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It’s getting awkward for Ayanna Pressley in the mayoral race

Councilor Ayanna Pressley chatted before a City Council meeting last week. John Tlumacki/Globe staff

So, what is Ayanna Pressley to do?

The race for mayor is just gearing up, and the two major contenders — Mayor Martin J. Walsh and City Councilor Tito Jackson — could benefit from Pressley’s broad political reach as the top vote-getter on the council.

Both men are associates and longtime allies of Pressley’s. And here is her predicament:

Jackson is a friend and key colleague of hers on the City Council.

And Walsh is her husband’s boss.

“It’s tough for her,’’ said political observer Kevin Peterson, who runs the New Democracy Coalition, a civic rights organization. “But she’s a very smart and very tough woman. She will have to really pull upon her extraordinary intellectual and moral reserves [to make a decision] in this mayoral race.”


Pressley, who is gearing up for own bid for a fifth term in office, would not weigh in on the mayoral race when reached by the Globe recently. Instead she said she is focused on the effect of controversial policies coming from President Trump’s White House and other issues.

“This is entirely too early,’’ said Pressley of the mayor’s race. “I’m not focused on any race or a contest right now, even my own. I’ve been focused on the work.”

Since Jackson officially threw his hat in the race last month, ardent supporters of Walsh and Jackson — both well-liked progressives — have been keeping their heads low and ducking questions about who they plan to support. Pressley’s case offers a unique window into that dilemma.

A Pressley backing would come with enormous benefits for either Jackson or Walsh: The at-large councilor has averaged about 43,000 votes in all of her four council elections.

Her support, and those voting numbers, could help even the playing field for Jackson, who some political watchers say is mounting a quixotic challenge against Walsh and his vast political and financial trove.


Political watchers say Pressley has shown enormous strength among black and left-of-center white voters, many of them upper-middle class — and votes that Jackson covets. But those observers caution that it remains unclear whether Pressley’s council support will transfer to a mayoral race.

Municipal elections tend to be low-voting affairs that draw many municipal workers to the polls. Walsh beat former city councilor John Connolly by just 4,889 votes in the 2013 mayoral election, according to results from the city’s Election Department.

Pressley, a 42-year-old Dorchester resident originally from Chicago, was elected in 2009 in a history-making campaign, becoming the first African-American woman to serve on the council.

But two years later she was in jeopardy of losing her seat and, out of necessity, formed a pact with her council colleague, Connolly. Connolly and Pressley agreed to share resources and campaign costs in an unusual alliance that defied political conventions in Boston.

Connolly, facing speculation about a 2013 mayoral run, needed more exposure in minority-dominated precincts — Pressley’s stronghold — and more credibility throughout the city. And Pressley needed access to his vast campaign finances and his broad appeal in Boston’s highest voting precincts.

That year, Pressley triumphed, placing first among all four at-large challengers. Connolly was third in the race.

When Connolly challenged Walsh in the 2013 mayor’s contest, Pressley decided to stay neutral. “I’m running my own race, and whoever the next mayor is, I look forward to partnering with him,’’ she said at the time.


As the city begins to turn its focus on this year’s mayoral contest, some political watchers say Pressley cannot afford to stay quiet as Jackson attempts his own shot at history

“She and Tito are good friends. But this is not about friendship. This is business,” said Darnell Williams, head of the local Urban League.

But Joyce Ferriabough-Bolling, a political consultant and Pressley supporter, said the councilor should stay focused on her own race.

“I think there’s a long way to go in the campaign, and endorsements sometimes can be a double-edged sword,” Ferriabough-Bolling said.

Jackson declined to comment for this story. Walsh said he has not asked Pressley — or anyone — for support.

In her seven years on the council, Pressley has been known for advocating for social issues affecting women and girls, and tackling causes that cut poverty, address trauma, and fight violence.

But some inside City Hall have wondered whether she, too, aspires to run for the mayor’s job, or for Congress. Pressley said she’s focused on her current job.

On the council, Jackson and Pressley are usually aligned on the same causes. She, along with other councilors, backed his lead in rejecting a proposed school budget last year. And he supported her last-minute — and unsuccessful — attempt to become City Council president in 2014. He also earned her support when he pushed his commission to address the plight of black and Latino men and boys.


After the council approved the commission, Walsh vetoed it and established his own initiative — Boston’s My Brother’s Keeper, after former President Barack Obama’s program, to address young men of color.

Last summer, Walsh named Pressley’s husband, Conan Harris, as director of the city’s My Brother’s Keeper program.

Walsh, in an interview, said he first met Harris for coffee in Dorchester in 2012 and the two became “instant friends.” He hired Harris in 2015 to work in the mayor’s office of public safety. Walsh, noting Harris’s long history of helping former gang members and at-risk youths find better opportunities, said Harris brings street cred, passion, and exemplary talents to the administration.

Walsh said he has previously backed campaigns for Jackson and Pressley. He said Pressley is entitled to her own choices.

“Ayanna can make a decision when and if she wants to make a decision in the mayor’s race. She also is a candidate for reelection. So she’s on the ballot as well,’’ Walsh said. “So I think it’s unfair to suggest that Ayanna is going to have to be with Marty Walsh because her husband works for Marty Walsh. Marty Walsh doesn’t care about that.”

Harris, in an interview, said that he, too, is focused on his job helping at-risk young men and will let his wife make up her own mind.

“I really have no decision in that,’’ he said, adding that he deliberately stays out of politics. “The wife is her own entity. She’s her own person and she has her own politics. Also, she’s on the ballot herself. When you are on the ballot, your priority focus is yourself.”


One thing is clear though for Harris. He said he has made up his mind on who he will vote for come November: Marty Walsh.

Meghan E. Irons can be reached at meghan.irons@globe.com. Follow her on Twitter @meghanirons.