In May, The Boston Globe conducted a poll to find out what Bostonians think of their city's mayor, Tom Menino. Most of the questions were common to public-opinion surveys about elected officials: Do you approve or disapprove of the way he is doing his job? Do you have a favorable or unfavorable opinion of him? But there was one question that seemed out of place, as if the Globe's pollsters had gotten their scripts mixed up and, rather than asking about a big-city mayor, were instead inquiring about a bucolic New England town selectman: "Have you, personally, ever met" Menino?
The question was presumably inspired by the fact that, in the 16 years he's served as Boston's mayor, Menino has yet to encounter a civic event he deems beneath his station to attend. Beauty-parlor openings, pancake breakfasts, Little League games--he shows up at all of them. ("If you're going to have your dog spayed, you call him, he'll be there," one Bostonian recently told the Globe's Scott Helman.) Still, in a major city of nearly 600,000 people, could a statistically significant portion of the populace actually have met their mayor? As it turns out, in Tom Menino's Boston, the answer is yes; according to the Globe's poll, a remarkable 57 percent of them, in fact.
"That's just me, Tom Menino--I'm out there listening to people, talking to people," the mayor told me one recent afternoon, at once shrugging off and trying to explain his omnipresence. That morning, he'd been at a ribbon-cutting for a new playground. At lunchtime, he'd visited a senior-citizens center. Now, Menino was sequestered in his campaign headquarters, which was unusually bustling for a Menino campaign headquarters three months before voting day. In the past, Menino hasn't had to put much effort into getting reelected, running against either token or no opposition. Even his initial entry to the office was frictionless: As then-city council president in 1993, he inherited the mayor's job when Bill Clinton made Ray Flynn his Vatican ambassador.
But this year, as Menino seeks an unprecedented fifth term--a feat that eluded all of the men who served as Boston mayor before him, including political legends James Michael Curley and Kevin White--he is facing not only a crippling budget crisis, but two credible challengers, both city councilmen. (The mayoral candidates will compete in a preliminary election in September, with the top two finishers facing off in November.) As a result, the 66-year-old Menino is campaigning earlier and harder than ever before. Paul Maslin, a pollster whom Menino recently hired, says, "I think it's a given that it's going to be his toughest race to date."
Menino points to any number of accomplishments that have occurred on his watch, from housing to health care. "I'll put my record up against anybody's record," he told me. And the Globe poll in May did find that 73 percent of Bostonians approve of the job he's done. But, in some ways, the upcoming election is less a referendum on Menino's record than a battle over Boston's self-image.
For a city whose residents like to think of their burg as "The Athens of America," Menino can be a confounding figure--especially to those who reside on the ever-growing-in-number gown side of Boston's long-standing town-and-gown divide. Unlike White, the ambitious liberal reformer with Williams and Harvard degrees who presided over Boston during the turbulent 1970s, Menino is a prosaic urban mechanic who not only got his B.A. from the University of Massachusetts in Boston, but did so at the age of 45. Of course, Curley, who dominated Boston's political scene for much of the first half of the twentieth century, had a similarly provincial outlook and pedigree; but what he lacked in ideological and educational distinction, he made up for in force of personality, ultimately becoming known across America as "The Rascal King." Menino, by contrast, exudes a sort of anti-charisma--even in his dapper suits, he appears lumpy--and has been saddled with the nickname "Mumbles," owing to his infamously poor locution ("dropping not just r's, but also t's, as if introducing an advanced strain of the Boston accent into the city," as Boston Magazine's Joe Keohane expertly described it).
The secret to Menino's longevity in office has been his knack for just muddling through. Parochial even by parochial Boston standards--he grew up and still lives in the white ethnic working-class neighborhood of Hyde Park--he has never aspired to any office beyond his current one. He tends to avoid doing anything that might draw significant attention--be it positive or negative. Indeed, about the only thing Menino is renowned for, besides being mayor, are his malapropisms--once referring to the city's shortage of parking spaces as "an Alcatraz around my neck" or promising to stop people from "conjugating" on Boston Common late at night. Now, as Menino seeks to make history in this history-obsessed city, the question confronting Bostonians is: Do they want this guy making it?
