Can a pro-choice, pro-amnesty "Libertarian for life" who backed Barack Obama in 2008, thinks the phrase "all lives matter" is "nothing but a dog whistle," and maintained throughout 2016 that Hillary Clinton is preferable to Donald Trump, truly be competitive in the 2020 Republican Party presidential primary? That's what Bill Weld is set to begin finding out in New Hampshire tomorrow morning, when he takes what his friends are forecasting as a substantial move toward declaring his candidacy for president.

Weld, the 2016 Libertarian Party vice presidential nominee and current* honorary chair of a nonprofit whose purpose is to "stop the political duopoly" (*Update: Our America Initiative announced this afternoon that Weld has resigned that post effective today), took the pre-primary step January 17 of switching his Massachusetts voter registration back to a Trump-led GOP that he has repeatedly compared to the xenophobic Know-Nothing Party of the 1850s. He has scheduled a second New Hampshire visit for February 26, he has recruited former New Hampshire Republican Party Chair Jennifer Horn to help, and his allies are writing thinkpieces about how "Democrats' hopes to take back the White House may lie in the hands of a Republican candidate." (Update 2: WMUR is reporting that Weld will announce Friday the formation of an exploratory committee.)

Like potential independent candidate Howard Schultz and Democrats, Weld's reception among Republicans has been on the chilly side, with even his own Trump-averse protégés, such as Massachusetts Gov. Charlie Baker, making cautious statements like, "I'm a big fan of Bill Weld the person, but the decision he makes to run for office is very much his own."

The northeastern moderate conservative was already an endangered species long before Donald Trump began reshaping the GOP; you can count the number of pro-choice Capitol Hill Republicans on half of one hand. Weld stands opposite Trump on trade wars, immigration crackdowns, the national debt, entitlement reform, the rule of law ("Well honestly, hasn't our incumbent done six times [more than Richard Nixon] in public with Manafort in the investigations?" Weld said to me last month), and what he described at the Libertarian Party National Convention last July as "this pitting of us against them and trying to divide everybody."

So why the interest in being a bug on Trump's windshield? Aside from the opportunity to be the first declared 2020 Republican competitor (and near his home turf, to boot), with all the national and local press attention that could generate, Weld has long been nurturing the theory that modern politics are inherently unpredictable. "You think about Donald Trump in 2014, you couldn't got 100 to one on Donald Trump," he said at the L.P. national convention last year. "Emanuel Macron from France in 2015, which is two years before he was elected, you couldn't count on 100 to one for him, because his party didn't exist."

With Trump shaking up the GOP even more than independent Sen. Bernie Sanders (I–Vt.) shook up the Democratic Party in 2016 and beyond, the perpetually bemused Weld might be thinking, so you're saying there's a chance. "I think he is probably noting that he won his first gubernatorial election in 1990 in a state where only 14 percent of voters were Republicans," New Hampshire Republican consultant and Weld confidant Tom Rath told WMUR. "[He] appears to savor a challenge at the point where he feels as though 'If nobody else does something, I'll do something.'"

If Weld indeed takes the Republican plunge, he'll have an awful lot of his own recent GOP bashing to contend with, including his statement at the Libertarian Party Massachusetts just four months ago that "I think [there's] going to be a crevasse in the two-party monopoly, which is our bounded duty to destroy by every means at our disposal….I feel that either the Libertarian Party has seeped into my veins, or I've seeped into the Libertarian Party a lot in the last couple of years."

Here are seven more occasions over the past 15 months that I have witnessed Weld lambast the leaders and followers of the political party about which he said upon leaving, "I feel free, free at last." All quotes are verbatim.

1) January 20, 2019: LibertyCon, in Washington, D.C.

Lately, I've become more and more concerned about what's going on in D.C. It seems to me that certain actions seem to go beyond lack of stability—which, as you know, I complained about throughout the 2016 cycle. Maybe even crossing the line into deranged decision-making.

2) October 13, 2018: Massachusetts Libertarian Party convention, Springfield.

Make no mistake about it, both the R Party and the D Party, they're both nanny-state parties….I never say "duopoly," because I think it doesn't register with a lot of people; I just call it the two-party monopoly in Washington, D.C. And there's an awful lot of people who think, for whatever reason, that they've got to do what mommy did and what daddy did. And that's the reason for a lot of the adherence to the R Party and the D Party. It's not rational at all.

3) July 30, 2018: Reason Podcast, Las Vegas.

If you recall, back in the 2016 convention they said "How do you feel?" after I became a Libertarian candidate, and I said, "Free! Free at last. Because I've been running for office for 20 years carrying around the Republican Party's social policies like a 30-pound weight on my back."… Matt Welch: Has Trump been as bad as you forecasted? How has he played out in your mind, compared to what you were warning about those two, three weeks before the election? Weld: Worse, worse. Welch: In what way? Weld: Well, to lie every day to the American people, that is something….To say to NATO, "We've got to go to four percent [of GDP spending on defense]," and to say the next day, "No, I never said that, I didn't say that," even when the things he said were on the public record. It's like he doesn't care whether what he says is true. And I don't think this is a vicious dig, I think this is right out there on top of the record. People say, "Well, he's invincibly ignorant, he can't be held to account." I don't buy that for a second, he's teaching lessons to our children, to the next generation, and that should not come out of the Oval office in the White House.

4) July 1, 2018: lunch talk at the Libertarian National Convention, New Orleans.

I've always been a liberal about immigration—part of it for economic reasons, not moral reasons. But I got the prize every year, the Golden Door Award, for being the most welcoming towards immigrants. Because I read the history books, I know that America's strength is that it has always been a melting pot. So just showing the snarl of teeth—which candidly, is what this president is doing—is really not helpful.

5) April 29, 2018: Interview at the California Libertarian Party Convention, Long Beach.

I did express [in 2016] the fact that I thought that [Hillary Clinton] was maybe more palatable than the Republican candidate, whom I've compared to certain figures in Germany in the 1930s and '40s, and never saw anything during the campaign that made me see fit to change my opinion there.

6) April 28, 2018: Speech at the California Libertarian Party Convention, Long Beach.

The number one thing we need to do by November 2020 is to elect a Libertarian president of the United States. This is entirely feasible….My own view is that both the R party and the D party are splitting in half right now; they just don't know it yet.

7) November 4, 2017: Students for Liberty Conference, New York.