Man Versus Machine

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).