Can Sam Yoon win?

By DAVID S. BERNSTEIN  |  February 11, 2009

Yoon has never raised anything close to that amount, and due to Massachusetts campaign-finance law, he cannot rely on a small group of wealthy benefactors. Individual donations are capped at a mere $500.

So he'll have to hope that his campaign catches fire, whereupon Yoon might find himself flooded with small-dollar progressive contributors. (That hasn't happened yet: a December push for online donations yielded little from that crowd.)

To spark his candidacy, he hopes to first tap into a national network of Asian-Americans, who may be eager to help elect the first Asian-American mayor of a major US city (and indeed one of the few major Asian-American politicians in any office). Yoon built up contacts during the Obama campaign, which sent him around the country to raise money from Asian-American communities in big cities. A "2009" drive will seek to get $500 contributions from 2009 Asian-Americans, according to a source close to the Yoon campaign — an effort that, if successful, would yield a cool million.

But that potential brings political peril: Yoon's opponents are wasting no time, and have already accused those donors of trying to buy the election from outside the state. Fair or not, attention on that source of funding could paint Yoon as a niche, racial candidate — the polar opposite of the post-racial image Patrick and Obama symbolize, one which Yoon wants to exploit.

2) HIS OPPONENTS MUST DRAG EACH OTHER INTO THE MUD To defeat Menino, a challenger must drive down the mayor's sky-high favorability — which, according to polls, currently finds nearly three-quarters of Boston residents satisfied with their current leader. For Yoon to stand a chance, someone will have to start throwing haymakers.

Some local observers speculate that if Menino is forced into a real, down-in-the-dirt public campaign, things could go very badly for him. The mayor is not only considered a poor public speaker, he is notoriously thin-skinned — a trait made worse the longer he has been shielded from criticism. His insistence that things are going well sometimes makes him seem out of touch — particularly when defending clear missteps by the city, such as when he blamed college students and bar owners, rather than Boston police, after the fatal 2004 shooting of Victoria Snelgrove.

At least one political veteran thinks the odds are good that Menino could, under months of constant criticism, let loose with a public display of anger, petulance, or disdain — which could become his "macaca moment," played endlessly on news outlets and YouTube, and demolishing his standing.

But then again, launching a harsh attack on a personally popular figure like Menino is a sure way to harm one's own image.

Yoon's savior, then, ironically, may be his City Council rival Flaherty, whose campaign strategy almost certainly includes plans for sustained, aggressive assaults on Menino. If effective, those attacks could leave voters looking for an alternative to both the attacker and his quarry — and finding Yoon standing above the fray, preaching his positive vision of the city's future.

As one local operative says, it's politics 101: A attacks B, and C wins the election.

But Yoon will still need to get his hands dirty, and engage in Menino-bashing, most locals agree. The criticisms of the current administration are more likely to take hold if they come from multiple voices. Also, by taking a few jabs himself, Yoon can demonstrate his own toughness, and prove his mettle for a job that all agree requires serious political-combat skills.

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