Money, Donald Trump, name recognition.
Conservative candidates for governor of Massachusetts are expected to face a difficult road to securing the state’s highest constitutional office, with Democrats already tying any potential challenger to Gov. Maura Healey to President Donald Trump, according to local political operatives.
The field of Republicans who have either officially entered the 2026 race for Massachusetts governor or who are still weighing a campaign is growing, with one former state cabinet secretary launching a bid this past week and a local GOP mega donor recently making inroads with top officials at the state Republican party.
And while several of the conservatives in the mix are wealthy and willing to contribute their own cash, any candidate who realistically wants to take on Healey will need to either fork over or raise tens of millions to compete with someone whose national profile could draw in out-of-state money and backing.
Rob Gray, a veteran political strategist who worked on campaigns for former Gov. Charlie Baker and Mitt Romney, said if a candidate is not willing or able to spend at least $20 million to take on Healey, then “you might as well not bother.”
“These candidates will succeed or fail largely based on that,” he told the Herald. “You’ve got to buy advertising to create the name ID to be able to beat a relatively popular Democratic incumbent in a highly Democratic state.”
Mike Keannely, who served as secretary of housing and economic development under Gov. Charlie Baker, officially kicked off his bid for governor Monday with a pledge to seed his campaign with $2 million of his own personal cash.
It is a sum that could put Kennealy on a somewhat level playing field with Healey’s more than $2.8 million campaign war chest. But his — or any other conservative candidate’s — ability to effectively fundraise through the entire election cycle will be key to success.
Other people considering running as a Republican are also wealthy.
Brian Shortsleeve, a venture capitalist and former MBTA official, told the Herald this past week that he is taking a close look at a run for governor. Shortsleeve also comes from the Baker political orbit and has a long history of donating to local political candidates on both sides of the aisle.
Michael Minogue of South Hamilton spoke with the head of the Massachusetts Republican Party and other top officials on the state committee about running for governor of Massachusetts.
The former head of the medical technology company Abiomed has shuttled hundreds of thousands of dollars to the Republican National Committee and a fundraising committee associated with President Donald Trump.
A February poll of 700 Massachusetts residents conducted by UMass Amherst found that Healey had a 52% overall approval rating.
The same survey showed that 15% of respondents would back Kennealy over Healey and 12% would vote for Shortsleeve. But in each instance, a large share of those polled said they were still unsure of who they would support in the 2026 election.
The president could also hurt Republicans running for governor.
Erin O’Brien, a professor of political science at UMass Boston, said Massachusetts has a history of electing Republicans to Beacon Hill’s corner office — Baker and former Gov. Mitt Romney are the most recent examples.
But the “big question in the room” is whether Trump’s efforts to slash the size of the federal government, cut off key funding sources that Massachusetts relies on, and his stances on social issues alter the trend, O’Brien said in an interview.
“Healey still has a lot of time. The election is far off, and if she establishes herself, as she did as AG, as a strong foe of the Trump administration, and if that’s what Massachusetts wants, as they did when Trump was in office the first time, then she’s going to be really hard to beat,” O’Brien said.
On the flip side, O’Brien said, the Trump-supporting elements of the local Republican party will need to let their candidate “not be completely MAGA.”
“Donald Trump makes it a lot harder in Massachusetts for a Republican to win,” she said. “They would have to be able to distance themselves from Trump, and they would have to assure Massachusetts voters that they wouldn’t become a Trump crony.”
The last Republican to hold the Governor’s Office, Baker, was known for regularly bucking Trump during the president’s first term. Baker even blanked the top of the presidential ticket each time the former television star ran for office.
Wendy Wakeman, a Republican strategist in Massachusetts, said being tied too closely to Baker could actually hurt candidates like Kennealy or Shortsleeve during the Republican primary.
“The Republican base needs to believe that you are not a never Trumper, that you are on board with the revolution in the Republican Party, and yet the very vocal press and Democratic Party are going to try to force you to be with Trump,” Wakeman told the Herald. “Denying Trump is not going to win the election. It’s a little bit like Peter in the Garden of Gethsemane denying Christ.”
