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John R. Connolly, 32, candidate for at-large councilor and the son of a former secretary of state, Michael J. Connolly, greeted his host, Paul McCarthy, at a recent house party in Dorchester.
John R. Connolly, 32, candidate for at-large councilor and the son of a former secretary of state, Michael J. Connolly, greeted his host, Paul McCarthy, at a recent house party in Dorchester. (Lisa Poole for the Boston Globe)
JOHN R. CONNOLLY

'I wanted to be like my dad . . . I wanted to make a difference'

(Clarification: A headline on a profile of City Council candidate John R. Connolly in yesterday's City & Region section linked two quotes by Connolly and gave the impression they were a related sequence of thought. The two quotes, ''I wanted to be like my dad . . . I wanted to make a difference," were made at different times, and the latter was in reference to Connolly's time as a teacher in a New York City high school.)

At rush hour on a busy Thursday, a group of women holding ''Connolly for Council" signs at a rotary in West Roxbury beam at the young man in the navy suit waving to the cars whizzing by. One talks about his prominent political family: ''Very down-to-earth, very smart." Another marvels at the first-time candidate's announcement speech: ''There must have been 800 or 1,000 people there." Another raves about his commitment to education.

Connolly, a clean-cut 32-year-old Harvard graduate with a self-effacing style, is used to such adoration. He is less accustomed to answering questions he doesn't like. Since his surprising third-place finish in the preliminary election made him a conspicuous target for his rivals, he has found himself fielding more of those lately.

These days the unions are criticizing him, landlords are complaining, and his opponents whisper that he has flip-flopped on everything from the city's residency rule to rent control to abortion rights. (For the record, he is for the residency rule, supports rent stabilization, and is personally against abortion but believes that it should be legal.)

Finding himself a target is uncomfortable for the newcomer, and sometimes, after long days on the trail, his usual athlete's ease and laid-back humor give way to furrowed brows and impatience.

''In 11 months of campaigning, I probably haven't faced as much pressure and as many people coming after me as I have in the last 10 days," he said.

Riding shotgun in his cranberry Ford Focus as a campaign aide drove him to a candidates' forum in Dorchester, Connolly said he always knew he would run for office one day. His father, Michael J. Connolly, was secretary of state for 16 years; his mother, Lynda, is chief justice of the state district court system; his uncle, James Michael Connolly, is a prominent Republican fund-raiser. As a boy, he loved dropping campaign literature and reading history books as much as playing baseball and football.

''I may have been the only kid who aspired to be secretary of state," he said with a laugh. ''I wanted to be like my dad."

A scholar-athlete at Roxbury Latin, he went on to Harvard, class of 1995, where he played football for two years and was elected class marshal and a Class Day speaker.

But in what he describes as a life-changing experience, he spent two years after graduation teaching at the Nativity Mission School, a Jesuit-run middle school for poor, mostly Hispanic boys on New York's Lower East Side. He lived in spare rooms above the school, took his meals with the priests, and subsisted on a $200-a-month stipend.

''I wanted to go work in a community where they needed teachers, and I wanted to make a difference," he said.

After two years at Nativity, he taught at Boston Renaissance Charter School. A year later, he left for Boston College Law School, then secured a job in corporate law at the old-line firm Ropes & Gray.

''I wanted to buy a wedding ring and a house, and I had massive student loans," he said. (In 2003, he married Meg Kassakian, a Harvard alumna who is earning her doctorate in psychology at the Boston College School of Education.)

He still found an outlet for his interest in public service, working pro bono for teachers and other groups. Laura Hoey, an attorney at Ropes & Gray, said he gained a reputation as a skilled lawyer with a winning personality.

''John stood out in the firm as someone who, whether you were a senior partner or a fellow associate or emptied trash cans, he knew your name," she said.

But last year, Connolly left the $200,000-a-year job for a smaller firm and took a nearly 40 percent pay cut.

This spring, he took a leave to run for City Council. He said he had watched many friends move to the suburbs to escape Boston's high cost of living and uneven public schools, and he saw an opportunity to begin his political career when a seat opened up on the council.

When campaigning, he refers constantly to his three years in the classroom, rarely to his experience as a corporate lawyer. At a candidates' forum in Fields Corner, he spent so much time talking about the need to increase parental involvement in the schools and forge ties between the public schools and local universities that he sometimes sounded as if he were auditioning for superintendent.

Despite his impressive finish in the preliminary election, Connolly's numbers were weaker in less-affluent, mostly minority neighborhoods. These days, he is trying to connect with voters in places like Mattapan and Dorchester, drawing on his experience as a teacher.

After the Fields Corner forum, he told a group of parents about his first parent-teachers' night at Nativity, when he tried to apologize for his poor Spanish by trying to say ''I'm embarrassed," not realizing that ''embarazado" means ''pregnant."

''They all burst out laughing," he grinned, and his small audience did, too.

Connolly would rather spend the last few weeks of the campaign engaging in friendly banter like this, but with seven rivals nipping at his heels, he is feeling the pressure of the fiercely competitive race. At a party in Brighton Saturday, he lamented to a supporter that a group opposed to rent control had launched an automated telephone campaign against him. In an interview, he complained about having a ''big target on my back."

Still, his drive to succeed, and a keen sense of political realities, seem to restrain him from lashing back.

''I like to think I've maintained my grace under pressure," he said. ''And certainly I have the benefit of having watched both of my parents live in the public eye. But, hey, it's tough when you campaign all day, each and every day and people throw stones. But that's part of the business, and I understood that when I began."

Lisa Wangsness can be reached at lwangsness@globe.com.

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