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.

photograph by the boston herald

From time to time, Tom Menino transcends the corporeal urban mechanic and begins to resemble something out of a ghost story. Never is this truer than during an election year.

An example: On a sunny day back in March, a campaign operative for councilor-at-large Michael Flaherty, son of Southie and 2009 candidate for mayor, walked into South Station to have coffee with a reporter. He sat down at the small round table under the chattering board, and mentioned he had parked his car, white, with a big green Flaherty sticker on the rear window, a few blocks away at a broken meter.

“There you go,” says the reporter. “Free parking.”

“Yeah,” says the operative. “Watch. When I get back to my car the meter will be fixed and there’ll be a ticket on my window.”

After leaving South Station, the reporter went one way, the aide the other. Moments later, the aide came running down the street, retrieved the reporter, led him two blocks south, and pointed at his car. Sure enough, the meter was fixed, and there was a nice fat orange ticket on the windshield. The paranoia is catching. A couple of days later, an aide to Sam Yoon, another at-large councilor and candidate for mayor, sat in a restaurant on Beacon Hill complaining that accurate polling is impossible in Boston because city workers—and there are some 20,000 of them—will lie to pollsters out of fear that if they let slip anything less than full-throated support of the mayor, it’ll get back to the boss. This is the sort of omnipotence usually reserved for Kim Jong Il, or Santa Claus, and Menino has achieved it.

And yet, as ever, in person he remains underwhelming. Yes, he dresses impeccably, supremely mayoral in a suit, tie, and (usually) cuff links. But he doesn’t radiate power or charisma, as you’d expect of one of the nation’s great urban bosses—as you’d expect of a man set to pass Kevin White this July as Boston’s longest-serving mayor, thereby becoming a legitimately historic figure. He’s a famously bad speaker, dropping not just r’s, but also t’s, as if introducing an advanced strain of the Boston accent into the city. He’s often photographed with his mouth slightly agape, even when posing for a shot taken by his own staff for a press release. As he sits in his office discussing his first campaign for city council back in 1983, he mentions how he was shy then, and insists he never quite got over it. “I’m not outgoing,” he says. “I’d rather hold back than go way up front. Some guys want to get way up front. I want—people respect you when you’re not that forward.”

The numbers, at least on the surface, appear to bear that out. According to a 2008 Globe poll, more than half the people in the city have met Menino, whose approval ratings hang in the 70s, suggesting widespread adoration. But seeing him in a diner and voting for him are two different things. And when the question is how many Bostonians feel moved to go pull the lever for him, you get far less imposing figures. Take 2005, when at-large councilor Maura Hennigan sought to unseat him. When people talk about that race (at least the minority aware it even occurred), they point out how Menino drew 68 percent of the ballots. But his 64,000 votes came out of 270,000 registered voters, and 450,000 potential ones. Factor in those 20,000 city workers who tend to go for the incumbent, and you’re left with a pretty thin foundation of support.

Menino must feel that acutely. Because if he cuts a weirdly humdrum figure for a man of such considerable accomplishments, he’s unique in another way, too. From the beginning he’s been remarkably clear-eyed about his limitations, a rare trait in historical-grade political mega-fauna. And so he has hustled every step of the way, determined to seize on every opportunity, even as he benefits from being constantly underestimated. At the same time, he’s also cannily retreated from the hurly-burly of elections, opting instead to work the system behind the scenes at a safe remove from the ballot boxes. Notwithstanding his fearsome reputation among those who work directly with the city, what Menino mostly does is benumb. His might has grown in inverse proportion to the interest that the people of this once peerlessly impassioned burg take in their politics.

Throughout Menino’s reign, his playbook has worked near perfectly. But it’s never been tested by a challenger with juice enough to stir the vast majority of Bostonians who have spent the past three mayoral elections on the sidelines. Assuming he runs (a safe bet), this year he’ll face three, in Flaherty, Yoon, and rabble-rousing businessman Kevin McCrea, plus a knee-buckling budget crunch and an open revolt among the firefighters and teachers unions to help keep the heat on—maybe enough to expose the key vulnerability built into the mayor’s long-preferred approach. Sixteen years into his mayoralty, and 27 after embarking on his political career, Tom Menino might finally have to battle it out tooth and claw in broad daylight. That’s the last thing he’s ever wanted to do, and in the Boston he came up in, he found a way to largely avoid it. His gamble is that in 2009, the Boston he’s made remains a place where in lieu of vast support, a leader can maintain power simply by preserving the populace’s indifference.


The Boston Park League is the oldest amateur baseball league in the United States. Started in 1929, it was once the passion of the neighborhoods. Games routinely drew crowds in the thousands. Before one contest in 1961, young city council candidate Joe Timilty came out to Kelly Field in Hyde Park to meet with a friend, Michael Donato, a great ballplayer out of B.C. High. The Bottomly Braves were playing that day, and Donato introduced Timilty to a guy who hung around the team, a well-liked 19-year-old neighborhood kid by the name of Tommy Menino. Tommy’s father, Carl, worked at the Westinghouse factory and was a popular figure in Hyde Park’s vote-rich Italian circles, and both of Menino’s parents had campaigned for a state rep named Charlie Patrone. Tommy had passed out pamphlets for Patrone, and, save for baseball, was interested in little else but politics. In a 1983 interview, Carl Menino said that after his son graduated from St. Thomas Aquinas High, he pushed him to go to college, to no avail. “He didn’t want to go to school no more…. He used to say, when I got after him to go to college, he’d say, ‘Truman never went to college.’ He told me that 1,000 times.”

