Mayor Michelle Wu’s first-term achievements shine, but challenges persist after her re-election.Was this email forwarded to you? Sign up here to get The Daily Prospect Monday through Friday. [link removed]
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**SEPTEMBER 25, 2025**
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I can recall the energy of Boston during the period when Michelle Wu pursued her first bid for mayor in 2020. It happened during the tail end of a year marked by the chaos and despair of the COVID-19 pandemic and the first presidency of Donald Trump. The nation was in a particularly vulnerable position, ripe for political change that felt long overdue. Boston was no exception. It’s a city defined by firsts, but also by rigid traditions, which created a distinctive backdrop for the buildup to the 2021 municipal election. I got the sense that Boston was ready for something different than what it was used to, and that eventually manifested itself in Wu’s successful campaign.
As a born-and-raised Bostonian, I had caught glimpses into the inner workings of City Hall and of the activities of the city’s previous mayors, but never fully grasped the intricacies of it all. During my time spent shadowing Wu in August, I was supplied with the opportunity to reconcile my understanding of her as a politician and as a person. In the weeks after, as I crafted a feature of her mayorship [link removed], I found myself drawing connections between my perception of Boston and the political intricacies that shaped it.
**–Naomi Bethune, writing fellow**
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Mary Schwalm/AP Photo
Michelle Wu, the Boston Beacon of Progress [link removed]
For decades, Boston has been in the thrall of its long-dominant “old guard” political tribe—which was Irish or Italian, and male. Although many other major Democratic cities have made strides in electing candidates who represented diverse groups and ideologies, Boston has also seemed like it was committed to sticking with a version of political power that prioritized frayed traditions over progressive innovations.
Deferring to the city’s real estate developers who have shaped the city’s residential and commercial policymaking to suit themselves has long been a feature, not a bug, of the old ways. Being the mayor of Boston meant that you needed deep connections with the city’s most influential groups, the desire to abide by the rules of its unique brand of conservative-to-moderate Democrats, and the drive to play a political game that had been chugging along unimpeded even by the boldest residents and civic leaders since the early 20th century.
Enter Michelle Wu. Born in Chicago to Taiwanese immigrants and educated at Harvard University and Harvard Law School, Wu is something of a wonder child. Her election in 2014 as the first Asian American woman to serve on the city council was monumental. Just two years later, her colleagues elected her to lead the body. Running for mayor was a natural next step, and in 2021, Wu, a progressive, won that contest with 64 percent [link removed] of the vote, stunning Boston and the country with a campaign centered on major policy changes in areas like housing that would have never been possible before.
She’ll get to carry on her work for another four years. Wu trounced [link removed] Josh Kraft, the millionaire son of NFL billionaire Robert Kraft, the New England Patriots owner, by nearly 50 percentage points in the nonpartisan race, winning all of the city’s 22 wards. Before the end of the week, he’d set aside [link removed] his bid for mayor.
To move ahead with her more ambitious aims, Wu faces considerable obstacles, including home-rule restrictions on taxes and rent control, which must be threaded through a resistant state legislature. She has had her share of blunders, among them having to shelve a controversial proposal to move the city’s most diverse exam school from Roxbury, Black Boston’s cultural hub, to West Roxbury, a mostly white neighborhood with poor public transit links. She also has been accused of ignoring residents’ concerns over a local stadium, a sore point for some in the multiracial coalition that backed her four years ago. Issues like these opened Wu up to intense criticism from Kraft, who’d been her highest-profile opponent.
In many ways, Wu personifies the profound social and economic changes that have unfolded in Boston over the past decade: She is the polar opposite of the leaders who steered the city before she came on the scene—which means she must grapple with the staggering task of redefining what it means to be the mayor of Boston in these perilous times.
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