Massachusetts State House in Boston
CNN  — 

For all but eight of the last 30 years, a Republican has occupied the governor’s office in Massachusetts.

The state that so many Americans equate with mainline liberalism – “Taxachusetts” was the GOP’s old derisive nickname – has a habit of electing Republicans to its top job, even as it sends prominent progressive leaders to Washington.

Republicans’ hold on the corner office in Beacon Hill held during the blue wave of 2018, with Gov. Charlie Baker cruising to a second term leading the Commonwealth. But as Baker now weighs seeking reelection again, Democrats are preparing for what is expected to be an uncharacteristically sharp clash over the political character and direction of the Bay State in next year’s gubernatorial race. The contest is already picking up steam as the early entrants to the Democratic primary ramp up their campaigns and try to rev up an intensifying base of progressive voters determined to break what has, for many on the left, become a maddening tradition.

“There’s this real mismatch,” Democratic State Sen. Sonia Chang-Díaz, who entered the race in June, told CNN. “People perceive Massachusetts to be a sort of Democratic and progressive bastion. That it’s the land of milk and honey of progressive policies and outcomes.”

The reality, she said, is much different – arguing that years of Republican leadership have been a “detriment to so many of the fundamental systems that people rely on in our Commonwealth. Schools, public safety, environment, traffic, transportation, economic development systems. These systems have been left to crumble and or haven’t been put in place in the right way in the first place.”

As summer comes to an end, there are three prominent Democratic primary candidates: Chang-Díaz, already the first Latina elected to the state senate (and daughter of the country’s first Latino astronaut), would be the state’s first Latina governor; Harvard professor Danielle Allen, an accomplished political theorist who has never run for office, would be the first Black woman to lead the Commonwealth; and Ben Downing, a Pittsfield native who served five terms in the state senate. A high-profile potential fourth entrant, two-term Massachusetts Attorney General Maura Healey – the nation’s first out gay state attorney general – has said she is weighing a bid, but cautioned in July that a decision might not come until the fall.

Asked to measure how Healey’s deliberations are affecting the race, Downing was blunt.

“It absolutely has an impact on the campaign, in fundraising and folks who are willing to make commitments one way or the other. And I think that does hold back candidates from starting to build any sense of momentum,” he said. “It’s one of many variables in a really crazy time to be running for office.”

Downing, Chang-Díaz and Allen all insisted that, despite Healey’s long shadow, they are focused on crafting the coalitions they believe necessary to defeat Baker – or, in the event he doesn’t run again, Republican Lt. Gov. Karyn Polito or former State Rep. Geoff Diehl, a Trump-friendly GOP primary candidate.

“There’s a heck of a lot of work to do to change the public understanding of the strengths and weaknesses of the Baker-Polito administration,” Allen said. “And that means it requires a heck of a lot of time and a grassroots movement. So the timetable required for beating Baker-Polito is… it’s already here. Those of us who are working on it, we’re on the timetable that’s necessary.”

Seeking a new coalition

Since former Gov. Michael Dukakis, the party’s 1988 presidential nominee, left office in 1991, following his second consecutive term and third overall, only one Democrat – former Gov. Deval Patrick – has (twice) defeated the GOP gubernatorial nominee. Former state Attorney General Martha Coakley lost narrowly to Baker in 2014.

During his nearly eight years in office, Baker has racked up some of the highest approval ratings among the nation’s governors. In an era when state leaders have taken on increasingly high profiles – first as Democratic executives tried to build a bulwark against former President Donald Trump, and now as Republicans defy President Joe Biden – Baker has earned a second title of sorts: one of the country’s most popular governors.

“The interesting dynamics are that his popularity is often higher among Democrats than among Republicans,” said MassINC Polling Group President Steve Koczela. “It was consistent for a while that his favorables were higher among Democrats and Trump’s were higher among Republicans than Baker’s were, even though Baker was extremely popular overall.”

That inversion of the typical partisan divide has driven the Democratic candidates to seek out broader coalitions by drawing in new voters.

“I have learned a lot of lessons from watching Stacey Abrams,” Allen told CNN. “And one of the things she has said consistently is that she goes out there with the goal of connecting with every community in the state.”

Chang-Díaz, the only office-holder in the Democratic race at the moment, has enjoyed the highest-profile success so far in attracting the support of movement progressives – including some of the same young political activists who helped key Massachusetts Sen. Ed Markey’s defeat of former Rep. Joe Kennedy III in a primary last year.

