'If I could do two terms, I'd be happy,' Menino said when he first won election. He's now in his 20th year as mayor.
Spencer Platt/EPA/AP Photo“If I could do two terms, I’d be happy,” Menino said when he first won election. He’s now in his 20th year as mayor.

Time has caught up with Thomas M. Menino, the mayor of Boston, who has spent 20 years in City Hall, longer than any previous occupant. Back in March, he told supporters that he wouldn’t run for a sixth term in the fall. The only thing holding him back, he made clear, was poor health; a long list of ailments includes Type 2 diabetes, blood clots, and a fractured spine. “I can run, I can win, and I can lead,” he declared. That wasn’t an idle boast. A poll published by the Boston Globe found that 74 percent of Bostonians approved of Menino’s performance in office and that he was a favorite for reelection, despite his frailty and 70 years.

On display in that rousing performance, and evident in much of Menino’s conduct over his five terms in office, was pride. He is an immensely proud man—proud of his accomplishments in Boston and proud of himself for surpassing everyone’s expectations. His own father once wondered whether his son, who got his start in politics as a driver for a local official, would ever find gainful employment.

How did he do it? How did Menino achieve iconic stature as Boston’s “mayor for life,” as he became known in political and media circles?

The usual answer to that question is, in a word, reform. Great mayors tend to be known (and rewarded) for overhauling some aspect of municipal government, whether it’s policing, the schools, or the tax system. Menino came to power in a reform-minded era, and several of his contemporaries, such as Rudy Giuliani of New York and Stephen Goldsmith of Indianapolis, made names for themselves as reformers.

Menino didn’t. He lacked the bold vision, the muscular policy agenda, and, above all, the ingrained sensibility and spirit of a committed reformer. “Visionaries don’t get the job done,” he once declared. That isn’t to say that he was inert or altogether bereft of ideas. He stood, as virtually all mayors do, for job creation, and he was a fervent, hands-on booster of a certain kind of economic development—as in his aggressive use of tax breaks to entice companies to move to his beloved Innovation District, comprising some 1,000 acres of South Boston waterfront. He often became intimately involved in the planning process for particular projects, down to the final choice of design elements, such as the dome atop a skyscraper at 111 Huntington Avenue. (He has an aversion to flat roofs.)

But none of this amounted to transformative governance. Even when something cried out for reform, Menino was hesitant. Take public education. The mayor wields great control over the schools in Boston, since all the members of the school committee, which runs the schools and picks the superintendent, are mayoral appointments. Menino, though, never consistently got behind any systematic approach to improving the schools. Instead, he zigged and zagged, as in his fitful support for the charter school movement. After 20 years of Menino, the public schools are much as he found them: mediocre. The rest of the state has seen academic achievement improve dramatically, thanks to reforms passed in the 1990s (see “The Massachusetts Exception,” Summer 2012). But Boston’s public schools are lagging; according to state tests, only 35 percent of third-graders read at a proficient or higher level in Boston, compared with 61 percent statewide. About 20 percent of students making it to ninth grade drop out before finishing high school. Middle-class families, especially white ones, have largely fled the public schools, in which a majority of the students are from families eligible for food stamps.

As for public safety, violent crime plunged in Menino’s early years to levels that seemed miraculous. Homicides, for example, fell from 98 in 1993, the year he took over, to 31 in 1999, a murder rate of 5.6 per 100,000 people. But then the rate began rising again. These days, Boston has about nine homicides a year for every 100,000 people, making the city less murderous than Baltimore, Cleveland, and Philadelphia but more so than New York City and even the Bronx. Gangs continue to plague poor neighborhoods like Dorchester, and various forms of graft, as ever, flourish. The city-regulated taxicab trade is a cesspool of corruption, as a recent Boston Globe investigation documented.

Menino’s middling performance only deepens the puzzle of his popularity. It pays, then, to look elsewhere for an understanding of his remarkable endurance in City Hall. Several factors stand out: his easily underrated political skills; his city’s underlying economic and cultural advantages; and, not least, his streak of good fortune.

In politics, it helps to be underestimated. The perception of unbounded promise can be a burden; just look at how Bill Clinton, in his wonder-boy years, nearly killed his prospects with an interminable, rambling speech at the Democratic National Convention in 1988. Menino has never had this problem. As Boston city councillor John Connolly, one of many candidates to replace Menino, recently told me, “He’s a guy people counted out for most of his life.”

Those people had reasons for counting Menino out. His education was spotty; for years, he bragged about not going to college, before entering UMass Boston in his early forties. He was an Italian-American in a city that had elected only Irish mayors since 1930. He did manage to get elected to the Boston city council in 1983, representing his home neighborhood of Hyde Park, on the city’s southwestern rim (where he grew up and still lives). But he wasn’t an especially distinguished presence in that body.

