While there’s been plenty of speculation about who may challenge Boston Mayor Michelle Wu in 2025, the two potential contenders subject to the most political chatter are remaining mum about whether they plan to jump into the race.
City Councilor Ed Flynn, a U.S. navy veteran and son of former Mayor Ray Flynn, said he is still weighing his options, and philanthropist Josh Kraft, the son of the billionaire New England Patriots owner Robert Kraft, is not currently a candidate, a spokesperson said.
“The speculation has been going on for a while,” Eileen O’Connor of Keyser Public Strategies, the political consulting firm working with Kraft, said in a Friday statement to the Herald. “Nothing has changed.”
“Josh is not currently a candidate and has no plans or timeline for any kind of announcement,” O’Connor added.
Kraft, the head of his family’s philanthropic arm, has been rumored to be a mayoral candidate for months. In May, O’Connor provided a statement from Kraft, where he said he was “looking at a lot of things” and had “nothing to report.”
Flynn, the City Council president last term, said in early May that he was not planning to run for mayor, but backed off that stance later that month, saying that he would not rule it out.
On Sunday, he offered a similar assessment, and batted away a rumor that he was planning to announce a mayoral bid at his Sept. 17 fundraiser reception, saying that it is typical for city councilors to host similar events.
“I’m going to consider it, consider my options, and how I can be helpful to the residents of Boston,” Flynn told the Herald. “But there will be absolutely no announcement there (on the 17th).”
Flynn added that he thinks it’s “too early” for him to “engage in campaigns,” saying that he has “a lot of work to do on the City Council and providing positive leadership.”
His campaign war chest currently stands at $787,075, far exceeding the city councilor with the second-highest fund, Council President Ruthzee Louijeune, who has $107,597 cash on hand, per the Office of Campaign and Political Finance.
As of now, Jorge Mendoza-Iturralde, a North End restaurateur clashing with the mayor and City Hall over outdoor dining restrictions, is the only candidate who has announced plans to challenge Wu in 2025.
Mendoza-Iturralde announced his mayoral bid in late May, but has not yet set up an official campaign fund with the Office of Campaign and Political Finance, which is required of political candidates.
He told the Herald Sunday that he plans to do so in the coming months, adding that he can’t pull papers to run for mayor until April, which he still plans to do.
“We are having the conversation with all the right people, but we haven’t got anything started yet,” Mendoza-Iturralde said. “It’s a very long campaign so we’re not there yet.”
Mendoza-Iturralde said he is registered as an Independent voter, while Flynn is a moderate Democrat and Kraft is said to have progressive views, but has a history of supporting and donating to Republican politicians.
The political consulting firm Kraft is working with has a bipartisan list of past and present clientele, including former Republican Gov. Charlie Baker and Senate President Karen Spilka, a Democrat.
Mayor Wu, the first woman and person of color to be elected mayor, is a progressive Democrat. While she hasn’t formally launched her bid for a second term, she stated her intention to run in July, when announcing she was pregnant with her third child.
“If anything, I feel even more motivated to make sure that the work that’s needed across the city, for families who are juggling so much, gets done,” Wu told the Herald at the time. “I plan to run for reelection, although I’ll make an official campaign launch announcement later. But this hasn’t changed my plans.”
Political insiders are split on whether Wu, who has amassed a campaign war chest of roughly $1.5 million, is vulnerable in the 2025 election.
An incumbent Boston mayor hasn’t been defeated since 1949, and Brian Jencunas, a political consultant, doesn’t see that streak changing next year. He cited the Hub’s status as arguably the “safest big city in America” where “property values continue to skyrocket,” when speaking to the Herald in July when a poll testing how Kraft would fare against Wu in a potential mayoral matchup was circulating.
A different political insider who requested anonymity sees Wu as vulnerable, however, to a potential candidate of color who’s willing to run “center-left” or a candidate with name recognition and resources.
In July, that political insider said the mayor has failed to build solid relationships and connections with community members who did not help to put her in office, pointing to pushback Wu has received from communities of color on proposals like moving the O’Bryant school, which failed, and her plan to renovate White Stadium to house a professional women’s soccer team, which led to a lawsuit by neighbors.
