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.