Yoon or Flaherty

Who will win the chance to challenge Menino?
By DAVID S. BERNSTEIN  |  August 20, 2009

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Boston voters will go to the polls in less than seven weeks to choose two candidates, out of the four now running, to face off against each other in November's mayoral election.

A statistician will tell you this preliminary round of voting can yield 24 possible outcomes. Anyone with an ounce of political savvy, however, will say that barring an earth-shattering electoral upset, Mayor Thomas Menino will come out on top and businessman and political maverick Kevin McCrea will finish last.

The Obama-Clinton Effect
Sam Yoon and Michael Flaherty have faced each other twice before — in at-large City Council elections, for which Bostonians could select both of them among their four votes. For a true head-to-head comparison, perhaps the 2008 presidential primary between Barack Obama and Hillary Clinton can serve as a surrogate. At least, Yoon might hope so: Obama bested Clinton here by 10,000 votes.

According to a Phoenix analysis of Boston election data, in 2007 Yoon received more votes than Flaherty in 90 percent of city precincts where Obama won a year later. Flaherty won 88 percent of precincts carried by Clinton.

The same pattern held for the 2006 gubernatorial primary, with Deval Patrick winning more than half the vote (in a three-way race against Tom Reilly and Chris Gabrieli) in almost all the precincts where Yoon topped Flaherty.

Yoon would be thrilled to repeat Obama and Patrick's success. But the same data reveals the reason why, in their own races, Flaherty has topped Yoon with room to spare. Turnout in the Obama-Yoon precincts declined far more — to less than a third, in many cases — than did the Clinton-Flaherty precincts for the 2007 city election. In Boston, Clinton voters are more likely than Obama voters to show up when local offices are on the line.

All eyes are therefore on City Councilors Michael Flaherty and Sam Yoon as they vie for the chance to unseat Menino, who with 16 years as Boston's political chief under his belt is the city's longest-serving mayor.

The final election may shape up to be the most serious challenge the incumbent has faced since winning election in 1993. But so far, at least, the race has been a sedate affair. Yoon and Flaherty focus their fire on Menino. They rarely take aim at each other: not on the stump, not in their literature, and not in interviews.

There are reasons for that, the primary one being that whoever survives the preliminary will need the others' voters in the general election. But that may be a difficult task since Flaherty and Yoon are chasing different types of voters for the September 22 contest. Flaherty is targeting the more traditional and reliable set that prefers him to Menino. Yoon, meanwhile, is after those elusive "New Boston" voters who turned out in droves for Barack Obama and Deval Patrick's elections, but who rarely show up for municipal contests.

Perhaps as the preliminary approaches the two will train their cannon fire on one another. But for now, their détente makes it difficult for a voter to decide which would be the more potent opponent in November.

Change vs. change
Flaherty and Yoon have much in common. They are only months apart in age, with the former recently turning 40 and the latter joining him in January. They hold the same job and similar progressive positions on major issues. On the stump, they criticize Menino for a similar litany of woes: lack of transparency; closed or rigged processes, particularly in city development; avoidance of responsibility; slow adoption of technology; and tolerance of mere adequacy, particularly in the city's schools.

There are differences, to be sure. Flaherty wants to reform the Boston Redevelopment Authority, while Yoon wants to shut it down. Flaherty has a more aggressive and comprehensive plan for reforming public schools. Yoon takes a harder line on reforming the police and fire departments (whose unions are major supporters of Flaherty).

More generally, Flaherty was born and raised in Southie — he's a Boston College and BC High double-Eagle with a Boston University law degree — which often gives his discussions of the city some depth. Yoon is a relative newcomer to Boston — not only born in South Korea but educated at Princeton before coming to Boston via Harvard's Kennedy School of Government — which makes it more compelling when he tells audiences that "we can't wait four more years" to put Boston on a new track.

But the real contrast in their rhetoric, and probably in fact, is similar to that which emerged between Obama and Hillary Clinton during their epic primary struggle. They, like Flaherty and Yoon, were striving to be the "change candidate" for primary voters who wanted to flush every trace of George W. Bush from the White House.

Obama embodied that spirit as an outsider, both in terms of race and political experience. Clinton, saddled with obvious "insider" experience, countered that she combined the desire for a new direction with the political skill and experience to make it happen.

Flaherty — a five-term councilor and son of an Irish Boston pol — is making the same argument when he frequently describes himself as a "bridge between old and new Boston."

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