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Geoff Diehl is kind of running for governor. Has a haphazard campaign strategy hurt his chances?

Republican gubernatorial candidate Geoff Diehl held a “Take Freedom Back Rally” at Faneuil Hall in Boston last week. It was one of the few campaign appearances in the final weeks of the campaign.Barry Chin/Globe Staff

The first of two profiles on the major candidates for governor. See Maura Healey’s profile here.

The campaign has advertised the wrong address. So six minutes after the event was scheduled to start on this warm September morning, reporters are milling around in front of the State House, wondering how Geoff Diehl intends to hold a news conference on steps that are being ripped out by a yellow excavator.

As it turns out, the team behind the Republican campaign for governor is on the other side of the majestic building, being ushered off State House grounds by security. A state official politely explains that political events aren’t allowed on public property.


When Diehl and his running mate finally appear on a nearby sidewalk, they rail against “failed Democrat policies” for four minutes and take questions for two more, as duck boats clatter by and tourists step around microphone wires. Then Diehl hops back into a white sedan. The show is over.

Greetings from the Republican campaign for Massachusetts governor, where the stakes for the state GOP are high but the intensity is often not. Embracing Donald Trump in a blue state that loathes the former president, as Diehl has, was never going to be the easiest path to victory. But Diehl has further diminished his chances, many observers argue, with a head-scratching and haphazard campaign strategy that has at times left even some Republicans wondering whether he is really trying to win.

As Election Day looms, the top Republican on the ballot is holding very few campaign events; his public schedule has been mostly fund-raisers. (He recently canceled a full-day swing through Eastern Massachusetts because of rain in the forecast.) Diehl’s most recent campaign finance report showed he had $89,000 — one-fortieth the cash of his opponent, Democrat Maura Healey. A recent digital ad attacking Healey had two spelling errors in a single sentence. And in a state where most voters are independents, Diehl snubs some mainstream media outlets but gives interviews to conservative platforms such as Newsmax.


Next week’s vote is an existential election for the state’s Republicans. If Diehl and the rest of the GOP ticket lose, the GOP will cede state government to one-party rule, with minimal bargaining power against Democratic supermajorities in the Legislature. A cherished tradition of divided state government will be broken.

Diehl’s team insists he still has a way to win. But political operatives on both sides of the aisle consider his loss inevitable. Every public poll of the race has shown Healey with a prohibitively wide lead — 28 points, then 18 points, then 26 points, 30 points, 23 points, and 27 points. Forecasters at Politico say Diehl is not mounting a “credible campaign” and label the contest “Solid Democratic.” (Diehl’s team slammed one recent University of Massachusetts poll as a “fraudulent” attempt “to suppress the vote,” while also pointing to growing support it found for him among independents.)

No cavalry is coming to help him. The state party is split into two uncooperative factions, and the side with money and a winning record appears to have no interest in helping Diehl, whose rise has been fueled by conservatives who deify Trump and despise Republican Governor Charlie Baker. Baker is staying silent on the race; the national Republican Governors Association, which poured millions into Baker’s campaign, has not spent a dime for Diehl.


‘His own man’

Diehl is sitcom-actor handsome, tall and serious-looking, with brown hair neatly parted on the side. He was an Eagle Scout, and you can tell. He really looks the part of governor, a number of political observers agree, in what some may intend as a backhanded compliment.

Diehl has run four successful campaigns for state representative and one losing race each for state Senate (2015) and US Senate (2018). The 53-year-old works now as the business development director for an auto parts company, and he lives in Whitman with his wife, Republican State Committee member KathyJo Boss, with whom he has two daughters. Outside politics, he owns and helps operate the family dance studio and has worked at two sign design companies and, briefly, as an Uber driver.

During his eight years in the Democratic-dominated Legislature, Diehl was known for fiscal and social conservatism. He vehemently opposed tax hikes, along with bills to cover birth control and to ban discrimination against transgender people. He notched few legislative accomplishments, according to a report compiled by the legislative analysis service Instatrac, and he filed fewer bills and spoke less during legislative debates than his Republican colleagues.

