Is Bill Weld the Hero Never Trumpers Have Been Waiting For?

It’s a long shot, but his audacious presidential bid is intriguing all the same.

Photos by Elizabeth Frantz

Bill Weld looks comfortable standing with his back to the mantelpiece of an antique-laden living room in a neighborhood inhabited by Washington’s deposed ruling class — perhaps too comfortable. As of this rainy Tuesday evening in late June, the fiscally conservative, socially liberal 74-year-old former governor of Massachusetts is the only Republican who has dared to mount a primary challenge against President Trump. The purpose of tonight’s invitation-only reception is to introduce his candidacy to about 175 members of the capital’s bipartisan upper crust.

The host committee and guests include a couple of Ronald Reagan’s White House social secretaries; George H.W. Bush-appointed former Federal Election Commission chairman Trevor Potter; Jimmy Carter’s White House communications director, Gerald Rafshoon; conservative commentator and arch Never Trumper Bill Kristol; and 2016 independent presidential candidate Evan McMullin. Coordinated by eminent Washington event planner Carolyn Peachey, the evening has all the makings of a planning session for the posh wing of the Resistance.

“Tonight I do pose this question,” Weld says. “Is it really too much to ask that senior members of the government in Washington observe those same rules that we teach our children? Apparently yes. More’s the pity.”

More’s the pity, perhaps, that Weld is not a take-the-ramparts kind of orator. To these potential troops perched on upholstered love seats, he serves barbs whittled and polished like intricate cherrywood clawfeet. “I do think it’s not a stretch to say that, at some level, Mr. Trump is a sick man,” Weld says. “And I don’t mean physically, I mean in his head. There’s lots of furies there. I wouldn’t want his demons. You know, I think that, like all bullies — and it’s clear beyond peradventure that he’s a bully — he is insecure. … Which is why anytime someone poses a slightest threat to him, he brands them a loser or an abject loser. The poor mayor of London has been called a loser so many times because he’s standing in Mr. Trump’s way of achieving in an untrammeled fashion what he wants — namely, everybody agreeing with him and telling him how fantastic he is.”

The guests laugh appreciatively. As far away as we are from Weld’s beloved New England trout ponds, this is the candidate’s natural habitat, where people know the definitions of “peradventure” and “untrammeled,” as they do “pardonably,” “ineluctable” and the “Gordian knot” of impeachment, all of which Weld will enunciate shortly.

Cerebral courtliness is not, to put it mildly, the dominant mode in Republican politics at the moment. As it happens, this evening, as Weld meets with a cell of elite resisters, Trump himself is launching his reelection campaign at a raucous rally in a nearly 20,000-seat arena in Orlando. The incumbent and his fans are braying back and forth to one another, revisiting some of their favorite gripes, such as Hillary Clinton’s emails. “If I got a subpoena for emails, if I deleted one email, like a love note to Melania, it’s the electric chair for Trump,” the president declaims.

Back in the D.C. living room with oil paintings of animals on the walls, Weld opens the floor to the skeptical questions on everyone’s minds: “Can you describe your path to the nomination?” Followed by, “How much [money] do you have to raise?”

The path begins, he says, “with a victory or close to it in the New Hampshire primary,” which is a phrase that would make us rich if we got a nickel every time a candidate said it. But as Weld lays out his case, his casual learnedness begins to serve him well. The outer parlors into which people are packed get quieter as the crowd gets more attentive. Weld reminds everyone that since the modern form of the New Hampshire primary began in 1952, when Estes Kefauver beat Harry Truman on the Democratic side, five incumbents who faced primary challenges in the Granite State were politically wounded. None returned to the White House — Truman, Lyndon Johnson in 1968 (challenged by Eugene McCarthy), Gerald Ford in 1976 (Ronald Reagan), Jimmy Carter in 1980 (Ted Kennedy), and George H.W. Bush in 1992 (Pat Buchanan). (Weld doesn’t mention the sixth case — that of Pete “I’ll run against Nixon if no one else will” McCloskey, who took on Richard Nixon in 1972. McCloskey won 20 percent of the vote in New Hampshire, and Nixon cruised to reelection — and Watergate.)