Still, Menino had certain qualities that can move a fellow up the ladder. For one thing, he understood and honored loyalty. As a city councillor, Menino established himself as a Flynn man—a supporter and, in some ways, a pupil of Mayor Raymond Flynn, who appreciated that fealty. From 1975 until 1988, Boston was subject to federal-court-ordered busing of students to desegregate the public schools. Many elected politicians on the city council and the school committee tried to turn an inflamed environment to their advantage—but not Menino, who followed Flynn’s example and took a conciliatory, healing stance on racial issues. He has never been a rabble-rouser.

Repayment comes to those who bide their time. In the early 1990s, Flynn began to think about choosing a successor. After settling on Menino, he got the city council to elect Menino its president—and thus in line to take over as mayor in the event of a vacancy. And that’s how Menino first moved into City Hall, as a supposedly accidental mayor, when Flynn departed in the summer of 1993 to be America’s ambassador to the Vatican. On winning election outright that fall, Menino told the Boston Globe, as if to underscore the happenstance of his triumph, “If I could do two terms, I’d be happy.”

Flynn shared this story of his plotting on Menino’s behalf in a recent conversation at his South Boston home. He recalled seeing in Menino a kindred spirit devoted to improving Boston’s neighborhoods. “He wasn’t Robert Redford, but I liked him,” Flynn said. “He had a good heart.”

Indeed, Menino’s heart may be his most valuable political asset. He isn’t weepy, but the words “I love”—as in “the people I love,” “the city I love,” and “the job that I love,” all phrases uttered in his farewell address at Faneuil Hall—sound heartfelt, all the more so for his halting, bumpy habit of speaking. Political rivals tend to precede their criticisms of the mayor with the acknowledgment that he “has his heart” in the city—that he cares. The concession helps explains why Menino, who has never aspired to any higher political office, has never had a serious challenger. His sentiment for Boston, especially as his time in office has grown, is often understood in paternal terms—the love of a father or a grandfather. He is frequently seen (and photographed) with children and young adults. “I think he goes to bat for the kids of the city,” for whom he has “a real feel,” a senior Boston attorney involved in mentoring programs told me.

Menino’s big heart fit in with an equally well-known trait: his approachability. “I am just Tommy Menino from Hyde Park,” he likes to say, with his thick-as-chowder Boston accent. (It’s compounded, possibly, by a speech impediment. Wags like Howie Carr, the conservative radio host and Boston Herald columnist, call the mayor “Mumbles Menino.”) In Boston, a class-aware town, “just Tommy . . . from Hyde Park” is a way of reminding people that the mayor isn’t a blueblood from a tony part of town like Beacon Hill. An oft-cited 2009 Boston Globe poll found that a remarkable 57 percent of Boston’s 450,000 adult-age residents had personally met the mayor—typically at the small-scale neighborhood events, such as funeral wakes and block parties, that he had made a habit of attending. In a more recent Globe poll this past March, that share dropped to a still amazing 49 percent.

These personal qualities, along with his expressed modesty of purpose, conspicuously set Menino apart from Flynn’s predecessor at City Hall, Kevin White. “King Kevin” was a charismatic figure who cut a bold, dashing, John F. Kennedyesque presence with big plans to transform sleepy Boston into a shining star of American cities. White captivated voters at first, but as his reign wore on, the public’s sentiments turned sour. Unlike Menino, White failed to go out on top: bruised by prosecutors’ investigations of dubious fund-raising activities, he opted not to run for a fifth term.

In taking a more cautious approach to his job, Menino has been happy to be known as an urban mechanic, a mayor who focuses on basic city services, such as picking up the trash, plowing the snow, and responding quickly to calls from constituents. (Until recently, he required workers at City Hall to answer the phones themselves—and not to use voice mail.) Probably it’s not a coincidence that most of his tenure occurred during an era of diminished political expectations in America. He appears to have sensed that Bostonians, like many Americans, had little faith in politicians who vowed to do big things. For much of the 1970s and ’80s, in the era of court-ordered busing, Boston was a traumatized, divided city. In that climate, a nonideological figure like Menino seemed a safe choice.

