William Weld Could Make 2020 Interesting. Here’s How.

The former Massachusetts governor could be popular enough in New Hampshire to damage Trump.
by Liz Mair
February 14, 2019
Featured Image
(Photo illustration by Hannah Yoest. Photo of William Weld by Getty Images.)

If you’re tracking 2020 presidential primary politics, you already know that former Massachusetts Gov. Bill Weld may announce a primary challenge to President Donald Trump on Friday.

The prospect is already ginning up giggles in some quarters. To wit, I had a small, and tepid, Twitter back and forth with a talk radio host friend who happens to be a former RNC digital director about it on Wednesday.

But let’s be clear: While it’s very unlikely that Weld (or anyone else, for that matter) is going to beat Trump in the totality of the 2020 primary contest, or even grab a substantial number of delegates, Weld running as the anti-Trump Republican might not be as stupid a move as a lot of people seem to think.

Weld hasn’t been in office for some time, so the presumption is that he just isn’t very well-known—a massive problem for anyone who wants to run for the presidency and achieve any measure of success.

But in Weld’s case, that broad assumption is wrong on a few fronts and that could matter greatly.

Weld was the governor of Massachusetts between 1991 and 1997. What state neighbors Massachusetts, sits within the Boston media market, and over the last 20 to 30 years happens to have become home to a huge number of moderate-conservative types who normally vote Republican and have exiled themselves from “Taxachusetts”—but many of whom still commute in to Boston for work every day?

That’s right, it’s New Hampshire, home to the first-in-the-nation primary, a virtually non-existent tax regime, and a propensity for the weird–like a protest that occurred in front of the state capitol there about 10 years ago featuring yoga practitioners doing “down dog” while exercising their Second Amendment rights, fully armed with big guns.

New Hampshire has been the migration point for the “Free State Movement,” which seeks to get libertarian-minded people to move more firmly entrench its standing as a home for individuals who favor free markets and free thinking.

Weld is well-known in the state whose motto is “Live Free or Die,” and he undoubtedly has better currency there, because of all these factors plus one more: He was the 2016 Libertarian vice presidential nominee in a year when the Libertarian ticket got about 3.3 percent of the vote nationwide and 4.2 percent in the Granite State itself. Tack on some aggrieved #NeverTrumpers who voted for Clinton in 2016 but will play in a GOP primary contest in 2020, plus independents and moderate-to-libertarian Republicans who have fond memories of Weld, and it’s pretty conceivable that Weld could get to 10 percent or higher.

That is especially so since during 2016, Weld arguably had higher visibility than the actual presidential nominee, Gary Johnson—a trend he’d likely continue in 2020, because Weld handles himself well on TV. He’s clever and funny, a good recipe for a cable news interview.

Weld is a former prosecutor and governor. And those who have fled Massachusetts since his tenure (many of whom are now prime voting age for a Republican primary) will remember his solid fiscal record. According to the Cato Institute’s Fiscal Policy Report Card on America’s Governors—compiled by Stephen Moore, a Trump economic policy advisor—Weld earned top marks for his fiscal stewardship (one of only two “As” awarded in 1992, and “Bs” placing him in the top four of his gubernatorial “class” in 1994 and 1996). That might matter for New Hampshire voters, who could reasonably be expected to be more pissed off than your average bear about a $22 trillion national debt. And let’s not forget that New Hampshire allows Independents to vote in its Republican primary.

The fact is, if Weld plays his cards right, he could come out of New Hampshire with a not-insignificant percentage of the vote. And what happens in New Hampshire has a tendency to totally upend presidential nomination assumptions and voting patterns afterward.

Remember: Trump did not win the Iowa caucuses in 2016. But he did win New Hampshire by a mile, re-establishing him as the frontrunner in 2016.

Also remember, in 2008, Hillary Clinton did not win the Iowa caucuses and her campaign was viewed as being in a downward spiral. But she did win in New Hampshire—a big surprise, so much so that her communications director was visibly sartorially unprepared for doing TV interviews to talk about her performance on the night— and it put her back in contention, helping to draw the Democratic nominating contest out far, far longer than Obama backers had predicted or hoped.

New Hampshire is also where President George H.W. Bush’s re-election vulnerability became visible in 1992. Contrary to popular belief, Pat Buchanan did not in fact defeat Bush there, but he gave him enough of a run for his money that Bush emerged very damaged.

Whether Bush’s soft underbelly was the reason Bush underdelivered in New Hampshire and subsequently lost to Bill Clinton in 1992, or whether Bush’s underdelivery in New Hampshire exposed the soft underbelly and caused him to lose in 1992 is a matter for debate. What we know for sure is that if someone racks up votes against a sitting GOP Ppresident in New Hampshire, the whole perception of a presidential race changes. And Weld looks like he has some ability to effectuate that in 2020.

Weld is going to need to raise a lot of money in order to make this project even semi-viable—assuming he does in fact announce on Friday.

But he’s always had a following with wealthy, New York and Boston GOP donors of the type who haven’t necessarily been thrilled with Trump and see him as responsible for the GOP’s pounding in 2018. He also probably has the ability to tap into small dollar, libertarian-y donors who would rightly credit him in part for the 2016 Libertarian ticket’s historically strong performance.

Ahead of Mitt Romney’s first run for president, Weld raised money for him– $50,000 for Romney’s exploratory committee in one day.

Weld is also not exactly poor himself. He comes from old money—very old money—so much so that he joked to Business Insider in 2016 that his ancestors weren’t on the Mayflower because they sent their servants over first to get the summer cottage ready, and that they came to the U.S. with nothing but the clothes on their back and £8,000 (the equivalent of about £1.1 million, or $1.4 million in today’s money).

Set aside that probable inherited wealth. Weld has been a partner and several firms known for their revenue-for-partner figures. Today he is on the board of a big cannabis company, Acreage Holdings—and cannabis is the fastest growing industry in the US.

The point here is, while I doubt anyone beats Trump for the 2020 nomination or forces an honest-to-God floor fight or redux of 1976, if Weld runs, there are a lot of reasons to project he won’t be a total nothingburger when push comes to shove. Watch what he does Friday—and if he does what he looks likely to, watch what comes next. It could be very, very interesting.

Liz Mair

Liz Mair is a former communications adviser to the Republican National Committee, Carly Fiorina, Rick Perry, Rand Paul, and Scott Walker. She supported and campaigned for Gary Johnson in 2016. She is also the founder, owner, and president of strategic communications firm Mair Strategies LLC.