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The year of living dangerously
Michael Flaherty, Southie populist with a citywide constituency, ran afoul of city-council progressives this year and now faces an uncertain long-term future
BY ADAM REILLY


FOR THE BETTER part of a decade, Michael Flaherty was a textbook example of how young, ambitious Boston politicians should build their careers. He began his foray into electoral politics early, making two high-profile bids for office by the time he was 27. Unlike some political legacies, Flaherty — the son of 12-term state representative Michael Flaherty Sr. — dealt with early defeats by regrouping rather than quitting. After finally winning election to the Boston City Council as the fourth of four at-large candidates in 1999, he continued to strengthen his position, finishing second overall in 2001, ascending to the council presidency in 2002, and topping the at-large ticket in 2003, at the age of 34. Just as important, he stayed true to his South Boston roots without being constrained by them, casting himself as a Southie guy but consistently reaching out to different constituencies across the city — blacks, Asians, Latinos, progressives, gays. By doing so, Flaherty garnered widespread praise as a new kind of South Boston politician, one capable of transcending that neighborhood’s conservative Irish Catholic parochialism while carrying on its storied tradition of political leadership.

It was an impressive run, and it had prompted widespread talk that Flaherty could become Boston’s next mayor if and when incumbent Tom Menino chooses to vacate the post. The speculation was intensified by the fact that Menino had publicly backed Flaherty on several occasions, most notably by brokering a compromise that gave Flaherty the council presidency in 2002. But in 2003, after nine years of making all the right moves, Flaherty stumbled. He alienated the council’s minority-progressive contingent by frequently using Rule 19 — a parliamentary maneuver that allows the council president to halt discussion of issues deemed irrelevant to council business — primarily against initiatives proposed by the council’s members of color (see "Local Color," News and Features, October 17). He antagonized District Four councilor Charles Yancey — one of the council’s two African-Americans — and large segments of Boston’s black community by openly backing Yancey’s opponent, challenger Ego Ezedi, and bad-mouthing Yancey in the press. He took aim at another long-time incumbent, at-large councilor Maura Hennigan, by lending counsel and support to at-large challenger Patricia White throughout the campaign season and then, shortly before the election, endorsing at-large incumbent Felix Arroyo, who many believed would be fighting with Hennigan for the fourth at-large slot.

On November 4, the day of the final election, Flaherty’s massive, well-oiled political machine was operating at full strength. Drawing on a war chest that approached $300,000, Flaherty flexed his muscle throughout the city, deploying food trucks to feed hungry volunteers, vans with loudspeakers blaring entreaties for Election Day support, and cars to transport the elderly and the infirm to the polls. But as the results trickled in, it became evident that Flaherty’s campaign gambits had failed. Yancey and Hennigan kept their seats. Arroyo pulled in a huge vote total that rendered Flaherty’s endorsement irrelevant. Despite spending over $110,000 in the second half of October alone, Flaherty’s margin of victory over Arroyo, his closest challenger, was a relatively slim 1705 votes. (In the same period, Arroyo spent about $36,000.) Furthermore, after the election, some White supporters speculated that Flaherty’s meddling had contributed to their candidate’s defeat.

Despite these setbacks, Flaherty’s short-term position remains strong. Campaign drama aside, the council’s make-up is unchanged, and chances are good that Flaherty, who was elected council president by a 9-4 vote this year, still has enough support to be re-elected in 2004. The future is murkier, however. Ten years from now, will Flaherty remember 2003 as the time he learned some tough but necessary political lessons? Or will he look back on it as the year his steady political rise was derailed by a series of blunders?

MICHAEL FLAHERTY’S election to the city council in 1999 was a watershed moment in city politics. By finishing fourth in the at-large field, the 30-year-old newcomer ended the career of Albert "Dapper" O’Neil, the stridently reactionary 14-term councilor from Roslindale who many thought embodied the worst qualities of Boston politics. The symbolism was appealing — out with the bad and the old, in with the good and the new — and the election results suggested that this neat formulation had a factual basis. Flaherty, the open-minded, inclusive newcomer, had triumphed by appealing to the very constituencies O’Neil reviled, finishing second in the Back Bay–Beacon Hill neighborhoods, the South End, and one of the Jamaica Plain wards.

But Flaherty’s heralded triumph also carried the burden of high expectations. He was the latest leader to emerge from the neighborhood that generated luminaries like Ray Flynn, William Bulger, Joe Moakley, and John McCormack, and his accomplishments would inevitably be compared to theirs. And while his inclusive campaign style had convinced many that Flaherty represented the New Face of South Boston, he’d now have to maintain that identity while governing.

He seemed eminently qualified for the role. In 1994, three years after he graduated from Boston College, Flaherty played a key role in Ralph Martin’s campaign for Suffolk County district attorney, serving as a campaign coordinator and helping Martin garner key votes in South Boston. (Thanks largely to Flaherty’s efforts, Martin — an African-American and liberal Republican — pulled in almost 50 percent of the South Boston vote.) The Martin campaign gave Flaherty an early opportunity to build bridges with Boston’s black community, according to political consultant Joyce Ferriabough. "That’s when people really started to see him, because he would campaign with Ralph," she says. "People saw Flaherty helping Ralph Martin, who was held in very high esteem in the black community, and that’s where folks first saw him actively working for someone of color." Ferriabough adds that Flaherty’s support was key to Martin’s victory: "Frankly, Ralph probably couldn’t have won that seat without Michael Flaherty’s help."

In 1995, when Flaherty made his first run for office, his newfound visibility in the African-American community couldn’t propel him to victory. Flaherty’s bid for one of the Boston City Council’s four at-large seats looked promising after the preliminary election, in which he finished a strong fifth. In the final, though, he slipped to seventh, a drop some observers linked to African-American and liberal support for sixth-place finisher Frank Jones.

