Bill Weld Has Nothing to Lose

Portrait by Ken Richardson

William Floyd Weld—6-foot-4, strawberry blond, and descended from Pilgrims—is delivering a speech at a Japanese-themed cocktail lounge on the mezzanine level of the Planet Hollywood Resort & Casino in Las Vegas. More accurately, he’s shouting the speech because this is Vegas and a bass line is pulsing from a speaker near his head. Roughly half of his remarks are audible: “The two-party system in Washington has been a monopoly for so long…. They’re dinosaurs!… And this year the Libertarian Party is going to be the comet that takes out the dinosaurs!” A few hoots register as Weld works his way to the kicker he’s been road-testing: “This year…let’s kick some…asteroid!” He grins sheepishly.

Not his best work. But given the circumstances, appropriate. It is a Friday in July and the setting is FreedomFest 2016, an outré political smorgasbord that bills itself as “The World’s Largest Gathering of Free Minds.” Weld, the former governor of Massachusetts, is here in his capacity as the vice-presidential nominee of the Libertarian Party, alongside his running mate, former New Mexico Governor Gary Johnson. FreedomFest leans conservative, but the vibe is more antiestablishment than it is pro-anything.

Quick tour of the premises: The Muslims4Liberty booth is handing out free Korans near the Libertarian Illness Prevention guy offering rides on a $14,000 exercise bike. Gold-bullion salesmen mingle with standard-issue “Big Brother Is Watching” pamphleteers. George Foreman and Don King are around, for some reason. “Bill wants me to be nearby in case any weirdo buttonholes him,” says Marshall Bradlee, Weld’s 24-year-old stepson and bodyman.

In Massachusetts politics, the adjective “Weldian” connotes a WASP-y, statesmanlike moderation shared by his Republican successors Mitt Romney and Charlie Baker, and not by the FreedomFest habitués dressed in flag-and-jeans. “He doesn’t come across as the kind of person running on a third-party ticket,” says David Boaz, the executive vice president of the libertarian Cato Institute. “He comes across as the kind of person having dinner with the Bushes.”

But the Bushes are out, Donald Trump is in, and Weld’s brand of Republicanism is no longer interesting to the GOP rank and file. Twenty years ago, Weld was the governor of Massachusetts and a rising star. Affable, wealthy, and quick-witted, he floated to two terms on Beacon Hill. He was POTUS material. A Republican Kennedy. Or maybe he was a comet. Almost as quickly as he ascended the national ranks, the party lurched rightward and Weld more or less disappeared from political life.

Until recently, Weld, 71, was living quietly in Canton with his second wife, journalist and novelist Leslie Marshall, and working for the powerful lobbying/consulting firm ML Strategies, headquartered across the street from South Station. The work was heady; he represented General Electric and Steve Wynn in their bids to set up shop in the area. But it wasn’t the political highlife he’d once envisioned. For a figure as singular (and wealthy) as Weld, corporate influence-peddling felt like an uninspired final chapter.

Then Donald Trump happened. And once the Grand Old Party officially staked its future on a television boss hawking 2,000 miles of raised concrete, there was renewed demand for sagacity in conservative circles. William Weld, Boston Brahmin, was suddenly back in vogue.

Part of this owed to personality. Temperamentally, at least, Weld is a near-perfect avatar for the #NeverTrump movement. Trump has conceded that he doesn’t read whole books, just “passages.” Weld might drop a casual reference to Walter Muir Whitehill’s Boston: A Topographical History into a conversation. Trump has the interior-decorating sensibility of a 1980s dictator. Shabby-chic, Weld looks like an extra in a Whit Stillman movie. Trump is a teetotaler, Weld a proud boozer. This list goes on forever.

But the peculiarity of the 2016 election suggests Johnson and Weld will be more than just a pressure-relief valve for disgruntled Never Trumpers (or Bernie Bros, for that matter). Hillary Clinton and Donald Trump, polling says, are among the least popular candidates ever to represent their respective tickets. At a time when both candidates have adopted aggressively interventionist platforms, the Whatever party is betting that its laissez-faire stance on social and economic issues will hold unprecedented appeal.

