The Making of a Mayor for Life
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.”
Ray Flynn went gangbusters through the first five years of his administration. He turned a $40 million shortfall into a surplus, secured barrels of state and federal aid, and presided over a period of prosperity that transformed Boston from blue collar to white. But late in his second term, he started bogging down. Scuttlebutt began circulating that he wanted out, maybe to run for higher office. He did little to discourage those rumors. He was frustrated. By early 1991, the flow of aid had slowed to a trickle, property values were sliding, crime was rising, and the budget was back into the red. There were escalating union problems. His critics piled on. Even Menino took a few shots. (In one rare heated moment, after Flynn stole an idea cold from Menino—today an even more notorious stealer of ideas—the latter spat, “This is Boston; this isn’t one person’s empire!”)
In July 1991, after playing hide-and-seek with reporters for months, Flynn announced he would run for reelection after all. He won easily, but the slide continued. Early the following year, a private poll conducted by his office (a rarity, as Flynn, a genuine populist, liked to do his own polling on the streets and in the pubs) showed him slipping by as much as 10 points. Worse, the slippage wasn’t tied to any one issue so much as a feeling of creeping malaise.
Flynn’s decision to go for another term was a turning point for Menino, but not in a way you’d expect. That June, Menino had announced he would run for the 11th Congressional seat. He was in the race for just over a month before redistricting erased the 11th altogether. But the bid had energized him. Though often critical of his TV performances, he’d actually made a capable showing on the big stage. He’d also discovered that the provincial politician doesn’t travel well. Sometimes literally. “I left my safe base and went down to Brockton and Carver, Mass., whatever the hell that is,” Menino recalls. “I remember going to Carver one night and we drove around in circles for an hour, couldn’t find a way out of Carver, Mass. I says, ‘This is a fish outta water for me.’” He came back sold on the idea that his best chance to move up lay within city limits. “He would say to me, ‘I have one big run in me, Bobby, because I love this game,’” says Finneran. “‘I did okay out there, those are some tough issues, oil imports and the Iraq war. I did all right. And Ray’s gonna leave.’ I can hear and feel the ambition in him. ‘And when he goes, I’ll be ready.’ And he was.”