How well would Weld have to do in New Hampshire to land a meaningful blow against Trump? For perspective, Buchanan took 37.5 percent in 1992 — that is, he lost — and Bush’s reelection campaign never really recovered.

To make it happen on New Hampshire’s primary day, Feb. 11, 2020, Weld has signed up longtime political hand Peter Spaulding to run his campaign in the state. Spaulding helped guide John McCain’s New Hampshire primary victories in 2000 and 2008. The rest of the path, Weld says, includes the other states in his home base of New England, the mountain states, the West Coast, and the 20 or so states with open primaries — where, as in New Hampshire, non-Republicans can vote.

And when it comes to money, “the amount required to do lasting damage to Mr. Trump in New Hampshire is probably not much more than $10 million,” Weld says. “I know where five of the 10 is, and I can get the rest. … The faintest whisper in November-December that I’m getting traction and busting out of the lower ranks against Trump in New Hampshire, there’s going to be an absolute flood.”

Bill Weld in New Hampshire. The former governor of Massachusetts has launched a campaign to win the Republican primary.

When he’s done speaking, the applause, to my ears, sounds more than courteous or friendly. It sounds grateful. These people have been waiting for 2½ years in the ruins of their America for someone to lead the way out. So many more predictable and arguably stronger potential Republican challengers — the likes of Larry Hogan, John Kasich, Jeff Flake, Ben Sasse, Bob Corker — remain on the sidelines. For now, Weld is their only hope. As I sample opinions, I sense genuine enthusiasm, which everyone is trying to curb because no one wants to sound naive.

“It’s not crazy that he could be competitive” in New Hampshire, Kristol tells me. He’s on the evening’s host committee but for now isn’t formally supporting any candidate. “I think winning would be really hard. But, you know, at that point, you just never know, maybe you get a break, something happens. Trump says something, implodes in some way, or there’s a recession … some foreign policy crisis. I think you can get to a point where it becomes serious, and [Weld] gets 35 percent of the vote in New Hampshire, 38 percent. That’s kind of a big moment. The whole Trump’s-invincible myth starts to fade.”

Says McMullin, whose appeal to principled conservatives earned him just 0.5 percent of the general-election vote in 2016: “The president is very popular right now within the Republican Party, but Trump and Trumpism are not forever. Eventually we’ll turn the corner, and things could change quickly. And if so, over the next year or so, [Weld] will be there.”

No one I talk to thinks Bill Weld will become president. (Except, possibly, Bill Weld: “I’m in it to win,” he says when asked by another guest.) But could he somehow make a mark on the campaign — even derail Trump’s reelection effort — by performing well in New Hampshire? Or is this whole exercise nothing more than a Never Trumper summer daydream: a wish-fulfilling fantasy spun from desperation and denial?

The conventional wisdom would hold that it’s fantasy. But in the spirit of anything is possible — which Trump himself validated in 2016 — let’s indulge the proposition. In a state like New Hampshire, where there are more independent voters than either Republicans or Democrats, isn’t it at least plausible that some critical mass of voters could find an appealing vehicle in Weld’s charmingly old-fashioned, ideologically heterodox pitch? “I think Bill — listen, he’d be a good president,” Rafshoon says. “But if he isn’t, he could still be a great hero.”

From top: Weld visits a Pride festival in Portsmouth, N.H., and the libertarian Porcupine Freedom Festival in Lancaster, N.H.
From left: Weld visits a Pride festival in Portsmouth, N.H., and the libertarian Porcupine Freedom Festival in Lancaster, N.H.

