Contrarian Boston

Contrarian Boston

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Contrarian Boston
Contrarian Boston
Embattled sheriff netted tens of thousands in campaign contributions from staffers | Emily Rooney on some strange mayoral race ads | Tentative winner in battle for pivotal Mass. Lottery contract |

Embattled sheriff netted tens of thousands in campaign contributions from staffers | Emily Rooney on some strange mayoral race ads | Tentative winner in battle for pivotal Mass. Lottery contract |

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Scott Van Voorhis
Aug 13, 2025
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Contrarian Boston
Contrarian Boston
Embattled sheriff netted tens of thousands in campaign contributions from staffers | Emily Rooney on some strange mayoral race ads | Tentative winner in battle for pivotal Mass. Lottery contract |
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Mixed messages: Between a strange ad featuring Michelle Wu and Big Papi as cartoon characters to Josh Kraft’s mystery trumpet, the multimillion-dollar mayoral ad blitz offers lots to critique

By Emily Rooney

Watching and dissecting political campaign ads is a sport for many journalists who like to hold them up to a truth meter. That’s fine, but my measure is whether the message, true or false, is effective.

This year’s Boston mayoral race ads have been a mixed bag, and interestingly, some of the most effective messages aren’t really ads at all.

Boston Mayor Michelle Wu has been using TikTok for some of her outreach, and particularly catchy is her interaction with the owner of Dynasty restaurant in Chinatown, who talks about how much better his business will be now that the city is allowing restaurants with beer and wine licenses to get full-blown liquor licenses in 2026. And says Wu, “That’s on top of the new 225 licenses issued this year.”

Also effective: A TikTok where Wu walks around Uphams Corner, pointing out how the city responded to neighborhood concerns about shoddy brick sidewalks. I couldn’t find anything comparable on TikTok from challenger Josh Kraft, except maybe a promise to fix a dangerous mash-up of wires and transformers hanging over Charlestown streets, one of which recently burst into flames. But his message lacked sufficient information about who controls the wires, who would be responsible for burying them, and at what cost.

I did, however, find some useful information about Kraft on the app Nextdoor. Once you get past the endless litany of reports of stolen packages and scolding over outdoor cats, there’s good stuff there.

Omnipresent neighborhood watchdog Ali Foley notes that while Wu is blasting Kraft for not providing traffic studies for the Kraft soccer stadium in Everett, Wu never responded to requests for bike lane studies back in 2023. Foley writes on the platform that while Wu is pressing a private business for transparency, her administration withheld information from constituents. That’s something Kraft could run with because while he has zero ties to the stadium - just in family name only - Wu is linking him to the soccer deal.

Meanwhile, an ad that might have blown into your cellphone recently, featuring cartoon characters of both Wu and former Red Sox great David Ortiz, aka Big Papi, is just plain weird.

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