By Brian Denitzio
Reporter Staff

His campaign literature states that John Connolly is more than just a name. A nod no doubt to his family's political activities. And while he is the son of a former Massachusetts Secretary of State and the current chief justice of the Massachusetts district court, Connolly has succeeded in moving from the shadow of his family's political past. But now that he's not just the name, he's taken up the perhaps more difficult task of showing exactly what else John Connolly is.

To be sure, Connolly is more than just a name. He's well educated with degrees from Harvard and Boston College Law. He's hard-working, a near-constant presence at civic meetings and events in Dorchester and across the city, and he has a resume that includes time as a teacher of at-risk youth in New York City and Boston, and as a corporate lawyer at one of Boston's largest law firms.

That's the John Connolly the candidate wants Boston voters to know, but despite his efforts to the contrary, voters still hold their own, perhaps misguided, opinions of the candidate.

The Harvard education is construed as a negative to some who choose to view Connolly as the entitled son of influential parents. By virtue of being a young, Irish-American candidate from the city's western reaches, he's often grouped with Matt O'Malley, a Roslindale candidate who placed sixth in the 2003 race, though the two diverge on the issues, notably on the residency requirement for city workers.

All these perceptions came up in a matter of moments during a conversation with a voter at a Dunkin' Donuts in West Roxbury last week. Spotting Connolly in a seat near the door, an older gentleman approached him and struck up a conversation during which he posited that Connolly was "born with a silver spoon in his mouth," questioned whether Connolly had spent much time in West Roxbury, spoke fondly of Connolly's father, noted that Matt O'Malley has been out there working hard, and promised Connolly his vote.

A victory in the end perhaps, but though Connolly never showed it to the voter, it was doubtless a frustrating encounter for a first-time candidate who believes that his issues will resonate with voters. And for a candidate who is also aware enough of how the electorate perceives him to remark that his whole story was played out in that one interaction.

Chief among the issues important to Connolly is education.

"Addressing education will help solve most of the other problems we face in the city," says Connolly. He believes he is uniquely qualified to lead on this issue, pointing to his three years of teaching in urban middle schools in New York City and Boston. He says he taught some of the most at-risk students who went on to graduate high school and college at rates far-outpacing their peers in other schools. He supports neighborhood schools as part of creating a similar educational environment, one that has strong parental involvement and after school programs that reinforce what's learned in the classroom.

Affordable housing is another issue important to Connolly, who owns a home in West Roxbury with his wife, Meg. He says that the motivation to run came about in part through the experience of purchasing their first home and conversations with Meg about raising a family in the city. He's troubled by seeing friends and neighbors leave the city as the cost of living makes staying unaffordable.

Not wanting to see families leave the city is one reason why Connolly says he supports the residency requirement.

"I support the residency requirement because I want people to be invested in their city, but at the same time I worry about the street sweepers and meter maids and DPW workers who are struggling to stay in the city," says Connolly.

Instead, he proposes a trust to fund down payments and a break on property taxes for city workers.

"At the end of the day, I want residency to work, which means that you have to make it affordable," says Connolly.

Supporting residency despite opposition from unions Connolly says is evidence that he's not afraid to stand up for his issues even though it might not make him any friends.

Friends however are not in short supply for Connolly judging by his fundraising efforts thus far. To date he's raised over $220,000, the most for any challenger this year, and as of his last campaign finance report sits on a war chest of over $140,000. Some in the field have charged that his support comes from moneyed interests from out of state. Connolly's tone in answering this and other digs at him is matter of fact, demonstrating he has as much confidence as he has campaign cash.

To the Dunkin' Donuts patron, he replied that you aren't born with an admission to Harvard, and to questions about the source of his funds he replies that "the vast majority of my contributions, and I mean the vast majority, are from Massachusetts and from Boston in particular."

The money, Connolly says, is simply another tool he'll use to get his message out there. As the preliminaries approach, Connolly plans to roll out other planks of his "Blueprint for Boston." The first, his 16-page plan for education, is available on his web site (connollyforcouncil.com).

First-time candidates rarely succeed in the at-large race, but Connolly's willingness to be everywhere, his fundraising prowess, and his firm grasp of the issues have many race watchers thinking he could make a name for himself come November.