Man Versus Machine

City councilor Michael Flaherty is young and full of ideas? But can he topple Menino?

Illustration by Daniel Adel

Illustration by Daniel Adel

At a Roxbury Senior Care event at the Charles Street AME church on a rainy day in June, 40-year-old mayoral candidate Michael Flaherty finds himself suddenly embroiled in competition. On one side is Sam Yoon, a fellow at-large city councilor who is also running for mayor, dressed like a prep schooler in blue blazer and khakis. On the other is Angela Menino, wife of the current boss, who eyes Flaherty warily. Straight ahead is a free buffet. The buffet is the mayor of this room. After a few words from the event’s organizers, the attendees, clad in Sunday best complete with fantastical hats, go for it. The politicians stand off to the side of the great rush, working the crowd. “He’s our guy, right there,” says one woman, pointing to Flaherty. “It’s time for some young stuff.” Another asks Flaherty who else is running. “Does it matter?” he says, grinning. Still another tells me, “I know it’s time for Mayor Menino to…” and makes a shoo-shoo motion.

Michael Flaherty is finally running for mayor, and the path before him is littered with carrion. Peggy Davis-Mullen and Maura Hennigan, both longtime city councilors, mounted campaigns against Tom Menino in the past two elections—and were effortlessly crushed by the mayor’s machine. The Southie-based Flaherty, on the other hand, represents the first real challenge Menino has faced in 16 years. Compared with past opponents, he’s got more money, a higher citywide profile, a pro-grade platform, substantial union support, and, more important, he really wants it. “You’ve got to give the son of a bitch his due,” says one local politico, who requested anonymity because he wants to stay on good terms with both Flaherty and Menino. “If he loses, at least he loses a job he really wanted to run for.”

But it will be a fight, and not only because Flaherty is up against the most enduring machine boss the city has ever seen. The key question is whether an Irish guy from Southie, the son of a pol, carrying the endorsement of the ignominious firefighters union, can convince a generation of voters weaned on Patrick and Obama that he is the new face of Boston. If he fails to do that, he loses, and the doctrine of mayoral infallibility lives on. But if he succeeds, he can do something once thought impossible. He can actually win.


Flaherty is sitting in a deli in Eastie’s Maverick Square, eating a sub. He had spent a couple of minutes chatting with an African-American resident while waiting in line for his lunch. The guy was in his thirties, carrying his young son. After Flaherty sits down to eat, the guy comes back over. “Okay,” he says, “tell me why you want to be mayor.” Flaherty leans over and taps the kid in the belly. “Right there,” he says. “You got my vote,” the guy says. Politics.

Shaking hands and kissing, or at least poking, babies is in Flaherty’s blood: His father is longtime Southie state legislator and judge Michael Flaherty Sr. After graduating from BU Law, the younger Flaherty took a job as assistant district attorney in the courthouse up the street from that Eastie deli, before moving on to prosecute youth violence cases in Roxbury. His frustration with the system inspired him to run for office, and after one failed bid, he ran a brilliant campaign for at-large in 1999. This was a blow for the new Boston, as he ousted old-school Southie powerhouse Dapper O’Neil (who, depending on where you live, was either a colorful scrapper or a racist vulgarian).

On the council, Flaherty quickly built a good relationship with Menino, who in 2002 engineered a deal that elevated the 32-year-old to council president. Flaherty frequently endorsed female and minority candidates, helping to efface the Southie stigma with progressives, but also fast developed a reputation as something of an autocrat as president. He was slapped down by a judge for repeatedly violating the state’s open meetings law (fellow mayoral candidate Kevin McCrea actually sued him for it), turning off the good-government types. He frequently invoked a parliamentary rule that allowed him to silence debate on issues he deemed immaterial to council business—like, for example, the Iraq war, which caused him problems among the city’s older lefty circles.

Despite that, Flaherty continued to grow his stature, and was widely seen as the heir to the throne. But Menino never stepped down, while Flaherty kept raising money and appearing in the papers. In 2005 he won 50,000 votes as a councilor, just 14,000 fewer than Menino got as mayor, and that was pretty much that. Menino put his weight behind Councilor Maureen Feeney for president in 2006 and knocked Flaherty back into the scrum. Ever since, Flaherty—the biggest vote-getter on the council for the past three elections—has been increasingly critical of Menino, never more so than during his successful campaign to kill the mayor’s plan to move City Hall to the waterfront. “It’s not personal,” Flaherty says, mainly because everyone seems to think it is. “I like the mayor. He’s done some good things. But good isn’t good enough.”

