Running Weld

William Weld in his Upper East Side apartment, December 29, 2005.Photo: Joseph Maida

Sometimes, it is easy to forget that Buffalo is 100 miles closer to Detroit than it is to Manhattan. Tonight isn’t one of those times. On an early December evening, the Grand Island Holiday Inn conference room is half-filled with Erie and Niagara County Republican Party regulars drinking bad coffee as the featured guest prepares to speak.

“I should have put up the Christmas lights today,” moans one man kicking at the green carpet with loafers lightly coated with road salt. “It’s probably going to be the last day above 20 degrees for four months.”

The faithful have turned out to hear from a long-shot gubernatorial candidate who could have sat next to them yesterday at the Bills-Panthers game without a flicker of recognition. What people out here know of William F. Weld, if anything, is that he was once the governor of a different state, might be in favor of gay marriage, at some point jumped into a river with all his clothes on, and once got into some inside-the-Beltway scrape with Jesse Helms. Those with Netflix subscriptions might recall his cameo in Traffic.

These are not Bill Weld’s people. Few are. Weld, the scion of two old-money Long Island families, grew up on a 600-acre oceanfront estate; was valedictorian at the Middlesex School, in Concord, Massachusetts; then headed to Harvard, Oxford, and Harvard again, for law school. As an undergrad in Cambridge, he was known for snoozing at the Fly Club, shuffling out pithy put-downs in Latin, and dressing in drag for Hasty Pudding shows. A Weld friend told me that he views a spirited squash game as the perfect metaphor for politics.

So here, not far from the Canadian border, the stage is prepped for comedy: Frasier Crane stumbling onto The Honeymooners set. Weld, a six-foot-four redhead, plays perfectly to type. He thrusts his hands, patrician-like, into his Brooks Brothers suit pockets and promptly drops a Waiting for Godot reference when mentioning Rochester billionaire Tom Golisano’s will-he-or-won’t-he run for governor. This is quickly followed by a shout-out to an “obscure French anarchist,” as if there were any other kind, who once said that “taxation is theft.” A few minutes later, he properly uses the word fricassée in regard to the carving up of his Democratic opposition in the Massachusetts Legislature.

And yet. And yet the 26 attendees in the Grand Island Holiday Inn eat it up. Maybe it’s his 60-going-on-6 demeanor or the mention of the nineteen tax cuts he signed as Massachusetts’s governor. Maybe it’s the argument that his years as a U.S. Attorney and then U.S. assistant attorney general will defuse Eliot Spitzer’s Eliot Ness shtick. Maybe it’s his self-deprecation—in 1990, when a Boston newscaster asked Weld to name his greatest flaw, he happily answered “laziness.”

Whatever. In the end, he gets a standing ovation. After shaking hands, Weld piles his lanky frame into the front seat of Erie County Republican chairman Bob Davis’s black SUV and stares into space as we motor toward Davis’s house for a cocktail party. “There’s nothing I like better than sitting in a car or an airplane seat, staring straight ahead for hours,” Weld had told me earlier. According to Weld, it was during one such moment that he came up with his plan to reform the Massachusetts penal code.

Davis, a brush-cut Buffalo adman, fields a blizzard of calls on his BlackBerry. “That’s another guy who was thinking of backing Golisano but now wants to bring two friends tonight,” says Davis. He clicks over and gushes to a Buffalo News reporter on deadline. Weld nods and continues his search for meaning somewhere far away in the electroclash of headlights and stars.

A few minutes later, Davis steers his cargo into the driveway of his split-level home. In the front yard stand three monumentally oversize snow globes—Christmas Snoopy, Frosty, and the Grinch—overkill at Rockefeller Center, strangely appropriate here. Inside, it’s clear the Davises do a fair amount of entertaining: There are two life-size televisions, a full-service bar, and a fully functioning Buffalo Bills Coke machine.

At the Davises’, everyone knows everyone’s favorite drink. Cocktails are mixed, and jabs traded about ne’er-do-well kids. Everyone is exceedingly friendly, but I feel like an intruder in a secret society. The toes curl up in my shoes as a platinumy Mrs. Davis steers me into a corner of the bar so she can show me dozens of pictures of her family’s alpaca farm. Just as I am about to fake thrombosis in order to extricate myself, a giant freckly hand pushes a tall vodka-tonic in my direction.

