John Connolly considers a run for Boston mayor

Councilor asserts city schools lacking

Councilor John R. Connolly said Tuesday he is seriously considering a run for mayor of Boston with a campaign focused on improv­ing city schools, a move that sets up a potential showdown with the five-term incumbent, Mayor Thomas M. Menino.

“I have become convinced that our schools won’t change without new leadership and new ideas and a bold desire to take on the status quo,” Connolly said in an interview with the Globe. “I really ­believe our schools are our future and if we do not make bold changes, then we are limiting Boston’s future in every way.”

In the past few months, the three-term city councilor from West Roxbury has been raising funds at a frantic pace, amassing $145,000 in December and January. To run a credible campaign, Connolly said he will need to raise a least $1 million, which is triple his current balance of $315,000.


“I won’t run unless I think I can win. I’ve been talking it over a lot with [my wife] Meg, and I’ve just begun reaching out to supporters to get their thoughts,” said ­Connolly, 39. “At this point, this is really about whether I can raise the money to mount a winning campaign.”

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With the city election season just months away, Connolly would be the first significant candidate to step forward.

He said he planned to make a final decision soon, but would not give a specific timeline. Menino, 70, has held the office since 1993, when Connolly was a 20-year-old undergraduate at Harvard ­College.

Menino has not said publicly whether he will seek a sixth term, and he must decide by May 13 whether he will file for nomination papers, the first step in launching another campaign.

Much of Boston’s political establishment believes Menino will run again, and a generation of mayoral hopefuls seems content to wait another four years for an open seat.

Jim Davis/Globe Staff
Councilor John Connolly raised $145,000 in December and January. He has $315,000 in his account, about a third of what he says he needs to run a credible campaign,

But Connolly said he will not wait. “I’m not making this decision based on what the mayor does,” Connolly said. “I think my [time] frame changed when my daughter entered the public schools, he said, referring to his 4-year-old daughter, Clare, who began kindergarten last fall at Trotter Elementary School. “I’m making this decision because I think I can bring about real change in our schools and bring a new generation of leadership to City Hall.”

Menino’s administration ­responded forcefully to ­Connolly’s charges.

“The Boston public schools have made great strides under the leadership of the mayor and his team,” said Menino’s spokeswoman, Dot Joyce, who rattled off a list of accomplishments. “It’s easy to use education as political fodder. It’s much more difficult to make real progress and get the job done.”

Aside from Connolly, ­William J. Dorcena has said he is running for mayor, but he had just $22.16 in his campaign account at the end of January.

“If [Menino] runs, I think he’ll win,” said Michael J. ­McCormack, a former councilor. “The question is his health and whether he wants to run again and serve four more years.”


At the end of 2012, Menino spent eight weeks hospitalized with a severe respiratory infection, a broken vertebra, and other aliments, including a new diagnosis of Type 2 diabetes. He has returned to work as he has regained strength, although he still has daily physical therapy sessions.

Menino has roughly $640,000 in his campaign ­account, which is about half the amount he had four years ago when he was preparing for a fight with former councilor ­Michael F. Flaherty Jr.

Menino’s political committee paid $32,000 in October 2012 for what campaign ­finance records described as a survey. The results were not made public.

“The mayor is playing ­Hamlet with this one, to run or not to run, that is the question,” said Paul Watanabe, a professor of political science at the University of Massachusetts Boston. “I don’t think he’s decided. He hasn’t given any clear clues in one direction or the other.”

Menino has something else on his side. No incumbent mayor in Boston has lost since 1949, when James Michael ­Curley was defeated after he spent part of his term in federal prison for mail fraud. Since Menino took office, he has easily dispatched challenges by three city councilors: Peggy Davis-­Mullen, whom he defeated by more than 50 percentage points; Maura Hennigan by 35 percentage points; and Flaherty by 15 percentage points.

The oldest of four, Connolly grew up in Roslindale. His mother, Lynda M. Connolly, is chief justice for the state’s district courts. His father, Michael J. Connolly, was secretary of state for 16 years and served on the Boston Licensing Board.

John Connolly graduated from Roxbury Latin in 1991 and Harvard College in 1995, before spending three years teaching in middle-school classrooms, first at Nativity Mission Center on the Lower East Side of Manhattan and then at ­Renaissance Charter School in Boston’s theater district.

He earned a law degree from Boston College in 2001. He lost his first bid for City Council in 2005, but won in 2007 and made schools the focus of his three terms in office.

Connolly lives in West Roxbury with his wife and their two children, Clare and Teddy, 3½. The couple is expecting their third child this summer.

“I know the history and it’s daunting, but if I run, I’m going to run to win,” Connolly said. “I think Mayor Menino is a good man whom I immensely ­respect, but I don’t think our schools will change without new ideas, new energy, and new leadership.”

Andrew Ryan can be reached at acryan@globe.