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The Boss of Boston: Mayor Thomas Menino

Boston's longest-serving mayor has started to think big. (But he still sweats the small stuff.)

David Kidd

Tom Menino needs a haircut.

The longtime Boston mayor wants to duck in for a trim at Johnny and Gino’s. It’s an old-school barbershop in the city’s Italian North End neighborhood, and Menino’s been going there ever since he first became mayor in July 1993, more than 18 years ago.

It’s a drizzly, chilly morning in early winter, and Menino’s already sat through a few meetings, made a couple of public appearances and chewed out at least one guy on his cellphone. Now he’s hustling from Brighton, a neighborhood on the west side of the city, back downtown toward Johnny and Gino’s. As a driver weaves the mayor’s black SUV through the slogging midday traffic, Menino talks shop. He talks about education and childhood obesity. He talks about economic development and urban crime. Or he tries to. He keeps interrupting himself. He points out noteworthy buildings and businesses he knows. He makes a couple of calls to his own constituent service line to report things that need the city’s attention -- graffiti on a building near Brookline Avenue, a busted streetlight at Commonwealth and Arlington. He starts talking policy again, but interrupts himself to expound on where to get the best deli sandwich in the city (it’s Sam La Grassa’s in the Financial District) or to point out the worst Italian restaurant in the North End (that one’s off the record).

It’s frenetic. And Thomas M. Menino wouldn’t have it any other way.

At 69 years old, Menino is midway through an unprecedented fifth term as the mayor of Boston. He’s the longest-serving leader in the city’s history. He’s also the longest-serving mayor currently in office in any major U.S. city. (Of course the senior-most mayor in the nation is Joseph Riley of Charleston, S.C. But with a population of 120,000, Charleston has less than one-fifth the population of Boston.) So it’s easy to think that someone in Menino’s position -- nearly two decades in the mayor’s office and 10 years on the City Council before that -- could be taking things a little bit easier.

But Menino seems as dogged as ever. If anything, his fifth term has been marked by a renewed energy. He has always been focused on building his city lot by lot, block by block. He’s the mayor of neighborhoods. When he talks about his successes, he’s still likely to mention small-scale triumphs like a grocery store he brought to Roslindale or a new police station in Dudley Square. Early in his tenure, a local columnist derided him as nothing but an “urban mechanic,” a guy too focused on tinkering and retooling to provide the city with any real direction. As it turns out, that approach has proven marvelously effective, but critics still charge that Menino is an “incrementalist” who lacks grand vision.

Beginning with his fifth term, however, the mayor seems hell-bent on shaking that image. Just after Election Day 2009, when Menino beat his opponent, former City Councilman Michael Flaherty, by a 15-point margin, the mayor told The Boston Globe that he was ready to “take more risks.” “The fifth term, I have more to accomplish,” he says today, on the way to Johnny and Gino’s. “More challenges. The danger you have when you’re in your third term, fourth term, fifth term, is that you might sit back and rest on your laurels. And that’s the worst thing you could do. If you’re staying status quo, you’re falling backward.” 

And right now, Boston is doing anything but staying status quo. Boston, in fact, is booming. While so many other cities are cutting back and scraping by, Boston is humming with an energy that may be unmatched anywhere else in the country right now. The city’s economy grew 4.8 percent in 2010, the fastest rate of growth in the nation. It’s one of only a handful of places in the country to have more private-sector jobs now than five years ago. It just surpassed Austin, Texas, as the city with the nation’s highest ratio of 20- to 34-year-olds. In September, The Atlantic ranked Boston the sixth most economically powerful city in the world, ahead of Hong Kong, Beijing, Sydney and others.

Menino is the first to admit that much of his city’s current economic vitality stems from its plethora of colleges and universities, and from its position as one of the world’s major biotechnology hubs. But he also seems more determined than ever to push that vitality further, to make his own mark. To help stoke that growth, Menino has worked to reimagine the city’s long-disused south waterfront as a new hub for high-tech firms and small startups, along with retail, housing, restaurants and green space. Two years ago, he rebranded the area as a new “Innovation District” and began targeted efforts to attract new companies there. The mayor of neighborhoods has essentially created a new neighborhood from whole cloth. It’s perhaps the biggest gamble of his 28 years in city government.

