The House That Ate Weston

What does a blue-collar North End kid turned hedge fund legend do with his prodigious fortune? If you’re Jim Pallotta, you build a 27,000-square-foot mansion to top them all, a Shangri-la capable of turning heads even in the state’s richest town. And you do it with such unerring efficiency, no one even notices—almost.

Sometime later this year, Jim Pallotta will be ready to celebrate his new home. He’ll invite a few good friends over for a tastefully extravagant housewarming party, and that night his first guests will pull off Weston’s idyllic Ash Street, stop in front of a pair of massive wooden gates, and push the button on a state-of-the-art call box. After a moment, the gates will swing open to a long, winding drive bordered by stone walls made to look as though they’ve been there forever and rows of young maples so big two hands could barely encircle their trunks.

As the house comes into view, Pallotta’s guests won’t help but notice its vertiginous size. A project four years in the making, it is a mansion to beat all other mansions in Massachusetts’ wealthiest enclave, a 27,000-square-foot, 22-room behemoth clad in fieldstone and slate, with a façade roughly the size of Fenway’s Green Monster. Add to that a basketball court, pool, and carriage house/garage with room for 10 cars on grounds 4 acres bigger than the Boston Public Garden, and it might be a lot for even longtime Pallotta pals like Denis Leary, Patrick Lyons, and Cam Neely to digest. The whole thing will have cost Pallotta about $22 million of his estimated $1 billion fortune. Not that he’ll want to talk about that.

Perhaps Pallotta’s guests, as they step from their cars onto a cut-granite parking court, will find the enigmatic man of the house leaning against a front door flanked by pillars, the pillars flanked by flowering dogwoods. Tall and fit, with black hair streaked gray at his temples, Pallotta will look a little like Mr. Fantastic, the comic-book superhero. Mr. Fantastic will be smiling.

That’s how I imagine it will happen, anyway. I can’t say for sure what Jim Pallotta is planning for a celebration, because Jim Pallotta isn’t speaking about his house (except to say, incredibly politely, that it’s his private business). If his new estate is the grandest gesture yet for a guy known to lavish money on charities and lucky friends, it would also seem, hard as this may be to believe, that he’s not building it to show off. When you earn an estimated $200 million a year, it’s difficult to remain inconspicuous, but the notoriously press-shy Pallotta has never wanted the attention. While workers hustle to complete his new compound, the driveway remains blocked by a chainlink fence secured by a heavy, fist-size padlock.

For many, moving from a Somerville apartment to, say, an East Cambridge condo is an accomplishment. Others work for years to get to Brattle Street, only to start dreaming of a place off Brattle, where everyone knows the real money is. Pallotta and his wife, Kim, have lived in Wellesley for 16 years, currently in a $2.4 million, 8,800-square-foot, five-bedroom colonial that is the second most expensive home on their street, and the only one that boasts a basketball court. If you’re going to trade up from such a place, chances are you’re looking at Weston. The town’s 3,700 families have the state’s highest per capita income and include several members of Pallotta’s circle: His Celtics co-owners, Wyc Grousbeck and Steve Pagliuca, live there, in homes worth $3.9 million and $5 million, respectively. Fellow hedge fund magnate Jeff Vinik has a $12.8 million spread nearby.

At a charity event in 2003, Jim and Kim Pallotta chatted with Diana Chaplin, a Coldwell Banker real estate agent with an interesting lead. Chaplin specializes in something called “whisper marketing,” in which agents get early scoops on yet-to-be-listed properties and put out discreet feelers to high-net-worth buyers—the kind who don’t spend time cruising open houses. These agents often close deals without ever putting homes on MLS,, or other listing services. According to Chaplin, about a fourth of the properties in Weston sell off-market; in the past four years, she herself has sold nearly 100 acres this way.

Chaplin knew Weston’s Regis College was unloading land it owned between Wellesley and Ash streets. The financially strapped school, located on the former estate of late-1800s Boston “copper king” Daniel Demmon, was hemorrhaging money and ready to strike a bargain. Chaplin approached Regis on behalf of a real estate trust managed by Jeffrey Allen, a Wellesley attorney. Allen, in turn, was working for the Pallottas. (Real estate buyers use trusts for a variety of reasons, sometimes because they’re too busy to do their own negotiating, other times to maintain their privacy.) The terms were simple: Regis would sell its 28 acres for $9.3 million, and the trust would informally agree to build only a single-family house on a lot big enough to accommodate an entire subdivision. The deal sailed through that June.

Pallotta snatched up an adjacent property last September in similarly under-the-radar fashion. When Panopticon Gallery owner Tony Decaneas wanted to sell his 4,218-square-foot, five-bedroom home, he went straight to his new neighbors. They quickly settled on a $1.2 million price. The purchase, however spontaneous, certainly fit within Pallotta’s budget. An old rule of thumb says you shouldn’t spend more than three times your annual income on a house. Pallotta’s mansion will eat up just 10 percent of his; barring a market crash, he should be able to pay off his entire property in less than six weeks.

