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Joan Vennochi

City Council race shows how far Boston has come

Ayanna Pressley of Dorchester won the most votes in Tuesday’s City Council election, but she wasn’t the first woman to do that. Louisa Day Hicks won the most votes in three elections.Bill Brett/Globe staff

MESSAGE TO Michael Flaherty: People don’t like encores unless they start the clapping.

Flaherty’s failure to win back a seat on the Boston City Council changes the dynamic of Boston politics. And so does incumbent Ayanna Pressley’s surprise top-of-the-ticket victory.

Pressley isn’t the first woman to accomplish that feat. Louise Day Hicks got the most votes three times. But the fact that Pressley, the first black woman elected to the council, could match even once what Hicks did, is truly a sign of a very different Boston and a different council.

“It’s looking less and less like an Irish rugby team,’’ said former councilor Michael McCormack.


“I wasn’t surprised by this at all,’’ said Maura Hennigan, a former city councilor and unsuccessful challenger to Boston Mayor Thomas M. Menino. “It’s a whole new day in the city. I felt it from listening to people, from West Roxbury to Charlestown.’’

Beyond gender and ethnicity, Pressley is the modern face of a city that has changed dramatically over the decades. When Hicks died in 2003, the headline over her Globe obituary identified the South Boston politician as an “icon of tumult.’’

Hicks, who came within 12,000 votes of being elected mayor of Boston in 1967, was a leading opponent of court-ordered school desegregation. Her passion for the cause turned her into a nationally known symbol of racial division.

In contrast, Pressley, a former aide to Senator John Kerry, describes her agenda as “eradicating poverty and ending cycles of violence.’’ She also took on controversial issues like expanding sex education in Boston public schools.

Pressley was cast as the weakest of the four at-large incumbents. Because of attendance issues relating to the illness and subsequent death of her mother, her commitment to the council was questioned.

With the retirement of veteran councilor Maureen Feeney, a Pressley loss would have left Boston with its first all-male council in nearly 40 years. As a result, women rallied to Pressley’s side, including Barbara Lee, the big Democratic fund-raiser, and supporters connected with the Massachusetts Women’s Political Caucus.


Pressley also got help from some powerful men. A core of Kerry volunteers joined forces with Pressley’s devoted campaign staff in the weeks leading up to election day. Kerry stood outside Grove Hall with Pressley the day before Tuesday’s election, and his team provided get-out-the-vote ground support on election day.

Menino also played a key role in the outcome by throwing his support, and the machine that goes with it, to the full slate of at-large incumbents. Menino didn’t want Flaherty back on the council, where his former rival could use the position to launch another challenge. In 2009, when Menino was running for his fifth term, Flaherty gave him his strongest challenge to date; even so, the mayor still won by 15 percentage points.

Flaherty blamed his defeat on a combination of political forces organized against him. But he was never able to formulate a message beyond ambition and his desire to take another shot at a mayoral run. “History has passed him by,’’ said Lawrence DiCara, who served on the council from 1972 to 1981.

Menino didn’t get everything he wanted in this week’s election. John O’Toole, the district councilor candidate he supported, lost an open seat to his opponent, Frank Baker. Still, the results prompted new speculation about who is now best-positioned for a mayoral run.


John Connolly, who partnered with Pressley, came in a disappointing third. Felix Arroyo finished in second place. That leaves Pressley in an enviable spot.

DiCara said his advice to Pressley is, “Don’t let it go to your head. . . The graveyards are full of people who topped the ticket and thought they were going to be mayor.’’ DiCara came in first in 1979, and lost a later mayoral bid.

Menino shows no signs of leaving office. To the contrary, political insiders believe he will run again. Whatever happens, this election is more proof that Boston is changing.

Still, some things never change. Pressley yesterday had to defend her victory as something more than “a historical footnote’’ brought about simply to prevent an all-male council.

So what if voters wanted to preserve a woman’s voice on the council? It’s as good a motive as wanting to preserve a spot for another man who would be mayor.

Joan Vennochi can be reached at vennochi@globe.com. Follow her on Twitter @Joan_Vennochi.