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Explaining The Mystery: Why Ayanna Pressley Is Running For Congress

Boston City Councilor Ayanna Pressley, a Dorchester resident.
Pressley for Congress

In declaring her candidacy for Congress Tuesday against Somerville’s Michael Capuano, Boston city councilor Ayanna Pressley willfully broke the longstanding code of Massachusetts politics—the one that forbids Democrats from challenging incumbents from their own party.

A lot of seasoned politicos have expressed some bafflement to me about Pressley’s decision, which will alienate her from the local and national Democratic establishment—which up to now has generally adored her—in hopes of a long-shot upset.

There is no room to run to the left of solidly liberal Capuano, they say. The district, although designed to be majority-minority, in practice leans toward the Capuano-strong Somerville-Chelsea-Everett side. She’ll have trouble getting the money, staff, endorsements, and foot soldiers she needs—and that she would be able to count on if she wasn’t taking on an incumbent political powerhouse.

All she’s doing, the skeptics say, is making enemies who will prevent her from winning higher office later.

All of that may be true. Still, the decision to run makes a lot of sense from another perspective—the one that says she’s spent enough time waiting her turn.

Pressley, 43, is in her fifth two-year term as an at-large councilor. As many have discovered before her, years on the Boston City Council quickly turn the freshest political talent stale. That’s why Sam Yoon, John Connolly, Felix G. Arroyo, and Tito Jackson took their shots at mayor after only a few years on the council. It’s why ambitious pols such as Paul Scapicchio and John Tobin walked away from the council after serving roughly as long as Pressley has now (and at younger ages).

And, it’s one reason why no sitting member of the council has won election to another office since Francis “Mickey” Roache became Register of Deeds in 2002. The last one to go council-to-Congress was Louise Day Hicks, in 1971—an interesting precedent for Pressley, to be sure.

The truth is, Pressley’s once-rising star as the first black woman ever elected to Boston’s City Council—the hype surrounding her had some in City Hall referring to her as “Elvis” in her first term—has aged into an almost motherly persona among the newer, diverse faces there. Pressley finished second in the at-large voting to Michelle Wu in 2017, while Lydia Edwards grabbed the biggest headlines for winning the East Boston district seat.

As one Boston political strategist said to me, in another few years Pressley might not stand out even among the women minorities in any bid for higher office.

Running now, one-on-one against Capuano, might be her one best shot before she becomes just one in a crowd.

It reminds some Boston political insiders of then-councilor John Connolly’s decision to run against Mayor Tom Menino, which he announced in January 2013. Connolly was disappointed when Menino later announced, that March, that he would not seek re-election. Connolly thought he had a better chance one-on-one as the symbol of change against the incumbent Goliath, rather than struggling to stand out as one among many vying for the open seat.

Pressley now has her one-one-one with Capuano—who, like Menino, is popular and formidable, but in some ways can’t help but represent a past political order out of sync with the current Democratic Party mood and energy.

That mood and energy has not been difficult to spot nationally and in the Massachusetts seventh congressional district. Think of the spontaneous protests last year against President Donald Trump’s travel ban, at Logan Airport and Copley Square; the huge women’s marches in Boston and Cambridge Common; the record-breaking list of women running for office nationally, including seven Democrats in Massachusetts congressional races before Pressley; the counter-demonstrations opposing white nationalists on Boston Common; and the Bernie Sanders-backed candidates who won alderman seats in Capuano’s hometown of Somerville.

Pressley can’t claim that Capuano is on the wrong side of those issues. She can, however, make the case that at this moment Congress needs more people like her.

That was no small part of her argument in what almost everyone I spoke with agree was Pressley’s best political campaign: her first re-election to City Council, in 2011, which many predicted she would lose. At the time, it could have meant a Council with no women on it—a scenario that Pressley and her team used to fire up support.

Feeling like the underdog seemed to help push Pressley, and her supporters, to a new level of passion and purpose. Many of those supporters have been waiting for her to light a similar fire under them with a race for higher office, and as one political insider I spoke with put it, “they’re ready to smash through walls like the Kool-Aid man for her.”

That insider, who asked not to be named because he knows and likes Capuano, predicts Pressley will win the race.

Others I spoke with gave her much longer odds, however.

She has a lot to do to prove them wrong. She’ll need to show a new level of discipline to quickly conquer the broad policy knowledge, raise whole new levels of campaign funds, and assemble and manage a large campaign team. She’ll need to demonstrate that she can both give and take a political punch, in ways that she never had to do in the multi-candidate dynamics of an at-large council race—for example, in that 2011 race she campaigned in mutuall-beneficial tandem with Connolly, one of her rivals for the four available seats. She’ll need to energize, organize, and mobilize Boston’s black community—during the political doldrums of summer—where Charlotte Golar Richie and Tito Jackson among others, could not.

It’s a tough task, against a very good opponent. But, win or lose, it’s hard to blame her for wanting to take on the fight.

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