Bill Weld Has Nothing to Lose

Bill Weld sharing a beer with John Kerry at McGann’s pub in Boston after failing to take Kerry’s U.S. Senate seat in 1996. / Photograph by Susan Walsh/AP

Alas, Libertarians were not. Weld could name-check The Road to Serfdom all he liked, but the party’s base found him suspect. And without their approval, he wouldn’t land on the ticket. The mistrust stemmed partly from past failing grades on acid tests such as gun control (for it) and criminal justice (hard-line). And partly it stemmed from Weld’s aborted 2006 run for governor of New York, when he opportunistically ran on a Libertarian ticket, then left the party in the lurch when he realized his actual goal—the Republican nomination—was unattainable. Most crucially, he didn’t really seem libertarian. “Gary [Johnson] is definitely a mountain-state, ‘Hey, I’m a triathlete, maybe I’ll smoke some Santeria’ kind of guy,” says Reason magazine editor at large Matt Welch. “Weld feels like yesterday’s news—the technocratic, good-government Republican governor.”

All of this resulted in an awkward Libertarian Party National Convention this past May in Orlando, where Johnson spent 75 hours trying to convince a large group of anarchists to vote for the man in pinstripes. (He was booed.) His basic pitch was that Weld would rescue the party from the sad periphery of American politics. Libertarians, though, kind of like the sad periphery. Faced with a choice between possible relevance and certain irrelevance, the party was split. “One of the interesting things about libertarianism,” says Massachusetts party official Dan Fishman, “is we don’t believe people need to be led, because people aren’t sheep.” On the second ballot, Weld barely secured the VP nomination with 50.5 percent of the vote.

Naturally, Weld and Johnson insist they’re gunning for the White House. Their opponents not only have historically crummy disapproval ratings, but they can seem weirdly out of step with the ideological trend lines of their respective parties. Libertarians, who skew left of Hillary Clinton on certain issues (war, drugs) and right of Trump on others (trade, healthcare) believe they’re poised to capitalize on the dissonance.

In the short term, though, the realistic goal is not to compete with Trump or Clinton, but to poll at 15 percent—the number needed to qualify for presidential debates. To get there, the two candidates have assumed different roles. Johnson, with his running shoes and Beaker-from-the-Muppets hairdo, has tried to pivot the party to a friendlier, less Ayn Randian place. (Until January he was CEO of the marijuana-products company Cannabis Sativa, essentially a high-end pot dealer.) Weld, in turn, is pitching the Never Trump people. He spends half his time hurling Jimmy Stewart–vintage insults at the Donald—Huckster! Pied Piper!—and the other half dialing depressed Republican donors with nowhere to park their cash.

By midsummer, before the campaign and its various semi-affiliated Super PACs began airing television ads, Johnson was in uncharted territory, polling as high as 13 percent. Weld, meanwhile, was running around comparing the Republican Party to extinct species like dinosaurs and Whigs. “My first reaction at not carrying around the Republican Party’s social policies on my back as I have been for 25 years was: ‘Free! Free at last!’” he told the audience at FreedomFest. “I think I’ve had a little bit of a conversion.”

The very first Weld to attend Harvard College, John Weld, was expelled in 1644 for stealing 11 pounds of cash and 30 shillings’ worth of gunpowder. Inaugural college president Henry Dunster personally issued the lad a whipping. Since then, the family has stayed more or less upright: Hundreds of Welds are rumored to have graduated from Harvard, and the letters W-E-L-D have long been etched all over Cambridge. Technically, the family made its fortune in railways, banking, and other plutocratic avocations, but the concept of earning a living has always been a little beside the point. As the unofficial family slogan goes, “The Welds don’t make money, they have money.”

William Weld, whose Brahmin name alone conjures images of sloe gin and tasseled loafers, did right by his lineage. Born onto a 600-acre estate on Long Island, he attended Middlesex School, Oxford University, and Harvard (twice). He married Susan Roosevelt, great-granddaughter of Teddy, and plunged into politics and law enforcement. In the 1970s, he worked alongside one Hillary Rodham on the House Judiciary Committee’s Nixon impeachment inquiry staff. As a Department of Justice prosecutor during the 1980s, he litigated high-profile public corruption (Mayor Kevin White’s staffers) and RICO (La Cosa Nostra) cases. When Ronald Reagan’s attorney general, Edwin Meese, was investigated for some graft of his own, in 1988, Weld resigned and returned to Boston. Two years later, he ran for governor.