Prerna Jagadeesh, a 22-year-old senior at UMass Amherst, was a fellow on Markey’s campaign and an early supporter of Chang-Díaz, who was the subject of an online campaign led by young progressives intent on drafting her into the race.

“I think Sonia is really the inheritor to the Ed Markey coalition because she and Ed both share that willingness to buck leadership in support of progressive ideals,” Jagadeesh told CNN, a specific reference to Chang-Díaz’s long fight to pass the state’s 2019 Student Opportunity Act, which guaranteed a new $1.5 billion in funding for K-12 public schools over seven years.

Asked why she saw a winner in Chang-Díaz, whose promise to unite and invigorate a progressive, multi-generational coalition has – in other campaigns, in other states and cities and congressional districts – met with mixed results, Jagadeesh offered a pointed case.

“What’s different is that (Chang-Díaz) is no backbencher, she’s no granola hippie who just showed up on the political scene,” Jagadeesh said. “She’s been doing this work, she’s been making these relationships, she’s been fighting.”

But can they beat Charlie Baker?

Mara Dolan, a Democratic state committeewoman and co-founder of Left of Center, a women-run super PAC, praised the “outstanding” field of Democratic primary candidates, but said that Healey, despite being on the sidelines for now, would have a head start if she jumped in, having already been elected twice statewide.

She also contended that Baker’s well-documented popularity with Democrats was not as transferable, at least not under the current political conditions, to the voting booth as some believe – and that he is not immune to the nationalization of state and local politics, especially with the GOP leaders in places like Texas escalating their efforts to undermine voting rights laws and effectively ban abortion.

“Democrats are going to vote for the Democratic nominee, Republicans are going to vote for the (Republican) nominee. In Massachusetts, though, it’s more true that what’s most important are the unenrolled voters, it’s the centrist voters – they’re the swing,” Dolan said. “Those voters are looking for someone who’s going to lead on these really important national issues. And that’s something that’s good for Maura Healey, because she’s been doing this all along.”

Baker could also face new pressure to tack right, or else risk an uncomfortably close primary race, if Diehl’s campaign picks up momentum and forces him to stick or twist on Trump-era Republican red meat causes.

“Whether it will be on issues or just discussion of Trump or voter fraud, the things that Geoff Diehl will say are the things that Republican primary voters might want to hear,” Koczela, the Massachusetts pollster, said. “And the things that Charlie Baker will say are probably not those things. So it does set up a very interesting contrast, given that that’s the contest he has to get to your first in order to get to the general.”

Baker, who has not yet made his intentions known, is steering clear of campaign chatter.

“Right now Governor Baker remains focused on leading the Commonwealth through the pandemic – not electoral politics,” a senior adviser to governor told CNN.

Still, there is some doubt among the progressives in the race now over the degree to which Baker’s shared party affiliation with Trump will disadvantage him in a general election, should he seek a third term and secure re-nomination. In many ways, Massachusetts Democrats say, the dominant Trumpist faction of the GOP has been a boon to the moderate, technocratically disposed Republican – and that the eventual Democratic nominee will need to do more to connect with voters in the state’s Gateway Cities and among those, across the state, who are increasingly focused on public transit issues and unrelenting traffic.

“Democrats tried to connect Charlie Baker to national Republicans (in 2018) and say, ‘He’s one of them. You don’t like them. Vote for us.’ Well, Charlie Baker’s not one of them,” said Downing, who is running on an ambitious climate agenda. “I have strong disagreements with Charlie Baker on policy, but he’s not a national Republican. And the second that we as Democrats in Massachusetts try to turn (him) into that, voters disregard anything else that comes out of our mouth.”

The challenge of defeating Baker, or any other Republican nominee, Chang-Díaz said, had in some ways been made more straightforward by the fallout from the coronavirus pandemic, which – as it has around the country – magnified inequities and frustrations, especially among working class and young voters, that had been papered over for generations.

“If you are a relatively well-off resident of Massachusetts, you live in the right zip codes, you have access to various forms of power, it’s really easy to want to believe that (things are better than they are),” she said. “And to let yourself be convinced that everything is OK. But this past year of pandemic and the beginnings of racial reckoning has really laid bare for people the depths of the problems that we have left to simmer for so long.”

Allen echoed the point, describing a “split screen economy” that, in her view, was merging into a singular, more troubling picture as the pandemic makes it more difficult to ignore government’s failings.

“We’ve all gotten used to settling,” Allen said. “We’ve gotten used to settling for less than we should be seeking.”