Nevertheless, Weld says, he’s itching to fight. “If this pans out the way I hope it will,” he told me, the campaign will be a “pay-to-get-in, knock-down-drag-out” battle. “Campaigns are completely exhilarating to me.”
“I think my dad might love the campaigns more than governing,” says David Weld, his eldest son, before catching himself. “Well, he loves campaigning as much as governing.”
Weld’s experience as governor of Massachusetts provides a sneak preview of what New Yorkers might expect from him here. In 1990, after toying with the idea of running against John Kerry, Weld decided to seek the governorship that Mike Dukakis was vacating. Nearly 25 points behind a month before the GOP primary, Weld was visited by Ray Shamie, the Massachusetts GOP state-party chair, who told Weld he was finished in elective politics if he didn’t clear the field for State Representative Steven Pierce. “He was contemplating getting out,” recalls Paul Cellucci, Weld’s lieutenant governor and eventual successor. “But when this guy came in threatening him, Bill said, ‘Screw it. We’re going to do it.’ ”
Helped by a million-dollar personal loan from himself, Weld won the primary and squared off in the general election against John Silber, a one-armed former Texan with more than a passing resemblance to Dr. Strangelove in both looks and demeanor. Weld campaigned, as Spitzer undoubtedly will in New York, as a tough-on-crime-and-corruption prosecutor hell-bent on fumigating state government. As the campaign moved into the final weeks, Weld trailed in most polls by almost ten points. Then, both candidates sat for long in-home interviews with Natalie Jacobsen, Boston’s preeminent newscaster. Weld was captured, shirttail out, making eggs for his brood. When Jacobsen asked him his greatest fault, Weld looked up from the pan, popped a smile, and told the viewers what a slacker he was.
“When I heard that first, I thought, What the hell is he thinking?” recalls Cellucci. “Telling the voter he is lazy didn’t seem that bright. But it worked.”
It worked because it was purely self-deprecating and plainly false. It also worked because when Jacobsen asked Silber the same question, the Boston University president had a What the hell kind of question is that? moment. Weld quickly instructed consultant Dick Morris and adman Stuart Stevens to make an anti-Silber ad using the footage. It played relentlessly until Election Day, and Weld won, 51 percent to 49 percent.
After the dour Dukakis years, Weld delighted Massachusetts with his freewheeling, libertine ways. The image of the Charles River dive was splashed across newspapers. Weld attended Grateful Dead shows and bragged that he raised a “wee small one” of booze before speaking at an annual Saint Patrick’s Day breakfast. His annual Christmas parties became legendary for the sheer volume of liquor, not to mention Weld’s predilection for doing duck calls after a few glasses of what he liked to call “the amber liquid.” At his second inauguration, Weld’s speech was more than a little slurred. The Boston Globe reported that at a Rolling Stones concert staged the year after Weld resigned, he had been intoxicated to a point that he had trouble standing up (Weld told the Globe he had only one glass of wine). When I asked him about his drinking, Weld dodged a bit, then said, “I used to see Governor Carey drinking at P.J. Clarke’s a lot, and he seemed to get things done.”
Weld flaunted his banker’s hours, intuitively knowing the guys in Dorchester could identify with a governor who admitted he cut corners and skated through days. During a blizzard, Weld’s director of emergency services told him at a meeting that he would call him at 5 a.m. with an update. Weld just smiled, nodded toward Cellucci and said, “No, I’ll be sleeping. You’ll call Paul.”
By 1994, the Massachusetts economy had rebounded from the recession of the final Dukakis years, with unemployment dropping by half. Weld, with his tax cuts and budget balancing, was able to take much of the credit. Spoiling for a high-profile campaign that might set him up for a 1996 presidential bid, Weld tried to bait either Congressman Joe Kennedy, RFK’s son, or former Boston mayor Ray Flynn into running against him. Both declined, and Weld was reelected with 71 percent of the vote.
Soon after his reelection, however, Weld grew restless and began planning his next move. He again considered a presidential bid but decided to challenge John Kerry for the U.S. Senate first. Unseating a Democratic senator in Massachusetts would cement Weld’s reputation as a comer and position him well for a 2000 presidential effort, Weld thought. In retrospect, the Senate race proved nearly as impossible as a national campaign—Weld lost by eight points. On Election Night, Weld gave a magnanimous concession speech, joking, almost prophetically, that he had propelled “Senator Kerry to the presidency.” Weld put up a happy front, even going out with Kerry for a beer. But the loss haunted him. Two months later, it was still such a sore spot that he broke into tears talking to a friend about it.