The math for Weld in New Hampshire appears brutal: As of mid-July, Trump was up 79 points — 86 to seven — according to a poll by CNN and the University of New Hampshire. Weld reported raising less than $1 million in the second quarter, including a $180,000 loan to himself, compared with $108 million raked in by Trump and the Republican National Committee for the reelection effort. Not to mention that Trump has already decisively won the New Hampshire primary once, in 2016 (although with just 35 percent of the vote in a crowded field). Weld is counting on New Hampshire households blanketed by the Boston media market to remember when he was a popular Massachusetts governor — yet he hasn’t been in the governor’s mansion since 1997, before an entire generation of voters was born or old enough to notice.

Weld fortifies himself with other data: For the 1992 primary, Buchanan didn’t even start campaigning until December. In the 2000 primary race, McCain polled at 2 percent in March and by August was only at 10 percent. Earlier this year, a poll by the Saint Anselm College Survey Center showed that although New Hampshire Republicans overwhelmingly support Trump, about half of them are open to considering a primary challenger. And a survey by Morning Consult showed that Trump’s approval rating with New Hampshire voters in July (including Democrats and independents) was only 40 percent, while his disapproval rating was 57 percent. As for fundraising, Weld told me the early numbers do not reflect money coming into a super PAC and a 501(c)4 organization working on his behalf, because they report separately. Spaulding added: “Money doesn’t count in New Hampshire. It’s organization and candidates spending time here and connecting with people. Money will come after you do well in New Hampshire.”

Numbers aside, Weld’s campaign is drawing on a full tank of moral conviction. “There’s fights that are worth having that you don’t say, ‘Well, you know, we’ve got a 58 ½ percent chance to win this fight, so I’ll get in that fight,’ ” says Stuart Stevens, a senior strategist on Mitt Romney’s 2012 presidential campaign who is advising Weld. “That’s not this kind of fight. … Bill Weld versus Donald Trump is a character test not just of the candidates but of each voter. And that’s unusual in politics. … What are the odds? We don’t care. If their arrows fill the sky, we’ll fight in the shade.”

What it will come down to in New Hampshire, Weld told me, is talking to residents and earning “one vote at a time.” He added: “When my obituary is written, this may be seen as the most important thing I’ve ever done.”

And so, a few days after the reception in Washington, Weld and Marshall Bradlee, his 27-year-old stepson and campaign aide-de-camp, made the relatively short drive to New Hampshire from Weld’s home in Canton, Mass. Their destination was the Porcupine Freedom Festival, or PorcFest, a six-day libertarian campout, policy seminar, trade show and dance party. I asked Jason Sorens, chairman of the Free State Project, why he had invited Weld. He gave me a version of what he told the audience of nearly 100 in the open-sided speaker’s shed: “This is a moment for those of us who are New Hampshire Republicans who don’t like the Trump agenda of protectionism and nativism and nationalism and open personal corruption to take a stand and make a statement in next year’s primary.”

“When my obituary is written, this may be seen as the most important thing I’ve ever done,” says Bill Weld of his campaign.

Weld wore jeans, boots, a checkered shirt and a fleece vest of the Guggenheim Motorcycle Club. “This is a visual,” he said, taking off the vest and holding it up to the audience. “I’m actually the international vice president of the Guggenheim Motorcycle Club, an honor which I won in a closely fought election in Bilbao, Spain, where the Guggenheim [Museum] was opening a new exhibit, ‘The Art of the Motorcycle,’ some years ago. But it gives you a sense that I do wander off the beaten path from time to time.” I could tell from the puzzled chuckles that the reference to the 1999 modernist exhibition was lost on almost everyone, but I decided the shout-out to anything motorcycle-related was a net political positive here, given the numerous helmetless freedom-loving posses roaring up and down the road in front of the campground.

After remarks attacking Trump’s lack of ethics and competence, and criticizing the administration’s policies, Weld shone in the Q&A, where several questions seemed designed to administer a hazing. Permitting New Hampshire to secede from the union “would be worth careful consideration,” he told an interrogator wearing a hat that looked identical to a red Trump MAGA hat, except it said, “Make Bitcoin Great Again.” Another asked Weld to read aloud his T-shirt, which was an ode to free trade. “Sir,” Weld said, “perhaps you’d care to join my policy team?” Perennial candidate-satirist Vermin Supreme, wearing a rubber boot hat, reminded Weld of the tradition of candidates raising money for the libertarian cause by getting pies in the face. “The store did not have whipped cream, but they did have snack pudding and I was wondering” — Supreme held up a pudding cup — “if you would agree to take a pie to the face?”