It’s a nice line, but also one that perfectly encapsulates the central challenges facing Flaherty’s bid. For one, he’s forced to acknowledge that Menino has done a “good” job. He can’t run an angry campaign, because people aren’t angry with the mayor. A few may be, but for the most part those outside the mayor’s base are either bored or don’t really care one way or the other, and attracting them will require tremendous finesse. How do you convert boredom into action without vilifying your opponent?

Moreover, how do you do it when you can’t play identity or ethnic politics? In order to win, Flaherty has to capture thousands of new, younger voters historically allergic to city politics. But the cool rhetoric of “good isn’t good enough” is hardly the stuff that will inspire them to turn out. This is doubly true when the genuinely progressive message is coming from an Irish guy from South Boston. It’s unfair, especially given Flaherty’s progressive record and vocal early support for marriage equality (two of his chiefs of staff have been openly gay), but even today Southie politics is still very much viewed in far-left circles as the province of guys like the Dap.

Altering that perception is critical. A Globe poll from late spring suggested that Flaherty and Yoon combined would make it a close race to beat Menino. The paper took that as a sign that Menino was sailing through this challenge; for others, it showed that, early in the race, a sizable percentage of people were already open to voting for someone else. The best-case scenario for Flaherty is that Yoon, despite having energized a respectable number of new voters, loses in the preliminary. Flaherty then morphs from an uninteresting Southie guy into a viable progressive choice, and those Yoon votes go over to him, perhaps even encouraged by Yoon, who maintains a good relationship with Flaherty. Add those votes to Flaherty’s solid base and whatever he’s able to take away from Menino, and that might be the ball game.


Because Flaherty isn’t exactly a man of sweeping oratorical prowess, the hook is vision. Namely, offer a grand one, and try not to get too disheartened when the mayor starts cherry-picking your initiatives. So far, Menino has poached readily from the Flaherty campaign, raising the cap on charters after years of resistance, implementing single-stream recycling after years of resistance, and introducing e-mapping technology so residents can track crime in their neighborhoods in real time, after years of resistance.

Provided Flaherty’s platform hasn’t been completely stripped of planks come the election, his vision of post-Mumbles Boston goes like this: Federal stimulus money will be combined with the city’s summer jobs program to help at-risk kids develop green skills that they can use in the future economy. The hated City Hall Plaza will be ripped up and replaced with grass and trees. The city will arrange cheap trash pickup for local restaurants, whose food waste will be composted for use in city parks. The firefighters will agree to mandatory drug testing, and not in exchange for a pay raise (Flaherty says he’s already gotten them to agree to it in exchange for long-overdue equipment upgrades). The city’s principals will be empowered to tailor their approach to education to the needs of their individual schools, with the same going for police district captains. This decentralization of power will foster a thriving marketplace of ideas.

Moreover, the Internet—long viewed warily by the Menino administration—will be summoned to satisfy all manner of goo-goo fantasies, from tracking the progress on a pothole, to monitoring the performance of individual city departments, to accessing a comprehensive list of city vendors (Flaherty swears he’s learned his lesson from that open meetings business). All in real time. He even says he’ll agree to term limits if the city council so wills it. And did we mention finally installing a voice-mail system at City Hall, as if the year 1997 had finally arrived? It’s all downright utopian.

In consciously raising people’s expectations of government, a politician is usually asking for trouble (hi, Governor), particularly in this case, where good-to-better is considerably more difficult than dismal-to-good. But after 16 years of all power and ideas radiating from a single room in City Hall, it’s an undeniably compelling vision. And a surprisingly practical one: Many of these initiatives are already in place in more-progressive cities. “This administration has always masterfully lowered people’s expectations,” Flaherty says. “So as Bostonians you come to expect filthy streets and underperforming schools. You’re almost immune to it.” He thinks he can attract those younger voters, and pick off enough traditional voters in the neighborhoods fed up with the status quo to carry it.

Whether he will succeed remains to be seen: It’s a long way from here to November. But the mere attempt has single-handedly reinvigorated a local political scene that’s been half-dead for what seems like ages. That alone makes his run worthwhile. “Boston needs an infusion of new energy and passion,” Flaherty says. “I’ll give this city the race it hasn’t had in 16 years.”