SOME FREE ADVICE for Josh Kraft — buy a new boat.
For once, getting a hole in the water you throw endless amounts of money into seem a wise decision, at least compared to running for mayor of Boston.
Kraft, the son of billionaire New England Patriots owner Robert Kraft is said to be preparing to announce next month that he’s running against Mayor Michelle Wu, who will be seeking a second term this fall.
Massachusetts voters are not kind to wealthy political neophytes. Just ask Steve Pagliuca, John Kingston, Shannon Liss-Riordan, or any of the other self-funders who spent big only to be disappointed on election night. And targeting a Boston mayor is a particularly steep challenge. It’s no coincidence that no Boston mayor has lost reelection since 1949. Boston’s mayor enjoy even more structural advantages than most incumbents.
Frequent media coverage leads to universal name recognition. A busy schedule of community meetings, ribbon cuttings, and other retail political events means that many voters have personally met their mayor. While our governor is checked by a powerful state Legislature, Boston’s mayor is the strongest executive in the Commonwealth, so it’s easy to make friends and even easier to raise money.
Kraft apparently thinks he could be the exception to this rule.
The argument is simple. Boston’s long economic boom is slowing down; national political dynamics are turning against progressive mayors; and Kraft’s background as head of the Boys & Girls Club and a supporter for other charities benefitting lower-income Bostonians will allow him to win support from Black and Hispanic voters. This will allow Kraft to win with a coalition that combines minority voters with moderate and conservative whites, stranding Michelle Wu with only progressive support.
That scenario is wishful thinking. The conditions are simply not right for the incumbent mayor to lose. Wu’s proposed remake of White Stadium in Franklin Park continues to go over budget, but the first question many people will ask is, “what’s White Stadium?” It does not impact day to day life, unlike, for example, Rhode Island’s damaged Washington Bridge and the resulting traffic jams.
Rents and home prices continue their meteoric rise but voters view it as a state issue, and Wu can remind them that the Legislature thwarted her rent control plan. Likewise, she can also blame the increase in property taxes on state legislators rejecting her proposal for a commercial tax hike.
When mayors lose, it’s typically because of crime or corruption. Whether it’s Republican Rudy Giuliani defeating David Dinkins in heavily Democratic New York City in 1993, Lori Lightfoot in 2023 becoming the first Chicago mayor to lose reelection in 40 years, or San Francisco’s London Breed being defeated in November by a moderate candidate in the city that’s a metonym for progressive excess — voters hold their mayor responsible for public safety and punish anyone who fails to deliver.
Michelle Wu doesn’t have this problem. As she will continuously remind voters until Election Day, Boston is the safest big city in America. Of the 50 largest cities, FBI statistics show our murder rate is the eighth lowest and overall violent crime is the lowest in the country.
To be sure, there’s more to the politics of crime than statistics. Visible disorder like open air drug markets, rampant homelessness, and gruesome, high-profile crimes like the woman recently set ablaze on the New York City subway all matter. Nobody thinks, “at least this was a statistical aberration” after being mugged.
However, Mayor Wu also has a strong position on the optics of crime and disorder. Two years ago, over the objections of progressive supporters, she removed homeless encampments from Mass. & Cass. Similar headline-grabbing action will almost certainly happen on Boston Common between now and Election Day.
Likewise, there is not even the faintest hint of corruption at City Hall. In fact, one of the biggest criticisms of Mayor Wu is that she’s not a typical wheeler and dealer, ignoring business leaders in favor of activists and academics. While this may limit economic development, nobody loses an election because they aren’t nice enough to the rich and powerful.
This election might be different if it were 2005 instead of 2025. The Patriots would have just won three Super Bowls in four years. That’s the bedrock of a winning campaign: an announcement after the duck boat parade flanked by Tom Brady and Troy Brown; speeches about “bringing a championship mindset to City Hall;” promises to “turn around our failing schools like we turned around a losing franchise;” and voter registration drives led by members of the world champion New England Patriots. None of that is possible when the only good thing to come from the Patriots recent season is their draft pick (and even that didn’t go as many had hoped).
The city’s electorate has also changed to one that votes for candidates like Michelle Wu over candidates like Josh Kraft. Traditionally, the highest municipal election turnout was in South Boston, eastern and southern Dorchester, and West Roxbury. Now, these more conservative areas have their turnout rivaled by ultra-progressive Jamaica Plain and Roslindale. What’s more, every year, those traditionally more conservative-voting neighborhoods change as cops and firefighters sell homes to biotech workers and college administrators.
The new Boston electorate is dominated by educated voters who moved to Boston for college or a job. This is true across income levels — whether it’s four 20-somethings splitting rent in Allston, a two-income professional household struggling to pay the mortgage in Hyde Park, or a surgeon and her venture capitalist husband living in a $4 million Seaport condo.
While these voters are different, they have major commonalities. They identify as living in Boston, not a particular neighborhood; they participate in politics for ideological reasons, not because they want a patronage job for themselves or a family member; and they care more about national than local politics. That is a recipe for reelecting Mayor Wu.
Finally, Michelle Wu received a political gift when Donald Trump won in November. Now she gets to wage her reelection campaign with an unpopular Republican president as a foil. Incoming border czar Tom Homan already attacked Mayor Wu and the coming immigration raids will likely target Boston.
Fighting mass deportation will let Wu frame her candidacy as a way to oppose Trump. As an added bonus, the visual of a young Asian woman mayor battling Donald Trump and Tom Homan — two angry old white men — will let Wu benefit from identity politics without ever having to explicitly invoke it in her campaign.
This all adds up to a huge problem for Kraft. Replacing the first woman and non-white mayor with a wealthy moderate who has donated to Republicans contradicts how most Boston voters perceive their city — as a cosmopolitan locale proudly at the forefront of social change.
Kraft hopes to counter this by highlighting his decades of admirable charity work benefiting the city’s poorest and most diverse neighborhoods. At best, this will be ignored by voters unless they directly benefited from his generosity.
By all accounts, Kraft is genuinely concerned about the direction of the city and especially its business climate. But elections are won by votes, not good intentions, and there is little reason to believe Michelle Wu is vulnerable in 2025.
Brian Jencunas is a political consultant and government affairs professional. He welcomes feedback at BrianJencunas@gmail.com
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