The Making of a Mayor for Life

As Tom Menino closes in on becoming our longest-serving mayor, we take a close look at his rise to the top and how it has profoundly changed Boston.

During his days in the wilderness, Menino managed to keep his hand in city affairs. He did so through a body called the Park Street Corporation, led by Paulist priest Robert Quinn. At his Bowdoin Street apartment and other venues around the city, Father Quinn would (and still does, as chaplain of the Massachusetts House) gather prominent Bostonians to discuss problems facing the city, away from the press. Doherty suggested that if Menino was serious about politics, he should come along. “One of his virtues, or weaknesses,” says Doherty, “is persistence. Once he started to go, and he bought into the idea that he could learn a lot, he kept going.” The other congregants, including early tech entrepreneur John Cullinane and developer Tom Flatley, “were not initially overwhelmed by him, but over time he grew on them,” says Doherty. Cullinane adds, “He used to bring the doughnuts, if I remember correctly.”

Doherty, who became close with Menino when they were both working on Timilty’s 1975 campaign, saw potential in the younger operative. “I sort of identified with him because I’m not charismatic, and he’s not charismatic,” Doherty says. “But he used to sweat. Most of the people you meet, they flash their teeth and shake your hand, while at the same time they’re looking over your shoulder. He didn’t do that. When he walked into a room, he wouldn’t galvanize it, but by the end of the night he could tell you exactly who was there, what they did, and what they didn’t do. He had a quietness of style.”

Eventually, Timilty found a spot in his Senate office for Menino, who worked his way up from driver to chief of staff. “He did everything. Everything,” says Timilty. “Knowing where the legislation was. Doing politics with other members of the Senate, their staffs, he got that all down. Any other fight we got involved in.” Menino was content to remain behind the scenes. He had developed into a master organizer, but lacked the flair he’d seem to need to compete as a candidate himself in what was a raucous era for Boston politics, characterized by Ray Flynn’s midnight jogging jags/pub crawls and the persistent lunacy and occasional brawls of guys like councilors Dapper O’Neil and Jimmy Kelly.

Nineteen-eighty-two changed that. That year, the city council was expanded from nine at-large seats to four at-large and seven district seats—one being District 5, covering Hyde Park, part of Roslindale, and a sliver of Forest Hills. Timilty territory. The change required legislative approval, which Timilty saw to. “We wanted a seat,” he says, “and it was obviously going to be [Menino’s]. We got the House and the Senate to pass that. It was created for him.” Menino, pushed by Timilty and heartened by the subpar quality of the other candidates, tossed in his hat. When he told his father about it, Carl Menino worried that Tom would be unemployed if he lost. “Dad, I won’t lose. Don’t worry about it,” he said.


Menino’s public persona hardly radiated the same confidence. WGBH made a short documentary of his 1983 run, capturing the then-40-year-old candidate on the trail, hustling, strategizing, pressing the flesh. He greets a roomful of seniors—”Hey, nice seein’ yiz, thank you, I need ya help, I need ya help”—but he’s awkward and seems unsure of what to do with his hands. He confesses he’s struggling with being the principal. “Bein’ the smilah, the shakah of hands, things like that, things that are not natural, that’s the part of the campaign that, uh, I have the most problems with.”

However underwhelming Menino was in candidate mode, his opponents, including a couple of ex-cops, lacked his political experience. They made the mistake of demagoguing crime and the death penalty, grand issues that might resonate citywide, but less so in the neighborhoods. Menino responded with a simple plan to revitalize Roslindale Square. “We have to bring it back,” he tells a roomful of voters in the documentary. “You only—in Roslindale Square today you have 13 pizza places. Which is crazy.” It was a modest pitch that voters could understand. He wasn’t promising them the world. He was just a regular guy looking to fix up Rozzie Square, with its crazy superabundance of pizza places.

Menino didn’t need to wow with his ideas—for that, he had his field organization. On the day he announced his candidacy in 1982, his campaign put 152 canvassers in all the district’s precincts. Mike McCormack, an at-large councilor from Brighton who had been elected the previous year, says he knew going into Election Day that Menino was a lock. “I was standing in Hyde Park. People were lined up to vote. And there was a woman standing for Menino, and she kept yelling at everyone going in, just yelling the name: ‘Menino!’ ‘Menino!’ I kept thinking everyone is going to go in there and vote for Menino, because she would know who didn’t and she would get them on the way out. He had some very aggressive people.” Menino won easily, with 75 percent of the vote.

It was a win for Timilty as well. “It was like having an extension of me in there,” he says. Not for long, though: A few years later, the two had a bitter falling-out. The most popular explanation is that Menino broke things off after Timilty, who left the Senate in 1984 to get into real estate, did business with questionable characters from East Boston. (Timilty would later serve four months in federal prison for conspiracy to commit wire fraud.) Menino was fastidious about avoiding the appearance of impropriety—he felt he had to be. “When you are an Italian guy in politics, and you keep your nose clean, you’re very careful about associating yourself with guys who are allegedly associated with organized crime,” says one political observer, who is of Italian heritage himself. Timilty, who looks as if he came off the boat from Ireland, could be seen with questionable characters, and no one would think anything of it. “If Menino did that, it would stick to him,” the observer says. So, just like that, Timilty had to go. He wouldn’t be the last mentor to get jettisoned.


