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Old Boston versus New Boston: Annissa Essaibi George is not the future

In a historically diverse mayoral election, Boston showed its lazy hand.

Annissa Essaibi George and Michelle Wu will face off in Boston's mayoral general election in November.Globe Staff photos

Michelle Wu was destined for the mayoral ticket.

She strategized. She listened. She learned. Her politics are smart, engaged, and intersectional. Wu was the first Asian American woman to serve on the City Council. And in 2016, she was unanimously voted council president. The first woman of color to serve in that role. A changemaker.

Wu, like Ayanna Pressley, like Rachael Rollins, like Kimberly S. Budd, made me believe Boston was ready to embrace the communities who live here. Are we ready to break the habit of being the birthplace of democracy by name while playing progressive and reliably resting on privilege?


In a historic mayoral race that broke the whitewashed ways of Boston politics, a race in which no major candidate was a white man and the front-runners were all women of color — two of them Black women — I was excited to see who would join Wu in pushing Boston into its next chapter.

I had hoped it would be Andrea Campbell, the first Black woman to serve as council president, a brilliant thinker who tenaciously won her council seat and whose concrete plans to create equity made her campaign stand out. Campbell’s lived experience as a native Black Bostonian showed her firsthand how uneven and oppressive the school-to-prison pipeline can be. Her late twin brother, Andre, was a victim of the systems she works to rebuild.

Or it might have been Kim Janey, who made history when she became the first Black person and first woman to ever hold the mayoral seat in Boston history — a fact both beautiful and sad.

Janey never planned to run for mayor. She inherited the office when Marty Walsh left to join the Biden administration.

One of the most heartbreaking realizations of the mayoral campaign was learning why she didn’t run until she took office. As a daughter of Roxbury, she didn’t believe it was possible.


Even with a lifetime of activism and organizing behind her, her experience as a city councilor and council president, she could not imagine Boston letting a Black person lead in that office. It didn’t matter that she had seen herself make change in local politics or that she had seen Pressley and Rollins make history in their roles.

“Imposter syndrome,” she told me over the summer. “I just didn’t think I could. You can’t be what you can’t see.”

She could not fathom a Black woman as mayor of this parochial and segregated city.

Apparently, neither could Boston. And no, Black folk did not split the vote between Campbell and Janey. We are not a monolith, fam.

In part, there was low voter turnout. Less than a sixth of our population, not even 110,000 people, voted. We still haven’t learned our lesson when it comes to local elections and primaries. Every vote matters and waiting for the big show can sacrifice real change.

But folk feel disempowered. If Janey herself didn’t think it was possible that a Black woman could hold that office, imagine how many Bostonians felt so discouraged by a lifetime lacking in representation that they just didn’t go to the polls.

People are tired, sad, and disillusioned. Between COVID-19, erasure, and enduring injustice, we must work hard to ignite the sense of duty and practice of hope required to make voting a lifestyle.


Still, in a historic mayoral race, the most diverse in Boston history, in which every candidate was of color and all front-runners were women, it is telling that the top two picks are the fairest skinned. Wu deserves this ticket. I gladly champion her vision for our future.

I also acknowledge colorism and racism played a role in this election. Annissa Essaibi George, y’all? Is this your mayor?

Essaibi George was the only candidate with a real sense of scandal this campaign, due to her husband’s capitalistic slummy practices and questions surrounding her complicity. Yet here we are: Essaibi George vs. Wu for the city’s next mayor.

There’s some talk this campaign is about who is in the neighborhoods doing the work. Essaibi George is not the only one in the community. Wu may be from Illinois, but she is a local politician. She is in Boston neighborhoods, in listening circles, in folk’s backyards having conversations and sharing solutions. Her ideas, like rent control and Free the T, are not abstract. They are only pie in the sky to someone who lacks the radical imagination to understand what it really takes to upend systems.

A moderate is not the answer Boston needs. Essaibi George supporters include police unions and Trump-loving New Balance chairman Jim Davis, who poured half a million into a super PAC supporting her. We know what pro-police, pro-big business fandom brings. You cannot straddle the fence on issues of justice and equity. And being from Dorchester doesn’t make her the better choice. In a race where no candidate fully catered to Old Boston, Essaibi George attracted the conservative base.


We’re wrestling with ourselves, Boston. We are a city primarily of people of color yet we wear a reputation of being racist and white. We are a city filled with young activists and new thinkers doing the work to re-imagine what it means to disrupt the narrative. We are a city in a tug of war between Old Boston bringing us down and New Boston building bridges to our future.

I say it’s out with the old and in with the Wu.

Jeneé Osterheldt can be reached at Follow her @sincerelyjenee and on Instagram @abeautifulresistance.