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.
“Whoever emerges the victor against Menino in the preliminary has a strong chance in the final,” he said.
Political pundits have pointed out several signs of vulnerability in Menino’s organization. While he mobilized his political machine in support of former Attorney General Thomas F. Reilly in the 2006 gubernatorial race, the city’s vote went to Deval Patrick. Last year, Menino lost again when the city cast its presidential support behind Barack Obama over Hillary Clinton, the mayor’s pick.
To win the race, Yoon will have to raise between $1 million and $1.5 million, Spencer said. He currently has $209,000 and $160,000 in pledges from last month’s fundraising.
One factor that could work against Yoon is turnout — or rather, the lack of it. The communities that comprise his supposed base of black, Latino and Asian voters have historically tended to have lower turnout in preliminary elections than the white, conservative communities on which Menino and Flaherty will be depending.
And there’s no guarantee that black voters, who have supported Menino in past elections, will choose Yoon over the incumbent.
Political organizer Mukiya Baker Gomez said Yoon’s association with other minority members of the City Council’s “Team Unity” bloc and his record of support for issues favored by black voters could help him.
He backed City Councilor Charles C. Yancey’s bid for a new library in Mattapan, has been a vocal advocate for reform of the state’s Criminal Offender Record Information law and supported youth activists who came to City Hall to advocate for more funding for youth programs, even as his colleagues had the youths forcibly ejected from the council chamber.
“Sam has done a number of things with Team Unity that directly impacted the black community,” Baker Gomez said. “The question is what’s his vision for the city and what role will the communities of color play in that vision.”
Yoon recalled the 2006 City Council meeting where more than 300 teenagers were escorted out of the chamber as a telling moment. The hearing came as the council were debating the city’s annual budget — the one vote where councilors have the power to veto the mayor’s will.
Yoon said he has worked to make the city’s budget process more transparent, holding hearings across the city and polling residents on his 20,000-name e-mail list.
But in the end, he said, the strong-mayor system undermines meaningful community participation.
“The power we have is an illusion,” said Yoon, who along with other members of Team Unity has consistently voted against the mayor’s budget. “The mayor meets individually with all city councilors and says, ‘What do you need?’ He always gets the seven votes he needs to pass the budget.”
Yoon said his years on the City Council have convinced him he can only make a meaningful change in the city from the executive office.
“Sixteen years is a long time for anyone to be mayor,” he said. “It’s time for a new approach. It’s time for new ideas.
“We need to have this conversation now. Especially now, given the bleak economic future we’re looking at; especially now, when we will have the most competitive mayoral race in 25 years. It’s like a perfect storm.”