Less than a year later, Flaherty tasted defeat again. This time, though, he was rejected by his own neighborhood in a contest rife with the complexities of Southie politics. In 1995, Senate president William Bulger left his post to become president of the University of Massachusetts. Then–state representative Stephen Lynch squared off against Bulger’s son, William Jr., for the elder Bulger’s state-Senate seat. Thanks in part to support from the well-connected Flaherty family, Lynch triumphed after an acrimonious campaign, leaving Lynch’s house seat — which Michael Flaherty Sr. had occupied for more than two decades — free for the taking. The only thing standing between Flaherty and his father’s old job was Jack Hart, a 35-year-old liaison for the Central Artery Project. Flaherty was initially regarded as the front-runner. But as the campaign progressed, Hart chipped away at his opponent, emphasizing the then-27-year-old Flaherty’s youth and portraying him as a liberal, still a dirty word in some corners of Southie. Hart also drew support from Bulger loyalists still smarting over William Bulger Jr.’s defeat. In the end, Hart defeated Flaherty in the Democratic primary and waltzed into the State House after running unopposed in the final election.

A conversation Flaherty had with Congressman Joe Moakley after his second defeat helped ease the sting. "I had received a phone call from the congressman asking me to come down and to sit down and talk with him," Flaherty recalls. "I went down to Joe Moakley’s office late one night, probably at 7:30 or eight — this is when his office was in the World Trade Center. He said, ‘What are you going to do now, kid?’ — that kind of stuff. And he went on to tell me about his whole career as an elected official. He said, ‘A lot of people talk about the things I’ve been able to do, and I’ve had some successes. But no one talked about the three defeats I suffered.’ I had never known that Joe Moakley lost a race. And he proceeded to tell me, ‘Hey, it wasn’t your day — my advice is to stay out there, be active in the community, continue doing the things you’ve been doing, stay active in the civic associations, continue to coach sports. At some point you’ll have another opportunity, and you’ll be able to make the most of it.’... That clearly was helpful to me personally."

Flaherty took a hiatus from politics, first joining Martin’s staff as an assistant district attorney and later working in private practice. But he took Moakley’s words to heart, and made another bid for city council in 1999. This time, he fared better. Flaherty ran what the Boston Globe described as a "flawless campaign," emphasizing affordable-housing issues and reaching out to groups Dapper O’Neil merely sneered at. Support from Martin, who mailed out statements promising that Flaherty would be "inclusive and progressive," helped his cause; so did an endorsement from Moakley and public backing from the Menino administration. City-council candidate Greg Timilty — son of former state senator Joe Timilty, who mounted three unsuccessful mayoral runs in the 1970s — attempted to paint Flaherty as a shill for the mayor. Indeed, during one campaign forum, Flaherty was the only candidate unable to say he was receiving no assistance from Menino. But Timilty’s strategy didn’t work. When the votes were tallied, Flaherty had captured the fourth at-large slot with 15.75 percent of the vote, some 1700 votes ahead of O’Neil. (Timilty came in sixth.) It was the first defeat for an at-large incumbent since the council moved to district representation in 1983.

In his four years on the council, the Boston College High School graduate has never been fully able to shake the perception that he’s a yes man for Mayor Thomas Menino. At times, Flaherty has shown his independence: in 2001, for example, he pursued the possibility of a new Red Sox stadium on the South Boston waterfront after Menino had made clear his preference for a new park near the current Fenway site. In 2002, his first year as council president, Flaherty opposed Menino’s proposed re-implementation of rent control, drawing praise from the Boston Herald for doing so articulately and effectively. In 2003, as Menino pushed for heightened powers for the Boston Redevelopment Authority, Flaherty urged that the council and neighborhood groups be kept in the loop on development issues. That same year, he also incurred Menino’s wrath by criticizing the mayor’s temporary closing of city fire stations due to alleged abuse of sick leave by firefighters. (Menino made his displeasure clear by refusing to transfer mayoral powers to Flaherty when Menino underwent surgery to remove a cancerous growth.)

Through it all, however, the dominant impression has been that Flaherty and Menino are a tad too cozy. In 2002, for example, the mayor brokered the deal that made Flaherty council president for the first time: he convinced Flaherty not to run for the newly vacated Suffolk County district attorney’s seat, and rewarded him by successfully urging then-councilor Dan Conley, who had planned to vote for Maureen Feeney as president, to back Flaherty instead. Conley, in turn, was rewarded when Acting Governor Jane Swift appointed him interim district attorney; he proceeded to win election to the office later that same year. Conley’s council seat was then filled by Rob Consalvo, an ally of the mayor’s, who defeated Adriana Cillo in a special election. This back-room dealing — coupled with Menino’s backing of Flaherty during his first victorious campaign for council, and Flaherty’s oft-stated desire for the council to work harmoniously with the mayor — has led some critics to raise their eyebrows knowingly when, say, the Flaherty-led council approves a Menino budget with a minimum of opposition. "At a time when people seem to be concerned about the lack of independence of the council from the mayor, Michael’s close relationship to the mayor doesn’t seem to have affected him negatively," observes Menino critic and former at-large councilor Peggy Davis-Mullen.

Flaherty, for his part, is wholly unapologetic about his close relationship with Menino. "I make no apology for being his friend and he mine. I am a supporter of the mayor," Flaherty says. "But as you’ve witnessed, I’ve also demonstrated my independence. I can point to rent control and the telecom tax as two big issues he felt strongly about and wanted to pass the council, and they didn’t — and they didn’t because I didn’t believe in them.... Put it this way: I am a friend, but I’m not afraid to disagree with him."

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Issue Date: December 5 - 11, 2003
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