Ray Flynn sits at a table at J. J. Foley’s in the South End, clad in a Notre Dame sweatshirt, drinking coffee and rocking his sleeping grandson in a stroller beside the table. Recently Raybo was in the paper lambasting his successor over his ongoing feud with the firefighters union. Flynn asks what people are saying about the mayor. “Did they tell you what kind of man he is?”

If Menino couldn’t have gotten to the council without Timilty, he couldn’t have risen beyond it without Flynn. As a councilor, Flynn had supported Timilty against White; after White stepped down in 1983 and Flynn jumped into the wide-open race to replace him, Menino repaid the favor. Flynn prevailed over community activist Mel King, the city’s first black mayoral candidate, in a hard-fought race that spurred record voter turnout. Counting an ally in the mayor’s office, Menino spent his first year on the council working to distinguish himself.

Many a councilor secretly hates the job’s endless succession of neighborhood meetings, usually attended by the same group of old people, complaining about the same issues, night after night unto eternity. Menino relished them. “He would just go after those meetings,” says McCormack. He would do three or four every single night. And if anyone—at-large candidates or even Flynn—was going to come into his district or so much as hold a meeting that might concern his constituents, Menino had to be notified. “He was very turf-oriented,” says former city councilor Bruce Bolling. Because his district was populated by reliable voters, Menino could get away with it. Come election season, citywide councilors would have to seek Menino out and pay their respects. McCormack found himself in that position. “When you were looking for endorsements—and everybody was, because people from Dorchester and Hyde Park thought people from Brighton were from another planet—it was a huge benefit to have Tommy’s. But it really was like going to meet Don Ciccio [from The Godfather: Part II]. ‘Have I offended you? If I did, I didn’t mean to!'”

However snarling he could be when protecting his district, Menino—with his deep neighborhood roots and support of progressive issues such as gay rights, arts funding, and affordable housing—got along equally well with the council’s conservative and liberal wings. Not to mention Flynn, with whom he was an inside player from the start. “Tommy used to come into my office and talk to me all the time,” Flynn says. “He came into my office more than all the other councilors put together.” Flynn liked him, liked the votes he could deliver. Most important, perhaps, he never saw him as a threat. “He was a team player,” says Flynn. “You could bring him in anytime, talk to him about what you needed. You could trust him.” In exchange for his support, Flynn allowed Menino greater leeway than the other district councilors. In time, Menino ventured outside his district more and more. He was forever after Bob Finneran, the mayor’s liaison to the council, for Flynn’s schedule. “I would say, ‘Tom, you’re gonna get me in trouble,'” Finneran says. “‘You can go to a few of these, but not all of them!'” And there were a lot of them. Flynn loved the attention, and Menino loved the chance to watch and learn.

At the same time, he was discovering the job’s inherent limitations. “I set a goal of 10 years on the city council, or out,” Menino says now. He kept an eye out for opportunities to enhance his visibility and clout, knowing that if you don’t keep moving you rot in place. He briefly considered running at-large, and put out a poll to get a sense of how much work it would take to get him there. “He was surprised at how many people in the city didn’t recognize the name,” recalls a former adviser. “So he stayed in the district.” In 1986, he mounted a brief run for Suffolk County sheriff, abandoning it upon realizing that if no one knew him in Boston, still fewer would in Winthrop.

Menino was also finding that his lack of a college education, which he never tired of mentioning to bolster his neighborhood-guy cred, was starting to look like a hindrance. Gerard Doherty had been on him for years to get a degree. “I don’t think you’re gonna be any smarter,” Doherty told him, “but you’ve got to go to school. If you don’t have a college degree, you’re going to get stuck.” Menino winced at the suggestion, but ultimately enrolled at UMass Boston to study community planning at the age of 41. He struggled, but didn’t miss a class. “I remember talking to him one day,” says Doherty. “…He said, ‘Damn you, I had a terrible weekend because of you.’ And I said, ‘Why?’ He said, ‘Well, my daughter is helping me with math. And my problem was, she stayed out late Saturday night, so I had to ground her. So I was prepping for my math class on Monday and she refused to help me!'”

That math homework was about to come in handy. When elected to the council in 1983, Menino had gotten a call from Michael Paul Feeney, a former long-serving rep who’d chaired Ways and Means. Feeney had Menino come up to his Beacon Hill office, where he told him, “Remember, he who knows the budget, controls the system.”

The city council’s budget oversight is the one check the oft-impotent body has on the mayor. But that power was sliced up when the council was expanded in 1982, with Flynn’s backing. As a councilor under White, Flynn had been continuously frustrated by the setup. “You’d sit there, nine of you, and whoever was the chair of Ways and Means, he would call the shots,” he says. “If he was buddy-buddy with the mayor, you would depend on him to even ask questions. It was a joke.” Under the reform Flynn helped push through, instead of one committee handling the entire budget, each councilor was given a department to work with, under the sweetly implausible pretext that this would school them in the inner workings of city government. Menino, however, saw it for what it was. He started pressing Flynn to bring back the old system.

In 1988, Flynn, throwing a bone to his key ally, agreed to reverse himself and reunite the budgetary power under one councilor: Tom Menino. “I says, ‘Reform. Let’s have one committee.’ And that was my committee,” laughs Menino. Amazingly, the rest of the council went along. “Some councilors viewed it as less heavy lifting,” quips Bolling. That backfired: “I used to be a pain in the neck on the budget,” Menino says. “I used to have hearings for eight hours. I used to bring them in at night.”

“A lot of us didn’t realize,” says Hennigan, “how much more powerful it would make him.”