The Boston Globe

Pounding the pavement with Connolly

The Boston Globe - Political Trail
By Michael Jonas - July 1, 2007

John Connolly has heard all the jokes, but he remains dead serious about another run for City Council - and about his belief that, if he wins, he can make a difference on issues that matter.

Barney Frank, the undisputed congressional king of quips, once described the trials and tribulations of a campaign for a Boston City Council seat this way: You could put a lot of effort into a run and lose. Or worse still, you might win.

Bada-bing.

The city's 13-member legislative body has long been derided because of its weak statutory authority under Boston's strong-mayor form of government. This year even more would-be councilors than usual seem to have taken Frank's warning to heart.

Just nine candidates have submitted nominating signatures in the at-large race for four seats, and Connolly looks to be the only credible challenger vying with the four incumbents, who are all seeking reelection.

Two years ago, with one open seat in the at-large field, the 33-year-old lawyer seemed to be coming on strong, finishing third in the September preliminary election. But his fortunes faded in the November final, when fellow challenger Sam Yoon, boosted by a big vote in progressive precincts, soared to third place, while veteran incumbent Steve Murphy held the fourth spot.

With fewer candidates and no mayor's race this fall, the off-year election is likely to be a particularly low-turnout affair. Which is why Connolly is already campaigning full tilt at a time when few voters are likely to have given even a passing thought to the city election.

Connolly comes from a politically prominent West Roxbury family, as the son of former secretary of state Michael Connolly, and he's counting on support from places like vote-rich Ward 20, where he grew up and now lives with his wife. But with degrees from Harvard and Boston College Law School and stints at two big downtown law firms, he's also trying to energize the growing swath of young professionals in Boston, a notoriously low-voting demographic in city elections.

That makes Connolly a bit of old and new Boston wrapped in one, and within his packed schedule of events last Monday night, he tried to touch all the bases.

"The City Council doesn't have a lot of power," he tells a group of 15 to 20 young lawyers from Ropes & Gray who have shown up for a Connolly fund-raiser after work at a Financial District eatery. "What we can do is push big ideas for the city that recognize what's going on out there." Connolly launches into a spiel about young families leaving because they can't afford to stay or lack confidence in the schools if they did. "Improvement in the schools is the key to people staying," he says.

A week earlier, Connolly won the endorsement of the Ward 5 Democratic Committee in the Back Bay. It's a nod he didn't come close to securing two years ago, and one he hopes will help tip support his way from other liberal locales.

"They come at you fast and furious on the issues," he says of the quizzing from the ward committee members. "It's not a slap-on-the-back crowd."

There is a lot of back-slapping going on later Monday night at the Hyatt Harborside, where Connolly ends his night after a stop at a Charlestown civic association meeting. The East Boston Athletic Board is holding its annual awards banquet, and the room is chock full of the neighborhood's most devoted boosters - and reliable voters.

"These are the bedrock East Boston families," says Connolly, standing at the back of the room. "The Carusos, the Schettinos," he says, pointing to tables around the room. Connolly says he has a lot more support in the neighborhood this time around than in 2005.

Anthony Albano, one of the neighborhood's legendary political operatives, offers Connolly a friendly greeting. Asked to size up Connolly's chances after the candidate has moved on to shake other hands, Albano, a longtime Steve Murphy loyalist, goes with the time-honored truism. "It's hard to beat incumbency," he says.

Connolly knows that, but says he's willing to challenge the odds - and seems to be having a good time doing so. "For whatever reason, I'm energized by criss-crossing the city," he says. "It's the same hours as my law firm work - but a whole different feeling."