In mayor’s race, Pressley’s endorsement packs the most power

But will the congresswoman choose a favorite?

Representative Ayanna Pressley spoke at the March on Washington at the Lincoln Memorial on Aug. 28 in Washington.Pool/Getty

As the two city councilors running for mayor of Boston announce endorsements to show their strength and try to stave off further challengers, one politician’s endorsement stands out as a singular, elusive prize: US Representative Ayanna Pressley’s.

The Seventh District congresswoman was a Boston city councilor until a little over two years ago, when she upset 10-term incumbent congressman Michael Capuano to become one of the most recognizable faces in the 116th Congress and a unifying leader in Boston’s Black community.

Now, some political observers think she could play queenmaker to the next mayor of Boston — and that she, more than any other political figure, has the clout to galvanize communities of color around a consensus candidate, if she chooses to do so.

But those who work closely with Pressley aren’t expecting her to weigh in anytime soon, particularly since the field includes two — and potentially four — of the women she served beside. City Councilors Michelle Wu and Andrea Campbell are declared candidates; Council President Kim Janey and Councilor Annissa Essaibi-George are considering campaigns.

“Policy is personal for Ayanna,” said James Chisholm, Pressley’s first campaign manager and former chief of staff, who noted the other councilors in the race aligned closely with Pressley on issues.

Chisholm does not expect Pressley to endorse early in the race. “She considers them her sisters in service,” he said. “Their voices need to be heard.”

Pressley has often balked at making endorsements, particularly in city races, and she is hardly one to discourage a long shot challenge; in 2018, she refused Democratic elders’ suggestion that she wait her turn and challenged Capuano on the campaign theme “Change Can’t Wait.”

US Senator Elizabeth Warren, who holds substantial sway among Massachusetts progressives, endorsed Wu just days after news broke that Mayor Martin J. Walsh would be heading to D.C. as labor secretary in President-elect Joe Biden’s Cabinet. Warren’s support of Wu, a longtime ally, was not a surprise. But her early endorsement was viewed as an indication that Wu may have an early advantage among progressives.

Campbell is also announcing prominent supporters, including former secretary of public safety Andrea Cabral; state Representative Liz Malia, a Jamaica Plain Democrat; 2013 mayoral candidate Bill Walczak; and Asian American Women’s Political Initiative founder Diana Hwang, among others.

Campbell did not endorse Pressley in her bid for Congress in 2018. Wu was among Pressley’s earliest supporters.

But Pressley and Wu have also diverged — most notably, when Wu strayed from Pressley’s bloc of councilors planning to elevate a council president of color. Wu instead backed the white district councilor from South Boston, a decision viewed as a political tradeoff that dismayed progressives.

Pressley, who was in a turbulent capital weighing a second impeachment of President Trump last week, before her husband tested positive for COVID-19, declined to comment about her intentions.

Wilnelia Rivera, who served as the chief political strategist for her 2018 campaign, said the congresswoman is “focused on D.C. right now, and making sure she gets us through this time.”

But with the nation embroiled in multiple crises — of racial injustice, a pandemic, and now, an effort to subvert democracy itself — Rivera suggested the mayor’s election will be won on big issues, not on endorsements. (She’s not working for any candidates, but she is personally supporting Wu.)

“Any candidate running for mayor right now shouldn’t be focusing on endorsements. It’s not that kind of a race,” she said. “We get to make a generational choice here.”

Endorsements are often downplayed as meaningless displays of ego by establishment figures, whose nods of approval carry little weight with the average voter. But they can sometimes give a candidate a boost.

“People have won with really fabulous endorsements and lost with really fabulous endorsements. What makes endorsements count is the people power that they bring to it,” said James Jennings, a Tufts University professor emeritus of Urban and Environmental Policy and Planning.

Pressley has backed several recent unsuccessful campaigns for higher office, including Jesse Mermell’s bid for the Fourth Congressional District and Warren’s presidential campaign.

But within the city, Pressley has proven to be an extremely popular and increasingly influential figure with deep grass-roots ties. The first Black woman elected to City Council in 2009, Pressley, an at-large member, was the council’s top vote-getter in 2011, when she was the only woman elected to council, as well as in 2013 and 2015.

Endorsements can also help voters distinguish among candidates in a crowded field, as this race may prove to be, said Charlotte Golar Richie, a former state legislator and city housing chief.

“When you have a lot of candidates running, there can be confusion,” said Golar Richie, who was one of a dozen candidates for mayor in 2013. ”When you have an endorsement from someone who is well-known, people can say, ‘Ok, that person has figured it out for me.’ ”

Democratic strategist Joyce Ferriabough Bolling, whose late husband, Bruce Bolling, ran for mayor in 1993, agreed Pressley holds unparalleled sway right now. But she noted that Pressley also has relationships with people who are still considering entering the race, including Essaibi-George and Janey, who will become acting mayor upon Walsh’s departure.

“Ayanna’s going to be very careful,” she said.

“The one thing I can say about Ayanna is that she ponders. She doesn’t go off and make decisions willy-nilly,” said Ferriabough Bolling. “She’s going to wait and see how this turns out.”