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An influential hype squad of prominent business leaders wants Baker to run for a third term

Governor Charlie Baker stood for a portrait in his office of the State House.Erin Clark/Globe Staff/file

One Wednesday morning earlier this month, in a swanky lobby in Boston’s Seaport, Governor Charlie Baker gathered with business leaders and fellow elected officials to cut the ribbon on the city’s newest luxury hotel.

Baker spoke early in the lineup. Then prominent real estate investor Richard Taylor took the podium.

“We have not had the talk yet, but I kept saying, he’s got to run at least one more time,” Taylor said. The polite applause ramped up as he continued: “What do you think about that? Hey, what do you think about that?”

With 14 months to go before the gubernatorial election, Baker, a second-term Republican with enviable approval ratings from constituents in both parties, has yet to say whether he’ll seek a third term.


But in boardrooms and at power breakfasts, in the top floors of Boston’s glass-windowed office towers and in Massachusetts’ other traditional halls of power, a well-moneyed, juggernaut constituency already has made up its mind. Many of the state’s power brokers and business elites would like four more years, thanks — and they’re making their pitch both to the public and to Baker himself.

“Yes, yes, yes. Emphatically yes,” said Karen Kaplan, CEO of the advertising agency Hill Holliday, when asked whether she’d like to see another term of Baker’s leadership.

“I would definitely like to see him run,” said Bob Reynolds, the CEO of Putnam Investments. “Everyone I’ve talked to would be in total agreement with that.”

“One hundred percent. Unconditional” is how Suffolk Construction CEO John Fish described his support for a Baker reelection bid.

Fish, an independent, said he has personally urged Baker to seek another term, as have many of his colleagues who lead the state’s most prominent businesses.

“I want to put the best players on the field. And I do believe Charlie Baker is the best player to govern the Commonwealth of Massachusetts,” Fish said.


Those high-profile supporters do not speak for everyone in the state’s business community, nor every wealthy resident of Massachusetts. But it’s an influential hype squad nonetheless, an informal coalition of powerful individuals who have the profile to sway some segment of public opinion and, in many cases, the bank accounts to fund a successful campaign.

Of course, Baker’s Democratic rivals — who say he has done too little to level the state’s inequities — could capitalize on the support he enjoys from so many titans of industry to argue he puts the interests of CEOs over those of average people.

While Baker hasn’t announced his intentions — campaign spokesman Jim Conroy said the governor is undecided and his focus remains on leading Massachusetts through the pandemic — there are tea leaves to be read in his political schedule.

Baker’s fund-raising remains anemic compared to where it was ahead of his 2018 reelection bid. At the end of August, he reported having just $537,802 in the bank, a fraction of the $6.3 million he had on hand at the same point in 2017.

But Baker also has begun to return, if only occasionally, to fund-raising events, including one in June at the UMass club in Boston and another in early September at the Cape Cod home of public relations executive George Regan.

In addition to musician James Montgomery and miniature horses Snowflake and Boo, the fund-raiser boasted big names in business and government, including former Legal Sea Foods restaurants owner Roger Berkowitz, who was on the host committee, and former Boston police commissioner William Gross.


Regan said the event’s attendance is a testament to the wide range of influential people who hope to see another term: “Their businesses are here, and it’s good for everyone to have Governor Baker as governor.”

The “cast of characters” currently seeking the office is “not in the major leagues,” Regan said.

“Charlie is in the major league,” he added.

Conservative former lawmaker Geoff Diehl, who has said Baker’s pandemic response imposed too many limits on businesses, is running on the Republican side; he attended a protest outside the Regan fund-raiser. Three major Democratic candidates also have launched campaigns: state Senator Sonia Chang-Díaz, former state senator Ben Downing, and Harvard professor Danielle Allen.

None has the name recognition of Baker, or of another potential candidate, Massachusetts Attorney General Maura Healey, a Democrat whose $3.3 million campaign account and national reputation would make her a formidable opponent. Healey has yet to announce her plans.

Pressed on why they prefer Baker to the rest of the field, the supporters pointed less to specific policy accomplishments than to what they described as a general approach of competent, bipartisan leadership. Several said his has been a steady hand on the wheel during the COVID-19 pandemic, and that it’s only logical to allow him to continue leading the state’s response.

“You can tell what he’ll do by what he’s done,” said Jack Connors, a philanthropist and former Hill Holliday executive who has personally encouraged Baker to run but said he understands that the governor must make the best choice for his family. (Lauren Baker, the governor’s wife, worked at Hill Holliday for more than a decade long before Baker was elected.) “While the world is going left and right, Governor Baker is, in my opinion, a steadfast and very impressive moderate.”


High-profile supporters from across the political spectrum insisted their enthusiasm for him is not about partisanship, but rather his overall approach.

The stereotype that Republicans are better for business “is not that simple in Massachusetts,” said Dan O’Connell, the former head of the Massachusetts Competitive Partnership and a government official who served under former governor Deval Patrick. In the case of the Baker support, O’Connell said, “it’s the individual.”

“The business community likes stability in government, they like predictability in government, and he brings those two things,” said O’Connell, who supports Baker’s running for a third term. “Why not continue success, if he’s willing to do it for a third term?”

The uncertainty over Baker’s plans comes as Boston selects its new mayor, a contest that could put city government in more progressive hands. With COVID-19 still spreading rapidly across the city, and a long recovery still ahead, some business leaders said a mayor who is new to the job would benefit from collaborating with a third-term governor.

To be sure, it’s not every Massachusetts business heavyweight who’s prepared to back Baker again. Some, in conversations with the Globe, had little to say on the still-developing 2022 field, or said they’d wait to assess all the candidates before making a decision.


Mohamad Ali, CEO of the technology media and research company International Data Group, which is headquartered in Needham, pointed to persistent problems plaguing Massachusetts — hunger, an underfunded transportation system, enduring wealth disparities along racial lines — as evidence that Baker has not done enough.

“Governor Baker has not made a meaningful impact on these inequities in his years in office,” Ali said. “We can do better; we can build a stronger economy, and we can give more citizens a chance to prosper. I would like to see additional candidates enter the race, such that we can have the possibility of finding one who can do both: Improve our economy and address our inequities.”

Should he run again, Baker will have to answer for moments in his tenure that cast doubt on his reputation for excellent management, including at the Holyoke Soldiers’ Home, where a COVID-19 outbreak killed 76 veterans, one of the highest death tolls of any senior-care facility in the country. A Boston Globe Spotlight Team investigation found that Baker and a top deputy played crucial roles in the lead-up to the tragedy.

Still, as Baker — along with his top advisers and family members — considers a third term, he can expect to keep hearing from high-profile supporters who hope to vote for him in 2022.

“Oh, of course,” laughed Steve DiFillippo, chief executive of the Davio’s restaurant group and a longtime friend of Baker. “I’m a broken record. . . . He knows how we feel.”

Shirley Leung of the Globe staff contributed to this report.

Emma Platoff can be reached at Follow her @emmaplatoff.