“It looks like you could use one of these,” says William Floyd Weld.

Weld at a November fund-raiser at the St. Regis.Photo: Courtesy of Steve Chavet

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.

The Times' Decker College story from Sunday, December 18, 2005.

That’s the bad news. But here’s the thing: It was precisely Weld’s never-let-them-see-you-sweat attitude that Massachusetts’s blue bloods and blue collars alike loved about him. “Like most people,” says Marty Linsky, a 30-year friend and political confidant of Weld’s, “Bill’s greatest weaknesses are also his greatness strengths, only more so.” In fact, the TV interview in which Weld breezily labeled “laziness” as his worst flaw played a significant role in Weld’s getting elected as a Republican in the country’s most Democratic state. Weld may have given the impression he was off playing contract bridge, but he wasn’t, at least not all of the time. As governor, he repeatedly cut taxes, reduced state spending, and balanced the budget in his first year—in a state where Republicans were outnumbered in the Legislature two to one—after his predecessor, Mike Dukakis, had left it $1 billion in the red. All the while, the goofball smile never left his face.

Weld’s mellow brand of Republicanism—a Pataki-esque, suburb-friendly mix of small government and live-and-let-live (unless-you’re-a-criminal-and-then-we-have-a-nice-lethal-injection-for-you) social policy—has a comfortable familiarity to New Yorkers. And while Spitzer is no doubt a talented and honorable man who may well go on someday to become president of this great land, no one is going to mistake his do-gooder goodness for charisma. The recent spate of “Spitzer as hothead” stories, fanned by Weld and his team, if not planted by them, suggests there may be traction in the idea that New Yorkers want a friendly face—and the Weld persona is nothing if not friendly—coming into their house on NewsChannel 4, not a humorless screamer perpetually reminding them how corrupt their state government is.

Can Bill Weld win? Those who say they know at this point are either fools or communications directors. This much is certain: New York is about to be vastly entertained and at times befuddled by a Republican blue-blood, patrician job-jumper who slurred his speech at his second gubernatorial inauguration, is a close friend of Bill and Hillary Clinton, has written three novels, and is a fan of Nabokov’s trilingual puns.

Bill Weld’s choice of Michael’s for a get-acquainted lunch seemed more appropriate for a Condé Nast raj than a GOP gubernatorial candidate. At first, our conversation was stilted, and we made small talk about our mutual love of Los Angeles. “Whenever I’m out there, I stay with my friend Terry Malick, off Doheny,” said Weld, alluding to lone-wolf filmmaker Terrence Malick, whom he met while studying at Oxford in the sixties. “I helped him raise money for Badlands. You can see my shoulder in a couple of frames.” Later, I made a joke about who in their right mind would want to spend four years in Albany. Weld didn’t offer any lofty response about his keen desire to help the people of the great state of New York or his intention to clean out the barn in Albany. Instead, he made the first of what would be many literary allusions. “Are you familiar with William Kennedy’s Ironweed?” Weld asked as he speared a scallop. “I can’t wait to walk the streets those characters walked.”

Weld is a Michael’s regular, it turns out, so we had a prime table in the front room. If the state were limited to this one posh precinct, Weld would win by acclamation. We were repeatedly interrupted by well-wishers, the last time by a Cablevision executive who pumped Weld’s arm for nearly 30 seconds. Weld is a favorite of the smart set, and has become known as a swell dinner guest in the five years since he returned to New York. It’s not hard to see why. By turns, our conversation touched on Malick, Weld’s squash game, and a new Edmund Wilson biography. Weld calls Wilson by his nickname, “Bunny.” Not that his New York friends would ever venture north for dinner. “I keep talking about how when I get to Albany we’re going to do a lot of entertaining,” he said with a wry smile. “No one seems excited about that but me.”

When George Pataki announced in July that he would not seek a fourth term, Bill Weld looked like the Republicans’ can’t-miss candidate (Weld declared he was running three weeks later). He had credibility in all the key areas: a proven track record as a fiscal conservative and social liberal, an established ability to raise money, seven years as a Justice Department hard-ass to counter Spitzer’s legal-crusader persona, and the tacit support of the GOP’s Big Three. Pataki and Weld are longtime friends, and Weld’s campaign offices are across the hall from the governor’s fund-raising team. Rudy Giuliani and Weld are even closer; they have been pals since their days as U.S. Attorneys in the eighties, and Giuliani sits on the board of Weld’s investment firm, Leeds Weld & Co. And if you went down a checklist, Weld’s and Mike Bloomberg’s policy stands are nearly identical. Weld seemed like a godsend to a party that was preparing to be steamrolled by Spitzer.

