Longtime friends wondered aloud whether Weld was surfing through a full-blown midlife crisis. “I think some people saw Leslie as a lightweight after Susan,” says Charlie Steele, a lifetime Weld pal who is godfather to Quentin. “But she’s brilliant and is interested in the same literary scene that Bill loves about New York. She completely reenergized him.”
Amid the chaos of dogs, Scrabble boards, roaring fireplaces, and the detritus of a Thanksgiving that featured 23 guests, the Bellport house exudes a mellow Gatsby-as-grandfather vibe. After settling in front of the fire, Marshall, a former InStyle writer who published her first novel, A Girl Could Stand Up, in 2003 and dedicated it to “ ‘Billy,’ my own wild boy,” went back to amplifying her husband’s sensitive side. According to Marshall, Weld took her to Elio’s on one of their first dates and began talking about a college friend who had died of cancer. “He started telling me about him, and the tears just started rolling down his face,” recalls Marshall. “We ate in silence, and it wasn’t until we were getting into the cab he was able to tell me the rest of the story.”
A few minutes later, Weld reemerged, his hair wet, calling to mind his days as Massachusetts governor, when his press conferences straight from the squash-court showers alternately charmed and alarmed the Boston press corps. “I just was talking to Baby Marshall,” Weld said, using the nickname of Marshall’s 13-year-old son, Marshall Bradlee. “I told him we would have lots of snow for Christmas. He was so excited.”
All you need to know about the financial circumstances of William Weld’s childhood is that his two boyhood homes make the Bellport place look like a cottage. Weld was once asked how his family made its money. He responded, “The Welds don’t make money; they have money.” His father, David Weld, was a successful investment banker from a long line of successful investment bankers, and his marriage to Mary Nichols united two of Long Island’s richest families. David Weld brought to the union a twenty-room mansion in Smithtown on a 600-acre spread with horses, chickens, and a 180-acre pond, the largest private body of water on Long Island, while Mary Nichols provided a Georgian mansion in Mastic, a home that once hosted Thomas Jefferson. “There was a fabulous seventeenth-century kitchen in Mastic where the whole family would have these great meals,” remembers Weld. “My maternal grandfather had been the curator of the fishes at the Museum of Natural History, and there was all matter of stuffed birds and animals on the wall.”
Talk with Bill Weld about politics and you can hear the arch, ironic tone of a clubby Ivy Leaguer, but mention his childhood and the lockjaw loosens. Weld was born in 1945, the last of four and a full four years younger than his closest sibling. As a young child, with his brothers and sisters away at boarding school, Weld was left alone to amuse himself. “From age 9 or so, I’d slip away in my Grumman Barnegat Bay scooter,” says Weld. “I’d go fishing all day, not even coming back for lunch. I was alone but never felt lonely. I could just spend hours fishing and thinking. Bellport has the same kind of feel as there.” (The Bellport mansion, which he bought in 2001, is just fifteen minutes away from his boyhood homes.)
Like his brothers before him, Weld headed off to Middlesex School. Although he went on to become class valedictorian, the first year was rough in a way Weld has never publicly talked about before. “I was a little fat kid when I got to Middlesex,” says Weld with a wan grin. “I felt on the receiving end of unwelcome pressure and hazing.” When I asked him if he had been beat up and bullied, Weld just nodded.
At Harvard, Weld majored in classics, so he was often cloistered away with a few classmates, which made his general insularity all the more possible. Somehow, he managed to make it well into the evening of November 22, 1963, without learning about the JFK assassination. “I was his proctor freshman year,” says Charlie Steele, who became Weld’s D.C. lobbyist during his gubernatorial years. “We played billiards a lot, and I didn’t get a sense that the outside world penetrated him much at that time.” The one thing Bill Weld made a point of everyone knowing was that Bill Weld wasn’t a grind. “I’m sure he did [grind],” says his friend Mitchell Adams, who would eventually serve as his revenue commissioner. “He just didn’t want anyone to see it.”
After graduating, Adams and Weld were roommates in Cambridge. In time, Adams told Weld that he was gay. “He could never ever understand why or how anyone could care that I was gay,” remembers Adams, who had Weld give the homily at his June 2004 wedding to Kevin Smith, a former Weld chief of staff. “And he could never understand how it was anyone else’s business but my own.” The championing of disenfranchised groups is something of a Weld family tradition: Weld is a direct descendant of the Theodore Dwight Weld who was the chief lieutenant of abolitionist William Lloyd Garrison. But Weld told me that his gay-rights advocacy grew out of the sympathy he developed for outsiders when he was at Middlesex. “I read a great deal as a teenager; the heroes of my literature were sensitive young souls who felt like they were being pushed around. That’s why I’ve always approved of [philosopher] Louis Hartz’s ‘Essence of Democracy’: ‘The individual shall not be thrust in the corner.’ That always resonated with me and, I think, came to describe my politics; it has always been about maximizing individual freedom.”