Pallotta—Jimmy to his friends—was born in 1958. His parents, James and Angelina, raised him and his two sisters, Carla and Christine, in a cramped North End apartment. Both parents worked hard, with James juggling three jobs, and instilled a tough work ethic in their kids. The girls would go on to open the restaurant Nebo just streets away from the family’s old home.

As a boy, Pallotta would cross under the elevated T tracks and sneak into the Boston Garden. There, he’d stand behind the cheap seats and watch Celtics stars John Havlicek and Bill Russell hustle across the parquet. After high school, Pallotta went to UMass Amherst, where he joined Beta Kappa Phi with guys who were also destined for big things: Jim Palermo is now vice chairman of Mellon Financial; Dave Andonian, still one of Pallotta’s closest friends, is a former president of CMGI. On Sundays, the frat brothers would gather for their weekly meeting, during which Pallotta would hunker down over the newspaper. “I always knew Jimmy was going places,” says Bruce Leaver, a Beta Phi who now owns the Best Western in Quincy. “He’d read two or three newspapers, and by the time the meeting was over he would have finished the New York Times crossword puzzle.”

Pallotta was also known for his fierce competitive streak. A hard-core intramural basketball player, he used quick hands and sharp court vision to lead his senior-year squad to victory at the UMass championship and the New England regionals. (When Pallotta bought his stake in the Celtics in 2002—for which he reportedly paid $15 million—he officially completed his transition from the nosebleeds to courtside seating. These days, he leads a weekly pickup game at a Harvard gym that includes former pros like Malcolm Huckaby and Bill Curley; Wyc Grousbeck asked to join in, but didn’t make the cut.)

After getting an M.B.A. at Northeastern in 1981, Pallotta signed on as a junior analyst at Essex Investment Management, where he developed a reputation for coolness under pressure and an almost preternatural grasp of financial markets. “It was obvious from the beginning that he had a gift,” says former Essex portfolio manager Stephen Demirjian, who worked alongside Pallotta for a decade. “If you looked around the office and could point to one guy you would bet with, Jim would have been that guy.” Word of the young ace stock-picker got around, reaching Paul Tudor Jones II in the early ’90s. Back then, Jones—whose own personal fortune is an estimated $2.5 billion—was looking for a manager for Tudor Investments, his $15.4 billion New York–based firm. The two men agreed to meet for a half-hour breakfast and, two and a half hours later, Jones knew he had his man. Pallotta opened Tudor’s Boston office in 1993, and has averaged 20 percent gains every year since, well above average annual hedge fund returns, which hover around 11.4 percent.

From his offices on Rowes Wharf, Pallotta now directs Tudor’s $11 billion Raptor Fund, which accounts for two-thirds of the money invested in the company. According to the hedge fund magazine Alpha, Pallotta himself makes more than all but 13 of the estimated 3,500 other managers nationwide. “Jim is clearly one of the top hedge fund managers, not just in Boston, but in the country,” Demirjian says. “There’s probably no one else in the city who has accumulated such a great amount of wealth in such a short amount of time. But more importantly, I guarantee you wouldn’t find anyone who has given away close to as much as he has.”

Indeed, Lenny Clarke calls Pallotta the most generous guy he’s ever met in his life. “But he doesn’t do anything to be noticed,” he adds. “Me, I donate 50 bucks and I want everyone to know about it. He’ll donate a million dollars if you promise not to tell anyone.” Pallotta and his wife, Kim, give tens of millions to local charities, while their own charitable trust is endowed with $11 million. Between them, they also serve on the boards of eight nonprofits, including the Institute of Contemporary Art (home to the Kim and Jim Pallotta Gallery) and, until recently, the Fessenden School in Newton (its James R. Pallotta Athletic Center is named for his father).

Pallotta has also quietly invested in a number of area restaurants. “Without his support, Radius and Via Matta wouldn’t exist today,” says their chef-owner, Michael Schlow. (Though it’s no longer on the menu, he still cooks Pallotta his favorite veal chop when Pallotta stops in.) Pallotta has also put money into Todd English’s Figs, Richie Balsbaugh’s Saint, and Ming Tsai’s Blue Ginger, and he frequently brings high-powered guests into his friends’ restaurants—hosting U2 at Radius and Samuel L. Jackson at the Pearl on Nantucket. But the billionaire also knows how to lay back and let loose. “He’s a chameleon,” adds Schlow. “He can fit in at a fancy dinner, then have a beer and eat chicken wings at the bar.”

