Battenfeld: Michelle Wu has earned a challenger, but is Josh Kraft the one?

At first glance, Wu has almost a perfect foil in Kraft, 57, a rich trust fund kid, a white carpetbagger from tony Chestnut Hill whose father, Robert, is a pal of President Trump.

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From her failure to get rent control launched, to her school closure plan and failure to get buses to run on time, to her administration’s refusal to listen to and engage with residents, Michelle Wu has quilted together enough dissent and dissatisfaction to earn a challenger. She’s invited it and deserves one. The question now is, is there a price to be paid for it? And is Josh Kraft really the man to break history and unseat a sitting Boston mayor, which hasn’t been done in 75 years.

At first glance, Wu has almost a perfect foil in Kraft, 57, a rich trust fund kid, a white carpetbagger from tony Chestnut Hill whose father, Robert, is a pal of President Trump. That’s how Wu will define her race unless Kraft gets out soon to define himself. Kraft has yet to sit down for interviews, giving Wu a head start on how to plan and organize her campaign after delivering her third child.



He is looking for a campaign headquarters in Roxbury, but better get going soon. But right now he’s the mystery candidate, saying nothing – not even articulating a vision for Boston and why he’s running. Wu sits on a $1.

7 million campaign warchest, which isn’t really that much considering Kraft will spend millions of his own money. But she will have access to plenty of money once her rank and file city workers and wealthy supporters get behind her. And Wu has a new political persona courtesy of Trump.

She’s the poster chiid for the birthright citizen movement, as she proudly points out that her parents were not citizens when she was born here. Trump is trying to remove it from the books, but a legal battle looms ahead. Which brings up another problem for Kraft: what does he stand for? He recently switched from unenrolled to Democrat, which doesn’t really mean anything because Boston’s elections are non-partisan.

But it does signal that Kraft intends to avoid being piegonholed as a Republican and run as a moderate or even progressive on some issues. And if he shares that title with Wu, the national darling of the progressive movement, how will Kraft separate himself from the incumbent mayor? Here are a few potential ways: Focus on the outrageous cost of housing and Wu’s failures to address it with her rent control plan, which was always going to be doomed in the Legislature. Wu also promised to make the T free, which is also never going to happen.

The most she could do is take some federal money and make a few bus lines fare-free. Focus on education and the poor shape of most Boston middle schools and high schools. This may be difficult for Kraft, a prep school kid himself, but Marty Walsh did it when he was running for mayor and sending his kids to private schools.

Most parents are outraged by the violence and poor condition of the schools in Boston, so come up with a few solutions while mocking Wu’s Green New Deal pledge to rebuild the city’s schools. The $100 million White Stadium fiasco is good fodder right now to focus on Wu’s my-way-or-the-highway governing style, but it will likely be just a blip by the time the campaign gets fully going. Focus on quality of life issues in the neighborhoods like potholes, stabbings and fear of walking the streets at night.

Wu has taken a victory lap because the murder rate has done down but there’s a lot more to crime fears than just that. And finally, try to exploit Wu’s rather weak connection to the Black community. Kraft has spent plenty of time in Roxbury and Dorchester, so articulate a vision for those residents that speaks to their problems.

And if after that Kraft is still getting blown away, he can always shift to a statewide campaign, which will be much more winnable against Maura Healey..