Gov. Healey’s 2026 message appears to take shape

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Welcome to another super-sized edition. We’re talking about the 2025 mayoral race, the 2026 governor’s race and everything in between. Let’s get right to it.

Is the Democratic Party in Massachusetts tilting towards populism? That was the question a Bloomberg News reporter posed to Gov. Maura Healey as she sat in the financial media giant’s Boston office, and her indirect answer indicated a possible outline of her 2026 reelection message.

The reporter pointed to the millionaires tax passed in 2022 – the same year voters carried Healey into the corner office – and a proposal for next year’s ballot to bring back rent control, asking whether it was a response to Donald Trump’s success at the ballot box.

Healey first jumped to the second part, arguing that Trump has not delivered on his 2024 campaign promises, such as lowering grocery bills. But when it came to what’s happening in Massachusetts, Healey didn’t address whether her fellow Democrats are turning towards populism, or whether she’s joining them. She instead touted free community college, without mentioning that it’s been largely paid by revenue from the millionaires tax.

As she continued by saying she was focused on lowering the costs of housing and energy – the basics in her view – Healey’s answer seemed to be a preview of possible campaign trail talking points as 2026 approaches and other contenders for the job are circling.

Brian Shortsleeve, one of two GOP candidates, hit Healey’s comments at the event supporting Eversource Energy’s proposal for a 10-year contract to buy natural gas from an expansion of a gas transmission pipeline.

“Healey was against natural gas before she was for it.  As Attorney General, she blatantly bragged about stopping two natural gas pipelines that would have lowered the cost on ratepayers,” he said. “Now facing a tough re-election battle, she is in favor.”

Back inside Bloomberg’s Boston office, the reporter who asked about populism was following up on a colleague’s question about the overall effectiveness of the Democratic Party in responding to Trump. The invite-only audience included bold-faced names from the business sector, such as Jon Hurst of the Retailers Association of Massachusetts, the Charles River Regional Chamber’s Greg Reibman and Tamara Small, who represents commercial real estate developers.

“Look, it’s a big party, it’s a big tent. You got a lot of voices,” Healey said. “I know that I am focused on telling the story of what I am doing as a Democratic leader. I tell people about the fact that I cut taxes.”

Healey went on to list off her backing of tax credits for developers, as well as easing rules about accessible dwelling units and money towards office-to-residential housing conversions.

If rent control moves ahead to the 2026 ballot, joined by business groups’ proposals to cut the income tax by a percentage point (5% to 4%) and increase potential taxpayer refunds, that will likely put Healey in an awkward position, as she and other top Democrats will be pulled into the ballot question fray like they were in 2024 on the MCAS test question and others. But for now, Healey seems to be about sticking with the basics.

Are you advising one of the potential 2026 candidates for governor, Alan Leventhal? Drop me a line: [email protected].

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MassDOT is rushing a secretive 35-year lease with Applegreen, despite inflated numbers, weak financials, and better alternatives. KPMG flagged serious flaws, yet the deal moves forward. Public oversight is missing, and $900M in rent is at risk. Legislators must act now. Before signing away public assets for decades, the MassDOT Board must pause and review. Learn more.

8:00 | The New England Council hosts "A Conversation with Former U.S. Ambassadors." Former U.S. Ambassador to Ireland Claire Cronin, who recently joined Boston-based firm Smith, Costello & Crawford, will offer welcome remarks. Former U.S. Ambassador to Portugal Robert Sherman will moderate a panel discussion with former U.S. Ambassador to Russia John Sullivan, and former U.S. Ambassador to Austria Victoria Reggie Kennedy. | Hampshire House, 84 Beacon St., Boston

8:00 | Mike Rowe, the host of the TV series "Dirty Jobs," joins Suffolk Chairman and CEO John Fish and others for a tribute to the tradespeople working with Suffolk to construct the MBTA Quincy Bus Maintenance Facility. | 599 Burgin Parkway, Quincy

10:00 | The Mass. Gaming Commission meets. Agenda includes presentation of a report titled, "Sports Betting Among Young Adults in Massachusetts: Preliminary Findings," briefings on at least two "noncompliance" issues related to sports betting companies, a vote related to proposed updates to the commission's event catalog to clarify the scope of permissible wagering on NCAA events. | Full Agenda and Access Info

In an extraordinary move days before the Sept. 9 preliminary election, Josh Kraft’s mayoral campaign parted ways with its top two consultants, the husband-and-wife team of Will Keyser and Eileen O’Connor. The pair had been working for Kraft in the run-up to his campaign, which launched in February but had been in the works long before that.

