Will anyone try to unseat Boston Mayor Michelle Wu?
Certainly within the business community — which has famously been at odds with Wu — there has been an active behind-the-scenes recruitment of a potential challenger. Consider it an anybody-but-Wu strategy.
For months, the town has been buzzing about Josh Kraft, son of billionaire Patriots owner Robert Kraft, who seems to be the white guy at every event for people of color.
Check out Josh Kraft’s recent posts on his LinkedIn profile: He was at an Amplify Latinx summit, the Urban League of Eastern Massachusetts’s inaugural Women’s Empowerment breakfast, and the graduation ceremony for the Marcus Anthony Hall Educational Institute in Roxbury.
The buzz reached a crescendo last week when the Globe put Kraft’s potential candidacy on its front page.
Is Kraft everywhere because he is laying the groundwork to be mayor? Possibly, but as one local pol reminded me, Kraft — as the former longtime head of the Boys & Girls Clubs of Boston — has always been a fixture in communities of color. And as the current chair of the Urban League of Eastern Massachusetts, it’s his job to be in rooms with people of color.
It’s only now the chattering class is paying attention because some in the business community desperately want Wu out of office.
My sense is that Kraft — who has never held political office before — is testing the waters only because so many people have begged him to run.
He’s not the only one being drafted. There’s always Jim Rooney, the outspoken CEO of the Greater Boston Chamber of Commerce. He grew up in South Boston, lives in Dorchester, and has become something of a Norma Rae-like figure in the eyes of developers and landlords for standing up for their rights at a time when Wu’s proposed policies have clashed with their livelihoods from raising property taxes to pushing for rent control.
Rooney — who ran the Massachusetts Convention Center Authority and served a stint as Mayor Tom Menino’s chief of staff — seems to be enjoying all the attention he’s getting. “People have called me or mentioned my name for every mayor and gov election for the past 30 years! But I admit it’s a little more this year,” Rooney told me in a text.
Typically, the City Council would produce a challenger. I thought City Councilor-at-large Erin Murphy — someone else who has been a public thorn in the side of Wu — might throw her hat in the ring. But she announced in March she’s running to be clerk of the Suffolk County Supreme Judicial Court.
Another City Councilor who has been a Wu critic is Ed Flynn, a Navy veteran and son of former Mayor Ray Flynn. Ed Flynn has close to $700,000 in his war chest, according to campaign filings, which is way more than anyone needs for a council reelection race. While the former City Council president recently told the Boston Herald he’s not running for mayor, he texted me to say that any discussions about 2025 “are premature.”
There has always been high hopes for Linda Dorcena Forry, the popular former state senator from Dorchester who, at the time, was the Legislature’s only Black senator. But she left politics for the private sector in 2018, and word is she’s focused on her consulting company and being co-publisher of the Dorchester Reporter and The Reporter Newspapers.
Talent abounds in the likes of state Senator Lydia Edwards and Attorney General Andrea Campbell, but I can’t see them wanting to upset the political apple cart to challenge their former Boston City Council colleague for her mayoralty.
And what about former mayor Marty Walsh? Walsh never really left Dorchester, even when he served as President Biden’s labor secretary, and still has $3.8 million in his campaign war chest, according to the latest filings from the Office of Campaign and Political Finance. He could be keeping his political options open, though he seems ensconced, making a reported $3 million a year as head of the National Hockey League Players’ Association.
Less viable would be one of the North End restaurateurs who have sued Wu over her outdoor dining restrictions. Still, Jorge Mendoza — owner of Vinoteca di Monica in the North End — could jump into the race just to spite Wu. I’m told he’s thinking about it. And lest you think Mendoza is some kind of lone wolf, think again. North End restaurant owners who have a beef with Wu are being represented by PR guru George Regan. Regan also repped the political action committee that bankrolled Annissa Essaibi George’s unsuccessful bid against Wu.
For her part, Wu has yet to formally announce whether she will run for reelection next year. But her fundraising indicates she’s gearing up for another term with about $1.4 million in her war chest, according to campaign filings. And the 64 percent of voters, who in 2021 made her the first woman and person of color elected as Boston mayor, remain a daunting base of support for any would-be challenger.
Historically, it has been hard to unseat an incumbent. But this time it could be different. Typically, business and civic leaders in Boston don’t publicly air their grievances about the all-powerful mayor. They’re too afraid. With Wu, there seems to be far less fear. Exhibit A: the array of lawsuits that have been filed against her administration from all corners of the city — whether it’s about outdoor dining in the North End, affordable housing in Charlestown, or the plan to redevelop White Stadium in Franklin Park.
That leads me to believe that if there was a viable candidate to challenge Wu, we can expect vast parts of the business community, in particular developers, to open their wallets to finance an upset. Watching this all unfold will be New Balance chairman Jim Davis, who coughed up more than $1 million for the PAC supporting Essaibi George. I’ve got to think Davis is once again ready to fund an underdog.
One thing’s for sure: This mayoral race won’t be politics as usual.
Shirley Leung is a Business columnist and host of the Globe Opinion podcast “Say More with Shirley Leung.” Find the podcast on Apple, Spotify, and globe.com/saymore. Follow her on Threads @shirley02186
Shirley Leung is a Business columnist. She can be reached at shirley.leung@globe.com.