At this January’s “Back to the Prom”–themed Big Brothers’ Big Night fundraiser—an event that has raked in nearly $14 million since he started it in 1999—Pallotta showed up in a tight black prom dress, long black gloves, and a corsage. (“He was a great-looking girl,” says Demirjian.) Not one to shy away from making a spectacle of himself for charity, Pallotta also bids big. At last year’s Spinazzola Gala (he’s on that board, too), he and his Tudor colleagues spent $100,000 to have nine celebrity chefs cook dinner for 30 at his Nantucket house. At a 2005 Mass General Hospital for Children benefit, he paid a record-breaking $200,000 for 424 Fenway seats. Even as an auction item himself, Pallotta has a way of generating interest. Once, when Clarke was collecting bids for a dinner with his buddy, he tried to sweeten the deal by noting, “This is a great way to get to know Jimmy.” All the arms in the room shot up. Clarke was incredulous. “People who couldn’t even afford it were raising their hands!”

In 2004, Pallotta flew a group of his friends to St. Louis to watch the World Series. Leary couldn’t make it, but Clarke, Neely, and Lyons were there, together with a handful of Pallotta’s old college buddies. He put everyone up at a golf resort outside the city—“We stayed in a castle, un-fucking-believable,” says Clarke—and hired a luxury bus to shuttle them around. On the way back from the stadium at 4 a.m. one morning, Pallotta told the driver to pull over at a White Castle. He and his friend ordered a whopping 200 hamburgers, 10 fries, 10 onion rings, and one water. “They were bringing the burgers out in suitcases,” says Clarke. “We ate maybe 10 of them, and then he had the bus pull over and gave the rest to some homeless people.”

To his famous friends, the one thing about Pallotta that’s not noteworthy is the fact that he’s building a personal Hermitage. (Michael Schlow calls it “inconsequential.”) Cornell University economist Robert Frank, who’s studied the purchasing decisions of the ultra¬rich for books like Luxury Fever, would tend to agree. “Everybody wants a nice home, but the scale you need to meet that threshold goes up as you climb the economic ladder. A twin-engine Cessna is a pretty nice plane, but when everybody else has a Gulfstream jet, it seems rinky-dink,” Frank says. (And in fact, Pallotta’s spread is dwarfed by that of his boss, Jones, whose palatial Greenwich, Connecticut, mansion is rumored to be worth up to $60 million.) For his part, Pallotta has ignored the buzz and the gibes from the likes of the Herald—which mocked him for insisting on calling his new place a mere “house”—and moved through his construction checklist with his trademark efficiency.

Once his land was secured, Pallotta handpicked his design team, hiring Greenwich-based architecture firm Shope Reno Wharton, best known locally for designing Reebok founder Paul Fireman’s $18.8 million Chestnut Hill home. Pallotta also chose Kenneth Vona Construction, a Waltham-based luxury homebuilder that relies almost exclusively on word-of-mouth recommendations. (When Extreme Makeover: Home Edition came to the Hub a few years ago, ABC producers enlisted 30 of Vona’s carpenters to work on the project throughout the night.) Other players include landscape architect Keith LeBlanc, who runs a national practice from Boston, and world-renowned Utah lighting designer Glenn Johnson, who, in addition to his work for Steven Spielberg and David Geffen, has lit houses for both Ernie Boch Jr. and New Balance owner Jim Davis. Pallotta’s interior designer, South Hamilton’s SLC Interiors, is an eight-person firm that regularly scours the world for Middle Eastern limestone, British handmade wallpaper, and rare antiques.

Perhaps most important to Pallotta, though, is that his team is experienced enough to smoothly shepherd his project through Weston’s thorny planning boards. Since 1996, the town has reserved the right of approval on all new houses that take up more than 10 percent of their lot space (i.e., McMansions), as well as all those over 6,000 square feet (i.e., just plain mansions). Town planner Susan Haber insists the process—rare, but not unique—isn’t any more challenging than those in Brookline or Lincoln. Some tradesmen disagree. “They have scenic-road restrictions, there are zoning boards, a house has to be below a certain height…. There’s a lot more control in Weston than in other towns,” says one contractor who has done work there.

That’s something Dr. John Meola learned the hard way. The Celtics’ team dentist bought his place, just down the road from Pallotta’s, in August 1996 for $700,000. Though the 2.8-acre lot came with a 1743 house on it, Meola set out to demolish the structure to make room for a modern home. Or he did, until he got a strongly worded warning letter from the historical society. “That’s when I started my 10-year odyssey with Weston,” he says. “I was dropped into this historic commission Twilight Zone.” Meola ultimately agreed to renovate, rather than knock down, the old house. After nearly a decade and three cease-and-desist orders from the town, he is in the unique position of owning both the second oldest house in Weston and an adjacent home that is by some measures Weston’s largest, at least for now (the whole package is on the market for $10.99 million). “Until Jim came along, I was the most talked-about guy in town,” he says. “It’s nice to have somebody take the heat off me.”

