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Harvard Alumnus Thrives on Boston City Council

For Connolly, a love of Boston complements a family history of political service

By Daniel A. Handlin, Crimson Staff Writer

As a city councilor, you may often find yourself acting as a salesman—whether that is selling yourself to your electorate or selling a policy proposal to your fellow councilors.

But for John R. Connolly ’95, these skills came at an early age as a hotdog vendor at Fenway Park.

Connolly, a Harvard class marshall and Boston city councilor who was elected last November, has worn many hats in devotion to his home town of Boston.

In high school and college, the former Currier House resident worked as a hotdog vendor at Fenway Park. This fall, Connolly, a lifelong Bostonian, launched a campaign to sell the Boston public something different—himself.

He found a buyer. The former Crimson football player earned a spot on the Boston City Council after upending a veteran councilor in a surprise victory.

“I spent eight months campaigning full time. I went into probably 75 homes to meet groups,” says Connolly, a Democrat. “I built support in every neighborhood of the city that began with my 2005 effort. In a sense this was a three year campaign.”

Before a reporter, Connolly speaks like a suave, practiced politician, the descendant of a well-connected political family. But once the interview is done, Connolly’s Boston accent slips out, a reminder of his roots and love for the area.

“I love this city. I’ve loved growing up here. I want to spend my whole life here. What energizes me is...each one of its different nooks and crannies and meeting all these people who make the city what it is,” Connolly says.


Connolly grew up in West Roxbury, a leafy neighborhood that was once the site of a utopian experiment led by the likes of Ralph Waldo Emerson. His interest in politics began at an early age, sparked by the public careers of his family. His father, Michael, served as secretary of the commonwealth from 1979 to 1994, and his mother works as a judge in the state district court system.

Lawrence DeCara ’71, who has known Connolly and his family for decades, said he thought being surrounded by politics from such an early age would help Connolly as a freshman councilor.

“He comes from an old political pedigree, that’s for sure,” DeCara says, “and even though he’s new to elected office he’s probably already halfway around the bases because he’s been around the business for so long.”

Connolly attended high school at Roxbury Latin, one of Boston’s elite private schools, then matriculated at Harvard, where he fed his passion for public service.

He wrote his senior thesis on governmental reform and volunteered for the Phillips Brooks House Association. During his senior year, his teaching fellow in a Spanish class put him in touch with a school on Manhattan’s lower east side, which catered to at-risk Latino youth. After graduation, he worked there for two years before returning to Boston and continuing his role as an educator there.

Education is now a key part of his platform, which emphasizes the benefits of after-school programs.

“A great public school system is key to a great city,” Connolly says. “That all grew out of my time at Harvard.”

Keith McLean ’95, Connolly’s Harvard blockmate who served as his finance chair during his campaign as city councilor, says that Connolly’s commitment to public service has been evident for years.

“He just really seemed like someone you can picture as doing something after Harvard to really help people,” says McLean.


After law school at Boston College, Connolly went into private practice. But after only a few years, he says he began to feel the pull of public service, and began a run for Boston City Council in 2005, which he lost.

Undaunted, Connolly put his hat in the ring for the 2007 race, hoping to benefit from the financial support networks he had built in 2005.

The campaign was a low-key affair—voter turnout dropped to under 14 percent—and Connolly drew fire for his campaign tactics after he distributed two anonymous flyers that attacked incumbent City Councilor Stephen J. Murphy.

“He’s a documented sneak and a liar,” Murphy told the Boston Globe at the time.

Though Connolly would win the race, he ended up besting a different councilor—the veteran progressive Felix Arroyo—to win one of the council’s four at-large seats.

Arroyo, for his part, bears no ill-will toward Connolly, saying that the newcomer will make an effective and enthusiastic councilor.

Arroyo—and Connolly—attributed the result to the extremely low voter turnout this year.

“My loss is one thing, but the loss for democracy participation is probably more important than my personal loss,” Arroyo says.


Connolly says he will devote his next two years in office to improving the school system and reforming the city’s property taxes.

Among his mentors, Connolly lists Thelma C. Burns, a leader of Action for Boston Community Development, a Boston antipoverty action group.

Burns says that Connolly’s enthusiasm for his hometown will stand him in good stead.

“He has the right ideas, he’s right on target with what’s going on in the school system, he knows the tax rates are going out and the property taxes are going up,” she says. “I’d like to give him a chance.”

In 2005, Connolly drew his weakest support from communities of color. But Connolly said his relationship with Burns, who is black, is emblematic of the sort of diversity and progress that he aims for in the city.

“[She’s] really become a mother to me—she is a civil rights leader in this city,” Connolly says of Burns. “Here she is helping a kid in his 30s get elected to the city council. We cross every conceivable line.”

“In a sense that relationship to me is what the future of Boston is all about,” he adds.

During his six years working at Fenway, Connolly saw the Red Sox work to shake off the legendary curse. His approach to his city shows that same dogged devotion.

“I will fight for the neighborhood with everything I’ve got. My number one commitment right now is to be the best city councilor I can be,” he says.

—Staff writer Daniel A. Handlin can be reached at

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