Man Versus Machine

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.

  • 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. http://www.samyoon.com/media/news/1784

  • 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.