Kraft 2.0 looks a lot like the first version

August 5, 2025
By Michael Jonas

As a reboot, it’s not clear it did much to clear the cache or restart the operating system.  

On Sunday, Josh Kraft gathered with supporters at the Ironworkers Local in South Boston to deliver what a press release billed as “an important campaign update and speech.” What followed in his remarks, however, was largely a restatement of positions he’s put forward on everything from rent control to bike lanes and the problems at Mass. and Cass.  

Kraft then turned to Mayor Michelle Wu and ripped her for spreading what the text of his speech called “falsehood after falsehood” about him. Kraft, who is Wu’s main opponent in this fall’s Boston mayoral election, took on the charge that he is “new to Boston,” questions about his family’s business dealings, and the relationship of his father, billionaire New England Patriots owner Robert Kraft, and Donald Trump.  

Kraft, who grew up in Boston’s tony suburbs and only moved into the city two years ago, ran through his admirable bio of decades of work in the city as CEO of the Boys and Girls Club of Boston. Reminding voters at the same time of Wu’s far-away roots, the 58-year-old Kraft said he was walking truant kids to school in tough Boston neighborhoods when Wu, 40, was being walked to elementary school by her parents in the suburbs of Chicago.  

He emphasized that he has no involvement in his family’s business dealings and then took on the issue of his father’s longstanding friendship with Trump. Josh Kraft, who has made clear that he has never voted for Trump and objects to his policies, doubled down on distancing himself from his dad’s connections to the president. Trump has “actively attacked democratic institutions, and stoked hatred and division throughout our country,” Kraft said.    

It was stronger language than Kraft has used to date, and it left little doubt that he shares the revulsion toward Trump of many Boston voters, only 1 in 5 of whom cast a ballot for the president last November. But it didn’t seem like much of a reset or “Do-over debut,” as Politico Playbook headlined its write-up.  

“If you’re explaining, you’re losing” is a well-known axiom of campaign strategy.  

Whether it’s making clear that he does not share his dad’s views on Trump, or looking to undercut attacks that he only recently moved into the city by pointing out that he’s spent years working in Boston neighborhoods, Kraft still seems to be doing a lot of explaining, six months after launching his campaign.

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