“Vermin,” Weld said, “I’m happy to work with you on raising funds for the Libertarian Party. But that’s what they call a bad photo op.”

The crowd repeatedly cheered Weld’s repartee. Another audience member, instead of asking a question, recalled the 1988 New Hampshire primaries. A canvasser for Michael Dukakis came to his door. Dukakis was a Democratic predecessor of Weld’s as Massachusetts governor, and the voter hadn’t appreciated what he considered Dukakis’s liberal, big-spending administration. He told the canvasser that he had moved to New Hampshire to get away from Dukakis. Now he told Weld, “But after I saw you for a year in Massachusetts, and what you’d done in just one year, I moved back to Massachusetts.”

After PorcFest, Weld’s next stop was a Pride festival in Portsmouth. He worked his way methodically through the crowd, trying his new favorite line to cajole Democrats and independents to help him beat Trump in the primary, even if they vote Democratic in the general election: “I will buy you a bar of expensive soap so you can go take a long, hot shower after voting in the Republican primary.”

Weld tells voters that a vote for him in the primary is a chance to vote twice against Trump — a tacit acknowledgment that Weld may not be in the general election. Some voters were more open to the soap-and-shower pitch than others. “I don’t know if I could do that,” Lauren Garza, a fundraiser for a community health center, told the candidate. But Dave Brackett, who works in IT, wasn’t ruling it out. “I could see myself voting for him in the primary,” he told me after Weld passed. “In the Democratic primary, I don’t really know who to vote for, so I might do a protest Trump vote.”

As I listened to these exchanges, I thought about how Weld is violating a fundamental quality of every other quirky-but-impactful New Hampshire primary challenger: They have always emerged from the more extreme wing of their parties. Democrats Kefauver, McCarthy and Kennedy attacked Truman, Johnson and Carter from the left; Republicans Reagan and Buchanan came at Ford and Bush from the right.

In contradiction of this history, “Weld’s bid to dump Trump invents a new political style: a moderate insurgency against an extremist establishment,” Adam Hilton, an assistant professor of politics at Mount Holyoke College, wrote in The Washington Post in April. “Primary voters are more ideologically extreme than general election voters,” Hilton noted, and so they may dismiss Weld’s invitation to the middle.

I couldn’t quite tell if this was a fatal flaw at the foundation of Weld’s crusade — or a brilliant innovation. It’s why he visits nontraditional Republican environments like PorcFest and a Pride festival. He’s not so much trying to convert Trump’s base as expand the GOP primary electorate. On the stump, while channeling the soul cries of Never Trumpers, he also tries to appeal to new categories of voters, such as millennials, who, he warns, will “reap the whirlwind” of Trump’s escalating budget deficits and indifference to climate change.

The old duck hunter says he likes to go hunting where the ducks are. “I don’t want Trump to hear me coming or feel me coming,” Weld told me later. “I don’t want them to feel threatened in New Hampshire. Oh no, I want them to wake up too late to how the shape of the electorate has changed, the shape and size of the electorate.”

Weld and wife Leslie Marshall in Canton, Mass. “His strategic mind is more wily than you think,” Marshall says. “He sees around corners, he sees way ahead.”

The son of a Wall Street banker and a descendant of a signer of the Declaration of Independence, Weld grew up on 600 acres on Long Island with a big pond where as a boy he spent hours in a boat, alone, fishing and watching the weeds reaching up from the bottom like beseeching hands. In Weld’s 2002 novel, “Stillwater” — yes, he has published three novels — about the real-life flooding of four Massachusetts towns in the 1930s to make way for a reservoir, the narrator projects the author’s passion for the water and the land: “America has both gentle and heartless in it. You can live a wonderful life in the gentle part of America, which is most of it, but if the heartless part notices you, it will come snuff you out, and the place you live.”

