He's trying. To launch the Quality Choice Plan, he partnered with a young, diverse set of Boston pols: state representatives Linda Dorcena Forry, Russell Holmes, Nick Collins, and Ed Coppinger, and Jamaica Plain councilor Matt O'Malley. And he's reaching out to voters with frequent education meetings, like his recent visit to Roxbury's Multi-Service Center.

Regardless of mayoral election politics, Connolly needs more widespread support and trust in those communities if he is to successfully lead a movement to dramatically change the city's schools — from whatever position he tries to do it.


Connolly has recently added a new perspective to his views on Boston's schools: that of a parent. His daughter's entrance into the system has revealed both political opportunity, and limitations.

Four-year-old Clare now pops up in her father's stump speeches, and in his conversations with parent groups all over the city. She was rejected from every school the Connollys selected in the lottery system — more than a dozen, he says. Connolly and wife Meg prepared to enroll her in Catholic school, before taking a last-ditch tour of Roxbury's Trotter School.

In that notoriously failing school, they found magic: under the state's 2009 education-reform law, the Trotter has been turned around, with a new principal and top-notch teachers.

Although Connolly does not explicitly say it, he is plainly telling Clare's tale as an indictment of the current system and its leader (and, secondarily, to claim credit for putting his own kids in public schools, without seeking favor through his position). If his daughter — and all the city's children — get a good education, he is implying, it will be despite 20-year mayor Menino, not because of him.

Yet earlier this month, hours before the State of the Commonwealth address, there was Menino standing with Governor Deval Patrick in front of the rejuvenated Orchard Garden school — like the Trotter, designated in 2010 a "Fresh Start"–level failure requiring state-led turnaround — celebrating and basking in success.

"I'm glad when [Menino] embraces bold change for our public schools, but I'm really skeptical," Connolly says. "He spent 20 years playing it safe. He was nowhere to be seen when we were fighting to get a lot of these changes."

This is the political genius of Menino at work, co-opting the very criticism an opponent might use against him. Just as he did with Flaherty's demands for charter schools, and as he has done with the revamped school assignment plans unveiled in the lead-up to the State of the City speech.

And it's a big part of the reason so many in the city think Connolly would be foolish to run against Menino — even as they may hope he has the balls to do it anyway.

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