Weld wasn’t supposed to win. The only other race he’d ever run—for attorney general in 1978—he’d lost by more than a million votes. His gubernatorial opponent, John Silber, was a pugnacious, whip-smart son of a bitch with a hook for a left hand and—more important—the support of the Democratic Party, which no longer seemed capable of losing elections in Massachusetts. “I remember once in 1990 we were running low on money, sitting in his living room in Cambridge,” says political consultant Stuart Stevens, who worked on Weld’s campaign. “He said kind of off-hand, ‘We can always sell this painting.’ Everybody thought it was a joke. And then as we were leaving, Weld was like, ‘No, I’m serious.’ I was like, ‘We’re going to be okay, man.’ It was a Singer Sargent.” Weld ultimately eked out the win.

On Beacon Hill, the effortless grace kept on coming. He’d pepper staff memos with Latin. Twice a week, he’d interrupt whatever he was doing to play squash. “He is old money, white, and fucking brilliant,” says a former staffer. “Everybody tries to distance himself from those traits when running for office, and he always embraced them and made them his own.” Weld intuited that voters would reward WASP authenticity over a feigned everyman shtick. Famously, after Senate President Billy Bulger ribbed him about his Mayflower ancestry, Weld rose to correct the record. “Actually,” he said, “they weren’t on the Mayflower. They sent the servants over to get the cottage ready first.”

Weld’s intellectual swagger trickled down. One night, he decided he needed a speech written at the last minute, but didn’t want to miss the Sox game at Fenway, Byrnes says. “So he taunted me: ‘You’re gonna come to the game too, right?’ First person I see is his buddy Charlie Steele, with seven beers in his hand. Susan Weld is sitting next to him, reading a book in Chinese. Then I went back afterwards and I wrote the speech.” Drunk, sober, gay, straight, Charlie Baker—Weld didn’t care who worked for him, as long as they were competent during business hours. During his first term, Weld balanced a bloated state budget without raising taxes and presided over a major drop in unemployment.

Voters found Weld’s swashbuckling energy irresistible, and in 1994 elected him to a second term by more than a 40-point margin (in a state that was 15 percent Republican). Afterward, a light bulb went off and Weld began traveling the country to gauge support for a 1996 presidential bid. “He was very serious,” says a former campaign official, but the GOP didn’t seem eager for a moderate. The new plan would be to establish DC cred by defeating fellow plutocrat John Kerry in a bid for the U.S. Senate. Weld’s strategy, which involved beating a popular incumbent Democrat during a high-turnout presidential-year election, in retrospect didn’t make much sense. He wound up resorting to absurd attacks on Kerry’s wealth—“Senator, if your name was John Six-Pack instead of John Forbes Kerry…”—and lost by eight points.

The Kerry defeat, Weld’s ex-staffers say, left their man disconsolate. So Weld, who suffers from a kind of political restless leg syndrome, decided it was as good a time as any to leave Beacon Hill. “He has a short attention span,” says a former top deputy. “He got bored being governor.”

And that’s when things started to get random. Weld decided it might be neat to serve as U.S. ambassador to Mexico, and in 1997 he announced his resignation before the end of his term. It was stunning enough that Weld would turn his back on an ascendant political trajectory to assume a second-rate ambassadorship. Even more baffling was the difficulty he had securing the post. At the time, archconservative North Carolina Senator Jesse Helms held the keys to the cabana. To Helms, Weld was the one-man amnesty/abortion/acid wing of the GOP and certainly didn’t deserve to be rewarded for his liberal heresies. Conventional wisdom held that Weld could have won over Helms by visiting him in his office and kissing his ring. Weld preferred otherwise. “I wouldn’t go on bended knee, and I wouldn’t kiss anything,” he reasoned, and he never received confirmation from the U.S. Senate.

There was a ballsy righteousness to Weld’s stand, though all it really did was ensure that he and his prodigious cojones wound up well north of sunny Mexico, in political Siberia. A figure who a few years earlier had generated serious White House consideration was suddenly a pariah to his party and an ex-governor without a job. “If I had to do it over again,” he says now, “I would serve out my second term and run again [for president] in 2000.”