When Ben Downing, the first candidate to jump into the 2022 governor’s race, ended his campaign a month ago, he warned his fellow Democrats not to take victory for granted. “I’ve heard too much, from too many Democrats … that with Gov. [Charlie] Baker and Lt. Gov. [Karen] Polito not running for reelection, that somehow this race is a slam dunk and a guarantee,” Downing said.

Given Baker’s high approval ratings, it’s easy to see why some Democrats might have celebrated his decision not to seek a third term. But the complacency Downing described also suggests a low regard for Geoff Diehl, the former state representative from Whitman who announced his run for governor last July.

Diehl served in the Legislature from 2011 to 2018, and in 2014, he helped lead a successful ballot-question campaign to end automatic hikes to the state’s gas tax. Lately, though, Diehl’s electoral fortunes have foundered. In 2015, he ran unsuccessfully in a special election for state Senate. In 2016, when he helped lead Donald Trump’s presidential campaign in Massachusetts, Trump lost the state to Hillary Clinton by 27 percentage points. And in 2018, after winning the Republican nomination for U.S. Senate, Diehl was routed by Elizabeth Warren in the general election, winning 36 percent of the vote to Warren’s 60.

Despite those setbacks, however, dismissing Diehl as unelectable would be a mistake. Thanks to the idiosyncrasies of Massachusetts politics, the 2022 governor’s race will offer him structural advantages the 2018 Senate race didn’t. And while Diehl’s strengths as a campaigner and candidate are debatable, he possesses one invaluable skill: an ability to intuit what various constituencies want to hear and to shape his message accordingly — even if that means, on occasion, saying different things to different people.

For the record, it’s not just Democratic partisans who struggle to take Diehl seriously. In 2021, when a primary contest pitting Baker against Diehl looked likely, former state GOP chair Jennifer Nassour told GBH News her party would be foolish to make Diehl its nominee. “If you cannot win for state Senate, and if you cannot win statewide office running for U.S. Senate, then the chance that you can actually win in a general election for governor is pretty slim to none,” Nassour said.

Paul Watanabe, a professor of political science and the director of the Institute for Asian American Studies at UMass Boston, is similarly pessimistic. For one thing, he thinks Diehl’s recent losses will keep Massachusetts voters from seeing him as a fresh political face in the mold of then-state Sen. Scott Brown, who stunned Democratic nominee Martha Coakley in the 2010 U.S. Senate special election that followed the death of Ted Kennedy.

What’s more, Watanabe sees Diehl’s pitch — which includes an early endorsement from Trump and staunch opposition to mask and vaccine mandates — as inherently limited, compared to those of Republicans who’ve previously become governor.

“You can get every Republican vote and still get [just] 10 percent of the vote in Massachusetts,” Watanabe said. “That’s not a substantial amount. You’ve got to be able to appeal broadly. … I don’t think Diehl’s message is one that’s going to appeal broadly in the way that [Mitt] Romney and Baker and [Bill] Weld have been able to do.”

Still, while Watanabe is skeptical, he allows that a Diehl nomination wouldn't mean an automatic Democratic victory. Democratic activist Liam Kerr is less charitable: in an opinion piece for GBH News, he argued that Baker's popularity has masked a protracted Republican collapse in Massachusetts, and that the 2022 Democratic primary will determine the next governor.

But Democratic strategist Doug Rubin, who helped Deval Patrick make the jump from unknown to governor in 2006, has a very different take on Diehl’s prospects.

“The most important thing in Massachusetts politics for governor — separate from every other race in the state — is that, for whatever reason, voters for governor don’t seem to see Democrat and Republican,” Rubin said. “They see insider-outsider. And they want an outsider in that governor’s office.”

In the past three decades, Rubin points out, that dynamic has resulted in just one Democrat, Patrick serving as governor. Every other occupant of the corner office has been a Republican.

“One reason Deval Patrick was able to break that Republican streak is because he was perceived as an outsider who was willing to stand up to the Legislature and fight for the people of Massachusetts,” Rubin said. “And look, if Geoff Diehl is able to paint the Democratic nominee as an insider, and is able to paint himself credibly as an outsider … that’s the path to victory for Republicans. It’s a pretty simple path.”

That outsider-insider narrative might be tough for Diehl to push if he’s the nominee and his opponent is Harvard political theorist Danielle Allen, who’s never held elected office. But against Sonia Chang-Díaz, an incumbent state Senator in the Democrat-dominated Legislature, it would be considerably easier. Against new entry Maura Healey — who’s in her second term as attorney general, and is widely seen as the preferred candidate of the Democratic establishment — it might be easiest of all.

Healey, it’s worth noting, brings important strengths to the race that Diehl lacks, including high name recognition and a campaign war chest of nearly $4 million. (Recent state filings show Diehl with less than $105,000 cash on hand.) Then again, after announcing her long-awaited candidacy earlier this month, Healey now has to contend with the burden of high expectations. Diehl may benefit from the exact opposite dynamic: since so few people outside the state’s small conservative base expect his campaign to succeed, pressure and scrutiny are, at this point, almost nonexistent.

That, too, is reminiscent of the 2006 campaign, in which Patrick was initially dismissed by many political observers — a response Rubin said can be liberating for a candidate.

“I think there’s an opportunity, as somebody who is written off or discounted, to appeal to different voters, to try different messages, to try different ways of campaigning,” Rubin said. “[And] in the environment we’re in right now – where people are frustrated and disappointed in their leaders, and checking out of politics because they don’t think it applies to them — that gives that person, if they run a smart campaign and have a good message. an opportunity to bring those people back in.”

