The Boston mayoral race is shaping up to be one of the most expensive and contentious elections the city has seen in recent memory, driven by significant financial backing from political fundraising groups.
This year, the Bold Boston Super PAC, which supports incumbent Mayor Michelle Wu, has raised $743,000, as per campaign finance disclosures.
In stark contrast, the Your City Your Future Super PAC, aligning with Wu’s leading challenger Josh Kraft, has amassed a remarkable $3.1 million, making a bid to unseat a Boston mayor for the first time since 1949.
Both organizations are heavily investing in attack ads across various mediums, including text messages, billboard trucks, cable TV, streaming services, and radio.
As the two candidates clash, tensions rise over transparency, city policies, and the nature of campaign finance itself.
Retired UMass Boston political science professor Mo Cunningham succinctly described the current atmosphere of the race as “negative.”
“The next five months are going to be negative, overwhelmingly so,” he said, predicting an election marked by hostile exchanges.
The Bold Boston Super PAC’s current campaign features a striking ad juxtaposing an image of a red “Make America Great Again” hat with Josh Kraft’s face.
“Hey Boston,” a voiceover states. “Trump donors gave big to Kraft’s Super PAC. That’s right, Kraft and his MAGA friends are attacking Michelle Wu to try to buy the election.”
While Kraft has publicly criticized President Donald Trump for his judgment, ethics, and temperament, he is tied to Trump’s influence through his father, Robert Kraft, owner of the New England Patriots.
The ads funded by Bold Boston effectively highlight that significant contributions to Kraft’s campaign have come from individuals who support Trump.
Through July 7, advertisements from Bold Boston have accounted for $375,000 in spending, according to spokesman Kevin Ready, marking a strong response to a provocative ad launched by Your City Your Future.
The latter features a woman’s voice claiming, “We tried to tell Mayor Wu: her ideas would only make things worse but she ignored us,” accompanied by a picture of Wu.
This ad critiques Wu’s decisions regarding bike lanes, the renovation of White Stadium in Franklin Park, and the Boston Public Schools.
In Boston, individual campaign donors can donate a maximum of $1,000 per year to a mayoral candidate.
However, Super PACs, or “independent expenditure only committees,” are allowed to raise and spend unlimited amounts, provided they do not coordinate directly with candidates or their campaigns.
A considerable portion of the funding for the Kraft-aligned Super PAC has originated from wealthy contributors linked to his family.
Significant donations include two $1 million contributions from New Balance chairman and Republican megadonor Jim Davis, alongside another large donation from Michael Rubin, CEO of the sports merchandising giant Fanatics.
When questioned about the negative tenor set by the Super PAC’s ads, Kraft sought to draw a line between his campaign and the activities of Your City, Your Future.
“Look, I have nothing to do with the [Independent Expenditure] group,” he stated.
“I’m focused on my campaign, running against an incumbent, and that’s a lot of work on the day to day.”
In contrast, Bold Boston’s financial support is supplemented by unions and environmental organizations, with a noteworthy $150,000 contribution from billionaire Amos Hostetter, the cable TV entrepreneur and co-founder of the Barr Foundation.
Hostetter’s charity subsequently contributed $175,000 to the Bold Boston Supper PAC.
Wu had previously urged Super PACs to refrain from negative attacks during her last election.
While remaining non-committal in a recent interview when asked about her stance on negativity, she expressed her intention to maintain a positive focus.
“We’re going to stay focused on making sure Boston is the positive example that the country needs right now,” she remarked.
Cunningham, who studies the influence of dark-money politics, contrasted the current situation with previous Boston elections.
In 2013, Marty Walsh and John Connolly steered clear of personal attacks, with Connolly even expressing admiration for Walsh until late in the campaign.
Similarly, the 2021 race between Wu and Annissa Essaibi George remained relatively civil until the final weeks, when debates turned contentious over issues such as homelessness and substance use in the city.
Super PACs played a noticeable role in both campaigns, but Cunningham noted the unprecedented flow of money in the 2025 election could dramatically affect voter perception and engagement.
“Super PACs, no matter what, to my mind are a curse on Democracy,” said Cunningham.
“They allow individuals to spend exorbitantly and independently of the candidate, creating a distance where the candidate can claim, ‘Oh, I’m not responsible for that.’”
In this charged political environment, two other candidates in the Boston mayoral race, Domingos DaRosa and Robert Cappucci, are running without Super PAC support.
Cappucci has disclosed personal investments of roughly $10,500 in his campaign this year, which will be reflected in upcoming public filings, while DaRosa has around $1,849 in his campaign fund with plans to contribute an additional $2,200 soon.
In contemplating the overwhelming influx of funds, DaRosa, a longtime community organizer from Hyde Park, expressed frustration over the lack of focus on practical issues.
“Because I’m not raising $100 million, I’m not a credible candidate?” he asked, lamenting the obstacles that arise from a system heavily driven by financial clout.
As millions of dollars flow into the race, the battle for Boston’s future is sure to intensify, revealing deep divides not only among the candidates but also within the electorate.
image source from：wbur
