In the Boston mayoral race, money vs. experience

The first woman mayor is battling to keep her job as a well-heeled newcomer steps in.

By Shalise Manza Young

Nearly two hours into a forum for Boston mayoral candidates last month came a simple question: Which ward do you live in?

Mayor Michelle Wu proudly shouted out Ward 18, quickly adding that she loves all of the city’s districts. But when the moderator came to Josh Kraft, he sheepishly admitted that he didn’t know.

It was an embarrassing moment, particularly for a candidate who has been fighting his outsider status since the moment he threw his hat into the ring.

Kraft is the third son of Robert Kraft, the billionaire owner of the New England Patriots. Largely content to fly under the radar for much of his adult life, he suddenly began appearing at events all over Boston last year, fueling talk that he was going to challenge Wu, who was elected in 2021. It’s the first time in the city’s nearly 400 years that a white man isn’t in charge.

Kraft is the embodiment of the current political landscape in America: a wealthy man who has never before shown an interest in politics and now wants to run things via his money and his similarly deep-pocketed allies.

Kraft was raised in Brookline, the tony town next door brimming with multi-million-dollar estates. He has worked in the city for years, serving as CEO of the Boys & Girls Clubs of Boston from 2008 to 2020. More recently, he ran Kraft Family Philanthropies.

But it wasn’t until October 2023 that Kraft got a residence in Boston. A $2.35 million waterfront condo was purchased by an LLC, the address of which is One Patriot Place, aka the stadium where the Patriots play and where his father and three brothers oversee the family empire.

Supporters say that one-on-one or in small groups, Kraft is engaging and personable, but that isn’t coming across in his public appearances and in front of cameras, and that’s how most Bostonians will experience him.

It feels worth noting that while Kraft is quick to tout his work in many of the city’s Black, Latino, and the more impoverished neighborhoods through his work with the Boys & Girls Clubs, when it came time for him to buy property, he picked the overwhelmingly white North End. His team, however, was savvy enough to put the campaign headquarters in Nubian Square, the heart of the city’s heavily Black Roxbury neighborhood.

For reasons entirely unclear to this Boston resident, bike lanes are becoming a significant issue in the election, with detractors like Kraft and his suburban supporters saying they’re worsening traffic on city streets. Because Boston is an old city, most streets are narrow, and congestion has long been a problem; bike lanes encourage people to commute another way and offer safety for those who do.

Yet they are at the centerpiece of an attack ad by the Kraft-supporting super PAC “Your City, Your Future,” which has gotten most of its funding from two billionaires who don’t live in the city: New Balance owner Jim Davis, who lives in Newton, Mass., and Fanatics founder (and friend of Robert Kraft) Michael Rubin, who doesn’t even live in the state.

The ad tries to tie the city’s traffic woes to the bike lanes, cutting from video of one such lane to gridlock inside the O’Neill Tunnel—which, for the record, has been a hot mess since it opened decades ago—as though bikers are riding on the interstate. In recent weeks, a rolling billboard paid for by YCYF has been photographed parked in bike lanes.

One other thing about those trucks: They say, “Josh will. Wu won’t,” a seeming dogwhistle using Wu’s Taiwanese last name and Kraft’s “American” first name, walking a well-worn path.

In 2021, Wu was the one painted as an interloper by her opponent because she was born in Chicago, though she had been on the City Council for over seven years. She graduated from Harvard in 2007 and has lived in Boston since 2009, fairly common in a city filled with residents who come to the city to attend one of the numerous highly regarded colleges and wind up staying or returning.

Like any politician, Wu has made missteps and hasn’t yet made good on some campaign promises, including rent control and free public transportation, though both require approval from the state legislature.

Her wins include a declining homicide rate, 5,500 affordable housing units built with more in the pipeline, implementation of initiatives tied to her Green New Deal for the city, a $10 million investment in advancing health equity, and an agreement with cultural institutions across the city giving free admission to all Boston families on the first two Sundays of every month.

If campaign contributions are any indication, Wu is in good standing with her constituents. Since Jan. 27, the day Kraft announced his candidacy, she’s gotten over 9,400 donations—42% from Boston residents and most $100 or less. Only one-third of Kraft’s contributors are Bostonians, and over half of his 1,655 donations are the $1,000 allowed maximum, including seven attorneys at Paul Weiss, the first major firm to bend the knee to President Donald Trump in a deal reportedly brokered by Robert Kraft.

Last month, Kraft, who has previously voted Republican and only recently registered as a Democrat, gave $2 million to his own campaign.

Wu is also getting an unexpected boost from the Trump administration. In March, she was one of four mayors of so-called “sanctuary cities” to appear on Capitol Hill. She received plaudits from many Bostonians for not cowering to the bad-faith representatives claiming the cities are overrun with criminals because of the presence of undocumented immigrants. She continues to be unflinching, standing up to Trump’s border bully, Tom Homan.

In the city that touched off the American Revolution, her fight has been well-received. Now she’s in a different kind of fight, with a neophyte politician with a lot of money but no concrete plans. Hopefully, he figures out his polling place by Nov. 4.

Shalise Manza Young was most recently a columnist at Yahoo Sports, focusing on the intersection of race, gender and culture in sports. The Associated Press Sports Editors named her one of the 10 best columnists in the country in 2020. She has also written for the Boston Globe and Providence Journal. Find her on Bluesky @shalisemyoung.

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