The race that began with a mischievous political jab will surely conclude by making history, as Boston is on the cusp of transforming into the city that many have long wanted but questioned whether they would ever see.
One year ago, almost to the day, Mayor Martin J. Walsh let drop that his political rival, City Councilor Michelle Wu, would run against him, preempting Wu’s own announcement. A few weeks later, Councilor Andrea Campbell announced that she, too, would run, creating the potential for a historic showdown.
More seismic shifts followed. In January, President Biden tapped Walsh to join his Cabinet, setting off a series of political moves that has brought one of the most durable bastions of white male political power in the country into an entirely new era: That “shining city on a hill,” which has had an uninterrupted string of white male mayors dating to 1822, will elect its first mayor of color, and odds are its first woman voted into the office, too.
It is nothing short of a sea change for a capital city that has a reputation for intolerance and is still recovering from the wounds of its past.
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A frame shot of last week’s first televised debate best set the scene: four women of color and a Black man, standing side by side at their podiums, challenging one another ahead of Tuesday’s preliminary election that will winnow the field to two. At one point, the camera zoomed in on Campbell and Acting Mayor Kim Janey, the two Black women in the race, who polls show in a neck-and-neck battle to advance to the Nov. 2 general election.
“As a kid, I could not imagine this field,” said Marie St. Fleur, a former state representative who was the first Haitian-American elected to office in the state and is backing Campbell. “Race is embedded in Boston’s psyche. Unfortunately, it is, and there’s an opportunity for us to shift the narrative, not only for Boston, but nationally and internationally.”
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For all the optimism, there is also a sense of uncertainty and trepidation, particularly within Boston’s Black communities. Polls show Wu as the front-runner, with Campbell, Janey, and Councilor Annissa Essaibi George locked in fierce competition for the second and final slot in the runoff. Essaibi George, who is of Arab American and Polish descent, identifies as a person of color.
Janey and Campbell could yet both make it to the runoff, but there is nonetheless concern that the city’s Black communities again may lose an opportunity for citywide power.
St. Fleur said such a loss would be an “indictment” of how far Boston has truly come, “a sad statement if we’re not able to do that.”
“Boston has a particular history, a particular set of experiences that requires us to address this issue of race head on,” she said. ”We’re just on the cusp of something here for Boston, there’s a bridge that’s happening from one generation to another, and I hope we don’t miss it.”
The other major candidate is John Barros, a Black man and a former economic development chief under Walsh. Polls show him consistently much further behind.
The four women of color, coming from the most diverse City Council in Boston’s history, have just about an equal shot at making the final — and history.
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Getting to this remarkable political threshold has taken decades of work. While previous electoral opportunities slipped away, this time the troops laboring for greater equity in city government are on the verge of wresting political power from the traditional strongholds that have long controlled city politics.
And Boston’s 13-member City Council could see yet another great transformation with a field of candidates that includes an unprecedented number of immigrants, many of them Black.
“We’re here,” said state Representative Russell Holmes, a Black man from Mattapan. “We have arrived at a moment that many of us did not imagine we would see. It’s an opportunity for women, and an opportunity for people of color.”
“This is our restorative justice moment right now, and an opportunity to right the wrongs,” added at-large City Councilor Julia Mejia, who is running for reelection. In 2019, she was the first Afro-Latina elected to the panel, by a single vote. “People are going to head to the polls, because they want to be seen and heard. It’s the power of the people, in its truest form.”
To be clear, the old Boston political machines will continue to play a role in the election. Groups such as unions for police and firefighters are flexing their muscle, endorsing and donating to more moderate candidates for mayor and for council.
Former police commissioner William Gross, whose abrupt retirement triggered a controversy over his designated successor, organized an independent political action committee on behalf of Essaibi George. Such groups can spend an unlimited amount, and Gross’s organization has already put nearly $450,000 into supporting her campaign. It’s received donations from police unions and New Balance chairman Jim Davis, who also donated heavily to former president Donald Trump.
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Essaibi George sought to distance herself from the super PAC, and told the Dorchester Reporter, the first to report on the donations, that the connections to Trump were “gross.” But she has defended her support of police and welcomed Gross’s endorsement.
Other political action groups involved in the campaign represent either developers, hotel workers, or environmental activists. One group backed by charter school supporters is supporting Campbell, which triggered criticism from a union-backed PAC.
Community groups and political activists that largely represent Boston’s Black and brown communities are keenly aware of past losses, including Mel King’s historic but unsuccessful run for the seat in 1983 and the 2013 election that produced the most diverse mayoral field in history yet resulted in two white men making the final. Walsh ultimately won.
But their efforts laid the groundwork for what we are seeing today: more diversity in all levels of government, and a city finally on the brink of major change.
Representative Ayanna Pressley was among the first to set the pace, in 2009 becoming the first Black woman elected to the City Council, and, in 2018, the first Black woman elected to Congress from Massachusetts.
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Wu also broke barriers: the first Asian-American woman elected to the City Council, in 2013, and the first woman of color to serve as council president. Essaibi George and Campbell were elected in 2015, with the latter becoming the first Black woman City Council president. Janey took office in 2017 and then succeeded Campbell as president. She was elevated to acting mayor upon Walsh’s departure to Washington, the first woman and Black person to hold the city’s highest office.
