New Boston vs. old Boston, in the Mayor Wu era – The Boston Globe

Whose city is it? As he wrapped up a recent rally to protest Boston’s ban on outdoor street dining in the North End, restaurant owner Jorge Mendoza described Mayor Michelle Wu as an out-of-touch out-of-towner “who wants to tell the rest of us how to live in our city.”

“This is not her city. This is our city. The citizens of Boston. And those citizens of Boston are tired of being pushed around by the Chicago political mob,” said Mendoza, taking a rude jab at Wu via her hometown.

Outsider vs. insider. New Boston vs. old. If Wu, the first woman and person of color elected to the mayor’s office, runs for a second term in 2025 and faces a challenger, those classic themes of Boston politics will surely get a reboot.

Mendoza and his family migrated from Argentina to the North End in 1984, so he is not a native Bostonian. Yet he still felt welcome to tap into the outsider/insider mentality that has shaped Boston’s culture and politics for centuries. Sometimes, it unites Boston. Remember the rallying cry of Red Sox slugger David Ortiz after the Boston Marathon bombing in 2013? “This is our f***ing city.” But too often, that us against them mind-set divides people along ethnic, racial, and religious lines.

Portraying Wu — who came to Boston to attend Harvard University — as an outsider is not new. In the 2021 mayoral race, Annissa Essaibi George tried to make ownership of a Boston accent an asset. Wu won that contest with over 64 percent of the vote. With her decisive victory came a progressive agenda of social and economic justice, one that critics now boil down to an over-abundance of bike and bus lanes and a controversial proposal to temporarily increase the commercial property tax rate.

Last summer, notice of a fund-raiser for then-City Council President Ed Flynn that was sent from the office of public relations executive George Regan referenced a mission to “save” the city from “the negative impacts of the ultra-progressive policies” that “dominate” the current administration in Boston City Hall. At the time, that fund-raiser also looked like a possible mayoral trial balloon by Flynn, a city councilor from South Boston and the son of former mayor Ray Flynn. However, Ed Flynn recently told the Boston Herald that he’s not planning such a run. His denial came after a North End appearance with three of the restaurant owners, represented by Regan’s firm, who are suing the city and Wu over the outdoor dining ban.

The latest rumors about a possible challenge to Wu focus on the younger son of New England Patriots owner Robert Kraft, Josh Kraft, who told the Globe’s Niki Griswold he’s “looking at a lot of opportunities now.” Where Josh Kraft stands on the political spectrum is unknown, since he has never run for office. But with his family name and money, he represents old Boston power with a new, younger twist. Through his philanthropy, Kraft also has strong ties to the city’s diverse nonprofit community.

To his potential advantage, it is in communities of color that Wu has faced challenges, from her plan to move the John D. O’Bryant School from Roxbury to the predominately white neighborhood of West Roxbury to her plan to redevelop White Stadium in partnership with a women’s professional soccer team. Wu rolled out both proposals without first getting buy-in from people affected by them. She backed off from the O’Bryant plan and faces a lawsuit regarding White Stadium. With both, she has given critics another chance to frame her as a mayor who, as Mendoza put it at that North End rally, “wants to tell the rest of us how to live in our city.”

Wu’s battle with the North End restaurant owners is a microcosm of her own “us vs. them” attitude. For sure, the restaurant owners are a loud and raucous bunch who have been holding weekly rallies to bring attention to their cause. The lawsuit they filed in federal court charges the Wu administration with “unequal, unfair and discriminatory treatment of Italian restaurants in Boston’s North End.” The city filed a motion to dismiss, and while the case is pending, Wu has said she can’t talk to the restaurant owners. So the strategy is to ignore them — or needle them.

For example, on her recent trip to Italy to meet with the pope, Wu visited the Italian city of Sulmona, which a press release from her office identified as “a town with strong ties through immigration to Boston’s North End.” That led to another North End rally, with restaurant owners noting that Wu had visited a place that celebrated outdoor dining. That in turn led Wu to tell GBH News that she “didn’t see a single example of a street in Italy with the outdoor dining set up that the litigants are pushing.”

To Wu, those restaurant owners, who surely love Boston as much as she does, are simply “the litigants.” New Boston, same old divide — unless she reaches across it.

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