Weld attended the best schools — Harvard, Oxford, Harvard Law — majoring in classics as an undergraduate and starring as the leading lady in Harvard’s Hasty Pudding cross-dressing theatrical farces, which always featured a kickline. Between scenes, he wrote his senior thesis, in which he argued that the commonly accepted Latin text of passages by the elegiac poet Sextus Propertius was wrong, because of mistranscription by scribes during the Middle Ages. “I remember vividly, in between acts, he was below the stage of Hasty Pudding with a legal pad, scratching out notes,” classmate Mitchell Adams says.

Embarking on a career, Weld kept finding ways to buck the establishment he was born into. As a young lawyer in Boston in the early 1970s, he abandoned the typical partner track and leaped at the chance to serve as a staff counsel to the House committee investigating Richard Nixon. He and another young lawyer then known as Hillary Rodham collaborated on a legal memo about what constitutes grounds for impeachment. (Now, on the campaign trail, Weld cites that work to argue that Trump’s conduct richly merits impeachment.)

In the early 1980s, as the Reagan-appointed U.S. attorney in Boston, Weld took on entrenched financial and political interests in public corruption prosecutions. He also served as head of the criminal division at the Justice Department, where his tenure may be best remembered for his splashily indignant exit: He quit in protest of what he said at the time were ethics violations by Reagan’s attorney general, Edwin Meese III.

In 1990, Weld was a laughably dark-horse candidate for governor. Not only was it unlikely that a Republican could win in overwhelmingly Democratic Massachusetts, but Weld was a long shot even to get the GOP nomination because of his support for abortion rights. The party activists soundly rejected him in a nonbinding convention and backed a more conservative favorite who opposed abortion. Weld started the primary race trailing by double digits in polls, but he handily beat his Republican rival by attracting large numbers of independents, then knocked off Democrat John Silber. In 1994, the former dark horse was reelected with 71 percent of the vote.

“Governor Weld, despite his patrician roots, is a street fighter,” Virginia Buckingham, a former chief of staff to Weld, told me. “I stood by his side and watched him take on the kind of Massachusetts culture on Beacon Hill and turn it upside down. … It was rough, but he showed that this theory that I think he’s positing for this [presidential] campaign actually is true: You can attract moderate, independent-thinking people to your party. … They’re looking for someone who espouses the philosophy of ‘Let people live the life they want to live and run the government well.’ ”

Massachusetts embraced Weld’s hybrid brand of cutting taxes and slashing budgets while standing for gay rights and supporting medical marijuana. Voters seemed to tolerate, more or less, a free spiritedness that set him apart. An avowed fan of the Grateful Dead, he attended concerts as governor and mourned lead guitarist Jerry Garcia’s death in 1995, saying: “More than any one song, it was just the consistently mellow approach they took to everything, life as well as music.” In 1996, after signing legislation to protect rivers and streams from development, Weld dived fully clothed into the Charles River.

“When people look at Bill Weld’s governorship as a stand-alone, I think they miss the real point,” says R.J. Lyman, a longtime friend and a colleague in Weld’s recent international business and consulting work, who helped launch the primary challenge. “The real point is not Bill Weld was an anti-tax crusading Reaganite Republican. It’s Bill Weld the speak-truth-to-power guy. That’s who he is. The irony is, the man of privilege is the speak-truth-to-power guy.”

Weld first imagined himself in the White House while still governor, when he challenged Democratic Sen. John Kerry for his seat in 1996. He thought it could be a steppingstone to the presidency. The race was tough, featuring epic debates. “Maybe I was too ambitious,” Weld told me. “I thought if I could knock off one of the two or three most liberal icons in the Senate, then the [Republican] Party would accept me. … But a funny thing happened on the way to the White House.” Kerry won by seven points.