To be sure, the mayor’s had some setbacks in his fifth term. He suffered a series of injuries and surgeries -- operations on each of his knees, a hospital stay for a bacterial infection on his elbow and another hospitalization for an adverse reaction to antibiotics -- that waylaid him for much of late 2009 and 2010, forcing him to spend weeks recovering at home. For a mayor who’s never known a pancake breakfast or neighborhood block party too small to attend, it was a frustrating slowdown. His 18 years as mayor have attracted plenty of accusations that he’s concentrated too much power, that he rules Boston more as an unchecked king than an elected official. He’s been accused of playing favorites with developers. And he still faces some perennial issues: He’s had to cut some city services after four years of reductions in local aid from the state; the city’s education system remains a thorny problem; and Menino’s been charged with lacking a cohesive approach to reducing crime. Boston’s crime rate has been at historic lows in recent years and 2011 saw an especially low rate. But the number of murders in the city spiked nearly 50 percent in 2010.

Menino has plenty of work to do. And he knows it. As he hops out of the chair at Johnny and Gino’s, he clambers back into the black SUV to head to City Hall for an afternoon of meetings and three different events that evening. But then he interrupts himself: “Who’s hungry? You guys want to get a sandwich? I know a place.”

A few years ago, The Boston Globe conducted a poll to gauge citizens’ satisfaction with the way Boston was running. The poll included typical questions about whether residents thought the mayor was doing a good job, and whether they had a favorable or unfavorable opinion of him. There was one question, though, that stood out: “Have you, personally, ever met Mayor Menino?”

That the newspaper would even pose such a question says a lot about Menino’s longevity and his leadership style. He’s always preferred being out in the city’s neighborhoods to spending his days at City Hall. What’s really surprising was the number of people who said they had, in fact, met the mayor: 57 percent.

“Being mayor, you have to have a sense of what the neighborhoods want,” he says over lunch at Mangia Mangia, a hole-in-the-wall carryout deli in the North End that’s a favorite spot of his. “You have to be out there every day listening to people. When you sit in your office, you don’t accomplish anything. You got to listen to people tell you what they think. That’s part of my success. I go out there and listen.”

Menino has lived in the same Boston neighborhood his entire life. He grew up in Hyde Park in the southernmost corner of Boston. His father worked nearby at the Westinghouse Electric plant on the Neponset River. Tom Menino and his wife, Angela Faletra, today live not far from his boyhood home, in an unassuming two-story house in the Readville section of Hyde Park. “He’s from a modest neighborhood in a modest home,” says Howard Husock, vice president for policy research at the conservative Manhattan Institute. Husock spent 20 years as an urban policy director at Harvard’s Kennedy School of Government, and he once directed a documentary on Menino. “He really understands what it’s like to be a lower-middle class homeowner in the outer neighborhoods of the city,” Husock says. “I think that self-understanding has really guided his mayoral tenure.”

First elected to the City Council in 1983, Menino was council president in July 1993 when Mayor Raymond Flynn left office to become the U.S. ambassador to the Vatican. Menino took over as interim mayor and was elected to his first full term that November. From the beginning, he’s been concerned with on-the-ground urban minutiae like potholes and trash pickup. That focus, combined with his omnipresence on the city’s streets and in its neighborhoods, has made Menino an extremely approachable guy. Spend a couple days bustling around the city with him, and you’ll be constantly struck by the number of people who come up to say hello. “Hey, mayor,” says a woman in line at Mangia Mangia. “How you doing? I’m Alexandra’s grandma.” Construction guys joke around with him; people stop him on the street to chat or to take their photo with him. When he stops in for a bite at D’Amelio’s, an Italian fish place in East Boston, two blue-collar guys -- total strangers -- rib him about disturbing their lunch.