Perhaps Diehl’s biggest political win came in 2014, after the Legislature had voted to have the state’s gas tax automatically increase each year in line with inflation. Diehl led a statewide campaign against the proposal, and, in a major conservative triumph, voters rejected the tax increase. That same year, Baker won the governor’s race, taking the office back from Democrats. Diehl was extremely disappointed, according to two people who spoke to him about it at the time, that Baker did not reward him for his work fighting the gas tax with a high-profile transportation role in the new administration.


It’s the 2014 election magic that Diehl’s team is hoping to recreate this year. Amanda Orlando, Diehl’s campaign manager, noted that, like 2014, this year features a controversial ballot question that could drive up turnout for conservatives, as well as an open-seat race for governor in which the Republican started as the underdog against a Democratic attorney general.

“It’s a late-breaking state for Republicans,” Diehl told reporters at a recent campaign event. “I think we have as good a chance as anybody.”

But the ballot question this time round — about whether undocumented immigrants should be able to obtain driver’s licenses — looks less likely to go Republicans’ way, according to polls. And by this time in 2014, Baker had closed the polling gap with his Democratic opponent, Martha Coakley, even leading her in some surveys.

When you ask Massachusetts Republicans how Diehl’s current campaign is going, many begin to chuckle — right before they ask if they can speak off the record. Matt LeBretton, the finance chairman for Baker’s gubernatorial runs, has a Maura Healey sign in his front yard. Former Republican acting governor Jane Swift said she hasn’t decided whom to vote for (Should this Globe reporter call her back to check? “Don’t hold your breath,” she advised.) Conservative radio host Howie Carr put it bluntly on Twitter: “Geoff Diehl cannot win in November.”


“I don’t see him doing anything that a major party candidate would do to try to win a race, from policy proposals, to field organizing, to raising money, to moderating some of his positions,” LeBretton said. “There’s nothing there that says to me that this campaign is about winning.”

Republicans have held the office of governor for 24 of the last 32 years, winning this blue state with the same battle-tested playbook: Strike a moderate tone; stick to the economy; avoid social issues and national controversies. It elected Bill Weld, Paul Cellucci, and Mitt Romney; it has made Baker the country’s most popular governor.

Diehl is trying something else. What exactly, is not always clear.

He does, to be sure, offer a consistent economic message, slamming President Biden for inflation and Healey for rising energy costs, and pledging to make life more affordable for working-class families. But he is also running hard on controversial social issues that are unlikely to attract centrist voters.

In a state where most people support vaccine mandates, Diehl has been one of their most prominent critics. He is fighting hard for the ballot question that would overturn the new law allowing undocumented immigrants to obtain driver’s licenses, saying it would roll out a “red carpet.” That’s a galvanizing issue for Republicans but a divisive one among independent voters, a recent poll showed. Diehl is also pushing a “parents’ bill of rights,” fighting to give families more influence over school curriculum, as well as the option of using public dollars to send their children to private or parochial schools. A recent ad spotlights school prayer and calls for restoring “our Christian foundational values.”

These are not issues that typically win general elections in Massachusetts, strategists in both parties say, questioning why Diehl would make them central to his campaign. But the nominee and his team say he’s focusing on the issues that move him most, even if they are unpopular.

“Geoff’s his own man,” said Jay McMahon, the GOP nominee for attorney general. “Geoff takes tough stances.”

The Diehl campaign’s approach is emblematic, some longtime Republicans say, of the division within the state party. The Baker faction argues for following the moderate message that has won in the past. The other, which Diehl represents, argues that a Republican who wins that way is no better than a Democrat. Principles, they argue, are the most important thing — even if they cost you the election, even if it means one-party rule.

“It doesn’t really matter if you win,” said Massachusetts GOP Chairman Jim Lyons, a Diehl ally who leads the conservative faction, at a candidate recruitment event in February. “What matters is to get into the fight to teach other people there is another viewpoint.”

‘Geoff “the real” Diehl’

Diehl’s viewpoints are not always clear, nor are they etched in stone. He’s running an ad accusing Healey of not caring about the state’s transportation infrastructure. But when asked at a recent debate when he had last taken public transit, all he could recall was using a moving walkway at the airport.

