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Could former Massachusetts Gov. Bill Weld be the candidate who can topple President Trump in the 2020 primary?
According to some Republicans, crazier things have happened.
“Trump has changed politics in a permanent way,” said Fergus Cullen, a former chair of the New Hampshire GOP and self-proclaimed “never Trump” Republican. “The traditional path to a presidential nomination is all out the window now.”
Weld could begin a bid for the White House Friday in New Hampshire, where he will be the featured speaker at a “Politics & Eggs” breakfast event in Bedford and make his case to anti-Trump Republicans, independents and disillusioned Trump voters who may be looking for an alternative in 2020.
Weld has been cagey about whether his speech will include a campaign announcement, telling the Boston Globe recently that his speech "will deal comprehensively with my thoughts about the 2020 election."
Weld didn't respond to questions for comment.
Weld has stoked presidential speculation with his vocal criticisms of Trump, and by his recent decision to return to the Republican Party after spending several years as a registered Libertarian. In his speech, Weld isn't expected to pull any punches when it comes to his views of the president.
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If he does declare his candidacy or announce the formation of an exploratory committee, Weld would become the first Republican to announce a primary challenge to Trump.
The road to the White House would be a difficult one for any Republican who enters the race. The odds against ousting an incumbent president are long, and Weld comes with a history of failed political campaigns in the years since he easily won two terms in Massachusetts’ corner office in 1990 and 1994.
Weld challenged John Kerry’s Senate reelection bid in 1996 and lost, and also launched an unsuccessful campaign for New York governor in 2006.
After leaving the Republican Party, he became the 2016 Libertarian vice presidential candidate — a move that could turn off some Republicans who would otherwise have given him a look in 2020.
But Weld wouldn’t necessarily have to win the primary to topple Trump, strategists said. They point to a number of recent presidents who fended off serious primary challengers only to lose in the general election: Gerald Ford, Jimmy Carter and George H.W. Bush.
“If Weld runs as a Republican, it’s a significant challenge to Trump,” said GOP strategist Rob Gray, Weld’s former press secretary. “Trump will be fighting two wars: one with the Republican challenger and the other with the Democratic candidate. That is very difficult for a president to do.”
But Republican strategist Ford O’Connell said the analogies to Ford, Carter and Bush “don’t work with Weld in the equation.”
“I see this, like his 2016 Libertarian vice presidential nomination, as a way to keep his name in the news,” O’Connell said. “Unless something dramatically changes, Trump has a stranglehold on the 2020 Republican presidential nomination.”
There are other perils for Weld should he throw his hat into the race. One is timing: It may simply be too early to launch a campaign that has the staying power to be effective.
Cullen, the former state GOP chair, noted that Pat Buchanan’s challenge to Bush was launched only 10 weeks before the 1992 New Hampshire primary, where he made a strong showing.
“There is a risk, whether you are Bill Weld or anyone else, of coming out too soon, and letting early media coverage of your race drive your campaign more than traditional grassroots efforts,” Cullen said.
There is also the prospect of becoming a target of the president. Trump has made no bones about using his Twitter feed and campaign stump speeches to criticize, insult and give pejorative nicknames to his political opponents, like Elizabeth Warren.
Gray said Weld could withstand the heat.
"I worked for Bill for a long, time, and he is the definition of having a thick skin," Gray said. "I doubt anybody would be more ready to sustain the Twitter blows that Trump will undoubtedly direct at him."
This segment aired on February 15, 2019.
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