Menino may be naturally comfortable around his constituents, but he’s never been a smooth politician. While he can be affable and crack a joke, he’s long said that smiling and shaking hands don’t come naturally to him. He’s not an eloquent speaker. His extremely strong Boston accent is full of dropped consonants and honking, flattened vowels. He stumbles through sentences, and he chews and muddles his words, a trait that long ago earned him the nickname Mumbles. When he says “commonwealth,” it comes out as “cawmulth.” The word “government” sounds more like “gubbin.” He’s prone to malapropisms: He memorably once described the lack of city parking spaces as “an Alcatraz around my neck,” and he recently said he wants to create a public food market in Boston “like Pikes Peak in Seattle.”

“People listen to him and they don’t understand how smart he is,” says Maurice Cunningham, a political science professor at the University of Massachusetts in Boston and a longtime observer of city politics. “He’s really smart. He’s forward-looking. He likes to say, you know, ‘I’m not a fancy talker but I get things done.’ I think he’s kept both of those promises.”

On the night after his haircut at Johnny and Gino’s, Thomas Menino attended a fundraiser for MassINC, a civic think tank. Before the mayor took the stage, a video began playing in front of the crowd. In it, the mayor appeared dressed as The Godfather, stroking a stuffed cat in a parody of the movie’s iconic opening scene. Godfather Menino addressed an actor portraying a well-known Boston developer who, in real life, is trying to develop a high-rise project the mayor doesn’t like. “What have I done that you treat me with such disrespect?” Menino rasps. “If you had come to me in friendship, your new tower would be up this very day.” At the end of the video, Godfather Menino turns to leave but stops an aide, and says: “Leave the blueprint. Take the cannoli.”

It was a rare bit of self-deprecation, but it spoke volumes about how Menino alone calls the shots when it comes to new projects in Boston. Nothing moves forward without his blessing. As a 2009 story in The Globe put it, “Never before in Boston, and perhaps nowhere else in the nation, has a mayor obsessed so mightily, and wielded power so exhaustively, over the look, feel and shape of the built city. Routine construction projects on remote streets need City Hall approval; prominent towers that climb the downtown skyline carry his mark; independent city boards bow to his will.”

Several years ago, the mayor was meeting in his conference room with a developer of a proposed 36-story skyscraper in the Back Bay neighborhood. Menino reportedly took one look at the design and dismissed it because he wasn’t a fan of flat roofs. The developer later returned with a scale model of the building and a dozen different miniature tops. He kept placing the tops on the building until the mayor pointed to the one he liked. Conversation over. Project good to go.

The mayor’s fanatical attention to detail has proven enormously successful for the city, helping to reclaim blighted neighborhoods like Grove Hall and Roslindale one street corner at a time. In recent years he’s set his sights on the Dudley Square neighborhood, which sits at the geographic heart of the city. In August, the city opened a gleaming new 35,000-square-foot, LEED silver police station in Dudley. Earlier last year, Menino announced plans to convert an abandoned historic building, formerly home to Ferdinand’s Furniture, into the new headquarters for the city’s education department. It’s a $115 million project that Menino says will be “a catalyst for Dudley redevelopment.”

By the same token, the mayor takes it personally when developments fail. The best example of that right now is the gaping, city-block-sized pit in the center of the city’s financial district. Five years ago, a developer announced plans to demolish an outdated building -- the home of the original Filene’s department store -- and replace it with a $700 million, 39-story, mixed-used tower to be known as One Franklin. The mayor and his team allowed the developer to demolish the existing building, even though the firm hadn’t yet lined up all the necessary funding. The economy tanked, the developer stalled and work on the project officially ceased in June 2008. Then, nothing. Nearly four years later, it’s still a bombed-out hole partially surrounded by ghostly historic facades. Tension mounted when officials began to publicly voice suspicions that the developer was effectively holding the property for ransom in order to get development incentives. Menino fired off a letter to the developer, saying he had “embraced a deliberate policy of long-term blight,” threatening to seize the property through eminent domain. Today the mayor vows that addressing One Franklin is a top goal in the remainder of his current term. “We’ll try everything we can to get them out,” he says.