So far, so good. When Weld and Johnson began bum-rushing newspaper editorial boards and cable news shows in their quest for free media, their poll numbers rose and disconsolate party elders began to perk up. If the Never Trump crowd had a complaint, it was that Big Red wasn’t featured prominently enough. “If Bill Weld were at the top of the ticket,” Mitt Romney said in June, “it would be very easy for me to vote for [him].”

Two decades removed from serious White House ambitions, Weld probably—okay, almost certainly—won’t get there on the Libertarian ticket. But he might play a larger role than just about anyone in deciding who does. Less than a couple of weeks before FreedomFest, a journalist asked if Johnson fretted playing “spoiler” to one of the two major candidates. Weld’s blue eyes twinkled—his eyes really twinkle—and he asked a question of his own: “What’s to spoil?”

Before our first interview, in June, Weld’s handlers tell me to meet the candidate at his hotel—the Holiday Inn, midtown Manhattan branch. Weld, wearing a pinstriped suit, is as surprised as I am at his low-budget accommodations. “One hundred fourteen a night!” he says, mystified. “I’ve never heard of a New York hotel where it starts with a ‘one.’”

Our meeting was originally scheduled at the venerable Algonquin Hotel, where the great American satirists of the early 20th century sat around getting hammered—the sort of oak-paneled watering hole with which Weld is familiar. The author of three books himself, Weld muses, “The Algonquin has the worst food in New York City. The food tastes like water.” By the time we move on to the drinking, he has a far-off look in his eyes. “I mean, you think about Robert Benchley and Dorothy Parker. All the pearls. God, what a wonderful time….”

Weld has a way of perpetuating his own myth: that of the old-money bon vivant who stumbles in and out of power, forever more interested in living well than in governing at all. The caricature isn’t completely inaccurate. Of Weld’s second inaugural address as governor, his former head speechwriter Robert Byrnes says, “He was wasted, no question about it. He said, ‘Let’s get these chairs out of the way; let’s dance the night away!’ There weren’t any chairs.’’

Indeed, from the cheap seats, much of Weld’s life has seemed like a jolly, meandering quest to stave off boredom. “I sat down in my twenties to write the Great American Novel and nothing came out the end of the pen because I had nothing to say,” he once said while doing publicity for one of his books. “I really still have nothing to say.” It would be fair to assume that a third-party vice- presidential run was Weld’s latest extracurricular diversion. “There’s nothing more he would like than to be flying around the country on somebody else’s dime, flying first class, and talking to political reporters all day,” says a former top adviser.

Putting aside the Libertarian ticket’s no-frills travel budget, Weld says he has other motivations. Doctrinally, Weld says, he’s always identified with the party. His political reincarnation isn’t a field trip. It’s a homecoming. “My first press conference as governor,” he says, “I greeted the press with the words ‘Fellow libertarians.’ They laughed rather nervously.”

On Beacon Hill, Weld ushered in an era of Republican gubernatorial dominance by upending assumptions about what the party could stand for. Weld was wide left of the Democratic Party on several social issues, most prominently gay rights. He was also a fiscal hawk. In the heyday of Ron Paul’s crypto-racist monthly newsletters, Weld was the rare high-rent practitioner of libertarian laissez-faire.

This made an impression on Johnson, who served as New Mexico’s governor from 1995 to 2003 and calls Weld his “role model.” Before the party’s nominating convention in May, a Johnson staffer emailed Weld out of the blue to gauge his interest in the veep slot. Weld was interested. “The stars were in alignment,” he explains. “If John Kasich were the nominee, would I be running? No, I don’t think so.” Weld hopped on the phone and accepted the offer. Johnson all but fainted: “I was just numb. Bill Weld was so far above the list that I had assembled. So I was numb beyond my wildest expectations.”