Can Sam Yoon win?

An Obama-loving city counselor aims to be mayor of Boston
By DAVID S. BERNSTEIN  |  February 11, 2009

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Recent elections, as you may have heard, have been about change.

Newcomer Deval Patrick beat back the candidate of Beacon Hill and City Hall, Attorney General Tom Reilly, in 2006. And while the good old boys and girls of Massachusetts backed Hillary Clinton over Barack Obama two years later, it was Obama who walked away with the nomination, and ultimately the presidency.

But before them, although on a much smaller stage, Sam Yoon turned the trick here in Boston, stunning the insiders by winning an at-large city council seat in 2005 as a virtual unknown, beating three scions of powerful political families: John Connolly, Ed Flynn, and Patricia White.

Since then, Yoon — who declared himself a candidate for mayor earlier this week — has joined the grassroots "change" coalition of progressives, minorities, college students, and young professionals who gave Patrick and Obama victories in Boston and nationally — while Mayor Tom Menino in both cases backed the establishment candidates, only to be left behind by his own city.

This recent history, of change triumphing over establishment, has not dimmed the view of political oddsmakers, who say this year's race remains Menino's to lose.

Change in Washington, or even on Beacon Hill, is abstract — decided on TV and YouTube, based on feelings and platitudes. Mayor of Boston, on the other hand, is more nuts and bolts than hope and change. It is a powerful job affecting daily lives. It is not glamorous — and neither is Menino.

And Yoon, many observers point out, is no Patrick or Obama. He is a slight man, without a commanding stump presence. Born in Korea, he has no clear claim on the African-American voters whose tallies went overwhelmingly to Patrick and Obama.

The most daunting difference: neither Patrick nor Obama faced the difficult challenge of having to unseat an incumbent, as Yoon must do — that is, assuming, as nearly everyone does, that Menino intends to run for a fifth term. Yoon also faces at least two other challengers — one of whom, his fellow councilor Michael Flaherty, received more votes than Yoon in the last two at-large council elections, and starts with more money and better political organization.

So, can Yoon catch the "change" lightning in a bottle? After discussing that question with city politicos and observers for the past several weeks, the Phoenix has compiled this list of seven things that must happen to make his bid to become Mayor Yoon a reality.

Many are beyond the candidate's control — as with Deval and Barack, Sam's success will depend as much on the moment as the man.

1) YOON MUST RAISE THE MONEY Yoon's supporters recognize that their candidate is well behind his two main rivals in the war-chest department, but argue that he can win despite having less campaign funding than his competitors because of the grassroots nature of his appeal. Perhaps, but even his top advisors realize that he can't prevail without the capital to get out his message.

That probably means he'll need at least $1.5 million — half to run the bulk of the campaign, and half for a sustained advertising presence in its final two or three weeks. Menino already has close to that amount banked, and will likely raise at least another million. Michael Flaherty has around $600,000, and a wide base of contributors.

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  Topics: Talking Politics , Deval Patrick, Deval Patrick, Malcolm Gladwell,  More more >
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