For all his focus on individual developments, though, Mayor Menino has started to dream bigger. That’s the idea behind the Innovation District at the old south seaport. For decades, it’s been an almost empty part of the city, despite comprising 1,000 acres a stone’s throw from downtown. With the completion of the Big Dig in 2006, the area suddenly became much more accessible and connected to the rest of the city. Developing it, however, has proven a little tricky. There were a few false starts with grand plans for office parks that didn’t pass muster with Menino. Then, at the beginning of 2010, the mayor rechristened it as the city’s Innovation District, and vowed to help companies large and small secure tax incentives to locate there, and to coordinate a continued network of support once they did. Since then, growth on the waterfront has exploded. More than 90 new companies have moved there, along with 2,300 new jobs, in the past two years. More than 50 retailers, bars and restaurants have opened. In June, construction began on a new global headquarters for Vertex Pharmaceuticals, a company currently based in Cambridge. With 1.1 million square feet of offices and lab space -- and a price tag of $900 million -- it’s currently the largest private-sector construction project in the nation.

In the past, says Husock of the Manhattan Institute, the waterfront “was nothing. It was really almost a wasteland.” What Menino has accomplished there, he says, “is not only the rebirth, but the complete refashioning of the entire area into what amounts to a new city. It’s quite an extraordinary achievement. The fact that they’ve guided that and continued to draw investment during the period we’re in now is tremendously to his credit.”

Menino hasn’t said whether he will seek a sixth term. But it’s clear he’s begun thinking more about his legacy. The Innovation District is certainly one. The mayor hopes education is another. Boston Public Schools have been a vexing problem since Menino took office. He’s logged some achievements: In 2006, the city school system was recognized by the Broad Foundation as the most improved urban school district in the country. Its graduation rate is at its highest level since Massachusetts started keeping track in the early 1980s. Still, many of the city’s schools are chronic underperformers. In the past couple years, Menino has tried to use contract negotiations with the city’s teachers union as an avenue for reform by seeking greater flexibility for principals, linking teachers’ salaries with student achievement and pushing for a longer school day. It’s been tough going so far. The city has gone more than 18 months without agreeing on a new contract for educators. “If I could wave a magic wand about education, I would,” Menino says. “When I leave office, I think people will say, ‘The mayor worked hard on education.’”

For the mayor, legacy-building may be about education reforms and bringing new development to Boston. But for many others, his lasting imprint on the city will be the very incrementalism that defined his first four terms in office. Menino has redefined what it means to be the mayor of Boston, says the University of Massachusetts’ Cunningham. “Anybody coming in is going to have to pay attention to every city block, the way he has. I think that’s an expectation people have now. I really think that’s a terrific thing to leave behind.”

In many ways, that’s an imprint that extends well beyond Boston. Menino’s approach -- fixing potholes, cleaning up parks and building neighborhoods through small-scale investments -- was derided as hopelessly myopic when he first took office. But along the way, as Boston thrived, Menino’s way became the way for mayors everywhere, says Husock. “I think that Mayor Menino has been an important mayor for Boston -- and for Democratic mayors across the country especially -- because he signaled that a focus on core, traditional services was important. That we should not only think that new projects and changing the face of the city should be the sole focus of a mayor. The delivery of core services is a message that any mayor can take to heart.”

It’s certainly a message that Boston citizens have embraced. As a couple of Menino staffers are headed back downtown after an event with the mayor in East Boston, a tollbooth operator catches sight of the city seal on their car. The toll plaza used to have some small trees, he tells them, and he’d really like to plant some new ones. “Tell your boss we’d like those trees back,” he says through the tollbooth window. “He runs a good city. If he says it’ll happen, it’ll happen.”

Tina Trenkner is the Deputy Editor for She edits the Technology and Health newsletters.
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