Yvonne Abraham

Mayoral candidates make most of missteps

If they’re living right, people learn a lot from their mistakes. And voters can learn a great deal from the mistakes candidates choose to acknowledge.

So for this last column before Tuesday’s mayoral election, I asked state Representative Marty Walsh and City Councilor John Connolly to talk about one regret, and how it changed them.

Their answers were true to their styles. Walsh went right to the personal, Connolly to a matter of policy. Their responses are reminders of something we often lose sight of in a bruising campaign: It takes courage to put yourself before the voters, to open yourself up and get picked apart publicly. It’s a quality they both have, in abundance.


In some ways, Walsh’s mistakes define him, and they’ve been central to his candidacy. His journey through addiction and recovery has been covered in depth, including here. So I asked him to talk about something else.

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“The one thing I regret in my life is not focusing more on high school,” Walsh says. He wasn’t a problem kid. He didn’t get into fights or get suspended. He was afraid enough of his mother to avoid that kind of thing. But he did spend a good deal of his sophomore year at Newman Prep hanging out in Copley Square instead of the classroom. He did just enough to get by. If he had a teacher he liked, he got A’s. But mostly, he was a C student.

“I was more motivated to get out of school and go to work,” he says.

Instead of going away to college like his friends, Walsh attended Quincy College, then Suffolk University, before dropping out. (He later got a bachelor’s degree from Boston College.) He visited buddies in college sometimes, and saw the broad range of people they were meeting, and he regrets missing out on that. He felt something like that gap again when he first got to the State House, though he also acknowledges the obvious: “I turned out OK.”

But as a kid, he didn’t aim high enough. And it still pains him.


“What would my life have been if I had gone that route?” Walsh wonders.

Connolly chose to talk about a vote he took last year, and you can still hear the sting of regret in his voice. As part of a plan to reorganize schools, the city proposed moving the very successful Mission Hill K-8 school to Jamaica Plain, then moving Fenway High from the crowded space it shares with Boston Arts Academy into Mission Hill. Parents at Mission Hill didn’t want their beloved school moved, but Connolly voted for it anyway.

“This was a situation where we pitted two school communities against each other, and yet I went with it, knowing in my gut it wasn’t the right vote,” he says. There was a lot of pressure from the mayor’s office, Connolly said, and he was trying to rebuild his relationship with Tom Menino. So he went against his instincts.

“I was supposed to be the voice for the families. That’s who I am on the council, their strongest advocate, and I totally let them down,” Connolly says.

It wasn’t as big a disaster as he feared. Mission Hill is a bigger and happier school now, while the other two schools are still crammed into the same building and the Academy may move again. Still, Connolly didn’t sleep well for a while after taking that vote.


“That was the turning point for me,” he says. “It made me look in the mirror and say ‘You’ve got to speak your mind, especially on schools and families. You can’t make deals and do the smart political thing.’ ”

Soon after, Connolly ripped School Superintendent Carol Johnson for allowing a headmaster to keep his job after he pleaded sufficient facts in a domestic violence case. He dug in on school assignment and the teachers’ contract. He became a burr in Johnson’s saddle, and, by extension, in Menino’s. It made Connolly some enemies, some of whom are with his opponent today.

“Ultimately, it gave me a much stronger voice,” he says.

Yvonne Abraham is a Globe columnist. She can be reached at