surprised that Jay would characterize their relationship in that way. He believes he has a good relationship with Jay Cashman.”

Zipping across Pleasant Bay, we finally arrived at Nauset Spit, and Cashman hopped into the water. He waded over to a pontoon boat that had ferried his wife and her family to the spit and grabbed a few cans of Coors Light. He handed me a can and we set out across the spit. As we walked, patches of sea grass peeking out of the white sand, Cashman told me about the first time he’d seen Strong Island, when he was a boy and he and his father were scouting summer rentals. “I kept bugging him about it,” he said. “One day in the garage—my father could be a real grouch—I asked him why we couldn’t rent the island. I still remember this; he said, ’Cause I don’t know if I want to spend seven thousand on it! I knew then to drop it.”

The Jay Cashman Inc. headquarters overlook the Charles River from the top two floors of the Modern Continental building on Memorial Drive in Cambridge. Cashman’s company has moved at least seven times in the past 15 years, and will soon vacate the Cambridge building as well now that Cashman’s work with Modern Continental is nearly finished. “We’re like gypsies,” he said.

Cashman’s office is overrun with photographs of his family and certificates of his achievement. On one wall is a framed yellowed flyer for Humpty Dumpty Construction, the snow removal company Cashman, then 12, founded with his brother Jamie, who was 10. Cashman was born into construction. He grew up in Quincy, where both his grandfather and father ran contracting companies. His father, Jack, had a reputation as “a bit of an Irish rogue,” says Paul Losordo, Cashman’s longtime friend and attorney. “You might find him after work at Jimmy’s Harborside with a bunch of the other Irishmen.”

Cashman has been known to enjoy the odd tavern himself. His daughter Jaclyn Cashman, a television news anchor, recalled the time her father disappeared during a family vacation in the Caribbean. Frantic, Jaclyn burst into a bar looking for him, tears streaming down her face. There was Cashman behind the bar, shirtless. “He says, ‘Jaci, you want a beer?’” Cashman was buying drinks for everyone, but only on the condition that he got to pour them. “One of the things I really liked about my father,” Cashman told me, “he’d go and thump a bar. He’d set it up, beer and champagne for everyone.” That was on the good days.

Cashman said his father also had a vicious temper, and his mood could blacken without warning. “We’d go places in the family car and we’d be singing. Other times, he’d be other ways. Why do you think my favorite charity is battered wives and children?” Cashman’s best friend, the auto magnate Herb Chambers, says the complicated relationship has affected Cashman throughout his life. “That’s part of what’s made Jay so loving,” Chambers said. Despite building a thriving business, Jack eventually ran into financial trouble and suffered a fatal heart attack at the age of 51.

Cashman played sports in high school, “but he was always more interested in making money,” his classmate, and now employee, W. Bruce Wood, once told the Patriot Ledger. When it came time to choose a quote for the yearbook, Cashman settled on “Why should the devil have all the good times?” He married at 19, fathering two daughters, and worked his way through Boston University. During college, he leased dorm room refrigerators to students across the city. By his junior year, he was worth $31,000.

While in school, Cashman founded a construction company with his brother. They ran J. M. Cashman out of a trailer in Weymouth. Paul Losordo remembers that he first represented them in 1977 on a $40,000 job for the town of Hull. The Blizzard of ’78 hit Boston the following year, doing millions of dollars in damage, much of it to seawalls and piers—precisely the sort of work the brothers specialized in. Losordo said the storm had an effect “of biblical proportions” on the company. Cashman won federal repair contracts worth more money than he’d ever dreamed of. “That’s when I became a millionaire,” he said. Two years later, Cashman stretched his company even further, winning a $3.5 million job to overhaul the Vineyard Haven ferry terminal.

By the time the brothers split in 1994, their company was bringing in $100 million a year, according to David Ferrari, who was hired to liquidate the business. After paying off the banks and shutting everything down, each brother walked away with about $17 million. By then, Cashman had already cashed in his 401(k) and mortgaged his house in order to seed his new business. “I hit a couple of big jobs right off the bat and I was back in the game,” he said.

