Battenfeld: Country’s sharp right turn could lead a pathway for Ed Flynn in Boston mayor’s race

The country’s sharp right turn in the 2024 election — even in pockets of liberal Boston – could provide a pathway for a potential Ed Flynn challenge to Mayor Michelle Wu in 2025.

Donald Trump’s gains across all of the voting wards in Boston – a 5% bump from 2020 that was even bigger in blue-collar districts and in South Boston and Dorchester — make it less daunting for a candidate like the Southie city councilor to take on Wu.

While Wu would still be a heavy favorite, Flynn or another moderate candidate like philanthropist Josh Kraft could make a case for a serious challenge to the far-left Boston Mayor if they are able to expand on Republican-leaning areas of the city.

Flynn, former council president and son of former Mayor Raymond L. Flynn has the name recognition and money to make it at least uncomfortable for Wu if she runs for reelection.

And Wu does not like to feel uncomfortable.

The Boston mayor, who is expecting a third child, prefers friendly settings like public radio interviews or packed supporter events where she is rarely challenged.

The jury is out about whether she has the stomach to withstand an aggressive campaign challenge. It’s going to require her to get out in public more, campaign in the neighborhoods, give constant media interviews and attend relentless campaign forums like her predecessors did.

Every place she goes she runs the risk of protesters harassing her with a megaphone.

When it happened before, she passed an ordinance outlawing protests outside her house in the early morning hours. That’s all going to change if Flynn challenges her. She has to come out of her protective bubble if she wants to win another term. No more safe spaces like climate change or bike lane press conferences. No more Zoom meetings when she has to announce difficult news like a school merger.

Once she’s pulled out of the shadows and into the heat of the spotlight, how will she fare? That’s the big question.

Democrat Kamala Harris won Boston with a whopping 76% of the vote, giving Wu a huge advantage as she heads into her reelection campaign.

But Wu has become the poster child for woke, progressive policies that were soundly rejected by voters nationwide last week. Now may be the time to test her popularity.

While Flynn is a Democrat and not a Trump supporter, there are pockets of Republican support in neighborhoods like South Boston where he is likely to pick up support in a potential mayoral bid next year.

Flynn may try to masquerade as a progressive but the fact is the progressive vote is going to Wu. So he needs to focus on the moderate and conservative precincts to pull out a win.

Flynn could also take advantage of pent-up anger out there against high taxes, crime, school bus snafus, and endless new bike lanes that have snarled traffic.

His father was a huge underdog in 1983 when he came out of a field of a half dozen candidates and won because of tireless campaigning.

In recent weeks Ed Flynn has been on a social media rampage, calling for the election department to be put in state receivership, the school bus system to be put in receivership, out-of-control bike lanes removed because of public safety concerns, a crack-down on downtown crime, more resources for schools, and an end to bullying on the city council.

It has amounted to a full-scale attack on the Wu administration.

“Boston was unprepared for yesterday’s election,” Flynn wrote last week after the city failed to deliver enough ballots to polling stations. “It was a failure in leadership at Boston City Hall. As I stated last night, we need a state and/or federal investigation…Voting is a civil rights issue!”

Flynn has said he’s keeping his options open, but has to decide soon whether to take the plunge in 2025. And Wu has yet to formally announce, triggering speculation about her intentions.

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