E-Mail This Article to a Friend Breaths of fresh air (continued)

In the coming months, one of his challenges will be to capitalize on the symbolic value of his candidacy without relying on it too heavily. Yoon seems aware that he’s about to walk a rhetorical tightrope. "I’m honored to be an Asian and to be running for the city council," he says. "The fact that I’m the first — it’s an honor and a privilege to have that. But the reason I’m pursuing the city council is because the stuff that they work on, I know. I care about the city, and I have the background and the training to do a really good job."

As the campaign intensifies, Yoon may also be hurt by his status as a relative newcomer to the city. Since graduating from Princeton University in 1992, he’s worn a number of hats: math teacher at a public school in New Jersey; project manager at several Boston-area nonprofits; grad student at Harvard’s Kennedy School of Government; and, for the last three years, director of housing at Chinatown’s Asian Community Development Corporation. But while he may be better versed on key challenges facing the city than many long-time Bostonians, he’s lived in Dorchester only since 2003. Recent arrivals may see Yoon as a kindred spirit. But some third- or fourth-generation families might view him with skepticism.

John Connolly won’t have this problem. Connolly, a 31-year-old West Roxbury resident, is just as steeped in Boston politics as Hennigan and Patricia White. His father, Michael Connolly, is a four-time secretary of state; his mother, Lynda, is chief justice of the state district court, and his uncle James Connolly topped the Boston City Council ticket back when the entire body was elected at-large. Furthermore, Connolly — who joined the law firm of Hanify & King after a stint at legal behemoth Ropes & Gray — headed Young Lawyers for John Kerry during the recent presidential campaign, and helped fundraise for Democratic gubernatorial candidate Shannon O’Brien during her 2002 campaign. All these ties should give him a ready-made fundraising base and help him assemble the sprawling campaign apparatus an at-large campaign demands.

But given the ubiquity of the "New Boston paradigm" (see "The New Bostonians," News and Features, December 10), Connolly’s background could also lead voters of color — or, for that matter, liberal white voters averse to supporting scions of Boston’s political establishment — to dismiss him as a relic of the past. This would be a mistake. Despite their different backgrounds, Connolly and Yoon actually have much in common. Both attended Ivy League schools as undergraduates: Connolly went to Harvard, Yoon to Princeton. Both worked as teachers after graduating from college: Yoon in New Jersey, and Connolly in both New York City (where he taught at a residential school for high-risk youth) and Boston (at the Boston Renaissance Charter School). Despite door-opening educational credentials, both are seeking to dedicate themselves to city government rather than maximizing their earnings in the private sector. And, finally, each now must make the vague notion of a New Boston work to his advantage. "The benefit is that I was raised to believe in the nobility of public service," Connolly says, when asked if his family background will be a liability. "I think the challenge is to get people to learn about the public service I’ve done — principally my teaching in urban schools, my work for a variety of Democrats, and my commitment to my community and the city — and to see that that translates into active work, far more than just relying on my name."

White and O’Malley face similar challenges. The latter’s task may be easier; as Cabral’s campaign manager, O’Malley had plenty of opportunities to forge connections with the various constituencies (voters of color, women, gays and lesbians) who propelled her to victory. "I’ve seen Matt with Cabral’s supporters," says one City Hall insider. "He’s treated like a star." But it’s hard to say whether Cabral’s supporters — many of whom became active in politics for the first time during her campaign — will shift this adulation, derived from his work for Cabral, to O’Malley the candidate. For her part, White is already planning a major shift in strategy in response to recent changes in Boston’s political landscape. Two years ago, White’s campaign literature relied heavily on images of her father, former mayor Kevin White, who served from 1968 to 1983 and holds a place of honor in Boston’s political pantheon (see "Running Start," News and Features, September 12, 2003). This time around, Patricia White promises, Kevin White’s image won’t be appearing on her palm cards or direct mailings. In addition, White seems to have learned from a wince-inducing misstep last fall, in which she was quoted — in a Globe story following up on Cabral’s victory — as stating: "I represent the future of Boston." In a recent interview with the Phoenix, White addressed the question of her place in contemporary Boston with considerably more finesse. "I think that people know there is a New Boston — they see the vibrancy of the city, they see the city growing, they see the new people coming in," White says. "They know there’s a New Boston — they can feel it — but we’re still trying to figure out what that New Boston is. I think New Boston is inclusion, New Boston is meritocracy, New Boston is where people run for office and they can win regardless of race or gender or religion."

THE UPCOMING at-large contest may highlight Boston’s shifting conception of itself, but it also demonstrates the power of inertia. Women are underrepresented on the council — currently made up of Hennigan, District Three councilor Maureen Feeney, and 11 men — and three of the four declared at-large challengers are male. And, once again, it seems the at-large field will lack an African-American candidate. (The last black candidate elected at large was Bruce Bolling, in 1981.)

Even so, the race should be fascinating. A host of unanswered questions could decide the outcome: will Flaherty aid Yoon as a way of cultivating support among Boston’s Asian communities? Does Yoon’s candidacy help or hurt Arroyo? Will Patricia White’s political career take flight or grind to a halt? If Murphy and Hennigan both yield their seats, will someone unexpected — like District Six councilor John Tobin or Charlotte Golar Richie, Menino’s director of neighborhood development — enter the fray to build his or her own mayoral credentials? Anything could happen between now and November, and much could change. But judging from the early signs, Boston’s 2005 election will be one worth watching.

Adam Reilly can be reached at areilly[a]phx.com