The Making of a Mayor for Life

In December 1992, Menino made a bid for council president. The job was somewhat coveted, in that the president got to make committee appointments and enjoyed a one-eyed-man-in-the-land-of-the-blind sort of clout. It wasn’t, though, widely viewed as a steppingstone. No one had jumped from council president to mayor in a century. Going for the post carried risks, too. If Menino lost, the victor would surely strip him of his Ways and Means chairmanship. He would be back to the district grind, just in time for his self-imposed 10-year deadline.

Menino faced Maura Hennigan, a gadfly at-large councilor. She rallied the support of women’s and minority blocs, positioned herself as a champion of lefty causes, and was the odds-on favorite. Flynn, understandably, didn’t want an outspoken antagonist heading the council, and so backed Menino. “We really pulled out all the stops for Tommy,” he says. To ensure Menino’s victory, Flynn broke off two councilors who had looked likely to go for Hennigan. One of them was a black freshman councilor named Anthony Crayton. While the rest of the council, recognizing its earlier error, was fighting to split up Ways and Means again, Crayton was dead-set against it. In fact, he could see himself chairing the committee. Offered that promotion, he took the deal. “Tony Crayton didn’t know what he was doing,” says Hennigan. Feeling betrayed, Crayton’s base in Roxbury voted him out of office two years later. (A well-liked but troubled man, he died at the age of 56 in 2006.) Menino won the presidency by a vote.

Things moved quickly after that. In March 1993, Flynn got word that he was being nominated as ambassador to the Vatican. A sign of how close the two men had become, Flynn called Menino to ask if he thought he should take the job. Naturally, Menino said he should. “I said, ‘Ray, some of us guys from the neighborhood get to be senators, congressmen—how many of us guys get to be ambassadors?’” On St. Patrick’s Day, the papers announced that Flynn was Rome-bound, with Menino, as council president, to replace him as acting mayor. The beginning of Menino’s record-breaking run, it also signaled the end of his relationship with Flynn.

“The day I was in my office leaving,” recalls Flynn, “I was asked by his staff…if I would say something very positive about Tommy before all the press. I said, ‘Look, I know [mayoral candidates] Jimmy Brett and Mickey Roache. Those guys were friends of mine and I don’t want to be dictating who the next mayor is gonna be.’ ‘Well, can you say something like, the city is in good hands?’ So I said, ‘Sure, I can say that.’ Of course that’s the front-page headline, with a picture of Tommy Menino. They asked me if I could hug him [for the photo]. So I did.

“Jimmy Brett was upset with me for that headline,” Flynn says. “I heard him say it cost him the election. And Mickey Roache wasn’t happy about it. And Tommy Menino never said, ‘Gee, thank you very much for what you said.’ Tommy’s been mayor for 16 years and he’s never called me.” Flynn, bitter over the snub, hasn’t shied from criticizing Menino in the press. (He even did it from the Vatican, which probably didn’t help.) Adding to the tension, Menino cultivated a warm relationship with Kevin White, the man who had fired him, taking to calling him “Kev.”

“After all I did for him,” Flynn says.

  • 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?