He told me what he’s worth these days but insisted I keep the information private. It’s a staggering figure, heavy on the “multi” part of multimillionaire. All told, Cashman employs a thousand people. He has offices in three states and in India, and did $250 million in sales last year.

“In my family, being a financial success was a source of pride,” he said as we talked in his office. “My father respected that. You were valuable if you were successful.”

Cashman is comfortable with the language of psychotherapy. He saw a therapist for 10 years, starting when his first marriage began to fall apart. Among his discoveries was the source of his need for constant activity. “Psychologically,” he said, “there is a fear with people that if they don’t have anything to do, they’ll be by themselves. They’ll have to face themselves.”

Cashman wound up alone in 1985, when he and his wife divorced. It’s debatable whether he used the time as an opportunity to face himself. He drank and caroused and hit Newbury Street in his flashy Rolls. He was romantically linked to glamorous models, and is said to have once offered $50,000 to anyone who could broker a date for him with Madonna. A worn-out Herb Chambers was once compelled to tell Cashman that it was not, in fact, a good idea for them to buy adjacent residences on Commonwealth Avenue. “I couldn’t possibly live next door to him,” Chambers told me with a laugh. “This guy would kill me!” In 1992, after too many appearances in the gossip columns, Cashman resolved to put some distance between his professional and personal lives, taking an apartment in Manhattan. There, he continued the high life, drinks on the town and fabulous parties at the apartment.

At one of his bashes, Cashman met a striking brunette who intrigued him. They lost track of each other, though, and he forgot all about her until a few years later, when she showed up at a party on a 180-foot yacht he had rented for a cruise to Atlantic City. Her name was Christy, a model, and she wanted to be an actress. She’s his wife today, the mother of his two young sons. Cashman spent hundreds of thousands of dollars on their wedding in 1999, renting a castle in Ireland. He hired actors dressed as leprechauns to leap out of bushes and startle guests. Cashman sometimes puts money into Christy’s independent films, and when she landed a small part in What’s the Worst That Could Happen?, a 2001 comedy starring Danny DeVito and Martin Lawrence, he opened up his Back Bay mansion for filming.

Everyone says Cashman is much happier and calmer since meeting Christy. “Before my dad and she were married, he was so much more short-tempered,” Jaclyn said. Cashman told me it can be embarrassing to think about his past antics. “When I look back at dating and I look at the hurt I caused people—you start to think about needing to change. If you’re a playboy, you’re selfish. You endear people to you and then you move on.”

These days, Cashman is putting most of his attention into his wind farm project. The people who know him say his passion for alternative energies is real, and that he will shrug off any setbacks he might encounter. “There’s almost a clairvoyant part of Jay,” said his attorney Losordo. “He’ll see over the horizon. If it’s not in Buzzards Bay, Jay will surface in Puerto Rico or Venezuela or wherever the wind’s blowing. And if wave-generated power proves more effective, he’ll go that way. This is not about putting windmills in Buzzards Bay. It’s about seeing into the future.” It’s also about profit. “If we’re half as successful as we think we can be, it will be a real score,” said David Ferrari, who’s involved in the project. But Ferrari did add one warning: “The only thing I worry about with him is that he spreads himself too thin. I worry that something might slip through the cracks. I’ve mentioned that to him.”

Cashman, for his part, said the project represents a chance to transcend his local roots, to be a part of the international solution to our energy problems. But there’s something else. With the wind farm, Cashman finally has the opportunity to rise out of the dirt, to create something more than a hole in the ground. “I’ve mastered making $10 million on a deal,” he said. “I just bought a company for $25 million and I know I made at least $15 million. Now I’ve got my eyes on something bigger. I’ve got something that I’ve always wanted—the higher order.”

Reaching the ocean side of Nauset Spit, Cashman spotted Christy and her family on the beach. He stripped down to a pair of bright orange swim trunks and dove into the water. “Jay!” Christy called to him from the shore. “There’s a seal right there!” Off to Cashman’s right, the animal poked its head from the rolling waves, regarding Cashman for a few seconds before darting away.

