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.

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.”


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.
At the time Menino became acting mayor, no one else in the city’s power structure realized yet quite what that meant. Many still considered it a caretaker gig. Besides, mayor, acting or otherwise, is not district councilor. The post came with a steep learning curve. Dan Payne, a Democratic strategist, was advising another of the 1993 hopefuls to eye the mayor’s office after Flynn’s announcement, Suffolk County Sheriff Bob Rufo. Rufo had a broad base of support, a good reputation, and a great field operation. He was considered the early frontrunner. “I can remember telling Rufo and others in the campaign that it’s entirely possible that the job of mayor is going to be too tough for Menino,” says Payne. “Not ultimately, but immediately. That he might not know where all levers of power were, so he might have a hard time convincing people he could handle it.”

It was on a Thursday that July when Flynn learned he was going to be confirmed. When he got word, Menino sat down with Gerard Doherty and John Cullinane, his old friend from the Park Street Corporation, to plan a fundraiser for the following Monday at the Meridien Hotel. Flynn’s news wasn’t made public until Sunday, but “we had the letters out already,” says Doherty. “That was the beginning of the mayor’s run.”

The trick, though, was to act as if there was no campaign, even as the fundraising engine revved up. Menino’s strategy was to behave as little like a candidate as possible, understanding that Boston voters traditionally value a proven ability to do the job far more than lofty promises of change (also that they tend to reelect incumbents, as if by muscle memory). The rest of the candidates—there were seven of them, including Roache, a former police commissioner; Bolling; radio host Chris Lydon; and councilor Rosaria Salerno—thought they would be running for an open seat, that it would be a race among equals. “But what happened when Tom became acting mayor was that the race changed,” says Jim Brett, a former legislator who made it to the final that year. “I didn’t see that coming.”

While his opponents complained he was abusing his position, Menino ordered police commissioner Bill Bratton to draft a new anticrime plan and announced a million dollars in improvements to security at elder housing and another half million for summer jobs. Because the news hole reserved for the mayor is far bigger than that reserved for mere candidates, Menino’s non-campaign was able to “blot out the sun, as far as coverage went,” Payne says. “They had a story at least once a week, a good story. We were forced to respond to everything he was doing.” Meanwhile, Menino, adopting another tactic central to his playbook, refused to debate his opponents, citing the crush of “city business.”

The other candidates’ numbers just evaporated. And still Menino waited until mid-August to announce his candidacy. He was the last one to declare. At the few forums he elected to participate in, he treaded water, playing to expectations and effectively negating his opponents’ performances. “That was the theme of the campaign,” says Payne. “You can’t get at him and he doesn’t hurt himself.”


And it’s been that way ever since. Though he promised in 1993 to serve no more than two terms, Tom Menino is still mayor. All the years learning from the rise and fall of other politicians made him steady, gave him the long view and kept him intensely focused. He doesn’t lose his composure or take his frustrations public, the way Flynn did. He won’t run for higher office, the way Kevin White did when he made his disastrous bid for governor in 1970 and was trounced by Frank Sargent. He’s successfully avoided serious scandal for 16 years, practically a miracle for a boss pol. The job is his life, and he doesn’t take it for granted. He still grinds it out anew. “He’s very surprised with where he is,” says Timilty. “This is something he never expected would happen.”

And because of that, he’s not going to take any chances. Facing a reelection challenge, he unfailingly reprises his 1993 strategy: Behind the scenes, his people are ferocious, but in person, it’s as though nothing is happening. He won’t engage; you can’t get at him and he doesn’t hurt himself. Asked about the approach that would become his signature, Menino says, “I had to make decisions, I had to do things, I couldn’t pander to the public.” He adds, sounding a vaguely monarchical note, “Sometimes on issues you want to say to the press what the public wants to hear. And what the public wants to hear and what the facts are are two different things. When you tell the truth, people don’t like it.” To this day, he largely refuses to debate, dismissing it as a forum for lawyer types spinning off sweet nothings. “Well, why not do one-on-one interviews? Get one person asking questions and I answer them? I just think so much is made of debates.” But that’s disingenuous. In 2005, he sat down for a one-on-one interview with a Globe reporter and testily dodged nearly every question. He wouldn’t speak then to the decline in minority students at Boston Latin “because I don’t want to make it political.” He declined to disclose his ideas for improving public housing, asking, “Why should I do it before the election?”

Many in City Hall assume that when he decides not to be mayor any longer, Menino won’t just leave his successor to be decided through a raucous open field, as White did. Instead he’ll return to the kind of furtive maneuvering that installed him in power. For several years it looked as if the beneficiary would be Mike Flaherty, who had long played Tommy to Tommy’s Ray. Flaherty rose to council president and waited and waited, and then in 2005 got 50,000 votes as a city councilor. That was just 14,000 less than Menino, and much too close for comfort. Menino decided he wasn’t ready to abdicate the throne quite yet and backed his ally Dorchester councilor Maureen Feeney for the council presidency, effectively knocking Flaherty out.

Now, Flaherty, still angered by the perceived betrayal, is running with a lot of money and considerable support, in a field that has Yoon and McCrea to ratchet up the heat. This time around, it will be more difficult for the mayor to act as though there is no election occurring, just some unimportant noises being made in the neighborhood weeklies by lesser men. Ray Flynn goes so far as to call the coming election “a bellwether.” He points to the 2008 presidential race that drew more than 232,000 voters in Boston, and the 2006 gubernatorial race that pulled 157,000. “There’s this notion that the people don’t care,” he says. “That’s bullshit. They do care, but they have to be encouraged and convinced.”

But that’s not part of the playbook. That wasn’t what elevated the mayor to power, and it certainly isn’t what’s held him there. Which cuts to the core of the strange phenomenon of Tom Menino: In order to do what he feels he needs to do to improve life for the city’s people, he has to paradoxically discourage those same people from taking an active interest themselves. The city may have his heart, but the process has his fealty.

This is what gets Ray Flynn the most exercised. “The happiest guy in the world would be Tom Menino if he had all these debates and he did well, and people said, ‘I like what he said, and I like his record. I’m gonna vote for him.’ Tom Menino would wake up one morning in November and say, ‘I did it,'” Flynn says. “I wouldn’t be too happy about climbing out of that bed if I won the election by default. I would say I manipulated the system. It’s not the way I would want to win elections.” Or it shouldn’t be, anyway. But Menino, as he has carved out a place for himself in city history, has made it so that the process is widely viewed as the only way in. It’s where the power now resides. It’s hard to remember a time when it was any other way.