Will Boston’s Next Mayor Be a Woman of Color?

Ready for the biggest race yet in New Boston politics? Here comes the 2021 mayoral election.

Illustration by Benjamen Purvis

A Black woman in a brightly colored floral-pattern dress stands on a front stoop and looks you right in the eyes through the camera. “Who’s with me?” she asks.

A quick camera shift provides an answer: Ama Edzie, a Black fitness instructor from Jamaica Plain. Another face replaces her, this one a white man, Dan Durgan. Then a Hispanic woman, greeting you with “Hola, yo soy Gina Razón.” More faces follow: Antonia, a Black woman; Lai Lai, an Asian-American woman; Lindsay, another Black woman; Sharma and Daniel Ross, a Black couple; Kyle and Phil, a white same-sex couple.

Who is this diverse coalition of Bostonians, and what, exactly, are they supporting? That would be the mayoral campaign of City Councilor Andrea Campbell, who announced this fall that she will challenge two-term incumbent Marty Walsh in next September’s primary election. Campbell isn’t the only woman with Walsh in her crosshairs. Fellow City Councilor Michelle Wu was the first to announce her candidacy, also launching her campaign with a multi-hued video montage, including a racially blended mother-son family, a woman in a hijab, and other diverse supporters. The message in both campaign videos was not terribly subtle: This is no longer the Boston of Irish and Italian white men, and it should no longer be run by them.

Change has been everywhere in Boston lately—especially in the voting booth. From Suffolk County District Attorney Rachael Rollins to U.S. Representative Ayanna Pressley, women of color have been winning office in record numbers. Of the 12 representing Bostonians in city, county, state, or federal elected office, 10 have entered their current positions in the past six years. Their elections have been not just about issues, or personal qualities, or even identity representation. They have been about redefining the very nature of the positions themselves: elevating activism, intersectionalism, and reform over voting record and bringing home the bacon.

Now Campbell and Wu have confirmed that 2021 is the year we’ll see if the wave sweeping local women of color into political office will finally break down the door to the mayor’s office. Even with the tide moving in their direction, though, they—and anyone else who decides to enter the race—face enormous odds. Assumed to be running for a third term, Walsh is extremely familiar to, and popular with, residents throughout the city. He has raised more than enough money for a full-scale campaign—so much, in fact, that he donated a cool half-million of it to the city’s coronavirus resiliency fund.

Besides, Boston literally never votes out an incumbent mayor. As progressive as the city might seem politically, people here generally don’t like change: They cling to their incumbents like they do to Fenway Park or their neighborhood Dunks. It may be no coincidence, though, that many candidates who have successfully persuaded locals to make a change recently are women of color. Perhaps their background and experiences were more likely to lead them to that paradigm-busting role. Maybe voters are more likely to see those candidates as change agents, because they are so clearly, even if superficially, different from the status quo. “It’s not a gender issue, but women have been part of that narrative—to approach things differently,” says City Councilor Lydia Edwards. In fact, she posits, it could very well be that in this coming mayoral election, “all roads lead to a woman of color.”

In many ways, Wu seems like a natural fit for the well-educated, professional-class progressives of all backgrounds who are increasingly driving Boston’s political conversation. After all, she’s one of them. After leaving Chicago for college in the Hub like Pressley did before her, Wu graduated from Harvard and Harvard Law; married her finance-industry boyfriend; moved from the South End to Roslindale; and had two children (now ages three and five) while advancing her career.

But there’s another side to her origin story, one that may resonate with working-class Bostonians, too—particularly the descendants of Irish immigrants who wrested political power away from the Brahmins generations ago. In her announcement video, Wu talks about her parents emigrating from Taiwan “with no money, no connections,” and about having to detour back to Chicago after college to care for her mother, who suffered from mental illness, and help raise her younger sisters. Still, bumps in the road didn’t get in the way of her political aspirations. She learned the ropes on the 2012 Senate campaign of her law school professor, Elizabeth Warren, and working in City Hall under Mayor Tom Menino. And as Walsh was defeating several city councilors for the mayor’s job in 2013, Wu was audaciously running for, and winning, one of the resulting open citywide seats—before she even turned 30.

Two years later, Andrea Campbell joined Wu on the council at age 33. Her path, too, had echoed that of many Irish pols from previous generations: escaping humble Roxbury and South End upbringings via a Boston Latin School education; furthering her education elsewhere (Princeton University and UCLA Law School, in her case); then returning to find a way to contribute to her community. While Campbell’s qualifications come from that success story, she is not shy about discussing her family’s challenges, including her twin brother’s death while in pretrial detention.

In the midst of the turmoil, Campbell kept on moving up, cutting her teeth in the Deval Patrick administration, and then—no less audacious than Wu—challenging Charles Yancey, one of the last older-generation Black politicians holding office in Boston, for a seat on the city council. In 2018, her fellow councilors made her president for the two-year session—succeeding Wu in that position.

Neither of these women is the type to quietly wait her turn in the political rotation. After all, that’s part of the status quo they intend to disrupt. “When you’re talking about changing the landscape, that requires challenging an incumbent,” Campbell said to me three weeks before announcing her mayoral intentions. That refusal to wait is precisely what excites her and Wu’s supporters in the upcoming race. “There is an energy for it,” says Chynah Tyler, a state representative from Roxbury.