Toweling off, Cashman talked with Christy’s brother Hans about the next day’s planned fishing trip. A tropical storm was heading for the Cape, Cashman told him, so it looked as if they might have to cancel the outing. “Those are no big deal,” joked Hans, an American Airlines pilot. “I’ve flown around them.” Cashman laughed, but the truth is he doesn’t like unnecessary risk. He hates sharks, aviation, and a lot of other things he can’t control. “Back when I was dating,” he told me, “I used to tell girls, ‘Let’s fly over for lunch on Nantucket.’ It was part of the bag of tricks, but I never liked flying.”

We headed back to the boat, and Mark brought us across the bay to the island. Once ashore, Cashman entered a boathouse and grabbed a couple of Coors Lights from a refrigerator. We cracked them open as we waited for Mark to bring around the golf cart. Cashman drove us up a path, eventually coming to a grassy clearing, in the middle of which sat his tastefully distressed summer home. Several landscapers and handymen worked the property. We stopped for a moment as Cashman chatted with his chef, passing by in another golf cart, about lunch for the fishing trip the next day. “You want me to make sandwiches?” the chef asked. “I don’t know if we’re going to go,” Cashman replied. “But make something anyway. And use those special cold cuts I bought at the deli.”

Inside the house, Cashman changed back into his clothes. He grabbed a couple of fresh Coors Lights and a cigar from a desk in the living room, then turned toward me. “You want to see something?” He led me downstairs into the basement. It was dark but I was able to make out a large metal box sitting atop a table. “I’m raising chickens!” Cashman said. There were 30 of them, just chicks, peeping in the box. Once big enough, they’ll be transferred to a proper coop Cashman is having built out by the old barn. “You know how they come?” he said. “They ship them live right to the post office. I couldn’t believe it.” Cashman said the chickens were mostly Christy’s idea, but he seemed pretty excited. He likes having things. He’s already accumulated about 40 19th-century paintings, and then there’s his latest passion, coins. He’d been buying them off eBay until receiving a letter from an expert appraiser, who informed him that he’d overpaid by double for nearly every piece in his collection, and advised him against buying rare coins from people who also have Barbie dolls for sale. Cashman laughed while reading me the letter. “I’ve spent like $300,000 on eBay, okay?” He said that he should probably stop drinking red wine when he makes his purchasing decisions.

Back in the golf cart, Cashman lit his cigar and we set off on a tour of the enormous island. A set of trails rings the perimeter, offering views of Pleasant Bay and the Atlantic. We ended up at a small shack outfitted with a couch, an easy chair, and an office workstation. Cashman settled into the chair and reached down to another small fridge stocked with Coors Lights. “I’m a little buzzed,” he said. He opened a new beer and relit his cigar.

I asked him about his plans for the wind farm. “My father always had a disdain for the construction business,” he said. “It hasn’t been until the last 10 years I’ve said, ‘You know something? The construction business is a good life. You build things that last.’ It wasn’t until I was 40 years old that I learned that. I finally decided that I was okay. I was okay with being a contractor. It’s okay.” The small room was growing hazy with cigar smoke and there was a drowsy calm to Cashman, not quite melancholy but a touch of sadness. “Maybe the windmills represent what my father always wanted.”

His father had also wanted Strong Island, but couldn’t afford it. “This was kind of his dream, so to speak, to have a place like this,” Cashman said. “One of his dreams was he was going to become a big national contractor. I went out and did that. Sons of carpenters become carpenters. Sons of doctors become doctors. Why does a guy who gets born pursue a certain path? Why did I come here? I’m so happy to be here. I’m so proud to be here. I’m living the life my father always thought was valuable.”

We walked out to the golf cart and Cashman drove me back to the water. It was a quarter past 8 and, with all his assistants gone, we were alone on the beach. The sun had set and the sky was streaked with purples and oranges that reflected off the now still bay. A small plane buzzed overhead. Cashman stretched out his arms, silently encompassing all of it. Then he grabbed a rope and, hand over hand, hauled in the boat.