That was on paper. Almost immediately after announcing his intentions, Weld found himself waging a multifront war with New York conservatives, who seemed offended by his very existence. Conservative Party chairman Michael Long quickly declared that Weld’s pro-choice, pro-gay-rights positions were anathema to his followers and stopped just short of saying there was no possible way he would consider Weld for his party (no Republican has won statewide in New York without the Conservative Party line in more than 30 years). In October, Tom Golisano announced he was registering as a Republican and considering a run (he promptly found an unlikely supporter in Majority Leader Joseph Bruno, who saw Golisano’s billions as a handy potential tool in maintaining control of the State Senate). It’s an extreme long shot, but rumors circulated last week that Nassau County Executive Tom Suozzi, previously seen as a potential Democratic challenger to Spitzer, might consider switching parties to take on the A.G.Meanwhile, Weld found himself entangled in the briar patch of Decker College. Leeds Weld had long specialized in buying for-profit schools, upgrading them, and flipping them. The firm was a major shareholder, for instance, in the purchase of Ross University, a medical-assistant training school, which was bought in 2000 and sold in 2003 for a $170 million profit. The previous year, Leeds Weld had purchased a 20 percent interest in Decker, a Louisville-based electrician-and-construction school. Decker had 3,700 students, mostly enrolled in programs that began with four weeks of classwork on campus, with the rest of the yearlong program to be completed online.

Early last year, when Weld was named the school’s CEO, he started commuting to Louisville to hire a new management team. The first sign of trouble came in June, when the Department of Education froze student-loan payments. During a routine program review, the DOE was told by the Atlanta-based accreditors of the school that they had been unaware that the school was primarily distance-based. The issue the DOE was raising by freezing the student loans was basically this: Is a for-profit distance-based institution purporting to teach hands-on skills like construction and the electrical trade a legitimate school or a bogus business?

In August and September, Weld commuted between Kentucky and Washington, D.C., meeting with DOE officials in an effort to restore the college’s loan eligibility. But on September 30, the DOE cut off all aid, claiming Decker owed the federal government nearly $7 million in improperly obtained loans. In October, Decker declared bankruptcy and the Louisville Courier-Journal began publishing a series of articles on Decker in which students alleged that instructors were incompetent and often absent, and that the training left them unqualified for the jobs recruiters promised awaited them. The paper also reported allegations that to keep students eligible for loans, answers to tests were provided in advance, attendance sheets were manipulated, and a student in jail was counted as attending on-campus classes. Decker stories started circulating in New York political circles and exploded when the Sunday Times ran a 3,200-word, above-the-fold investigation on December 18, followed by two more stories before the New Year.

Weld has not been accused of any wrongdoing, merely gross, career-torpedoing negligence. But he maintains that Decker was legitimate. He says that no one ever concealed the fact that the program was distance-based. He can’t understand why, he says, the Atlanta accreditors claimed not to know that it was. “I sat through a three-hour meeting with the very regulators from the Atlanta operation who went on to say they had no idea we’re a distance education program,” he says. “There is a PowerPoint presentation including the exact amount that was distance education and the exact amount that was residential.” Weld notes that he didn’t gain personally from his involvement with the school. The $430,000 in salary he drew during his eight months as CEO (his annual salary was $700,000) was more than offset, he says, by the $530,000 he personally invested. “No one feels worse about Decker closing than I do,” Weld says. “But I don’t know what I could have done differently.” He paused and half-grimaced. “Except not take the job.”

Weld’s detractors say he’s covering up a bogus business scheme or, at best, was asleep at the wheel. Either way, Weld handed his opponents a ready weapon. Golisano aides have been whispering that their man would carpet-bomb Weld over the issue. Spitzer? “Any mileage Governor Weld was going to get out of saying, ‘Hey, I was a prosecutor, too,’ is lost with Decker,” says a Democratic consultant with ties to the attorney general. “It just fits perfect for Eliot: He built his record on putting away rich people cutting corners and screwing the poor, and that’s exactly what Weld did.” Weld himself concedes, “I’d turn that into a 30-second negative ad if I was running against me.”

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.

