Yoon looking to beat odds in mayor’s race

Yawu Miller | 2/25/2009, 3:51 a.m.

Sam Yoon surprised political pundits in 2005 when he emerged victorious from a packed field of political insiders to grab one of the four at-large seats on Boston’s City Council, beating out two children of former mayors in the process.

Now, mid­way through his second term on the council, Yoon is seeking to once again defy the conventional wisdom about what’s politically possible in Boston — this time, with a bid for the mayor’s seat. And while he hasn’t officially announced plans to run for a fifth term in office, there’s no indication that sitting Mayor Thomas M. Menino is ready to end his 16-year hold on City Hall.

Yoon recently joined fellow at-large Councilor Michael Flaherty and South End developer Kevin McCrea in what is now seen as a four-way race for mayor, though Menino has yet to declare his status. The top-two vote-getters in September’s preliminary municipal election will face off against each other in the November final election.

Yoon said the inspiration for his mayoral run comes from his desire to challenge the political culture in Boston.

“Boston has a lot of potential to be a truly great city,” he said. “What’s holding us back is the old ways of doing business. It’s our politics. In this city, those who are in power have a huge advantage in terms of staying in power.”

You don’t need a degree in political science to see the truth in Yoon’s critique. Not when the last time an incumbent mayor was voted out of office was 1949, when James Michael Curley was ousted after serving part of his last term in jail.

Yoon attributed much of the difficulty in defeating an incumbent to the city’s strong-mayor system, where virtually all decision-making powers rest with one person.

“It gives a 16-year-incumbent who has a pay-to-play fundraising operation a massive advantage,” Yoon said. “We don’t have term limits in Boston. I think we need to start thinking about whether that makes sense for our city.”

From the picture that Yoon paints, taking on an incumbent mayor in Boston seems, at best, a daunting proposition with long-shot odds. Yoon has hired veteran Boston campaign strategist Jim Spencer as a general consultant, nationally recognized consultant Jim Trippi to run his media operation and Massachusetts pollster Tom Kiley to crunch numbers.

The polls, Yoon said, are encouraging.

“We have good survey research that tells us there is a path to victory for us,” he said.

“It’s going to be tough for a single challenger,” Spencer added. “But with multiple fronts, it changes the dynamic.”

Spencer said Flaherty provides a strong challenge to Menino in West Roxbury and South Boston, two predominantly Irish American neighborhoods where the former City Council president has enjoyed his strongest support.

In contrast, “Sam’s base has traditionally been in communities of color and progressive white communities like Jamaica Plain and Back Bay,” Spencer said. “And he’s popular with senior citizens.”

According to Spencer, Yoon would have to make a strong showing in the preliminary balloting with those communities.