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Last Tuesday, Boston city councilor Michael Flaherty was schmoozing the adoring hometown crowd at South Boston’s National Night Out celebration, a neighborhood party recognizing crime-prevention efforts. There was the couple who went to South Boston High with Flaherty’s father, who would later go on to become a 12-term state representative. And the woman who lived in the same apartment complex as Flaherty’s wife’s grandmother. Countless people asked for reports about his infant twins, born earlier this summer. The at-large councilor chatted amiably, calling out to friends in " Richie, what’s going on?!? " style — a loyal son of Catholic, conservative Southie.

But the next day, on the council floor, Flaherty spearheaded the successful vote on a resolution urging the state legislature to enact domestic-partnership benefits. It was a striking move, but one in character for the 32-year-old Flaherty, who has built his political reputation on the premise that being liberal and being from Southie aren’t mutually exclusive.

Not that Flaherty is the first to combine those attributes. During the mid 1990s, at-large councilor Peggy Davis-Mullen, another Southie native, reached out to citywide progressives, capping these efforts with her courageous 1996 vote in favor of domestic-partnership benefits. (Those benefits were approved, but were later thrown out by the state’s Supreme Judicial Court as an unconstitutional usurpation of state authority — hence the current appeal to the state legislature.) It was a risky move back then, and Davis-Mullen (who moved to West Roxbury last year and is now running for mayor) faced criticism in the neighborhood. But it paved the way for Flaherty, who is now perfecting the model.

Says South End gay activist Mark Merante, " He’s very much of South Boston, but recognizes that he represents the whole city and really has done very effective and aggressive and heartfelt outreach. It’s really paid off for him. " And Southie is changing, too — enough so that its district councilor, Jimmy Kelly, a social conservative who is perhaps the neighborhood’s most powerful elected official, sent signals on the council floor last week that he, too, might support domestic-partnership benefits in the future. Never mind that his comments immediately preceded his latest negative vote (see " Surprise Vote, " posted last Thursday, August 9, on bostonphoenix.com).

But in the coming months, Flaherty may be forced from the middle ground he’s so carefully cultivated. After all, the South Boston waterfront is home to some of the most dramatic, and controversial, development proposals in the city. One contentious issue Flaherty has been willing to step out on — albeit cautiously — is the proposed new stadium for the Red Sox. While seven city councilors took the lead last year in opposing Mayor Menino’s plan for a new park in the Fenway, Flaherty hung back — and still hasn’t ruled out supporting it, he notes. But he recently wrote an op-ed piece for the Boston Globe about the possibility of building a park along the waterfront, a move that downtown lawyer and former city councilor Larry DiCara calls " courageous. " Flaherty is clear, however, that he intends to follow the community rather than lead it on this matter. " To this point, I’m willing to raise the issue and call for a thorough review, " he says. " I’ve yet to endorse this proposal, and will not until I see significant support from the South Boston community. "

Another issue that could put Flaherty in a bind is the infamous Southie linkage deal. In 1998 — before Flaherty joined the council, he takes pains to note — Kelly and a number of other South Boston elected officials negotiated a lucrative agreement for the neighborhood. Southie, in return for the disruption that would be created by construction along the waterfront, would receive 51 percent of the " linkage benefits " the city extracts from developers — far higher than the 10 percent to 20 percent that affected communities usually receive in such agreements. When the deal came under fire last year, Menino reneged — prompting outrage from South Boston and a lawsuit from Kelly. Some citywide councilors, such as Stephen Murphy of Hyde Park, publicly criticized the deal. But Flaherty — an at-large councilor whose base is in Southie — has remained extremely careful.

" All along I felt there should be a citywide distribution " of linkage benefits, he says. " But the directly impacted community of South Boston should get a share that’s proportionate with the share of disruption they’d have to endure. No neighborhood should benefit more than the directly impacted community of South Boston. " He refuses to say what an appropriate share would be, however. " To put a specific percentage? I probably wouldn’t want to do that, " he says.

Flaherty — an ambitious pol who first ran for the council in 1995, at age 26 — is eventually hoping to parlay his skills into higher office. He insists that he’s concentrating fully on his re-election bid this fall, considered a lock by local political observers. Former at-large councilor John Nucci, now the Suffolk County court clerk, praises Flaherty’s " citywide organization and strong Southie base, " as well as his progressive appeal. Adds DiCara, " I don’t think there’s a person out there who questions whether he’ll be re-elected. It’s a given. "

Be that as it may, the Suffolk County district attorney’s office is an alluring prospect. In May, current DA Ralph Martin — for whom Flaherty worked as a South Boston campaign field director in 1994, and as an assistant DA from 1995 to 1998 — announced that he won’t be running for re-election next fall. Flaherty was almost immediately viewed as a front-runner. He plans to decide on entering the race after the November 6 council election. " I’m going to look at the numbers across the city, " he says. " It’s a job I’m interested in, a job I thoroughly enjoyed as assistant DA. "

But if either the linkage deal or the Red Sox issue heats up again, Flaherty could be forced to take an uncomfortable stand. Though so far he’s succeeded in being a Southie progressive, conflicts like the linkage deal — which pit South Boston against the rest of the city — make it clear that Flaherty will eventually have to choose sides. If he makes his decisions with enough political savvy, he could be on the fast track to higher office. But in a city known for its contentious political battles, it won’t be easy.

Issue Date: August 16 - 23, 2001