Menino signed on as a foot soldier with Timilty’s campaign, and became close with the candidate and his family. “He was exactly what I was looking for,” says Timilty. “He worked at it.” Timilty won the seat, assuring Menino a recurring gig in politics, at least come reelection time. In 1968, he quit selling insurance for Metropolitan Life, where he’d been since 1963, and got his first public job when Timilty fixed him up with a low-level position with the Boston Redevelopment Authority.

Three years later, and then in 1975, and again in 1979, Timilty tried to do what his uncle, a former protégé turned opponent of James Michael Curley, had failed at. Namely, wrest power from a ruthless, charismatic mayor. In this case the incumbent was Kevin White, and each time Menino enlisted to serve the cause. “This is Boston politics,” says Timilty. “It’s like a sport. When the season comes around, you get involved.” It was also a gamble. Timilty was a legitimate contender, and if he prevailed, Menino would get a job in his administration. If White won, however, he might seek revenge on this kid who’d had the audacity to try to oust the man who signed his checks. Menino, unfazed, dug in. “With

Timilty, everyone would go out and drink after a campaign day,” says Skinner Donohue, a veteran political operative who now advises Menino. “Tom would hang in with us, but he wouldn’t drink. Timilty would yell at him because the day was going bad, and he’d never push back. He’s just a rock.”

Timilty, by this point a state senator, had given White the strongest challenge in 1975, falling a mere 7,528 votes short. It was a nasty campaign, and when it was over, White finally came for Menino. It’s a little-known fact, more salient than ever now that Menino is poised to break White’s record, that Kevin White actually fired Tom Menino from the BRA. Sitting in his office on the fifth floor of City Hall, Menino doesn’t try to duck questions on the episode, as some former associates suggested he would. “He fired me,” he says. “He fired me! That dirty scoundrel.” He laughs, slapping his leg. “Probably the best thing that ever happened to me. I probably would have been stuck there still today.”

At the time, however, it was a painful setback. To help Menino out, Timilty fixed him up with a job with the state Department of Housing and Community Development. The posting wasn’t exactly ideal for an ambitious young political operative, “[but] at that point he can’t be that fussy,” says Gerard Doherty, a longtime counselor to the Kennedys and Timilty who became Menino’s chief political mentor. “He had two young kids, he had no job, he had no degree. He got the state job and he had to hang on to it.”

During his days in the wilderness, Menino managed to keep his hand in city affairs. He did so through a body called the Park Street Corporation, led by Paulist priest Robert Quinn. At his Bowdoin Street apartment and other venues around the city, Father Quinn would (and still does, as chaplain of the Massachusetts House) gather prominent Bostonians to discuss problems facing the city, away from the press. Doherty suggested that if Menino was serious about politics, he should come along. “One of his virtues, or weaknesses,” says Doherty, “is persistence. Once he started to go, and he bought into the idea that he could learn a lot, he kept going.” The other congregants, including early tech entrepreneur John Cullinane and developer Tom Flatley, “were not initially overwhelmed by him, but over time he grew on them,” says Doherty. Cullinane adds, “He used to bring the doughnuts, if I remember correctly.”

Doherty, who became close with Menino when they were both working on Timilty’s 1975 campaign, saw potential in the younger operative. “I sort of identified with him because I’m not charismatic, and he’s not charismatic,” Doherty says. “But he used to sweat. Most of the people you meet, they flash their teeth and shake your hand, while at the same time they’re looking over your shoulder. He didn’t do that. When he walked into a room, he wouldn’t galvanize it, but by the end of the night he could tell you exactly who was there, what they did, and what they didn’t do. He had a quietness of style.”

Eventually, Timilty found a spot in his Senate office for Menino, who worked his way up from driver to chief of staff. “He did everything. Everything,” says Timilty. “Knowing where the legislation was. Doing politics with other members of the Senate, their staffs, he got that all down. Any other fight we got involved in.” Menino was content to remain behind the scenes. He had developed into a master organizer, but lacked the flair he’d seem to need to compete as a candidate himself in what was a raucous era for Boston politics, characterized by Ray Flynn’s midnight jogging jags/pub crawls and the persistent lunacy and occasional brawls of guys like councilors Dapper O’Neil and Jimmy Kelly.

Nineteen-eighty-two changed that. That year, the city council was expanded from nine at-large seats to four at-large and seven district seats—one being District 5, covering Hyde Park, part of Roslindale, and a sliver of Forest Hills. Timilty territory. The change required legislative approval, which Timilty saw to. “We wanted a seat,” he says, “and it was obviously going to be [Menino’s]. We got the House and the Senate to pass that. It was created for him.” Menino, pushed by Timilty and heartened by the subpar quality of the other candidates, tossed in his hat. When he told his father about it, Carl Menino worried that Tom would be unemployed if he lost. “Dad, I won’t lose. Don’t worry about it,” he said.


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.


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!'”
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.”


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.


  • 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?