Weld turned to novel-writing and a private law practice. He moved to New York City, where he initiated a bid for New York governor in 2005, but dropped out before the primary. Over the years, detractors have accused him of a certain ideological fluidity. In the 2008 presidential race, he supported Romney in the primary and Barack Obama in the general election. In 2012, he endorsed Romney in the primary and the general-election campaigns. In 2016, he was former New Mexico governor Gary Johnson’s running mate on the Libertarian ticket. By Libertarian standards, the race was a smashing success, garnering 4.5 million votes, or 3 percent of the total, the most in party history. Through all his partisan wandering, Weld maintains that his principles have never wavered — it’s the meaning of political labels that has changed, particularly the meaning of “Republican.”

After the New York governor’s race, the Boston Globe wrote a midcareer political obituary that still seems instructive: “He was only interested in campaigns that were quixotic, or at least uphill,” former Weld aide Raymond Howell told the paper. “The least fun was his landslide re-election victory in 1994. … He was never in politics for the power. He was always in politics for the gamesmanship. He was more interested in the intellectual chess game than in being crowned champion.”

We will know if Weld ever gets under Trump’s skin when the president starts tweeting about him.

At both PorcFest and the Pride celebration, Weld didn’t spend much time mingling with potential voters. And after those two events, he called it a day and left the state. For all of July, he attended only a handful of events in New Hampshire. Was it possible that all the Never Trump ardor I saw at the gathering in D.C. was being projected onto someone whose heart wasn’t in the tough work of campaigning? Is this how to wage a Buchanan-style insurgency in New Hampshire in 2019?

Buchanan declined to comment when I contacted him, but I reached David Carney, who was on the other side of Buchanan’s primary challenge, serving as a national field director for George H.W. Bush’s reelection effort. “It’s a half-assed vanity project,” Carney said of Weld’s campaign. “He’s not running a serious campaign. Gene McCarthy had hundreds of kids, you know, ‘Clean for Gene,’ who cut their hair and shaved their beards and [went] all over New Hampshire going door to door for the guy. Pat Buchanan — it was a show race, it was 10 weeks — but he [practically] lived in New Hampshire. … He had brigades, Buchanan brigades of activists. … And he had a message. Agree with it or disagree with it, it was a message about Washington and the establishment and Bush and raising taxes.”

Carney said that he probably will vote for Trump but that he is not involved in the primary. He and I spoke in the second week of July, when Weld acknowledged to me that his ground game needed to become more “intense,” and he promised it would in short order.

Only four young people were wearing Weld T-shirts at PorcFest, but nearly two weeks later, many more trailed the candidate as he walked the Fourth of July parade in Amherst. The campaign is counting on building momentum in the fall; after all, Buchanan didn’t fully engage until December. “If you look at New Hampshire, it really tends to be a kind of post-Thanksgiving race,” Stevens told me in the last week of July. Most of the media’s and voters’ attention was on the Democratic primary race, he said, but “there’s going to come a time when there’s going to be a focus on this Republican primary.”

We’ll know if Weld ever gets under Trump’s skin when the president starts tweeting about him. Trump’s reelection campaign and the Republican National Committee both declined to comment on Weld specifically. Tim Murtaugh, director of communications for Trump’s campaign, said in an email: “President Trump came within a whisper of winning New Hampshire in 2016” — referring to the general election — “and we are confident that he can add the Granite State to his win column in 2020. The Trump economy is benefitting all Americans, and nowhere is that more true than in New Hampshire, which enjoys one of the lowest unemployment rates in the nation.” An RNC spokeswoman said in an email: “President Trump enjoys unprecedented support among Republicans. … Any effort to challenge the president’s nomination is bound to go absolutely nowhere.”

Yet other observers are less dismissive. “He was a very successful governor, he’s extremely articulate, he’s pretty straight up about the case he makes against the president and how he differs from him, and I think independents will listen to him and Republicans who may not like the president will listen to him,” says Stephen Duprey, one of New Hampshire’s three members of the Republican National Committee. He emphasized that he is neutral in the race (and also that Trump has, needless to say, significant advantages).