Their tenures over the last decade have coincided with a demographic and ideological shift in the city. Boston’s population grew by close to 60,000 over the last decade, to roughly 675,000, a total not seen in a half century. The city is more diverse, though the number of Black residents slightly dropped.
And Boston is even more liberal, and politically progressive, according to recent polls, evidenced by the success of people of color and women in politics: Pressley, and Suffolk District Attorney Rachael Rollins, the first Black woman elected to the post and Biden’s nominee for US attorney. They both overcame more established, white male opponents.
Now comes the last position to see that shift: mayor.
Pressley, who has declined to endorse in the race, said of her 2009 election: “I could only dream of where we’d be today, with a historically diverse field of candidates for both mayor and City Council.”
“The increased diversity of Boston’s elected leaders is critically important, because it means greater diversity of perspective, of lived experience, and, ultimately, policies that better reflect the needs of every person in our city,” she said.
Charlotte Golar Richie was the only woman in the preliminary mayoral round in 2013 and finished third — dashing hopes for a Black candidate in the final. She viewed the race as a political lesson: She had been in the private sector and had lost some of the political chops developed from earlier experience in government. The current candidates, Golar Richie said, are seasoned veterans with professional and personal stakes in their community.
“We are going to have a woman mayor, no offense to the guys,” she said. “Boston is going to make history in November, with a woman and with a person of color … very possibly with a Black woman.”
She added, “Ready or not, here she comes.”
So far, Wu has raised $1.8 million, and Campbell $1.6 million; Janey and Essaibi George have each raised around $1.3 million, while Barros is at about $650,000. Those figures do not account for spending by outside PACS, which exceeds $2 million to date.
Voting has already begun, via mail and early-voting locations. Turnout could be crucial for the tight cluster of candidates scrambling for second, based on recent polls. For example, Wu was in command with 31 percent in a poll last week by the Globe and Suffolk University, and then Janey at 20 percent, Essaibi George at 19, and Campbell at 18.
Though all the candidates are people of color, interest in the race has also centered on Campbell and Janey, and whether either one or both can make it to the final and be elected Boston’s first Black mayor.
Campbell has been needling Janey on a range of issues, which seems to have helped her climb in the polls, while Janey has slipped. But with Essaibi George running close, there’s a real possibility that neither will make the final. Both have balked at stepping aside to let the other advance, taking umbrage at the insinuation that their candidacies and qualifications are interchangeable.
Holmes, who has not endorsed a candidate, suggested it is inappropriate to focus on Janey and Campbell when Barros’s candidacy will also influence the outcome.
“Both [women] are strong and should be able to have this opportunity to go to voters to see who has this stronger message, that’s how I look at it,” he said.
The race will ultimately come down to get-out-the-vote efforts and political strategies, as all of the candidates seem to have core support in different demographic areas, according to the recent Globe poll.
Of poll respondents, all likely voters, 61 percent approved of Janey’s work as mayor. She also leads among Black voters, with 46 percent, among people age 65 and older, and among voters without college degrees.
Campbell, riding momentum from her recent endorsement from the Globe editorial board, has different mix of support. She is popular among liberal voters who are philosophically aligned with Wu, said David Paleologos, who conducted the Globe poll; 43 percent of voters who picked Wu as their first choice for mayor named Campbell as their second, he said.
For her part, Wu gets support from multiple demographics, including Boston’s newest residents. She has support from 50 percent of people who have lived in Boston for 10 years or fewer, 45 percent of voters with advanced degrees, and she is also popular among younger voters and those who identify as very liberal.
Essaibi George’s base is among moderate voters: Those who cited public safety as their greatest concern in the Globe poll named her as their top choice. She also has loyal support in some of Boston’s more conservative neighborhoods, including in South Boston, parts of Dorchester, and West Roxbury. Those areas were also loyal to Walsh, a longtime ally, though he has not endorsed anyone in the race. He and Essaibi George grew up on the same street in Dorchester. On Thursday, Essaibi George escorted Walsh’s mother, Mary, along with her own mother, to the polls for early voting.
Essaibi George has focused on quality of life and neighborhood issues, while Wu has proposed bold initiatives to address climate change and equal access to transportation. Campbell built her campaign on reform, particularly in policing, and Janey bills herself as the progressive who is already doing the job.
Suffolk Superior Court Clerk Michael Donovan, the longest consecutively serving elected official in Boston, has seen the transformation of politics in the city. While he’s endorsed Wu, Donovan has praised all four front-runners, and said the city is ready for a woman mayor, and one of color.
“It’s time for change,” he said. “They are bright, intelligent, all fighters, all scrappers. I’ve known them, I’ve seen them. I think their time has come.”
Milton J. Valencia can be reached at milton.valencia@globe.com. Follow him on Twitter @miltonvalencia and on Instagram @miltonvalencia617. Meghan E. Irons can be reached at meghan.irons@globe.com. Follow her on Twitter @meghanirons.