Raised In A Middle-Class Enclave, Connolly Branches Out

It was perhaps the emotional high point of City Councilor At-Large John Connolly's mayoral campaign.

More than a hundred ministers, activists and moms — most of them black, some Latino and Asian — gathered to declare their support for him in Dudley Square.

"John! John! John! John!," the crowd thundered, partway through the first of several testimonials on his behalf.

"It humbles me greatly," said a visibly moved Connolly, taking the microphone at the end of the event. "And I really don't know what to say for the first time in my life."

The event was primarily a political counterpunch: an attempt to show that Connolly has strong support in the minority communities at the heart of the city, even as his opponent, state Rep. Marty Walsh, was racking up endorsements from prominent black and Latino political figures.

But the gathering, at the century-old Hibernian Hall in Dudley Square, had broader symbolic value.

The hall — once an Irish social club and now a fixture of black Boston — is a potent symbol for the trajectory and ambition of the man who would be mayor.

Raised in a middle-class, Irish-Catholic enclave in Roslindale, this scion of a prominent political family has drawn plenty from the traditional wells of power; his campaign runs, in part, on hefty donations from lawyers and developers.

But he's also sought a broader experience — and a broader political appeal.

Connolly has worked with low-income kids as a teacher, reached out to the parents of murder victims as a city councilor and cultivated the entrepreneurs behind Boston's bubbling innovation economy.

He needs those relationships now more than ever. In the waning days of the mayoral race, his critics are focusing on the early part of his story, on the advantages of his childhood; mailers from outside labor groups backing Walsh dubbed Connolly a "son of privilege."

His task is to tell a broader story.

Origins

Connolly's story starts in Roslindale, in a neighborhood of handsome — though hardly opulent — homes.

"It was great," he says. "It was a place where you could go through backyards and doors were open and you'd just see piles of kids everywhere. It was a very tight-knit neighborhood and a wonderful place to grow up."

Connolly's father Michael was a state representative and later a quirky four-term Massachusetts secretary of state — his nickname: "secretary of space." His mother Lynda was a lawyer and, later, a judge.

The couple sent Connolly to Roxbury Latin, an elite college preparatory school with just a handful of kids from the city. There were a lot of late nights. There were some tears.

"They really just push you to your bounds intellectually, academically," said Connolly. "There was a growth-through-suffering element."

Connolly, 40, says the talk of a privileged upbringing is a bit overblown: Roslindale, he quips, is no Beverly Hills.

That's a crucial corrective in a race against Walsh, a longtime labor leader who grew up in a triple-decker in Dorchester and has pitched himself as a champion of the working class.

Still, Connolly is acutely aware of the advantages he had — advantages that were particularly pronounced in the Boston of the 1970s and 1980s.

"There was a real polarization in Boston along racial and class lines," he says. "There was just some real terrible hatred that often felt palpable. And I think it gave a lot of us a real sense that things weren't right. Certainly for me, while I was very lucky to grow up in Roslindale, I knew that there were so many people in my generation who were not getting the opportunities I did."

The Classroom

Connolly says it was that sense of inequity that drove him to teach in urban schools for three years after graduating from Harvard University — two years at a Jesuit school on New York City's Lower East Side and a year at the Boston Renaissance Charter Public School.

He calls the experience pivotal.

"I think I made a difference for my students and in their lives," he says. "But I know they transformed my life. This is where I really saw firsthand that poverty just becomes an incredible obstacle to someone's success."

Connolly says his final year in the classroom was a "disaster." Boston Renaissance was poorly run, he says. The young teacher was drowning.

Connolly left to attend Boston College Law School and went on to practice corporate law at two downtown firms — the heavyweight Ropes and Gray and the smaller Hanify and King. Later, he started a smaller firm with two partners.

He has declined to offer many specifics about his legal work, citing attorney-client privilege. But he has said he engaged in a number of standard business transactions.

"My heart," he says, "was never in it."

The Council

Connolly, who lives in West Roxbury with his wife and three young children, made a first, unsuccessful bid for City Council in 2005.

Two years later, he won an at-large seat on the panel and has won re-election twice since. He's worked on environmental issues on the council. But his signature issue is education.

Two years ago, he made a splash when he uncovered expired food in school freezers. Last year, he was the lone vote against the teachers' contract, citing its failure to extend the school day.

Along the way, he spent countless hours talking with teachers and policymakers and mothers — mothers worried about a child left on a bus or a special education plan gone awry.

One call from a parent begat another and another. “I didn’t understand the void we were stepping into,” he says. “There was nobody who did education in more than a big, bumper stickery, banner way.”

The mothers he met along the way have become a vital part of his campaign apparatus. Among them: Valerie Madden, an actress and secretary who lives in the Fort Hill section of Roxbury.

She says she got to know Connolly when he was working on an alternative to the school assignment plans weighed by the School Committee. She was most impressed, she says, by his willingness to listen — no small thing for a parent who often felt unheard advocating on behalf of her kids.

Now, she says, "I have yard signs, I have bumper stickers — I have friends and neighbors who didn't want to have bumper stickers who have bumper stickers."

'We're All Connected'

Connolly has embraced a market-based education reform movement that favors charter schools, accountability and more flexibility for principals at traditional schools to hire, fire and set the curriculum.

That's drawn the ire of the Boston Teachers Union and other defenders of traditional public education.

And his focus on education comes with other risks: there are only so many voters with school-aged children, after all.

But Connolly has worked to connect education to other issues — good schools mean fewer dropouts, healthier and safer neighborhoods and a better economy, he says.

And good schools appeal not just to low-income families, but to middle-class families hoping to stay in the city.

They are, in short, a way to stitch together the city — and, for Connolly, a broad electoral coalition.

That seemed the aim on a recent weekday night, when the candidate spoke at a "Women for Connolly" fundraiser at the sleek offices of a private equity firm in the Back Bay.

He talked of the successful Bostonians who walk past teenage dropouts at Downtown Crossing every day. And he spoke of a friend — a woman he met at his daughter's elementary school — who lost a loved one in a shooting.

"At the end of this, we're all connected," he said. "It's just about whether we're going to choose to see it or not."

Next week, voters will decide whether the guy from Roslindale — the guy who attended Harvard and taught school, practiced law and dug into education policy — is the one to knit the city together.