At the same time, Menino wasn’t modest in the least about putting his personal stamp on the city—the mark of the all-knowing, all-seeing, all-caring paternalist. There is a comic aspect to the obsessive enshrinement of self that characterizes Menino’s Boston. Possibly no major city in America goes to greater lengths to imprint the mayor’s name on parks, playgrounds, libraries, and traffic islands. A sign stamped with his name and title welcomes visitors to Roslindale, Jamaica Plain, Mission Hill, and other venerable neighborhoods. His name is etched on a stone bench at a memorial to World War II veterans at South Boston’s City Point. At public thoroughfares like Quincy Market, passersby are surrounded by green circular signs offering a free Wi-Fi connection, courtesy of Thomas M. Menino, Mayor.

The comic element is amplified by Menino’s protestations that, as he once asserted, “I don’t like having my name on stuff.” It’s a glaring contradiction, and yet he gets away with it. Perhaps because he’s viewed not only as good-hearted but as honest and unambitious for higher office, Bostonians are willing to abide his pharaonic sense of civic possessiveness. And to forgive, too, his less than stellar results in such areas as education.

He’s good-hearted, he professes humility, and yet he’s not an altogether nice guy. In fact, he can be exceedingly un-nice. And that’s another key to Menino’s success: his understanding that, at times, you have to show your teeth. One way the mayor is strategically ill-mannered is his penchant for stealing other people’s policy ideas. The practice is so prevalent that city councillors have coined a name for it: “Wi-Fi-ing.” It was a city councillor, John Tobin, who had the notion of making public Wi-Fi available in Boston. But Menino beat him to the punch by announcing it as his own. City Councillor Michael Ross, who is also running to replace Menino, defends the mayor: “Stealing good ideas from other cities and other people is the hallmark of good public policy,” he tells me.

In any case, Menino’s machinations have a darker side. He is known to hold grudges, to shut out dissenting voices, and to chew out anyone he believes is tendering unwelcome notions. “The mayor is notoriously thin-skinned,” says Paul Grogan, president of the Boston Foundation and a veteran of Boston politics who has known Menino “forever,” as he says. “He does take offense easily. There’s a walking-on-eggshells mentality when talking to the mayor. People spend an enormous amount of time thinking about how to please him and how not to piss him off. It’s a cottage industry in town.”

Possibly this is a personality flaw—but Menino seems to choose his feuds cannily, taking on people who are unlikely to have a strong claim on public sympathy. Such was his schoolyard brawl with the blustery developer Don Chiofaro, a former Harvard College linebacker. At a press conference in 2010, Chiofaro brazenly declared that he would force Menino to accept his proposal for Aquarium Place, a luxury project for the harbor area featuring a pair of skyscrapers that were, city hall objected, too big for the neighborhood. Menino had said that “the chances of Don Chiofaro building is about as likely as an 80-degree day in January.” Eventually, Chiofaro caved. Yet even though Menino seems to relish tussles with bigwigs, business leaders have been among his most stalwart supporters. Even with his poor health, many hoped that he would hang on for another term.

The reason for their support is Menino’s pragmatism. He hasn’t always insisted on getting his own way. The business establishment, for example, was successful in its drive, initially opposed by Menino, for a runway expansion of Logan Airport in East Boston. “He didn’t have a death match about it,” a senior business official told me. A mayor for life need not be a dictator; in fact, trying to be a dictator may be a formula for failure.

Of course, there’s only so much that even the craftiest mayors can do to promote their political success. Any assessment of Menino’s staying power has to weigh heavily Boston’s formidable economic and cultural strengths, no matter who’s occupying City Hall. Recall first that the city of Boston, only about 625,000 people strong, is lodged in a metropolitan area of 4.6 million from which the city draws many of its most able workers. While the public schools in Boston are generally second- or third-rate, many of the suburban schools, in well-off towns such as Newton, Needham, Wellesley, Lexington, and Concord, are first-class and train excellent workers for Boston’s economy.

Moreover, metropolitan Boston may have the country’s greatest concentration of fine institutions of higher education: Harvard, the Massachusetts Institute of Technology, Tufts, Brandeis, Wellesley, Boston College, and Boston University. Year after year, these institutions attract smart, ambitious students, teachers, and administrators from not only an American but a global pool of talent, and they, too, help build Boston’s tax base. Similarly, Boston has 15 teaching hospitals, including such renowned names as Massachusetts General Hospital, Brigham and Women’s Hospital, and Beth Israel Deaconess Medical Center. The hospitals and medical schools have established Boston as a world-class center of health care and medicine; the city is America’s top recipient of National Institutes of Health research grants. And the universities, especially MIT, also train entrepreneurs in high-technology industries that have benefited Boston’s economy for decades. Some $4 billion gets spent annually on academic research and development in Cambridge, home to MIT and just across the Charles River from Boston—a greater amount than in any other place in the nation, according to the National Science Foundation.