Fergus Cullen, a former chairman of the New Hampshire Republican Party, held the first house party in the state for Weld in the spring — although, when we spoke at the end of June, he said he was still keeping his options open, in case others enter the race. He is an avowed Never Trumper — he supported John Kasich in the primary four years ago — and the author of the 2015 book “Granite Steps,” an authoritative history of the New Hampshire primary.

“What people like me are looking for is someone to serve as a vehicle to register opposition and disgust with the current administration,” Cullen told me. “And there’s a market for that. Now whether that market is 10 percent, whether it’s 20 percent, whether it’s 37 percent — which is what Buchanan got against Bush — I don’t know. But it’s greater than zero. And it’s probably greater than single digits.”

Cullen observed Weld keenly at the house party and came to a depressing conclusion. “His retail skills are excellent,” he says. “He is a natural-born politician. … He was able to speak with some level of depth on all sorts of issues, foreign and domestic. I remember thinking, ‘Boy, if he was running in a primary for governor of Massachusetts right now, he’d be really doing great, he’d be impressing people.’ But he’s running against not just any incumbent — it’s Donald Trump. So none of that stuff matters.”

Put another way, this primary won’t be won with issues and reason. It’s about something more elemental: identity and values. Weld must tap into the anti-Trump id, Cullen says: “He has to be [more] explicit in saying, ‘Look, if you’re uncomfortable with this president and his style, if you’re concerned that he’s not a role model for kids, if you think that he’s changing politics in a negative way, that he’s obstructed justice, that you don’t think it’s a good thing that he’s paid off porn stars and Playboy models, then we need to send a message that we can do better and that this isn’t the vision of the Republican Party or the conservative movement that we stand for. And I’m here to help you express that message.’ ”

Of course, there’s an argument against basing the campaign too much on this conceit. Democrats also are blasting away on those points. Why should a New Hampshire independent — who can vote in either primary — choose Weld to send that message rather than, say, Joe Biden, Elizabeth Warren, Kamala Harris, Pete Buttigieg or Bernie Sanders?

According to this line of thinking, Weld should focus on what distinguishes him ideologically — from Trump and from every Democrat. “Bill’s strongest point against Trump is that Trump’s a big spender and is exploding the deficit,” says Rob Gray, who served as press secretary to Weld in the 1990s. “That point is true to Bill’s record as governor, it’s true about Trump and it works in New Hampshire. I think if his campaign is going to take flight, it’s going to be on spending and the deficit and not just imitating the Democrats’ line about scandals and the Mueller investigation. That’s the lane that could give Bill a following in New Hampshire and other states.”

Gray adds: “This is the longest of long shots. But Weld damaging Trump enough so that he loses to the Democratic nominee is not the longest of long shots.”

Three weeks after I saw Weld in New Hampshire, he and his wife, Leslie Marshall, visited Manhattan. Weld did some fundraising and attended a directors meeting of a cannabis company, where he sits on the board with Republican former House speaker John Boehner.

Marshall and I chatted while Weld went to be interviewed by CNN. They wed in 2003 after his 25-year marriage to Susan Roosevelt Weld ended. Marshall, a novelist and magazine writer, had previously been married to Dino Bradlee, a son of then-Washington Post Executive Editor Ben Bradlee. Marshall also worked at The Post for two stints in the late 1970s and 1980s, including as a writer and an editor for The Washington Post Magazine. She and Weld reconnected in New York about 20 years after they had met briefly at a fundraiser in the late 1970s. Marshall has a clearer recollection of another early encounter a few years later, at a cocktail party around a swimming pool in Virginia. “I was talking to somebody standing by the side of the pool,” Marshall recalled to me. “And suddenly I am airborne. And then I’m in the water with another person who, when we come up, says, ‘Hi! I’m Billy Weld!’ I said, ‘What was that?’ He just said, ‘I don’t know, you just looked like you needed to be in the water.’ ”

Marshall told me she was charmed more than annoyed by the impromptu dunking. We both recalled Weld’s dive into the Charles, and Marshall noted: “I’ve always said he has a penchant for leaping into bodies of water fully clothed.”

