GOV. MAURA HEALEY is gearing up for reelection in 2026, and with nobody on her left in sight, much of the political scrumming is happening to her right. 

A state GOP primary is looking likely: Two people from former governor Charlie Baker’s administration jumped in, both with backgrounds in private equity. Mike Kennealy, Baker’s economic development chief, and Brian Shortsleeve, who was part of efforts to overhaul the MBTA, threw their hats in a month apart. Others may join in soon. 

If the 2026 GOP primary for governor is anything like the 2024 primary for US Senate, when three candidates jockeyed to take on US Sen. Elizabeth Warren, Donald Trump and the state of the Republican Party will be part of the discussion. Backed by crypto interests, John Deaton won that primary, keeping his distance from Trump while praising Elon Musk. 

The 57-year-old Kennealy, who left his presidential ballot blank rather than vote for Trump, joined The Codcast to discuss being a Republican in Massachusetts, his time in the Baker administration, and several other topics. He says he’s someone who has “always been a free market guy,” though that comes as Trump has shifted the party away from free trade and championed tariffs, which are largely passed on as a tax on consumers.  

“When I talk about the core values of the party, I’m looking over a very, very long period of time. That’s how I look at it. And different policies will come and go, and ebb and flow,” said Kennealy, whose daily media diet includes The Wall Street Journal, which has been critical of Trump’s erratic push for tariffs. “But I look at the Republican Party and what it stood for, and free markets, and strong [economic] growth, and limited government, that’s been kind of the core of it for a very long time.” 

Asked what led him to join the party, Kennealy pointed to his late father Paul, a steelworker who spent nine years of night school at Bentley College getting an accounting degree. He later went to work for one of his accounting clients, Roche Bros. Supermarkets, and eventually became the CEO. 

“I grew up with a dad who went from the factory floor to the CEO suite and ran kind of the ultimate Main Street business, a grocery store,” Kennealy said. “Thinking about our Main Street businesses in our communities, what their needs are, what their opportunities are — that definitely informed my philosophy around being a Republican.” 

In the episode, Kennealy discusses the MBTA Communities Act at the 5:30 mark, in addition to why he’s a Republican (7:00), the immigration crisis affecting the state’s shelter system (14:35), transparency in government (18:44), and his media diet (27:35).