The Stage is Set: Wu and Kraft to Square Off in Boston’s Mayoral Election
BOSTON – The political battlefield for Boston’s future is now clearly drawn. Incumbent Mayor Michelle Wu, a progressive Democrat and frequent target of the Trump administration, has advanced through Tuesday’s preliminary election. She will face Josh Kraft, the non-profit leader and son of New England Patriots owner Robert Kraft, in a high-stakes November general election that pits a national symbol against a local philanthropist betting millions on a message of change.
The race promises to be a dramatic clash of styles, records, and resources, reflecting the broader tensions shaping urban American politics today.
A National Lightning Rod vs. Local Criticism
Mayor Wu’s first term has been defined, in part, by her unwavering defense of Boston’s identity as a “sanctuary city.” This stance has made her a prime target for the Trump administration. Just last week, the Trump Department of Justice filed a lawsuit against Wu, the city, and its police department, claiming their policies interfere with federal immigration enforcement.
The attacks continued on election day itself, with the Department of Homeland Security announcing arrests in Massachusetts and directly blaming Wu’s policies for “attract[ing] and harbor[ing] criminals.” Wu has met this fire with fire, framing the onslaught as a badge of honor. She argues that Boston is targeted because it “represents all that is good about our democracy.”
“We are proof of what’s possible when people come together, and we’re proof of everything that shows why they are wrong,” Wu said while visiting polls on Tuesday.
Her challenger, Josh Kraft, also a Democrat, has been critical of the Trump administration’s tactics. However, he has sought to keep the campaign focused on local issues, particularly hammering Wu on her record regarding housing affordability, arguing she hasn’t done enough to increase options for Bostonians.
The Money Race: A Self-Funder vs. a Fundraising Incumbent
One of the most staggering aspects of the race is the financial disparity in spending. Kraft, heading the Kraft Family Philanthropies, has injected his campaign with over $5 million of his own money. This massive personal investment allowed him to shatter spending records for a Boston preliminary, outspending Wu by a margin of $5.5 million to $1.1 million as of August.
However, this strategy has its limits. While the spending bought a flood of ads and name recognition, Wu entered the final stretch with a significant war chest for the general election, boasting $2.4 million in cash on hand to Kraft’s $1.3 million.
Political analyst Jeffrey Berry, a professor emeritus at Tufts University, notes that money alone can’t win. “Wu has become a symbol of democratic resistance to the president,” he said. “That will be hard for Kraft to overcome in a city like Boston.”
Kraft’s campaign has also shown signs of internal struggle, with his team announcing a “mutual parting of ways” with two top advisers just last week.
Contrasting Visions: A Proven Progressive vs. A Grassroots Connector
Wu’s campaign is a testament to building a broad coalition. She enjoys strong support on the City Council, a string of endorsements from Democratic leaders, and a energized progressive base. She has spent the summer tirelessly highlighting her administration’s work on her key pillars: housing, climate change, and reducing crime, often with her infant daughter by her side.
For supporters like David Woodruff, a retired MIT specialist, she represents the direction the city and country need to go. “I like the way she stands up to Trump, I like what she’s been doing on the national scene,” he said. “I want people who are progressive and are strengthening democracy in office.”
Kraft, the former CEO of the Boys & Girls Clubs of Boston, is campaigning on a different kind of connection: a personal, neighborhood-level touch. He argues that City Hall has become disconnected from the people it serves.
“Everywhere we go… we hear the same thing: People don’t feel listened to, people don’t feel connected to the mayor and the mayoral administration,” Kraft told The Associated Press.
This message resonates deeply with voters like Remy Lawrence of Dorchester, who was personally consoled by Kraft after her 13-year-old son, a participant in Kraft’s youth programs, was tragically killed in 2023. “I believe we need change in this city,” Lawrence said. “We need a leader who is accessible, who’s accountable, who’s connected.”
With the preliminary field cleared, Boston voters now have a clear choice this November: reaffirm the progressive, nationally-focused leadership of Michelle Wu or opt for the hands-on, philanthropic localism of Josh Kraft. The outcome will define the city’s direction for years to come.
