The Making of a Mayor for Life
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.