The Making of a Mayor for Life

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!’”

  • Chris

    Is it not possible for the media to admit that Mayor Menino has done an excellent job for our City- That is why he is still Mayor? The article mentions his promise to help Roslindale square, but doesn't say how he has delivered on that promise. The Mayor consistently keeps his promises. A trait that is lacking in most politicians. This is why he is popular- why he has won- apathy has nothing to do with it.

  • Mike

    If the mayor has done such an excellent job, why are the schools in such awful shape? Why his sudden election-year conversion of Charter Schools? Why the dearth of middle-class and upper class kids in the schools?