But he also went to Roxbury Latin School, and spent time teaching at the Nativity Mission School in New York City and the Boston Renaissance Charter School. Speaking to the public, across all classes and races, Connolly comes across as an easygoing, well-informed, concerned parent. In 2011 he campaigned in tandem with Ayanna Pressley, and dramatically raised his share of the vote in black and progressive neighborhoods.
And he has occasionally used his position on the council, and as chair of its education committee since 2009, to take on the entrenched powers — as in early 2011, when he dramatically uncovered expired food in school kitchens.
"He's a much greater risk to Menino than Flaherty was," says political consultant Jim Spencer, who managed Sam Yoon's 2009 mayoral campaign.
"He's very smart, he's very grounded, and he understands the city as well as anybody," says well-connected attorney and former city councilor Larry DiCara. "It's been smart for John to focus on education."
In recent months, as Connolly has shifted toward the role of full-time oppositionist, he has been talking about the need for "transformative change" in Boston's public schools. He cast the lone vote against the teachers' union contract negotiated by the Menino administration, calling it a squandered opportunity to win concessions for a longer school day and rewarding quality over seniority.
And he is leading an effort to promote his own "Quality Choice Plan" — with a website and citizen petition (qualitychoiceplan.com) — in opposition to the school-assignment reforms under consideration by the Boston School Committee. The proposed plans, he says, deal only with the logistics of moving kids around the city, and not about ensuring high-quality schools for everyone.
Skeptics call the new Connolly just another calculated step. But, according to him, he has been "deeply changed" by a sequence of events last year.
FROM THE TANK TO THE DOGHOUSE
The transition began, Connolly says, with a council vote in May to approve and authorize funding for a Boston Public Schools (BPS) plan that included closing Mission Hill's only remaining elementary school. Michael Ross and four other councilors voted to save the school, but Connolly says that, despite reservations about the plan, he gave in to pressure from the mayor's office.
"I tanked that vote for the administration," Connolly says. He ruminated over it afterward; he says he eventually apologized to some parents who were losing their school. "It was the first time I couldn't sleep — I felt like I let parents down."
"I do think something changed for him after that Mission Hill vote," says Mary Tamer, a school committee member who opposed that school closing. "There has been a certain fearlessness in him after that."
Regret was still weighing on him a few weeks later, Connolly says, when news broke in the BostonGlobe about Rodney Peterson.
Peterson, the headmaster of the John D. O'Bryant School of Mathematics & Science, had been allowed to keep his job after a 2011 arrest for domestic-assault charges. The details of the case were shocking; even worse, to many, was Superintendent Carol Johnson's decision not to remove him, her failure to inform city officials of the situation, and her personal penning of a glowing reference to Peterson's judge.
