Two years ago, outgoing City Councillor Michael Flaherty stood in the ballroom of the Venezia restaurant with a darkened Dorchester Bay behind him. The election returns were in, and he had just gotten off the phone with Thomas Menino after congratulating the mayor on handily winning a fifth four-year term.
Let’s do it again in a few years, Flaherty said he told Menino.
Now, Flaherty is back on the ballot and the mayor remains his primary target. But this time, the South Boston pol, who spent nearly a decade as one of four at-large city councillors, is running to win back one of those seats.
Flaherty’s entrance radically re-jiggered a municipal election since in many parts of the city the seven-person at-large field will be the only item on the ballot. Dorchester, with an open district seat for the first time in nearly two decades, is one of the exceptions. Voters will get to pick a district councillor and fill in four slots for City Council At-Large.
Most political observers are predicting a citywide voter turnout of 12 percent – barely one in 10 voters – and an election similar to 2007. That was the year City Councillor At-Large Felix D. Arroyo was knocked off the council by West Roxbury’s John Connolly.
But it’s unclear who will be clearing out their desks come January, if Flaherty manages to get back on the council.
In Felix G. Arroyo’s office hangs the Serenity Prayer, which asks for help “to accept the things I cannot change; courage to change the things I can; and wisdom to know the difference.” The prayer was the first thing that came to his mind when the younger Arroyo was asked about the at-large race earlier this week.
“My father lost in 2007. That’s a fact,” said Arroyo, who managed to grab one of the seats that opened up due to the departure of Flaherty and Sam Yoon in 2009. “And what I understand in politics is, politics is temporary and the important thing is not really whether you win or lose but what you did with your time.”
Arroyo pointed to his efforts in preserving youth jobs in the city budget and opposing library branch closures. The Jamaica Plain resident has maintained a heavy presence in Dorchester, attending neighborhood meetings and local events.
On his “year in review tour” earlier this year, he visited over 40 neighborhood associations. In summer 2010, he dropped by 20 small business districts, according to his office.
“I’m in every neighborhood all the time,” Arroyo said. “I’m a very accessible.”
Given the unpredictability of what will happen on Nov. 8, Arroyo isn’t the only one to be considered vulnerable. Fellow incumbents Ayanna Pressley, an Ashmont area resident, and Stephen Murphy, born in Dorchester and now living in Hyde Park, are also on the list. John Connolly is not, positioned similarly to Flaherty in 2007: an at-large city councillor who is expected to top the ticket again and widely viewed as an eventual mayoral contender.
Connolly’s campaign had volunteers manning polling locations across the city during the preliminary election for district races in Dorchester, Roxbury and South Boston on Sept. 27. The at-large race wasn’t on the ballot – not enough candidates were able to sign up – but it was a clear show of strength.
In the first half of October, Connolly raised over $40,000, outpacing all the other candidates and continuing a financial trend.
He also sent out a mailer that highlighted his investigation into expired frozen food being served: “WARNING: Contents inside were not suitable for children…Until John Connolly Took Action.” In another year and in another election, that type of mailer would have drawn the ire of the Menino administration. But its focus is currently on Dorchester’s District 3 race and ensuring Flaherty doesn’t return to the council.
At a recent house party on Carruth St., Connolly was “running on fumes” as he sat with several parents who vented their frustrations with the school system, including the Menino administration’s plan to close Lee Academy. He is getting four to five hours of sleep a night, Connolly said.
He was soon joined by Pressley. The Boston Sunday Globe’s report that the two had formed an alliance left their colleagues feeling blindsided, but the pair sought to downplay it at the house party, saying they had been campaigning together for a long time, and knew one another before either was elected to public office.
Their partnership makes for an “intriguing and compelling narrative,” said Pressley, the city’s first woman of color to serve as an at-large councillor.
But “this is not about a white guy trying to meet black voters,” Connolly said. And, Pressley adds, “he’s not my white knight.”
Her supporters remain appreciative, though. At the ribbon-cutting for the Ashmont MBTA station, U.S. Sen. John Kerry, Pressley’s former boss, approached Connolly to personally thank him for helping Pressley’s campaign.
A Chicago native, Pressley was raised by a single mother. Connolly is a former teacher whose father is a former secretary of state and whose mother is a judge. The joint pitch: He works for strong schools, she works for strong families.
“My agenda is to eradicate poverty and end violence,” Pressley said, citing her spearheading of hearings on teen pregnancy issues and neighborhood homicides.
Asked about the Connolly-Pressley partnership, Flaherty said, “As far as pacts and alliances, at the end of the day, what matters most to people is who they feel is going to work hard for them on their issues.”
He maintained he would be a strong and independent voice on a council that has sometimes been “bullied” by the mayor, standing up to him only a few times a year, instead of living up to its duty as the “last bastion” of checks and balances in a strong mayor form of government.
In a sign of Flaherty’s potential to crack into the incumbents’ club, Dorchester’s gay, lesbian, bisexual and transgender organization DotOUT— which is influential in the larger progressive community locally— gave Flaherty their endorsement on Sunday. Arroyo, Connolly and Pressley also won the group’s support, while City Council President Steve Murphy, who did not attend the group’s meeting in Savin Hill, was not endorsed.
Murphy, a Dorchester native who now lives in Hyde Park, has vigorously pushed back against Flaherty’s charges. “We don’t always agree on everything but…we’ve learned to kind of coexist and support each other,” Murphy said Tuesday in a forum on WGBH’s “The Callie Crossley Show.”
Murphy frequently points out that the council worked together to wring around $40 million in savings from a firefighter union contract with the city while upholding collective bargaining rights, and limited the number of custodians who were laid off in the city budget.
Flaherty’s candidacy has reshaped the relationships between the four incumbents, and put a City Council At-Large seat farther out of reach for two other candidates on the ballot: Hyde Park’s Will Dorcena and Jamaica Plain’s Sean Ryan.
Dorcena, the brother of state Rep. Linda Dorcena Forry, is running for the first time, while Ryan has previously campaigned for at-large seat.
Dorcena’s campaign has sometimes taken on a bitter tone, noting in forums and online that his candidacy isn’t getting much media coverage. “I am the invisible man in the race,” he said at the Savin Hill forum put together by DotOUT.
But Dorcena did not attend a sit-down between City Council At-Large candidates with WickedLocal.com editors and he did not respond to a request for comment for this article.