She plans to be active in the campaign. “He’s way more [politically] dangerous than people are perceiving him as right now, but maybe that’s good for us,” she said. “I mean, this is a man who played simultaneous games of chess blindfolded.” Really? I asked. Yes, it turns out that at cocktail parties in law school, Weld used to beat three opponents at a time with his back to the chessboards, while they played normally. “His strategic mind is more wily than you think,” Marshall said. “He sees around corners, he sees way ahead.”

This must be the first primary campaign in American history where the challenger’s spouse has written a nine-page magazine spread about the incumbent. Marshall’s piece on Trump and his Trump Tower penthouse for InStyle magazine in the mid-1990s featured pictures of the ostentatious decor and glimpses of then-wife Marla Maples, and daughters Tiffany, 2, and Ivanka, 13. Trump bragged about his onyx bathroom fixtures and purported to take a conference call while snuggling on the titanic bed with Maples and Ivanka.

“Trying to track Donald Trump’s daily movement through his made-to-order tower, the glittering-gold complex that commands both a prime spot on Fifth Avenue and the highest rentals in New York, is a little like reading ‘Eloise,’ the children’s book about a mischievous 6-year-old who blitzes her way around New York’s Plaza Hotel,” Marshall wrote at the time. These days, she is traveling with “Tyrant,” by Stephen Greenblatt, a Shakespearean scholar’s take on, as she sums it up, “how it is that an entire country can fall and become enthralled with a man who is as bad as it gets.”

What are the odds that her husband could actually play a meaningful role in rescuing us from this fate? The answer may ultimately depend on whether there is a constituency in New Hampshire for a candidate who — in his manner, his worldview, his very essence — is almost like a laboratory-designed anti-Trump. “I can’t think of a single demand that Donald Trump makes on himself — not decency, not truth, not character, not integrity, not consistency,” Weld had told me after the Pride event. In a similar vein, to the audience at PorcFest, he had said, “My sense of what’s a democracy is it’s a form of organization where the individual shall never be thrust in a corner. I say this with a heavy heart, but all too often the first reaction of the current incumbent in the White House is, ‘Let’s by all means thrust the individual into a corner so we can maximize the amount of power that’s being centralized in Washington, D.C., and more particularly in my White House’ — Donald Trump’s White House.” (After the mass shooting this month in El Paso, Weld sharpened his attacks on Trump’s divisive rhetoric, declaring on MSNBC: “There’s no longer any doubt that the president has blood on his hands.”)

But Weld’s prospects may depend on one other thing, too: whether his interest in the chess-like aspects of campaigning can carry over into a world where Donald Trump has changed all the rules. Over lunch in New York, after my conversation with Marshall, I asked him how he used to take on three opponents simultaneously with his back turned to the chessboards. Weld demonstrated in the noisy restaurant by calling out nearly a dozen chess moves and the responses of a standard opponent. “Pawn to king 4 … pawn to king 3 … knight to knight-bishop 3 … knight to queen-bishop 3. …” The strategy, he explained, is to get “the king’s bishop, the king’s knight and the queen all focused on the same spot, which is diagonally adjacent to the king on the other side. People don’t see it coming. That’s too much firepower. … So that’s how [checkmate] happens in eight or 10 moves.”

When I returned home, I dug out a chessboard and set up the pieces. I had transcribed Weld’s recitation of chess moves, and now I tried to duplicate them. I pushed the pieces across the board, captured some pawns, focused the firepower. I tried it a few times before I realized Weld’s game plan didn’t quite work. The old chess player had left out one or two moves necessary for checkmate.

But I noticed something else: The king was grievously compromised anyway. It was, in other words, an outcome that Bill Weld’s Never Trump fans would happily claim as victory. Peradventure there’s a chance.

David Montgomery is a staff writer for the magazine.

Credits: Story by David Montgomery. Photos by Elizabeth Frantz. Designed by Christian Font. Photo Editing by Dudley M. Brooks.