For Campbell, changing Boston’s political landscape means tackling issues of equity and race more aggressively. It also means holding the city’s departments and agencies to account. Campbell made waves in City Hall by calling for an independent inspector general to tackle corruption and inefficiencies without political interference. She has been a leading voice demanding an independent police-review board, and wants to make the central Boston Public Schools administration more responsible and transparent to individual schools, and thus to parents.

Wu, for her part, is looking to harness the energy for change with big ideas. “Next year’s election needs to be about redefining what’s possible for our city,” she told me 10 days before her announcement. “To address our challenges is to recognize and affirm that change is about more than one individual—especially one elected official.” She talks about reimagining the mayor’s role as a “community-based” model of leadership, to replace the classic top-down imposition of the mayor’s will—usually benefitting those with the best connections.

Judging by whom they’ve elected to the council lately, Bostonians are eager for a city government that addresses big issues—such as climate change and transportation—that have previously been thought of as federal or state problems. “Michelle has positioned herself as a big thinker,” Edwards says. “It’s not enough to talk about which person is going to be the mayor—we need to talk about what it means to be mayor.”

Regardless of their individual platforms, the candidates have one thing in common: They represent systemic change, a current buzz phrase in Boston and pretty much everywhere else, says former Suffolk County sheriff Andrea Cabral. Recently, there have been plenty of people “looking at who has been in power, and saying this isn’t working,” she says. “You can’t run on the same old same old.”

It’s also worth noting that after Wu and Campbell, Kim Janey of Roxbury took over as city council president, meaning that since 2016 a woman of color has been poised to become acting mayor if Walsh were to vacate his position. Some speculate that could happen if he gets offered a role in a Joe Biden administration.

As Edwards says: All roads seem to lead to a woman of color.

One afternoon in late June 2018, Michelle Wu left her office at City Hall, an aide in tow, en route to a downtown coffee shop. But this outing wouldn’t be a quick latte break: Wu had agreed to meet with Ayanna Pressley’s campaign manager and Boston coordinator, who had organized a number of discreet sit-downs aimed at convincing local pols to endorse Pressley’s long-shot challenge to sitting Congressman Michael Capuano.

Many of those discussions were about relationships, history, and shared aspirations. Wu, however, already knew what she liked about her fellow councilwoman. Instead, she wanted to dig into the game plan. Peppering Pressley’s staff with questions, Wu began offering a tutorial on the granular micro-targeting of Boston votes. She gave advice on winning specific precincts, even blocks: You need to be at this ward meeting; meet with this influential person. Emphasizing this particular message will boost those “ones and twos”—definite and likely supporters, on coding sheets—in this part of the South End. And on and on through portions of the city within the congressional district.

Two weeks later, Wu endorsed Pressley. The lesson is that while Boston’s fast-rising women in politics may have lofty notions about transforming public office, they reinforce it with plenty of practical, street-level political savvy. They also have resources and networks available that didn’t exist for past female candidates and candidates of color in Boston. Campbell and Wu are both graduates of Emerge Massachusetts, which trains women for political careers. So are Edwards and Rollins, among other local politicians.

Those networks spread within and beyond Boston through digital organizing and fundraising. “This race is largely going to be decided by the online community,” predicts Sharon Durkan, a campaign professional who once served as finance director for Wu and most recently worked on Ed Markey’s Senate reelection campaign. Durkan witnessed how important digital organizing was for the Markey campaign—which surprised many with its fundraising acumen, and stunned people by beating Joe Kennedy 55 percent to 45 percent.

Markey’s online success—ultimately comprising a self-defined social media #markeyverse—centered around his fan base among climate activists, including those in the Sunrise Movement. Wu’s embrace of a local Green New Deal could pay big dividends with those same voters. When Bill McKibben, godfather of this progressive online climate movement, excitedly retweeted Wu’s mayoral announcement to his 360,000 Twitter followers, a #wuniverse hashtag sprang up immediately from many of the #markeyverse influencers. “The Sunrise Movement helped Markey,” Durkan says. “Those kids will be with Michelle.”

There are still challenges for both candidates, of course. Thanks to glaring racial wealth inequities as well as a reticence among donors to irk powerful incumbent pols, female candidates of color can have trouble raising money locally for their campaigns. Neither Wu nor Campbell is likely to come close to matching what Walsh has to spend, but that might not be necessary. Eager progressive communities outside of Boston can make up some of the difference—Wu, for instance, has built relationships with other Asian-
American political leaders across the country, in addition to climate activists and young progressives. Campbell has national networks of her own to tap into. Besides, Sam Yoon ran a strong preliminary mayoral campaign in 2009 on about $750,000; Michael Flaherty, who competed through to the final election, spent less than $1.5 million. And Pressley spent $1.3 million in winning her 2018 Congressional election.

Not everyone can excite a coalition of voters the way Pressley did, of course. But if anybody is going to do it in 2021, well, all roads seem to lead to a woman of color.