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John Connolly was outspent and out-organized

Early front-runner became underdog by Election Day

John R. Connolly, with his wife, Meg, thanked supporters at the Westin Copley Place.
John R. Connolly, with his wife, Meg, thanked supporters at the Westin Copley Place.Barry Chin/Globe Staff

He was the first in the race, announcing his candidacy for mayor even before Mayor Thomas M. Menino said he would bow out. He had spent years establishing himself as the mayor’s chief political antagonist on the City Council and the chief agitator for reform in the Boston public schools. He came in a solid second in the September preliminary election, when his well-established citywide campaign organization turned out in force.

But on Tuesday night, Councilor John R. Connolly was edged out by state Representative Martin J. Walsh, whose massive campaign team, assembled with the help of organized labor, outmanned, outspent, and out-maneuvered Connolly’s campaign.


“We came up short tonight, but I am very proud of how we ran this campaign,” Connolly said in his concession speech last night. “This campaign looked like the entire city of Boston and I’m so proud of that.”

The tight results ended a roller-coaster campaign for Connolly, who began the race as an underdog taking on an all-powerful incumbent. But when Menino announced he would not run for reelection, Connolly became the sudden front-runner, the best-established and one of the best-financed candidates in a field of 12. He came in second in the preliminary election but was still considered the favorite to win the general, until a series of key endorsements and a flood of union money made him the underdog again.

Connolly, 40, a father of three who lives in West Roxbury, had made school reform the cornerstone of his campaigns even before his oldest child was assigned to a failing city school. The chairman of the City Council’s Education Committee, he crusaded on expired food in school cafeterias and on changing the schools’ student assignment system.

His efforts attracted many mothers of Boston Public School students to volunteer for his campaign, leading his aides to try to frame the campaign narrative as “moms vs. the machine.”


But Connolly has also had difficult relationships with some in the schools. Last year, he sparked a backlash from the black community by calling for the resignation of then-superintendent Carol Johnson, who is black, for not firing a principal who was arrested on assault charges.

He alienated teachers by calling for raising the limit on charter schools, and voting against their last contract because it did not require longer school days. On Election Day, the Boston Teachers’ Union made its displeasure official, offering a last-minute endorsement to his opponent.

Connolly attracted support from school groups, including Democrats for Education Reform, which spent money independently on his candidacy. But during the preliminary campaign, he swore off a pledge of $500,000 in support from Stand For Children, an at-times controversial national education group.

He had hoped Walsh would agree to a “People’s Pledge,” in which the candidates would swear off any outside expenditures by special interest groups. Walsh refused, allowing millions to be spent on his behalf by national labor groups.

“I’ve got no regrets with how we handled it,” Connolly said on Monday. “We made the decision that we didn’t want this race taken over by outside money. Unfortunately, [Walsh] did not sign onto that idea as well.”

Born and raised in Roslindale, Connolly is the eldest of four children of Michael Connolly, a former state representative and secretary of the commonwealth, and Lynda Connolly, who was chief justice of the state’s district courts for eight years.


He graduated from Roxbury Latin and Harvard College and spent two years as a teacher in Manhattan and another year teaching in a Boston charter school. But he turned to law, graduating from Boston College Law School and practicing law in Boston for 12 years.

In running for mayor, he is surrendering the at-large City Council seat he won in 2007.

Despite the loss, Connolly insisted Tuesday night that he would not have changed anything about how he ran his campaign.

“I would run it the same way. I was never going to go negative. I’m proud of the race that we ran,” Connolly said.

Asked about his next steps, Connolly said he does not see himself seeking office in the future and he does not see a spot for himself in the Walsh administration.

“I spent eight months not seeing my kids enough. The next step for me is to do something that allows me to be home a lot,” Connolly said. “At this point, it’s just about putting one foot in front of the next. So I’m thinking about going to my city council meeting tomorrow.”

He has previously expressed interest in working for an education reform group or a charter school. But his dream was to become the mayor of Boston.

“Nobody believes me, but I don’t have any desire to run for governor or senator or another elected office,” Connolly told the Globe in August. Mayor “would be the dream job for me,” he said. “I love cities, and if I’m not mayor, I’m going to find a way to work in urban policy and schools. It’s been my love for the city driving me.”


Wesley Lowery of the Globe Staff contributed. Stephanie Ebbert can be reached at Stephanie.Ebbert@globe.com. Follow her on Twitter @StephanieEbbert.