His Pink tie liberated from the stiff collar of his tattersall shirt, the man who wants to be your next governor is now behind the bar, taking orders. As the hour wanders toward midnight, Weld leads the crowd in a rousing rendition of “Happy Birthday” to the Erie County’s sheriff’s fiancée; kisses his late-arriving novelist-wife, Leslie Marshall, on the lips; and jokes he might be for Tom Golisano if he lived in Buffalo, since the billionaire bought the Sabres and promised to keep them in town. After a couple of hours of happy mayhem that feature a guest breaking out a Cuban cigar that Weld politely refuses, the would-be governor asks for a moment.
“Thanks for having me here,” says Weld. “To quote Dennis Quaid, right before he was about to have sex with Ellen Barkin in The Big Easy, ‘I like the way you people do things around here.’ We will be back many times.”
More laughter, more booze, and more merriment ensue. At that moment, if William Weld were to suggest a moonlight nude ice-fishing expedition, there would be no naysayers.
On the way back to his hotel, Weld chuckles in the backseat, squeezes Marshall’s hand, and giddily talks about the evening like a Bluebird recapping her first sleepover. “That was a lot of fun.” He dreamily stares into the stars. “Golly, those snow globes sure were big.”
At Harvard, Bill Weld majored in classics. Right now, Sisyphus has a better chance against the rock than Weld has of becoming New York’s next governor. Where to start? Well, how about the fact that he’s a Republican running in a state where, recent GOP victories notwithstanding, Democrats hold a five-to-three advantage in registration. Until 2000, Weld had spent the previous 30 years living in Massachusetts and has no political organization in New York. In a primary, he might have to fight off the deep pockets of Golisano, who could drop $50 million exploiting Weld’s involvement with Decker College, where, as CEO of the Kentucky-based for-profit school that came under scrutiny from federal Education officials and went bankrupt in 2005, Weld was exposed to charges of sham business dealings and poor management. Al D’Amato hates him (a Weld protégé prosecuted D’Amato’s brother in the eighties), and the influential New York State Conservative Party claims there’s no way the pro-gay-rights, pro-choice Weld will be its standard-bearer. If he maneuvers that minefield, likely Democratic nominee Eliot Spitzer awaits. You may have heard of him. He’s the wildly popular state attorney general who cleaned up Wall Street in the name of the little guy. Spitzer, with $18 million already in the bank, has been thinking about being New York governor since the age of reason, which gives him a monster head start on Weld. Currently, Weld trails Spitzer by 40 points. If this were a game show, the keyboardist would be cuing the “thanks for playing” music.
But wait, that’s not all! Bill Weld comes to New York with a serious case of occupational ADD. A year into his second term as Massachusetts governor, Weld launched an unsuccessful bid for John Kerry’s U.S. Senate seat, then, after losing, resigned from the statehouse to pursue a failed bid to be the U.S. ambassador to Mexico. There is also a quirky “look at me, I’m wacky” quality to Weld’s political career that leaves some with the feeling that he’s not serious about anything. Probably the indelible image of Weld’s years as governor was his impromptu 1996 dive into the Charles River, a PR stunt designed to prove how the ecofriendly he was. (“The river wasn’t as clean as I thought,” Weld recently told me. “I had an earache for three weeks.”) Weld is given to occasional glib, devil-may-care comments that don’t exactly put the gravitas question to rest. When Paul Cellucci replaced him as governor, Weld handed over the ceremonial keys to the statehouse and quipped, “I am reliably informed it works on weekends.” At times, Weld’s march-to-the-beat-of-his-own-drum-machine spirit seems to indicate borderline-suicidal career tendencies. Weld’s doomed bid to become an ambassador might have been saved with a standard suck-up visit to then–Senate Foreign Relations chairman Jesse Helms’s office (Helms had made it plain that he wasn’t a fan), but Weld wouldn’t do it. “People said I should go down and kiss Jesse Helms’s ring,” Weld said in a speech recently. “I just didn’t feel like it.” The non-visit was so inexplicable that Tucker Carlson theorized in The Weekly Standard that it must have been the first step toward a Weld party-switch, because otherwise, it defied logic. All of which makes more than a few people wonder just how serious Bill Weld really is about being governor. To them, Weld’s trying to become the chief executive of a second state is the political equivalent of Evel Knievel’s trying to clear the Snake River Canyon; a neat trick concocted mainly to see if he can pull it off.