The ancestral home of the moderate Republican faces Trumpian swing

BOSTON — Massachusetts voters have twice rejected former President Donald Trump. That may not stop one of his acolytes from becoming the Republican nominee for governor Tuesday.

Although the Bay State’s rank-and-file GOP have long promoted socially agnostic fiscal conservatives who can win over independents and frustrated Democrats, Trump is hoping to bulldoze that tradition with former state Rep. Geoff Diehl.

State party leaders have been torn between embracing the former president and eschewing his rhetoric. Now, Republican voters are heading to the polls to either support a Trump-backed conservative for governor or a political newcomer who’s become a beacon for the once-dominant strain of New England GOP moderates. And while the few public polls available show Trump’s pick leading, September surprises have kept party insiders, advisers and even the candidates guessing about Tuesday’s outcome.

Trump declared Diehl the “only conservative” running for governor in deep-blue Massachusetts during a telephone rally Monday night. Chris Doughty, Diehl’s rival for the nomination, Trump said, is just a “tool” of outgoing Republican Gov. Charlie Baker, a Trump nemesis who has not endorsed in the primary.

“Doughty will do nothing but surrender to the left-wing extremists,” Trump said in his five-minute speech, painting the businessman who was virtually unknown a year ago as a puppet of the establishment. “If you want to save Massachusetts from the radical left … you must vote Republican up and down the ballot, and vote for Geoff Diehl.”

A Trump endorsement also looms over a contest next week in New Hampshire, among the last primaries in the country. It’s a race where insiders say the former president’s nod could propel either a far-right candidate who champions his election denials or the establishment-backed state Senate president against vulnerable Democratic Sen. Maggie Hassan.

In Massachusetts, Diehl is looking to capitalize on the vocal pro-Trump faction of the state’s Republican base and those who believe Baker has shifted too far left during his eight years in office.

Trump’s endorsement is “certainly something that’s going to help make sure that we have a victory,” Diehl told reporters while campaigning in Boston last weekend.

But his opponents, a mix of conservative and moderate Republicans that include allies of Baker, say Trump’s endorsement can only spell trouble in a general election in one of the most anti-Trump states in the country. And presumptive Democratic nominee Maura Healey, who election handicappers say is likely to flip the governor’s seat blue in November, burnished her profile by repeatedly suing the Trump administration as state attorney general.

The Massachusetts gubernatorial primary is as much a proxy war between the Trump wing of the GOP and more moderate New England Republicans as it is a battle for control of the state Republican Party. The Massachusetts GOP has in recent years been defined by the power struggle between conservative, pro-Trump Chair Jim Lyons and the moderate Baker. But Baker’s decision not to seek a third term left his wing of the party with a power vacuum, and Doughty is now the one standing in the way of a Trump takeover.

“Our party is headed off a cliff in Massachusetts by supporting candidates that are frankly unelectable,” Amy Carnevale, a GOP state committeewoman who voted for Trump but is backing Doughty in the gubernatorial primary, said in an interview. “This primary has essentially become a referendum on the future of the Republican Party in Massachusetts.”

Voters in solidly blue Massachusetts have elected fiscally minded yet socially moderate Republican governors like Baker and Bill Weld for the better part of 30 years.

But Diehl rejects that mold. The conservative former state representative describes himself as “pro-life” in a state where more than three-quarters of residents believe abortion should be legal in all or most cases. He opposes the coronavirus vaccine mandate for state workers implemented by the ever-popular Baker.

And, after initially veering away from Trump, Diehl tied his fate to the former president and his rhetoric. He brought in Trump’s former campaign manager, Corey Lewandowski, as a senior adviser and has falsely claimed the 2020 election was “rigged.”

Diehl’s hard-right Trump turn played well at the state GOP convention in May, where he walked away with the party’s endorsement for governor after winning a resounding 71 percent support from roughly 1,200 party activists. He followed it up by campaigning with South Dakota Gov. Kristi Noem, a Trump ally, in August.

But Trump — who jumped into the GOP primary back when it seemed like Baker would seek a third term and who again made clear he’s “not a fan” of the governor during his telephone rally for Diehl — could walk away from Tuesday’s primary a loser.

Republicans make up less than 10 percent of registered voters in Massachusetts. The majority, 57 percent, of voters are unenrolled and can pull a Republican ballot in the state’s open primary.

That larger electorate has little love for the former president. Voters here resoundingly rejected Trump in both of his presidential bids and sent likeminded down-ballot candidates packing in 2020. Diehl, who co-chaired Trump’s 2016 campaign in Massachusetts, also lost his 2018 campaign against Democratic Sen. Elizabeth Warren by 24 points.

Diehl argues that his experience running a statewide campaign will help him this time around and that his platform of “restoring people’s freedoms” will appeal across party lines to parents who want more say in their children’s education and people tired of living under pandemic rules.

“Obviously, things like having the president’s endorsement help with Republicans in the primary, but my messaging has always been targeted towards that independent voice out there,” Diehl told reporters while campaigning in Boston over the weekend. “I understand that there’s going to be Democrats who are going to have a tough time thinking of voting for me. But I think there are event ‘light’ Democrats who are looking at me and saying ‘he’s talking about the things that are important to us.’”

Still, Doughty’s supporters say their candidate is more electable. They argue the wealthy businessman who’s poured more than $2 million of his own money into his first campaign is better positioned to take on Healey — a fundraising juggernaut who had more than $4.7 million in her campaign coffers at the end of August — than Diehl, who ended last month with less than $17,000 in his bank account.

And they point to the fact that, in a bizarre turn of events, influential conservative talk radio host and Boston Herald columnist Howie Carr — a Trump ally who backed Diehl in his bid against Warren — started urging his listeners last week to vote for Doughty.

Doughty’s political leanings are murky at best. He initially labeled himself a moderate, then eschewed the term. He opposes vaccine mandates, describes himself as “pro-life” — though he’s vowed not to try and change state law protecting abortion access — and has left the door open to voting for Trump in a future presidential run.

“I’m pragmatic and common-sense. I’m not extreme,” Doughty said in an interview. “I speak to everybody that’s just sort of sick of the extreme on both sides of the parties.”

And he’s won the support of more moderate Republicans — including New Hampshire Gov. Chris Sununu — through what they describe as his willingness to embrace bipartisanship in a state where Democrats control the Legislature with supermajorities in both chambers.

“He’s not a moderate,” Carnevale, the state commiteewoman, said. “But I think he understands what it takes to govern in Massachusetts — and that’s the winning formula that we’ve seen time and time again on the Republican side for governor.”