Bill Weld Has Nothing to Lose

A look at our former governor's last (and wildest) hurrah.


Bill Weld sharing a laugh with presidential candidate Gary Johnson at the Libertarian Party National Convention last May. / Photograph by Phelan M. Ebenhack/AP

Instead, what followed were nearly two decades of alternately predictable and baffling career choices. He worked in law. He moved to Manhattan’s Upper East Side, joined a private equity firm, where it appears he schmoozed clients while his colleagues did the quant work, and remarried. He finished his third fictional potboiler. He launched a kamikaze gubernatorial bid in a state he hadn’t lived in since the 1960s. He spent several weeks a year in Ulan Bator, Mongolia, helping run the world’s largest gold and copper mine. By 2012, he was back in Boston, working for ML Strategies.

Even Weld can’t ignore the fact that as his political career petered out, two lesser Massachusetts politicians—Mitt Romney and John Kerry—were busy scoring presidential nominations or running the State Department. Both conspicuously lack Weld’s personal charm and political instincts, but they’re better at coloring inside party lines. A quixotic third-party run, though, plays to Weld’s strengths. Staring down a GOP completely unrecognizable to him, Weld is now free to adopt the same insurgent mentality he did when disrupting Massachusetts’ one-party hegemony in the 1990s. “This is sort of a triple bank shot,” says a former aide. “He loves triple bank shots.”


It is dusk on a Thursday in late June as Weld and I recline in our Adirondack chairs, looking out at the Atlantic Ocean. From the back we look like the stars of an edgy new Cialis commercial. Weld is being honored by Boston Harbor Now, at a $500-a-plate fundraiser on Georges Island. The usual suspects—Foley Hoag, Suffolk Construction, the Dewey Square Group—are well represented. Weld’s frenemy, former Governor Mike Dukakis, also being feted, is in attendance. The occasion is as clubby, white, and middle-aged as you’d hope. Those who do not wear Sebago Docksides wear Sperry Top-Siders.

Compared with, say, FreedomFest 2016, Weld is in his comfort zone. And the politically homeless Republicans swaying to Earth Wind & Fire tonight are his target voters. Weld’s strategy isn’t to try to defend libertarian ideas. Instead he articulates the ones he thinks disaffected centrists want to hear. When Johnson suggests abolishing the Internal Revenue Service, Weld raises an eyebrow and clarifies that he wouldn’t go that far. When asked about gun control, Weld suggests the formation—cue a million Libertarians choking on their dinner—of a massive new FBI task force.

Keep up the Reagan act, the thinking goes, and he’s back on prime time come October. “There were these debates with 16 candidates,” Weld says. “‘Little Marco and Lyin’ Ted and Crooked Hillary.’ That’s all [Trump] said. There’s no content there…. It’s like everyone else was scared of him.” In their place, Weld says, he’d zing Trump with that vintage demagogue rejoinder: “Have you, alas sir, no sense of decency or shame?” “That’s exactly what I’m going to say,” Weld pledges.

All of that sounds convincing enough until you start to think about it: Because it’s not the silver-tongued Weld who would be appearing before 67 million television viewers to disembowel Trump, but his utterly charming but not so articulate running mate, Gary Johnson. Meanwhile, nobody will be watching Weld trade jabs with Mike Pence.

With few exceptions—Weld’s ex-great-grandfather-in-law Teddy Roosevelt scored 27 percent of the vote in 1912; Ross Perot tallied 19 percent in 1992—third parties in America do not perform well. In 1980, the Libertarian Party’s VP nominee was Koch brother David Koch, who advocated the elimination of every major governmental agency. Today, the party has broadened considerably under Johnson and is more likely to be associated with Willie Nelson and Edward Snowden than granny-starving budget cuts and Mad Max–style paramilitary groups. Even if Johnson and Weld don’t win the election outright, party strategists argue that they could deny both Trump and Clinton the 270 electoral votes necessary to win. From there, the Republican-controlled House of Representatives, which doesn’t seem particularly keen on either major nominee, could split the difference and hand the presidency to Johnson.

Still, it’s a long shot. The party may have had a record showing in 2012, but that record showing garnered just one percent of the general election vote. Assuming Clinton doesn’t succumb to unforeseen scandal, or Trump doesn’t drop out of the race, or Johnson doesn’t morph into a world-class orator, the ticket can best make its presence felt not by taking the White House, but by denying it to someone else. The question is, who?

The answer is…not clear. Polls show that Clinton’s overall lead over Trump tends to dip about a percentage point when Johnson’s name is included. “Trump voters are mainly Trump voters,” Monmouth University pollster Patrick Murray told Politico in August. “But Clinton voters are still not quite happy that they’re going to end up voting for her.” Which is to say: If Weld siphons support from Never Trumpers who have already defected from the Donald, he’s more likely to pull from Hillary Clinton. And come November 9, he could be generating comparisons to the dread Ralph Nader.

At the start of the campaign, Weld might have been haunted by the thought. Here was a man who compared Trump’s immigration proposal to Kristallnacht. When a CNN anchor asked him which candidate was more qualified to be president, he answered Clinton without hesitation. But by midsummer, he had stopped vouching for her. “All I’m thinking about now is winning the whole shooting match,” he said during a panel discussion at FreedomFest. Next time a TV anchor asked him the Trump versus Hillary question, he added, he’d merely respond, “I’m voting Libertarian and I’m not going to lose any sleep over it.”

Considering the Libertarian Party will not, in fact, be winning the whole shooting match, one might naturally wonder why else Weld might be running for high office. Several loyalists surmised that the specter of Trump was appalling enough to pull him out of political retirement. But the majority of the Weldologists I spoke with suggested that to understand Weld’s late-career renaissance, one had to take into account the rest of his peripatetic résumé.

Weld’s brother Tim, a doctor on Nantucket, once told a reporter that “Bill will do anything as long as he’s challenged. He can’t stand repetition.” Weld himself has said his “greatest motivation in life is fear of boredom.” In the context of a disruptive third-party run that could deliver the nuclear codes to a certain billionaire man-child, Weld is making the same mischief he always has. “From the very beginning of his political career,” says his former press secretary, Ginny Buckingham, “he’s always been the skunk at the garden party.”

On the morning of the last day of FreedomFest, after watching a 15-minute rom-com about the perils of the surveillance state, I sit down with Weld for a final interview. He’s shed his pinstripes for light-washed blue jeans and a rugged brown suede jacket. He could be a rancher fresh off an armed protest against the federal tyranny of environmental regulation. But he doesn’t sound like one. I ask him, at random, about climate change. He advocates pragmatic, mainstream, and essentially unlibertarian ideas about the urgent need for governing bodies to prevent the rise of global temperatures by 2 degrees Celsius.

These aren’t ideas his free-market brethren take kindly to. He smiles. He doesn’t care: “I’m running as myself.”