That makes for three drivers of economic opportunity in the Boston area—higher education, health care, technology—that have almost nothing to do with city hall. They were a major reason that Boston suffered less than other cities did from the 2008 financial crisis. University students kept enrolling; sick people kept showing up for treatment. In fact, the health-care sector—by far, Boston’s single largest source of employment, with some 120,000 workers, nearly 19 percent of the total workforce—kept adding employees as America reeled from its worst economic calamity since the Great Depression. The number of jobs in that sector in Boston increased by 27 percent from 2001 to 2010. In 2009, as Menino campaigned for his fifth term in office, about the most that his challengers could say was that, as well as Boston was doing, things could nevertheless improve. It wasn’t much of a slogan.

Menino also profited from sheer good luck. He had little to do with two gargantuan public-works projects that have made “his” Boston a more livable and attractive place. The first, a $4 billion cleanup of Boston Harbor paid for by higher water and sewer rates across the metropolitan area, was compelled by a federal judge after lawsuits were filed to stop the dumping of raw sewage into the sea. The second, the so-called Big Dig—which buried the city’s Central Artery highway underground and built an underwater tunnel to Logan Airport—was the brainchild of Massachusetts state officials and had backing from powerful Massachusetts politicians in Washington. Despite the jaw-dropping $15 billion price tag, the project has proved a boon for Boston, nourishing pedestrian traffic and tourism and pumping up commercial and residential real-estate values in and around the wharf district and the North End (see “Lessons of Boston’s Big Dig,” Autumn 2007).

Menino’s good-luck streak even included being mayor when the Boston Red Sox won the World Series in 2004, for the first time since 1918. For a moment, Boston was the happiest place on the planet. The Sox repeated the feat in 2007. (At Menino’s tightly scripted good-bye ceremony, an introductory video played before his speech showed him with Sox hero David Ortiz, also known as Big Papi.) Such streaks don’t last forever, as the Boston Marathon bombings showed, jolting the city a few weeks after Menino’s farewell event. But in general, Menino successfully concocted a fable that had him at the center of everything good happening in Boston. Nearly everyone subscribed to this narrative, even the president. “Boston is the vibrant, welcoming, and world-class city it is today because of Tom Menino,” Barack Obama said in a statement responding to Menino’s decision not to run for another term.

It’s tempting to conclude that a mayor for life is a bad thing. There are certainly people in Boston who feel that way. Ray Flynn himself told me that the mayor had stayed in office too long. The city needed an infusion of fresh leadership, Flynn said. (Our meeting took place before Menino announced his departure.) Boston ought to have term limits for its mayors, as many cities do, Flynn added.

Longevity in office can certainly concentrate power, inviting abuse and calcification and stifling fresh thinking. Boss figures often become remote from the people, surrounded by yes-men, and interested mostly in perpetuating their rule. Menino did grow more prickly as the years passed, and he nourished a punitive culture. In 2009, a young city councillor, Sam Yoon, took on Menino in the race for mayor and lost, only to find that prospective private-sector employers, who needed to do business with city hall, didn’t want to risk hiring him for fear of getting on Menino’s bad side. (Yoon, who left Boston for northern Virginia, told me that the story, well known in political circles, is true.)

Yet such abuses, all told, don’t amount to much. Menino’s temperamental flaws, if that’s what they are, haven’t left an indelible bruise on Boston. In fact, the surprise, given what the political-science textbooks tell us we should expect, is that matters aren’t much worse—that Menino hasn’t been more selfish and aggrandizing. Chicago’s Richard J. Daley ran for a sixth term in 1975 despite having been afflicted the previous year by a stroke that kept him from doing his job for months. He seemed determined to die in office—which he did in 1976, after easily winning reelection. Menino, given the same chance for a sixth term that voters would probably have granted him, said no. That was a good decision for Boston. (And good, surely, for his legacy.)

Bostonians now get to determine the contours of a post-Menino landscape. There is no obvious successor—not surprisingly, Menino didn’t groom anyone to take his place—which means that any number of comers feel that they have a shot in the open primary, scheduled for September. The top two vote getters will then square off in the general election in November. Perhaps 20 years of Menino will prove to have sated the popular appetite for a reassuring father figure with no particular policy bent. A swinging back of the pendulum toward a younger, more dynamic figure with a clearly articulated program for change seems overdue. The public schools present an obvious target for a reformer. But then, the city’s robust economic performance shows no sign of fizzling out—and that could be a formula for inertia even under a new mayor.

At any rate, the candidates bidding to succeed Menino must tread carefully when discussing his legacy. To talk about what is less than first-rate in Boston is to risk imprudent criticism of its beloved mayor for life. Which means that a true post-Menino era—a sharp break with his person and example—may be years away.


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