Geoff Diehl, a pro-Trump Republican, hopes to ride red wave into Mass. governor’s office

Republican Geoff Diehl has charted an unlikely path to the governor's office in Massachusetts.

The former state representative is running as a pro-Trump candidate in a state so blue that residents voted against the former president by a 2-1 margin. Twice.

Diehl's last attempt to win statewide office did not go much better. In 2018, he challenged Sen. Elizabeth Warren and lost by a wide margin. But Diehl pledged not to give up his quest for higher office.

After the race was called, Diehl told supporters: “I am a firm believer that when God shuts a door, he opens a window somewhere, so together we're going to find that window."

Now Diehl thinks he has found that window. He has Donald Trump's endorsement again. Charlie Baker, the popular Republican governor, declined to seek a third term, creating an open race. And polls show Diehl has a big lead over businessman Chris Doughty in the GOP primary in September. The winner will face off against Attorney General Maura Healey, a Democrat, who is widely considered the front runner in the governor's race.

Moreover, many Republicans are hopeful a red wave this fall will sweep conservatives like Diehl into office across the country — even in blue states like Massachusetts, where Healey holds a huge lead in early polls.

Diehl has overcome challenges before. He shared his personal story in an interview at his campaign headquarters in downtown Plymouth, as campaign volunteers delivered a stack of new, bright red Diehl-for-Governor lawn signs.

“When my Mom was raising me after she was single, it was difficult times,” Diehl said. “Economically, we didn’t have a lot.”

Diehl was born in a steel town in eastern Pennsylvania, where his parents divorced when he was 8 — an experience that he described as scarring. He still recalls the time he was brought before a judge, who asked him which parent he wanted to live with.

“How incredibly hard is it to have a kid answer that question,” Diehl said. He paused for a moment, as if taken back to that moment in the courtroom, before continuing. “Yeah, that’s painful.”

Diehl said that as he grew up, he searched for stability, “a reaction” to those difficult times. He became an Eagle Scout, studied government at Lehigh University and started a family.

He met his wife, KathyJo Boss, on a blind date. Five months later, they were married and eventually moved to her hometown of Whitman, next door to Brockton. They have been together 26 years and have two daughters.

Diehl was drawn to Republican politics, even though he grew up in a family of Democrats and was a Democrat himself. But he left the party in 2008, when Barack Obama ran for president and called for higher taxes on the wealthy, including many business owners.

Diehl, who owns a small performing arts company with his wife, was outraged by Obama's proposal.

“That that was like the last straw,” Diehl said. “We know what it's like to put our life savings into something and not expect government to help us out.”

In 2010, Diehl ran for state representative as a Republican and won. He pushed successfully for a ballot initiative that stopped the state gas tax from automatically going up with inflation. And he won three more terms in the House.

But Diehl has struggled to win higher office. He lost a special election for the state senate in 2015. And when he challenged Warren four years ago, he got clobbered — 60% to 36% — despite Trump's endorsement.

Trump himself lost Massachusetts by an even bigger margin two years ago. But Diehl credits the former president with strengthening the economy and prioritizing American interests.

And while Diehl does not fully embrace Trump's baseless claim that the 2020 election was stolen, he comes close.

“It was highly suspicious that in the 2020 election, five states stopped counting ballots at 10:00 p.m.,” he said in a recent online chat with supporters.

And back in December, Diehl told WBUR the election would have been “a lot closer if all the states had conducted themselves correctly.”

Diehl acknowledged that Congress has certified the election, and the party needs to move on. But he supports stricter voting rules for future elections, including limits on mail-in ballots, which he calls an invitation to voter fraud.

The former state rep had to give up seeking another term in the state Legislature to challenge Warren in 2018. For the past two years, he has worked as an executive for an auto parts distributor owned by a Republican donor.

But Diehl never completely left politics. In 2021, he launched a YouTube series showing him driving across the state in a Ford Bronco, reminiscent of Scott Brown's statewide tour in a pickup truck during Brown's successful campaign for the U.S. Senate.

And in May, Diehl overwhelmingly won the endorsement at the state GOP convention in Springfield, where he pledged to challenge liberal policies. 

"No more drivers licenses for illegal immigrants," Diehl declared to cheering delegates. "No more putting masks on kids in schools and teaching our children to be ashamed to be Americans.”

At a recent rally in Lowell, Diehl said he was the conservative who had the guts to challenge Elizabeth Warren, who he described as the state's "most liberal politician." Though he lost that race, Diehl said this year is different — because Republicans are riding a wave of discontent that will sweep them into office.

“We’ve got to make a change in 2024, but it starts right here in 2022,” Diehl declared.

State GOP Chairman Jim Lyons said the Republican case for change in Massachusetts comes down to one person: President Biden.

“The best argument that we have is the Democrats,” Lyons said at the rally in Lowell. “Who sits around … at their dinner table and says, 'Let’s talk about gender transition in the third grade?’ I mean, $5 gallon gasoline? These people are off the charts.”

But Republicans have typically won the governor's office in Massachusetts in recent decades with moderates like Charlie Baker, Mitt Romney and William Weld — who appealed to independents and even some Democrats.

Loring Barnes, a Republican from Millis running for state representative, says Diehl’s ties to Trump make him unelectable in Massachusetts.

“I think people are exhausted by that,” said Barnes, who is backing Doughty, Diehl's GOP rival. “They want someone who’s more inclusive and doesn’t only see the world through one perspective.” 

Still, many conservative Republicans say they don't want to settle for another moderate, like Baker.

Mary Lotze, a Republican from Fitchburg, said she’s backing Diehl because he’s "a real conservative" and calls Baker  “a RINO” — a Republican in name only. 

“We need to have a definite distinction between the Democrats and the Republicans because without that we have just this mishmash, which is what we have now in the State House,” Lotze said.

For his part, Diehl says he's running for governor to make a difference, inspired by the Scouting motto: "Leave the campground better than you found it." But he knows that politics have divided that campground.

“The problem is we're starting to see politics continue to diverge further and further away nationally, and it seems to seep into Massachusetts, as well,” he said.

For Diehl’s longshot campaign to be successful, he will need to convince lots of independents and moderate Republicans — and perhaps even some Democrats — to cross an ever-widening political divide and vote for a conservative Republican.

In this politically divisive moment that’s a tall order, something Diehl understands personally. In a candid moment, Diehl said he can no longer even talk about politics with Democrats in his own family. Not even with his own mother.