Campaign against Michelle Wu could be rude reality check for Josh Kraft

If Michelle Wu was looking to script her reelection race, she couldn’t do much better than run against a rich white guy from tony Chestnut Hill backed by the disgruntled business community.

Somebody like Josh Kraft, son of Patriots owner Robert Kraft, if he decides to challenge the popular progressive Boston mayor.

Kraft is being urged by the business community to challenge Wu, but a rich guy trying to buy the seat has never worked in Boston and probably won’t again. Kraft may be in for a rude reality check. He may not be the bigfoot people think he would be as a candidate.

Wu won 64% of the vote three years ago and while she has her angry opponents like North End restaurant owners, they don’t have the power to unseat her.

Then there’s the small problem of Kraft donating $1,000 to Wu’s mayoral campaign a few years ago, plus more than $33,000 in donations to other mostly liberal pols like Attorney General Andrea Joy Campbell, according to records reviewed by the Herald.

Kraft lists his current address in campaign finance records as both Beresford Road in Chestnut Hill – which is not in Boston – and Battery Wharf in the North End.

This year alone, Kraft has donated $1,000 to Campbell, $1,000 to Suffolk County District Attorney Kevin Hayden and $1,000 to Boston State Rep. Christopher Worrell.

In 2023 Kraft gave $500 to Boston City Councilor Ed Flynn, another potential Wu opponent, as well as numerous other Democrats and one Republican, Plymouth County District Attorney Timothy Cruz.

Kraft certainly has plenty of money to throw at politicians. And he works with several charities that do great work in the inner city. But can the son of a billionaire truly understand the real problems of people in the city, people who can’t afford gas or groceries some weeks?

That would be the major question that could stumble Kraft, who is head of the Kraft family philanthropies. Josh Kraft would be painted by Wu as out of touch with the city’s real needs like affordable housing and low cost health care.

Plus, there’s the issue of his father, Robert, who was embroiled in scandal several years ago for allegedly paying for sex at a massage parlor in Florida as part of an investigation into human trafficking. The charge of soliciting prostitution was eventually dropped by prosecutors.

Kraft issued an apology for his actions but pleaded not guilty.

“I am truly sorry. I know I have hurt and disappointed my family, my close friends, my co-workers, our fans and many others who rightfully hold me to a higher standard,” Kraft said.

Josh Kraft had nothing to do with the scandal but many voters only know the Kraft name because of Robert, and it’s a potential blemish on the Kraft brand. It could potentially loom in the minds of women voters who aren’t sports fans.

Most Boston voters have never heard Kraft speak, so he would have to go on a whirlwind tour to introduce himself should he decide to run.

The second he announces he will have to prove himself and the question is, is he up to challenging the Wu powerhouse?

Will he show aggressiveness or dynamic leadership to challenge Wu?

Will he be bold enough to call out her failures?

Can he be another Mitt Romney, who overcame his wealth and out of touch with average people baggage to be elected governor of Massachusetts?

Kraft will be backed by rich developers, and pigeonholed by Wu as the candidate of wealth and the elite.

You couldn’t think of a better optics for the first term Boston mayor – a mother of two who made history as the first non-white male to be elected mayor of Boston.

Wu has $1.4 million in campaign cash, which is not a lot for an incumbent mayor, so she would probably be outspent by Kraft. But that often matters little to voters.

Mayor Michelle Wu. (Nancy Lane/Boston Herald)
Mayor Michelle Wu. (Nancy Lane/Boston Herald)

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