As Rubin points out, the Patrick analogy has its limits. Despite being a neophyte candidate in 2006, Patrick was a political natural blessed with eloquence, charisma, and unerring instincts, at least during the campaign.

Diehl is less sure footed. In December 2021, GBH News asked his campaign to comment on racist remarks left on Diehl’s Facebook page as he decried vaccine mandates issued by Boston Mayor Michelle Wu. The politically smart move, for a would-be governor, would have been to decry any and all racism while reiterating his avowed commitment to personal freedom. Instead, Diehl’s campaign provided a statement saying Diehl shouldn’t be judged by his supporters’ actions on social media.

In his stronger moments, though, Diehl comes across as an affable everyman-turned-politician — the neighbor who you might not always agree with, but whose earnestness and civic-mindedness you have to respect. That persona was on full display in “Bay State With A Bronco,” the folksy, upbeat web series Diehl produced while mulling a run for governor. In a May 2021 episode, he fretted about the future of the country during an outdoor chat with GOP chair Jim Lyons. “Just hopefully, you know, we have respectful discussions between people who are elected and the people who support them,” Diehl said. “Because our country’s really taken a hard turn lately.” Even if you weren’t totally sure what Diehl meant, it was a statement that invited tentative head nods across the political spectrum.

But that example doesn’t do justice to Diehl’s nimbleness as a communicator. Consider the varied ways in which he’s discussed the 2020 election, suggesting to different groups of potential voters that his understanding matches their own.

In July 2021, GBH’s Greater Boston host Jim Braude asked Diehl if Trump’s claim that he won the election was correct. “Uh, no,” Diehl replied. “Look, those states — obviously, they’ve got to clear — sort out if they had any problems with voting, but look, I don’t think it was a stolen election.” It was time, Diehl added, for Republicans to “move forward [and] stop crying over spilled milk.”

It was a perfect response for wooing public-television viewers — and substantially different from what Diehl said, a couple weeks later, when WCVB’s Janet Wu asked Diehl if the election had been stolen from Trump. “I don’t know,” Diehl answered. “I don’t think you or anybody knows at this point.”

In September 2021, when Diehl spoke outside the State House at a conservative “freedom rally,” he seemed far less ambivalent. Responding to shouts of “Stop the steal!” — the mantra of Trump supporters who believe Biden's presidency is illegitimate — Diehl said, “We got a concern about elections being fixed. You guys — you guys think that 2020 was a problem? You guys think that mail-in voting was a problem? I agree with you!”

Collectively, these campaign-trail snippets evoke the approach used by Glenn Youngkin, the new governor of Virginia, to oust Democratic incumbent Terry McAuliffe last year. In that race, Youngkin was able to appeal to Trump loyalists while simultaneously keeping the former president at bay, even after Trump endorsed him. “Furious Democratic attacks that he was a Trumpian wolf in suburban-dad fleece never quite stuck because, in both biography and manner, Mr. Youngkin did not fit the former president’s bullying, self-aggrandizing profile,” the New York Times concluded. “[Youngkin’s] ability to direct multiple messages — red meat to the G.O.P. base via interviews with right-wing media, and a less divisive pitch to swing voters — will serve as a blueprint for his party in the midterms.” Massachusetts is not Virginia, and Diehl does not have Youngkin’s personal wealth. But the strategic parallels are evident.

Of course, for Diehl to fully emulate Youngkin, he’ll have to get through the Republican primary. As of last week, he has some competition: Chris Doughty, a Wrentham businessman, announced his own bid for governor Wednesday, touting himself as a process-oriented job-creator in a kickoff video. But Doughty, who’s never run for office before, may find that the appetite for his political profile is limited these days. In an interview with the Boston Globe, Doughty acknowledged voting for Hillary Clinton in 2016, which is unlikely to please the Republican base. He also said he voted for Trump in 2020, which is unlikely to please moderate Republicans and Republican-leaning unenrolled voters concerned with the party’s ongoing shift rightward.

In addition, even if Doughty proves to be a quick study, Diehl has already forged a strong relationship with the voters who’ll choose the next Republican nominee. In October 2021, a poll commissioned by the Democratic Governors Association showed Diehl leading Baker by 21 points in a hypothetical primary matchup — with the margin growing to 32 points when respondents were told of Trump’s endorsement.

And yet, for Massachusetts electorate as a whole, Diehl remains a largely unknown quantity, even after running statewide in 2018. A survey released this week by the MassINC Polling Group found that 18 percent of registered voters know of Diehl but haven’t formed an opinion about him, and that 51 percent haven’t heard of him at all.

Those findings make it clear that Diehl — who did not comment for this story — has plenty of work to do if he wants to become governor. But they also suggest that he has an enviable opportunity, even after a decade in public life, to re-introduce himself to voters in a way that maximizes his appeal and viability.

The shadow state-of-the-state address Diehl delivered this week, hooked to Baker's final such speech as governor, suggests he plans to take full advantage. After nodding to the right with a call to unmask kids and provide more parental control of education, Diehl spoke of making Massachusetts more affordable, and panned the Legislature’s decision to spend federal COVID-19 pandemic relief funds on “pet projects." He closed by referencing his own experience as an Eagle Scout — saying it taught him to “leave the campsite better than you found it,” and vowing to apply that maxim to Massachusetts. If, like nearly half the state's voters, you didn’t have an opinion of Diehl before watching it, you might have liked what you heard.