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).


  • Frank

    It's easy to tell that Boston magazine now has its roots in the mid-west. How is it that Flaherty will appeal to the young voters you talk about. He has ignored them for years. How about when he threw a couple hundred kids out of city hall? Sam Yoon is the only candidate who can – and is – appealing to these voters. Why not read an article by someone who lives in Boston – and know politics! Here's the link.

  • Brad

    Sorry Frank, I really like Sam and think he is a good person. However, he thought that his campaign was going to miraculously arise out of the progressive sand and its hasn't. Words about change are good, but one needs to really build a grassroots campaign and the only one I have seen do that is Michael Flaherty.

  • Will

    Brad is totally off the mark on this one…Flaherty has paid insiders in each community but not base of disaffected voters. Flaherty is more of an insider than he is an outsider. He's burned through a lot of his cash on trivial things. I can't walk 10 feet without stepping over a piece of Flaherty lit on the ground, unread. Sam Yoon is the real candidate for change in this race.

  • Anonymous

    Brad, have you really not seen the grassroots campaign that Yoon has been building? It seems far more prominent to me than Flaherty's grassroots base… in fact, Flaherty hardly seems to have that grassroots campaign going at all. Honestly, he seems like just another politician to me, whereas Yoon doesn't. I feel like Sam is so different from the Flaherty / Menino typical politician types, and it's that difference that makes him seem, at least to me, like the only candidate who can really bring change to Boston.

  • barbara

    Michael Flaherty is the reason this discussion is going on and if it weren't for his tireless efforts to bring forward change for the children and the community this debate wouldn't be going on. Sam Yoon may be a good person but has he put himself out there for public debate and ridicule? Has he opened up his life to ridicule or is he hoping to stay in the shadows and then jump in? Hat's off to Michael Flaherty!

  • Sadie

    Flaherty is running a campaign for thugs. Nothing fresh about that. Anyone miss him at the shark-slashing tournament last weekend? Guess he was too busy ripping down signs to keep up the olde tradition.

  • Zach

    In what bizarro universe is Flaherty the young and hip candidate? He's as much of an institutional figurehead as Mayor Menino, and a less successful politician at that. Stick to the thuggery and intimidation, and leave the actual campaigning to the respectable candidates.

  • Tom

    So the fact that Flaherty has volunteers going to neighbors house with literature is not proof of a grassroots campaign? Top vote getter in the city the last three city elections including getting over 50k votes in 2005? Interesting analysis. I love the Sam Yoon astroturf campaign being run. Every comment is the same. XXXXX sucks. Sam Yoon is change. Three people from Cambridge with 30 user names.

  • Griselda

    People are not bored with Menino, they are content. Many, in fact, are excited about what he has done and for his plans for the future! Flaherty's campaign is almost identical to the Mayor's – so why not let the experienced man take the lead and send the so-called "young" Flaherty packing. Menino's got things under control. He's the one who has made Boston the third greenest city in the USA…on a smaller scale, many Boston residents also praise the simple details that Menino pays attention like removing snow from their driveways.

  • Brian

    I really can't stand this good/better thing. Ready Flaherty's platform. It's every idea the Mayor has had…but whenever there's a number, he makes it bigger. I don't think an orignial thought has passed through Flaherty's head.

  • Brian

    I really can't stand this good/better thing. Ready Flaherty's platform. It's every idea the Mayor has had…but whenever there's a number, he makes it bigger. I don't think an original thought has passed through Flaherty's head.

  • Brian

    I really can't stand this good/better thing. Read Flaherty's platform. It's every idea the Mayor has had…but whenever there's a number, he makes it bigger. I don't think an original thought has passed through Flaherty's head.

  • Paul

    I've read all the anti Michael Flaherty comments. However, I'm not convinced that most of you know what you are talking about. As a volunteer worker for Michael I can personally tell you that Michael has been constantly telling us to "keep it clean" and "stay above the frey"! Although I don't care for being called a "thug" who supports Michael Flaherty I will take the high road and let you people be the "thugs" tossing all the bombs and insults. Sam Yoon has a long way to go before he'll be able to run a City like Boston. I would suggest that Sam start actually going to the Council Meetings and learn City Government. May the best Man win!

  • Ed

    Michael Flaherty is the right blend of Ray Flynn type, walking the neighborhoods campaigner, he's street smart, a solid family man and someone who is very much aware of the procedural disciplines necessary to run city government. This race is a little like comparing Wii to Atari Pong, the Mayor is going to be overturned before he realizes it's too late. Michael your time is now. Someone in the big office is hearing footsteps!

  • Ed

    I think Menino is underestimating Flaherty. Yoon is a good candidate but he is too young. I agree with the article and his supporters will go to Flaherty. McCrae is too much of an outsider and after Deval Patrick campaign of change, I don't think that is going to fly. When I drive thru the streets of Dorchester, I see Flahery signs and bumper stickers. I don't see Yoon signs or McCrae signs. I don't see Menino signs. I see Flaherty signs and I see bumper stickers everywhere. Some might claim that doesn't mean anything and it is only in one part of the city. I disagree. Menino owned this city for 16 yrears and now he doesn't.

  • Duncan

    I just love how Menino shows up to an event and leaves right after it begins or even before it officially starts. Flaherty and Yoon not only spend time meeting people at events but they actually listen. It would be nice to see a mayor in office that actually cares about the people instead of just themselves and their power.