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An uncommon alliance crosses old battle lines

Two city councilors, one white, one black, are fusing their campaigns, a move driven by idealism — and politics

By Andrew Ryan
Globe Staff / October 16, 2011

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City Councilor John R. Connolly has something Ayanna Pressley, his council colleague, covets - an overflowing campaign treasury and strong appeal in some of Boston’s highest voting precincts. Pressley, meanwhile, has something Connolly wants - more pull in minority precincts, more credibility with the full rainbow of the electorate in the city he would like to run someday.

Together they have something people have said for years that Boston needs - unity. A white politician and a black one, putative rivals, working together. Not just words - common ground, in fact.

It may well be the first partnership of its kind, at least in this town. Connolly and Pressley have agreed to share resources and split campaign costs in a fierce reelection fight. The alliance defies the entrenched norms of politics of Boston, where voting has historically been defined by neighborhood and ethnic loyalties.

The pact was born of necessity: Pressley is in danger of losing her seat just two years after becoming the first woman of color ever to serve on the 13-member City Council. And of ambition: Connolly doesn’t talk about it this way, but he has long been spoken of as a likely mayoral contender, and taking a stand as bridge-builder can only burnish his citywide image.

On the campaign trail, where Connolly and Pressley have been making daily appearances together for more than a week, they describe the partnership as a “natural progression’’ of a longstanding friendship and close working relationship. But they also speak bluntly about the dynamics of an off-year municipal election without a mayoral race to draw people to the polls.

“Conventional wisdom says that in this municipal election, traditional voters - code words for white - will not vote for me,’’ Pressley told Connolly supporters last week as they sipped white wine at an intimate South End fund-raiser hosted by one of his former classmates. “I think that’s insulting to me. And to white voters.’’

Pressley needs a boost as Michael F. Flaherty, a mayoral finalist in the last election, is attempting to win back the seat he held for years on the City Council. His presence on the ballot could put the squeeze on other incumbents, with Pressley likely the most vulnerable.

Connolly has a war chest brimming with $245,000, which dwarfs Pressley’s $38,000 and totals almost as much as all the other at-large city council candidates combined. Sharing campaign costs is allowed under state campaign finance laws as long as the expenses are divided equally.

The 38-year-old incumbent has strong support in his home neighborhood of West Roxbury and other predominantly white enclaves of Boston, where voter turnout is traditional higher in municipal elections.

“I take very seriously representing the whole city. I’m always trying to work with people to bring neighborhoods together and people together,’’ Connolly said, dismissing speculation about ambition for higher office. “Ayanna Pressley and I have had very different life experiences, but we share a common vision for a city coming together.’’

The Boston City Council has four at-large seats that represent the entire city. All four incumbents – Connolly, Pressley, Stephen J. Murphy, and Felix G. Arroyo – are running for reelection.

The most substantial challenge will come from Flaherty, who served on the council for a decade before leaving to run unsuccessfully for mayor last year. Two other competitors, Will Dorcena and Sean H. Ryan, will also be on the ballot, though they have been slow to raise money and gain traction.

In Boston, it will be a first for two at-large candidates competing for the same votes to form a team and split campaign costs, said Lawrence S. DiCara, a former City Councilor and longtime watcher of city politics.

“It is ingenious and risky simultaneously,’’ DiCara said. “It’s risky because no one can accurately predict the numerous combinations of votes in a multiple candidate, at large election.’’

Pressley and Connolly seem to be aware of the pitfalls.

“I’d never want to take my own reelection for granted,’’ Connolly told supporters at his South End fund-raiser. “But according to the political pundits [Pressley] is most at risk of losing. That would be a tragedy. I couldn’t look my wife or daughter in the eye If I didn’t do everything I could to make sure that doesn’t happen.’’

Pressley became the first woman of color ever elected to the City Council in 2009, when she captured an open seat by finishing fourth in the at-large race with almost 42,000 votes. She won by a comfortable margin, beating the fifth place candidate by almost 12,000.

But the Menino-Flaherty mayor’s contest drove 111,190 voters to the polls, which represented a citywide turnout of 31 percent. Less than half of that turnout is expected on Nov. 8. The last off-year municipal election in 2007 saw just over 46,000 ballots cast.

Those who show up for low-interest elections tend to be older, white, and more conservative, a dynamic that could hurt Pressley.

Some believe that no matter what Connolly and Pressley do to bolster their collective candidacies, few voters are likely to head to the polls on Election Day. That’s particularly true in communities of color, said Paul Watanabe, a professor at the University of Massachusetts Boston who specializes in ethnic politics.

“In a low turnout election, maybe moving a few votes this way or that may have some immediate impact,’’ said Watanabe. “But the notion of deriving some future political benefits from this, I actually don’t see it.’’

Partnerships between two candidates is most common at the gubernatorial level, where teams often join forces and run simultaneously for governor and lieutenant governor. But it also happens on occasion at the local level, said Jason Tait, a spokesman for the state Office Campaign & Political Finance.

“Joint expenditures are OK so long as the costs are shared proportionally,’’ Tait said.

Connolly grew up in Roslindale. His father served as a state representative and secretary of state. His mother is the chief justice of the state’s district courts. Connolly graduated from Roxbury Latin School, Harvard University, and Boston College Law School. He taught middle school for three years before becoming a lawyer and has made education the focus of his work on the City Council. The last election, he won the most votes in the at-large race.

Pressley, 37, has a very different biography. Born in Chicago, she was raised by her mother because her father struggled with addiction. Pressley has talked publicly about being sexually abused as a child and sexually assaulted as a college student when she attended Boston University. But she went on to work for former US Representative Joseph P. Kennedy II, and ultimately became political director for US Senator John F. Kerry.

In West Roxbury on Friday, Ann Sullivan, 78, said she votes for Connolly “every time’’ because she meets him in her neighborhood so often. Connolly was there again that day to talk to Sullivan and a few dozen other seniors at a turkey, stuffing, and gravy lunch at the Roche Family Community Center. This time he appeared with Pressley and actively urged the seniors to give her one of their four votes.

“I’ll think about it,’’ Sullivan said with a shrug after the candidates were out of earshot.

But then Pressley took the stage. She told the seniors about her tough upbringing, her work with Kennedy and Kerry, and quipped that as the only woman running for reelection, “Somebody, ladies you know this, has to keep these men in line.’’

Sullivan laughed. So did others. And they listened as Pressley outlined her efforts to combat poverty, teen pregnancy, and stabilize families.

“I like her,’’ Sullivan said.