Whatever the reason, friends and critics universally note that Bill Weld has to have a massive challenge in front of him or he quickly loses interest. “You know how some CEOs are maintenance guys and some are turnaround guys?” asks Robinson, who has worked with Weld on and off for two decades. “Bill’s a turnaround guy.”
After Weld’s failed ambassadorial bid in 1997, he retreated to the comforts of corporate law, second love, and writing. He sturdily kept up his “what, me worry?” attitude. When his first novel was released in 1998, a Washington Post reporter delicately asked him about his precipitous drop from presidential contender to middling novelist. “Downward mobility is the secret of the American system,” Weld exclaimed. “That’s what makes room for upward mobility!”
Weld’s downward mobility took him to New York in 1998 to head the local office of McDermott. Within a year, he had fallen in love with Marshall, left the law firm, and partnered with Jeffrey Leeds in Leeds Weld (Leeds and Weld became fast friends, taking fishing trips to Iceland, among other vacations, together). It was yet another job switch for Weld, and an odd one at that, particularly as his investment-banker father had given him little occupational advice other than avoid investment banking at all costs. “He thought it could be soul-crushing and intellectually limiting,” admits Weld. “But I like it. It’s like the Wild West. After all those years in public service, I needed to put a little more water in the well.” In the aftermath of the Decker fiasco, he probably wishes he had followed his father’s advice.
Last week, I stopped into the Weld for Governor offices in midtown. A jovial Weld took a break from drafting a Medicaid speech and belly-laughed at my question of whether the Decker College affair might drive him from the race. “The more I think about Decker, the more I think I’m picking leaves off an artichoke, and there’s nothing there,” he said. “George Bush was made fun of for the Texas Rangers deal, and they had him drooling and saying he was a fool in business. And next thing you know, he’s president of the United States.”
This Wednesday is a big day for the Weld campaign. It’s the first official filing date for fund-raising, and although Weld wouldn’t give away how much his campaign has in its coffers, a Weld source puts the current take at between $2 million and $3 million (it’s likely that Weld will eventually add at least $1 million of his own money). As rough as his early campaign has been, Weld has some reason for optimism. Privately, supporters are confident that Weld can win the Republican nomination. Golisano’s entry into the race is manageable, they believe; his wealth, they say, will be offset by his years of anti-Republican rants, a dislike of retail politicking, and, as Weld puts it, “a tendency to get lost when he goes off his cue cards.”
A general-election victory is harder to see. Weld will need to draw the equivalent of an inside straight to beat Spitzer, who already has more than $18 million in the bank (a figure that’s likely to go up to $20 million or more on Wednesday), not to mention sky-high approval ratings and—oh, yeah—that 40-point lead.
But the way Bill Weld sees it, there’s reason to believe. If he manages to win the Republican primary, he told me, his moderate brand of Republicanism could reduce Spitzer’s margins in traditionally Democratic strongholds from the Upper West Side to Westchester. The A.G.’s prosecutorial zeal, he said, might be stanched by Weld’s Boston years as U.S. Attorney, and in a year when Albany teeters again toward economic collapse, his Massachusetts budget-balancing and government reforms could have traction. Weld is also counting on Spitzer to lose his temper, à la John Silber. “The question is, ‘Is this guy tightly wound?’ ” said Weld. “Might he be prone to a misstep in the heat of a high-profile, fast-moving race?”
With his reading glasses slipping down his nose, Weld went on to deliver a dizzying soliloquy on Medicaid, pension reform, and job creation for upstate counties, the three policy cornerstones of his campaign.
When I wondered aloud how he could break the Albany logjam that had stymied his good friend Pataki, Weld said, “I’m not scared of anybody. I don’t care what anybody thinks about me. I don’t want to win a high-school popularity contest.” Later he added, “I don’t owe anybody anything.”
And then William Floyd Weld gave off the easy laugh of the well-heeled, and flashed his goofball smile.