Close watchers of the race were left to parse statements released Wednesday night by a Kraft spokesman and Keyser Public Strategies, whose client list has included Gov. Charlie Baker, Senate President Karen Spilka and commuter rail operator Keolis.

The announcement of their departure came just as Kraft finished a NBC10 forum in which he and Mayor Michelle Wu fielded questions on immigration and housing issues. “Earlier this week, a mutual decision was made to part ways based on strategic differences as the campaign narrows to two candidates,” the Kraft spokesman said. O’Connor and Keyser in their own statement said they “deeply respect and admire” Kraft’s years in the nonprofit sector and wish him well.

Fresh campaign finance filings filed yesterday revealed the state of play ahead of the prelim. Kraft, who is relying on wealthy donors and his own funds to power the campaign, spent $2.4 million in August, and had $1.3 million in cash on hand at the end of the month. (His campaign’s total 2025 spending stands at $5.6 million, according to online records.)

Wu’s camp had $2.4 million in cash on hand. Her campaign’s spending in the same period — February through end of August — totaled $1.1 million.

Josh Kraft's campaign payroll has been a source of fascination for political junkies as he is spending more than $100,000 a month on the tall task of unseating an incumbent Boston mayor. (See above item.) One of the paid staffers happens to be a Hollywood name: Kevin Chapman. Known for playing cops and criminals, the Dorchester native had just finished shooting an HBO show when he told his agent to put a hold on his film and TV career so he could help Kraft’s mayoral campaign. Chapman had worked on the late Mayor Tom Menino’s campaign in 1993 and in City Hall as a neighborhood services coordinator, and he got to know Kraft through the Boys and Girls Clubs. “His family has considerable wealth but he could be doing other things than local politics,” said Chapman, who now lives on the South Shore. "He’s a good guy and I believe in him"....

… Annissa Essaibi George, the former Boston city councilor at-large who ran for mayor in 2021, is keeping a hand in politics. The most recent example was a Wednesday morning email blast to supporters. She encouraged them to support a fellow Dorchester resident, Frank Baker, the former district-level councilor now running for one of the four at-large positions. She also plans a meet-and-greet at her home for him on Sept. 23. Essaibi George returned to running her yarn store, the Stitch House, after the merger of her Big Sister Association of Greater Boston with Big Brothers Big Sisters of Eastern Mass. Asked whether she plans to run for office again, she said, “I’m always looking for an opportunity to serve. I want to be productive, I want to be helpful and I want to continue to have impact. I’m always looking for roles where I can do that.” When I mentioned that doesn’t sound like she’s ruling anything out, she chuckled and said, “I don’t think any politician ever does.”

VACCINE POLICY: Gov. Maura Healey “essentially wrote a prescription” for COVID vaccine shots for every person in Massachusetts over the age of 5. The move comes as vaccine skeptics have taken over the federal health care bureaucracy. – Boston Globe

BALLOT ROYALE: Forty-four ballot question proposals, including a return to rent control and placing the state Legislature under the public records law, advanced another step, clearing a legal review from Attorney General Andrea Campbell’s office. – State House News Service

NATIONAL GUARD: Gov. Maura Healey said there is “no need” for President Trump to federalize and deploy the Massachusetts National Guard in city streets, and it would be an “abuse” of their mission. – MassLive

BAR ADVOCATES: Some private Massachusetts attorneys, assigned indigent clients, aren’t taking new cases and considering unionizing despite receiving a pay bump from Beacon Hill last month. – GBH News

Boston is at an economic crossroads. The vitality of its downtown business district, drained by the COVID-19 epidemic, continues to slowly rebound but has yet to return to pre-pandemic levels. Commercial property values have declined, creating the potential for major budget challenges for the most property-tax dependent big city in America. With Boston’s financial underpinnings at risk, what is the strategy and vision for Boston’s future, particularly for its major business districts? Join business and community leaders to explore challenges and opportunities ahead. Register here!

HARVARD V. TRUMP: A federal judge ruled in favor of Harvard University as classes got underway, saying the Trump administration acted illegally in freezing funds. – Boston Business Journal

ROLLINS WEIGHS IN: Former U.S. Attorney Rachael Rollins, who resigned in disgrace in 2023, waded into the controversy of the White Stadium rebuild, siding with opponents and mayoral candidate Josh Kraft. Rollins recently moderated a panel with New England Patriots owner Robert Kraft, who later in the event took the stage to tout his son’s candidacy. – WBUR

QUICK STRIKE: Mount Holyoke College workers ended their strike after 24 hours, saying they felt administrators had heard their concerns. – Daily Hampshire Gazette

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