Compared with Meola’s, Pallotta’s plans breezed through the approval process, perhaps because he agreed to all the town’s recommendations. Pallotta—who Lenny Clarke says once gave a New York cabbie $100 for speeding them 90 blocks up Madison Avenue without hitting a light—kept things moving by quickly giving up several items on his original wish list. He removed 20 of the estate’s exterior light fixtures (leaving 113 behind); downgraded the size of his lawn from 10½ acres; drilled new wells rather than draw water from Weston’s reservoirs; and planted an additional 50 trees to screen the house from Wellesley Street.

On April 27, 2005, the planning board voted unanimously to approve Pallotta’s plans. There’s a sense of wonder in Haber’s final report: The new house would be seven times larger than the average neighbor’s, yet cover only 3 percent of the lot. Weston building permits used to be among the cheapest in the state—Meola paid $1,000 for his—but now the town charges $10 for every $1,000 of the building’s estimated value. Before construction started in fall 2005, Pallotta handed over $10,000 for the carriage house permit and an additional $100,000 for the main residence.

Many Westonians seem to be looking forward to having Pallotta as a neighbor, no doubt partly because it means there will be just one house on the land, rather than an unsightly development. But that doesn’t mean they’re not curious about what he’s up to. “What are they building there?” a perplexed resident asked a town board member when the skeleton of the main house was still visible through the trees. “It looks like a Wal-Mart.”

Sometimes curiosity makes you do things you’re not particularly proud of. Which is how I came to be camped out in an empty auditorium at Weston Town Hall, poring over Pallotta’s 27-page architectural plan. (In my defense, the plans are public record, and I got the feeling the building department is used to handing them over.) I hesitated at first, but once I got a look at just what fits into a house as gigantic as this one, I couldn’t tear myself away.

According to the most recent set of plans on file, the ground floor of Pallotta’s two-story main home will hold a vast kitchen with two islands, an eight-burner stove, and multiple ovens. Off to one side will be an office, a command center of sorts for entertaining. Upstairs, the couple’s two sons will each get a roughly 500-square-foot suite with a walk-in closet and private bathroom…in their own wing, which will include two guest bedrooms and a two-washer/two-dryer laundry room. In the opposite wing, the Pallottas’ 2,000-square-foot master suite reigns. It has nine distinct spaces—including a pair of 375-square-foot closets and an exercise room—and is only about a Pallotta-sized closet smaller than the average American house.

The basement is almost completely dedicated to entertainment. The “lower gallery,” a 50-foot-long curving hallway, leads past a home theater; farther down the hallway will be a bar (an extra-nice perk, considering Weston is a dry town) and a game room, not to mention a 27-by-19-foot music room where Pallotta can gather with his friends Peter Wolf and Berklee School of Music president Roger Brown, whose school recently appointed Pallotta to its board. (“I don’t think he plays an instrument, at least not in public,” notes Pallotta buddy Cam Neely. “He certainly can’t sing; I’ve heard him try.”) At the very end of the hallway lies a wine cellar large enough for thousands of bottles, and a long, narrow room labeled simply “Santa Storage.”

After I left Weston Town Hall, I took a wrong turn and ended up at a stoplight. That’s when a local cop spotted my expired emissions sticker and slapped me with a $50 fine. I felt like a drifter who didn’t belong, about to get an escort to the town line. Looking back, though, I think it might have been karma. I bet Jim Pallotta never lets his emissions sticker expire.

On my way home I drove past Pallotta’s property one more time. The fences were still up and, with all the new trees, it was impossible to see the house, even though it was the dead of winter. Construction vehicles circled, and much of the estimated 7,000 cubic yards of fill for Pallotta’s gardens was still waiting in a massive pile. Someday soon, though, the last slate tile will be affixed to the roof, the last doorknob polished, the last speck of dust swept from the driveway—construction will have taken less than two years, which is almost unheard of with a project this large. Pallotta’s old furniture will be moved in from Wellesley, along with the new pieces he’ll probably need to buy to fill his additional 18,200 square feet of floor space.

On his first morning in his new house, he might wake up and slip downstairs to check his Bloomberg box, before showering and selecting a suit from his cavernous closet. Maybe he’ll sip his coffee and watch the sun rise from his first-floor breakfast room, then check the markets again. Then he’ll walk the 70 yards or so through his house to one of his attached garages, and get into his car. He’ll circle around the house, and pass under the rows of 22 maple trees. And then he’ll turn onto Ash Street, joining the steady stream of commuting cars, as the gates to his dream home swing quietly closed behind him.