The Kerry loss didn’t exactly send Weld back to the statehouse with a renewed focus on Massachusetts. Not long after the election, Weld received feelers from the Clinton administration (Weld and Bill became friends when both men were governors; Weld’s friendship with Hillary dates back to Watergate, when they were junior staffers on the House Impeachment Committee). “There were two cabinet positions, but after neither happened, there was a segue to a discussion of ambassadorial appointments,” says Weld, who was long rumored to be Clinton’s choice to replace Attorney General Janet Reno if she resigned. “I gave them six, and I got back a list of three: the Court of St. James, India, and Mexico. I chose Mexico, which is the one that Bill and Hillary hoped I would choose.”

In July 1997, Weld resigned as governor. He said publicly that pursuing the ambassadorship was a full-time job, but he also wanted to repay Cellucci’s loyalty by giving Cellucci sixteen months as acting governor before the next election.

Even before Weld’s ambassadorial nomination was publicly announced, Jesse Helms made it clear he wasn’t a fan. Weld had dodged a question in the Kerry debate about whether he would vote to keep Helms as committee chair, but the animosity went back further. Helms had been close friends with Reagan attorney general Ed Meese, who had appointed Weld assistant attorney general in 1986. When Weld resigned two years later, citing Meese’s ethical lapses, conservatives, Helms included, were furious. After Weld refused to court Helms, Helms saw to it that Weld never received a hearing, and a month after announcing his nomination, the Clinton administration quietly withdrew Weld’s name.

Back in Massachusetts, Weld’s abrupt departure had undone much of the goodwill he had built up there. Did Weld feel he had betrayed his Bay State constituents? “I wouldn’t have resigned if Paul hadn’t been my co-partner in governing Massachusetts,” he says. “The state was in good hands.”

In Bellport, a quaint Long Island town 90 minutes from Manhattan, the stately homes on Howells Point Road are tastefully appointed and set back from the street. However, none of them prepare you for the one at the end of the road whose only neighbor is the Great South Bay. The rambling white mansion is a three-story affair with giant glass windows that afford bay views. On a damp December Sunday, Bill Weld opens the screen door in a white shirt and shorts, sweat pouring from his perpetually ruddy face. “This was the first moment the treadmill was available,” he explained. “Let me grab a shower. Leslie will entertain you: She’s better company anyway.”

On Decker College: “I’d turn that into a 30-second negative ad if I was running against me,” Weld says.

Leslie Marshall walked me back to the kitchen so she could finish her phone call with her daughter Josephine, one of three children she had with ex-husband Dino Bradlee, one of Ben’s sons. I had mentioned to a Weld aide that I was throwing a party the night before. Apparently he had told Marshall, because the first thing she asked me was “Would you like a Bloody Mary? I heard you might need one.”

Susan Roosevelt Weld, the great-granddaughter of Teddy and the mother of Bill Weld’s five children, never hid her disdain for her then-husband’s political obligations. Marshall is the opposite, a gregarious 52-year-old novelist who is CC’d on all campaign e-mails. In the early days of the campaign, Marshall has been traveling with her husband as much as possible. She has taken on the task of injecting her new husband with a caring side as her pet project. On the second day in Buffalo, Weld held a breakfast meeting with twenty Republican donors and talked at length about ways to revitalize Buffalo’s downtown and dying port. Toward the end of the talk, a gentleman mentioned that he was impressed but wanted to know what was at the essence of Weld, what were two or three facts that he could take back to his friends? For a moment, Weld seemed at a loss, offering policy analysis when the man was looking for the personal. After a few minutes, Marshall chimed in from across the room. “Bill Weld is the greatest provider I have ever met in my life,” said Marshall. “He has a real preternatural need to take care of people. He wants to do that for New York.”

Weld and Marshall had been casual friends for decades and started dining together regularly in 2000, after Weld took a job with McDermott, Will & Emery, a law firm that had him spending more than half his time in New York. Eventually, Weld separated from Susan Weld and moved into the same Upper East Side building where the divorced Marshall was raising her three children. Weld is loath to discuss his divorce, but his son Quentin told me, “The happy thing is, the plane didn’t fly into the mountain. They are both very happy now.”

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.”

