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Do George Regan and friends help or hurt Annissa Essaibi George?

News that New Balance chairman Jim Davis poured $495,000 into a super PAC is turning into a liability, due to Davis’s previous support for Trump’s reelection.

Annissa Essaibi George helped distribute food while volunteering at the Chinatown Main Street, Food Access Program in Chinatown on Sept. 25.Craig F. Walker/Globe Staff

First it helped Annissa Essaibi George, then it hurt her.

“Real Progress Boston,” a political action committee that’s chaired by William Gross, the city’s first Black police commissioner, helped Essaibi George win a spot in November’s mayoral final. But the news that New Balance chairman Jim Davis poured $495,000 into the PAC is turning into a liability, due to Davis’s previous support for Donald Trump’s reelection.

That Trump connection is a problem for Essaibi George, who is now trying to separate herself from it. “Any affiliation, any commentary, any implication that I am connected to Donald Trump, to me, is a gross statement,” she told WBZ-TV political analyst Jon Keller. “I don’t want this PAC involved. I don’t want them to speak for me. I’m more than capable to speak for myself.”


The official issue driving the PAC is support for police. Essaibi George has been calling for more police funding, while mayoral rival Michelle Wu, who finished first in the preliminary election, is stressing police reform. Meanwhile, in Boston, there is always a personal side to politics, and as often is the case, it involves public relations executive George Regan.

Davis is a client of Regan’s and Regan describes Gross as “a good friend.” Regan’s company designed and placed ads for the political action committee during the preliminary election, and as the Dorchester Reporter reported, Regan and his dog hit the campaign trail with Gross the day before the preliminary. Regan also played a behind-the-scenes role in advising Dennis White, who was appointed as Gross’s successor by former mayor Marty Walsh; put on leave after allegations of domestic abuse surfaced; and then fired by Acting Mayor Kim Janey.

In a telephone interview, Regan said Janey’s role in White’s firing has nothing to do with his support for Essaibi George or his involvement in the PAC. “The schools are a disaster, the police department is upside down,” he said. He said he supports Essaibi George because “she doesn’t talk in headlines and theories. She’s the right woman for the job.”


Gross, who resigned abruptly as commissioner in January, endorsed Essaibi George in May and set up the political action committee in August. In a statement released through Regan Communications, he said he created it “to raise money for the best person to lead Boston through the multiple challenges ahead. . . . The people that I am talking with every day care about Boston and have never once mentioned Trump or any other candidate to me.”

Whatever the motivation behind the PAC, Doug Rubin, an adviser to the Janey campaign, said there’s “no question” it had an impact. “In the last few weeks of the election, they were able to significantly increase the overall spending and support of Annissa Essaibi George,” he told me. “And I think they were able to target voters and do things Essaibi George didn’t have the resources to do.” That, said Rubin, helped her claim one of the top two spots, ahead of Janey, who finished fourth, and Andrea Campbell, who finished third.

Asked about the relationship between Janey and Gross, he said he believed it was good “pre-Dennis White. Afterwards, Gross may have been upset with how Janey handled Dennis White.”

Janey just endorsed Wu, which is significant given that Janey was the top vote-getter in voting precincts with the highest concentration of Black voters, according to the MassInc Polling Group.


Focusing strictly on the politics, Rubin said that public safety is “not a clean issue” for either finalist. “I think there are a lot of voters, Black and brown, who supported Kim Janey and wanted to keep neighborhoods safe. . . . Both (Wu and Essaibi George) have to figure out how to make that appeal,” he said.

As for Davis’s role in the PAC, Rubin said he thinks of the New Balance CEO as “a respected businessperson in the city”— not a Trump supporter.

But “Trump supporter” is the label that‘s drawing all the headlines. Can Essaibi George keep her distance from Davis while embracing Gross? The former commissioner is a popular figure who is treated like a rock star in Boston neighborhoods that she needs to win over.

For Essaibi George, it’s complicated.

Joan Vennochi is a Globe columnist. She can be reached at Follow her @joan_vennochi.