And, on Trump’s false claims of fraud in the 2020 election, Diehl said in July 2021 that “I don’t think it was a stolen election,” but in August 2022 said it “definitely was an election that was stolen from Trump, and it was rigged.” Then, at the first gubernatorial debate in October, Diehl backpedaled again, cracking that, “Obviously Joe Biden won the election, look at the economy.”

And of course, there is Trump’s endorsement of Diehl, which helps in a Republican primary here but hurts in the general. Democrats are giddy over the opportunity to tie Diehl to the former president, whose brand is toxic in Massachusetts; Diehl is neither advertising nor running from the endorsement. Trump is listed in small type at the bottom of an online list of Diehl’s supporters, beneath members of the Chicopee School Committee and Agawam City Council, several former NFL players, and a Middleborough couple who go by “Mr. and Mrs. Gunrunner.”

In 2018, when Diehl ran for Senate against Elizabeth Warren, he faced similar long odds and ultimately lost by 24 percentage points. Still, he ran a spirited, energetic campaign, holding events at train stops, doughnut shops, parades, Patriots games, and scallop boats. In a single weekend in mid-October 2018, he advertised nine campaign stops, including six local fall festivals.

His schedule this time round is different: There hasn’t been much of one. Even in the final weeks of the campaign, Diehl listed just one appearance on most days: a fund-raiser. This year, on that same mid-October weekend, he held only two events, one of which was a fund-raiser in Connecticut.

Orlando said Diehl works full time and pointed to the light schedule for Healey. Strategists say the relatively slow pace of this campaign may be an indication that both sides consider the outcome — a Healey victory — all but guaranteed.

Diehl has been far outraised and outspent by the Healey campaign. He has only recently begun running television ads, spending just $200,000 on airtime so far, a fraction of Healey’s spending on commercials that have been running for months. In lieu of more paid outreach, he told reporters earlier this fall, “I’m hoping that, obviously, the news carries our message.”

But he declined repeated requests for an interview with the Globe. (“No offense,” Diehl said, “but I’m not sure what that achieves.”) Diehl does speak with other mainstream outlets, but more often, he takes his message to conservative platforms including Fox News and Newsmax. He has a regular appearance with Jeff Kuhner, a conservative talk radio host who railed recently against the “RINO Judases” he said are “crucifying [Diehl], stabbing him, shanking him at every single turn.”

With early voting already underway, Republican strategists said that Diehl can’t afford to focus only on a conservative audience, that he needs to be speaking to independent voters and trying to sway some Democrats. He’s still acting as if he’s trying to win a Republican primary, some critics say.

Others in his party wonder whether Diehl has another goal in mind.

“You have to really be focused on what the electorate wants in order to be successful,” said Jennifer Nassour, a former chair of the MassGOP. “I don’t think he thinks he can actually win. But I think he thinks he can get some other position after he’s done,” possibly as a TV personality, she speculated.

Orlando of the Diehl campaign said she is “very confident that our message is resonating with the right voters.” As for Diehl’s Republican critics, she added, “it’s unfortunate that anybody who claims to be a Republican isn’t doing everything they can” to defeat Healey.

At a campaign rally last week in Boston, Diehl sat placidly on stage in a large, throne-like wooden chair, legs crossed and hands folded, as the speakers before him pumped up the audience. They praised him as the one man standing between them and a liberal-run wasteland: “Geoff ‘the real’ Diehl.”

Then he rose to address the spirited crowd. Diehl was greeted like a champion quarterback, and his speech, two weeks before Election Day, was among the last opportunities to rally his team as it trailed badly with just minutes on the clock. Plowing through his stump speech, Diehl hit all the talking points: gas pipelines, taxes, vaccine mandates.

But — perhaps with his eye on that scoreboard — he also talked about the wins he has found in his losses.

“We didn’t win that race, I understand that,” Diehl said of his 2018 loss to Warren. “However,” he added, “we set the stage for what’s happening now.”

Emma Platoff can be reached at emma.platoff@globe.com. Follow her on Twitter @emmaplatoff.