During his law-school summers, Weld interned in the Boston office of State Representative Martin Linsky, negotiating his way through antiwar marches without ever publicly taking a position on the war (Weld got a medical deferment for a back problem). In 1973, as the Watergate crisis exploded, Linsky was asked by Republican friends on the House Impeachment Committee for help in hiring a smart, nonideological young lawyer to research the legal grounds for impeachment. Linsky immediately called Weld, who was working as a young lawyer-drone in the Boston office of Hill & Barlow. Linsky offered the job, and Weld blithely said no, not wanting to lose his place at the firm. Weld then looked out his window, thought for a minute, called Linsky back, and took the job. It was on that D.C. trip that he met a young Democratic lawyer doing the same work named Hillary Rodham. Thirty years later, when asked what he took from the experience, Weld answers, “We researched and realized impeachment was whatever the Congress and the public thought it was.” The answer comes across as glib, dismissive, and, as Hillary’s husband found out 25 years later, absolutely correct.

Weld returned to private practice in 1974, and in 1978 launched his bid to unseat then-Massachusetts Attorney General Francis Bellotti. When I asked Weld what inspired him to first seek elective office, he didn’t cite policy reform or any of the obscure political philosophers that he drops into conversation like the rest of us drop the names of Yankees outfielders. “I had been electrified by Teddy White’s The Making of the President book about JFK,” Weld told me. “It seemed like great fun.”

Weld lost his first political battle, 80 percent to 20 percent, and carried only two towns in the state. Still, he impressed state GOP leaders and was named U.S. Attorney for Massachusetts after Reagan’s 1980 victory. Like his possible opponent, Spitzer, Weld earned a reputation for taking on high-profile targets. He drew headlines, for example, for his aggressive attacks on political corruption in Massachusetts, indicting 48 officials and convicting 46 of them, including ten staffers in the administration of Boston mayor Kevin White. Only a U.S. Attorney from New York named Rudolph Giuliani scored more positive buzz.

In September 1986, Attorney General Ed Meese nabbed Weld to run the criminal division at the Justice Department. Some saw it as an odd fit—the libertarian blue blood taking a job with Reagan’s right-hand man—and, in fact, it took just a few months for the two men to clash. In November 1986, the Iran/contra scandal began to break and Meese decided he and a few cronies would conduct the initial investigation themselves. Weld strenuously disagreed and announced at a staff meeting that it was inappropriate for the attorney general and his lieutenants to handle the case. He argued that his criminal division and the FBI should handle it. After several related ethical disputes, Weld lobbied for Meese’s resignation. “It got to the point where Meese was defending himself by saying, ‘If I’m so corrupt, then why is Mr. Anti-Corruption Bill Weld still saluting me every day?’ ” says Mark Robinson, Weld’s top aide at the time. “That just became intolerable for Bill.”

On March 29, 1987, Weld resigned along with Deputy Attorney General Arnold Burns. That day, he went over to the White House to explain his resignation to President Reagan, who promptly fell asleep during their meeting.

At a November speech before a lunchtime crowd of bankers at the St. Regis Hotel, Weld began by bringing up Sam Houston. “Sam was governor of the state of Tennessee and then the first governor of Texas,” said Weld. “When my friend Lamar Alexander from Tennessee heard about my interest in running for governor here in New York, he gave me a copy of the famous Sam Houston biography, The Raven, and told me, ‘You’ll like Sam. He’s a quitter, just like you.’ I told him he was right. I think, like Sam Houston, I’ve always been a principled quitter.”

The line didn’t ring true, not entirely, anyway. Later, a Weld confidant suggested another reason for his friend’s peripatetic career. Shortly after his second Massachusetts inauguration, Weld sat in his office with the friend and expressed private amazement at his accomplishment. “I never thought I would live this long,” Weld said. “I have so much I want to do, and I don’t know how much time I have to do it.”

Weld’s father died in 1972, at 61. “It was a heart attack, clear out of the blue sky. He was never sick a day in his life,” Weld told me at Bellport. In June, Weld buried his brother David at the age of 66. “The Welds have never had the longest life expectancy,” Weld said. I asked him if that fact might explain some of his career impatience. “It’s possible,” he answered. “I certainly was very taken with Achilles as a figure. Achilles was vouchsafed to a brilliant life full of valor but a short one, and he knew it was coming. I think Aeneas is down in book six in the underworld and he sees someone there, and I think it’s Achilles, and he says, ‘I would rather be a slave among the living than a king among the dead.’ ”

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.

Running Weld