Of the two city council members who are running for mayor, Michael Flaherty and Sam Yoon, it's Yoon who appears to be the more formidable challenger. While the 40-year-old Flaherty has a sizable war chest and deep roots in the vote-rich Irish enclave of South Boston, he often comes across as merely a less tongue-tied version of Menino. Indeed, Flaherty was once considered Menino's chosen successor, until he evidently tired of waiting for his turn and challenged his mentor. But, if Flaherty represents a difference in degree from the current mayor, Yoon represents a difference in kind.
Born in South Korea and raised in Amish country in Pennsylvania, Yoon first came to Boston in 1993 to get his master's degree at Harvard's Kennedy School of Government. (He attended Princeton for undergrad.) After Harvard, he spent the next ten years as a community organizer in Boston before becoming the first Asian American in the city's history to run for public office. His election to the city council in 2005 prompted The Boston Globe Magazine to name him one of its people of the year, declaring: "The best thing about Sam Yoon is not just that he makes us look good. He makes us feel good."
Yoon is now hoping there are enough Bostonians looking for that sort of uplift to propel him to the mayor's office. An earnest wonk who frequently feels the need to mention that he is 39--not to emphasize his youth but to reassure people he's not still in college--Yoon is counting on minority voters and, more importantly, those who (like him) are newer arrivals to the city, lured by jobs in academia, medicine, and finance. In short, yuppies. "At a certain point, there will be more and more people here who have lived in the city for less than twenty years or less than ten years," Yoon told me one recent evening, as he sat on the patio of an upscale pizzeria in the city's hipper-than-thou South End neighborhood.
Yoon's platform seems designed to stroke these voters' erogenous zones: building educational partnerships between the city's public schools and local universities like Harvard and MIT; creating a 311 number to call for non--emergency municipal services; replacing the city's motor fleet with Zipcars; and, in general, looking to Seattle as a model for urban policy. "There is more to governing than just handshaking and ribbon-cutting and going to neighborhood barbeques," he told me. Later that evening, Yoon said to a group of supporters who'd gathered over hummus and beers at a home in a gentrifying section of the Roxbury neighborhood, "Our city needs to make a fundamental, systemic change to bring our city government into the twenty-first century, because we are really stuck, we're still operating like it's 1945."
History is not on Yoon's side: The last time a Boston mayor lost his race for reelection was in 1949, when Curley went down to defeat after spending much of his previous term in prison. What's more, Yoon begins the race in a money hole, with (as of the end of 2008) $137,000, compared with Menino's $1.4 million. But there is one number that gives Yoon hope: 192,000. That's the number of Bostonians who, spurred by the candidacies of Deval Patrick and Barack Obama, voted in the state and federal elections in 2006 and 2008 but didn't vote in Boston's two most recent municipal elections. And, when you consider that Menino was last elected in 2005 with just 64,000 votes, it's not hard to see how a big increase in voter turnout could spell trouble for him. "I do this thing at events where I say, 'How many of you voted in last year's presidential election?' Most of the hands go up," Yoon explained. "Then I say, 'Well, how many of you have paid little or no attention to the mayor's races?' It's about the same number of hands that go up. I say, 'Listen, you're going to determine the next mayor of Boston, this election is going to be yours to decide.'"
Menino, meanwhile, maintains that he welcomes the competition. In the past, he's been reluctant to engage his opponents, typically participating in only one debate, which he's then scheduled for Sunday morning or the night of a Yankees-Red Sox game. But this year, he has agreed to three debates. Sitting in his campaign office, Menino was asked to respond to Yoon's charge that he's an "incrementalist." "What does that mean?" the mayor replied. After the term was defined for him, Menino said, "I do what I think is right for Boston." In his 16 years in office, Menino has rarely not known what Bostonians want from their mayor--including when they don't want much. He was confident that he still understood--and, in fact, embodied--the true character of what he called "my city." "Now that people see I have two opponents, I've got more people coming to me and saying, 'I want to help,'" he said, as he looked out a window that afforded a view of City Hall. "I've been in the business a long time, I've never seen the reaction I've gotten this time, people coming forward saying, 'Hey, we gotta help, we're gonna keep you in office.'"
Jason Zengerle is a senior editor at The New Republic.