If William Floyd Weld wins his primary challenge against President Trump, it will be the greatest political miracle since Jesus Christ intervened to advise Emperor Constantine before the Battle of Milvian Bridge.
Weld has no fan base, no name recognition, no political machine. His brand of let-them-eat-cake libertarianism has zero traction in either major party. His complaint to CNN that ‘the President does not exhibit curiosity about history’ probably won’t resonate with the party’s base, given how quickly they took to demanding Trump imprison his opponent once he was elected. 89 percent of Republicans approve of the President’s job performance, and the remaining 11 percent might be weary of voting for another Massachusetts governor.
The one thing Weld does possess is what we might call ‘the WASP Factor’. Following President George Bush’s death in November, Ross Douthat penned a tribute, not only to the late president, but also to his near-extinct race of Yankee patricians. Douthat extolled the WASPs for their ‘personal austerity and piety’ and ‘distinctive competence and effectiveness in statesmanship.’
And the Welds, if you can believe it, are even WASPier than the Bushes. The Governor’s ancestor Captain Joseph Weld was one of Harvard’s original donors. His namesake, William Floyd, signed the Declaration of Independence.
Yet Bill Weld is best understood as the antithesis of Bush 41. Where the former president exemplified the virtues of WASP statesmanship, Weld embodies its vices. Granted, they’re rather charming, as far as vices go. But if Poppy is the archetype, Big Red is the stereotype.
In 1978, Weld made his first go at public office, running for Attorney General of Massachusetts. When asked why he was seeking public office, he said: ‘I had been electrified by Teddy White’s The Making of the President book about JFK. It seemed like great fun.’
He first ran for governor in 1990 against Boston University president and arch-Ivory Tower liberal John Silber. When his campaign flagged due to lack of funds, he summoned his inner circle to his Cambridge living room. At the conclusion of their strategy meeting Weld supposedly pointed to a John Singer Sargent hanging on the wall and said, ‘We can always sell this painting.’ A staffer convinced him that wasn’t necessary; he kept the painting and he still won by three per cent.
Weld developed a friendly rivalry with William Bulger, the state senate’s longtime president. The two enjoyed ribbing one another over their ancestry. When Bulger made a crack about the governor’s ancestors coming over on the Mayflower, Weld famously shot back: ‘Actually they weren’t on the Mayflower. They sent the servants over to get the cottage ready first.’ Weld got him back on the St Patrick’s Day party by joking about Bulger’s brother James, the former leader of the Winter Hill Gang and FBI ten most wanted fugitive. Ha ha!
In 1994, Weld ran for re-election against his wife Susan’s cousin, Mark Roosevelt. (The hero of San Juan Hill is their common ancestor.) Bill won by the largest margin in Massachusetts history. But colleges complained that he ‘quickly seemed bored with the job.’ A former aid explained: ‘You know how some CEOs are maintenance guys and some are turnaround guys? Bill’s a turnaround guy.’
So, in 1996, he contested John Kerry’s Senate seat (why not?) and lost. The next year he resigned as governor to accept an appointment as ambassador to Mexico, but the Republican-controlled Senate Foreign Relations Committee refused to even give him a hearing. Weld then decided to move to Manhattan and take a job in the private sector. He ran for governor of New York in 2006, losing by an almost 3-to-1 margin.
Then, to the bafflement of many veteran libertarians, Gary Johnson chose Weld as his running-mate in 2016. They were right to be suspicious: on no fewer than two occasions during the race, Weld suggested Hillary Clinton was best-suited for the job. He and Hillary are old friends, going back to their days as counsels to the House Judiciary Committee during the Watergate hearing. A long-awaited biopic called Rodham casts Weld as a rival suitor during the early days of Bill and Hillary’s courtship.
There was speculation that Weld would run for the Libertarian party’s nomination in 2020. He even appeared at the Students for Liberty’s LibertyCon this January. Then, about two weeks later, he re-registered as a Republican and…well, I suppose we’ll have to wait and see what comes next.
I have one anecdote about Weld that seems pertinent. Shortly after graduating prep school, I – a wee blue-blazered WASP myself – landed a job with the Massachusetts Republican party’s campaign arm. Weld’s protégé Charlie Baker had recently lost his first tilt at the State House but was already calling the shots. Our efforts were concentrated on yet another Massachusetts governor whom the Republicans had recently nominated for the 2012 election – not a WASP, but a Mormon. This was my political baptism.
Fast-forward four years. Though I voted for Trump in the 2016 Republican primary, I still feel an ingrained loyalty to the GOP’s liberal Northeastern wing. So, after the Libertarian party nominated Weld for Vice President, I offered my services as liaison to New England’s liberal Republicans.
I remember pacing the parking lot outside the local Brooks Brothers, chain-smoking and ringing up every hack and donor in my Rolodex. Each and every one responded the same way. First, they’d laugh themselves into a coughing fit. Next they would say something to the effect of: ‘That useless old drunk? You gotta be kidding.’ Then the line would go dead.
I can’t fault anyone who pines for a return to the temperate, genteel rule of the American optimates. But take it from those who know him best: anyone looking to Weld for leadership will be sorely disappointed.