Odd man out
That precedent would seem to bode well for Yoon: Obama won in Boston — as did Patrick, who trounced Tom Reilly in the similarly themed 2006 gubernatorial primary. And yet, in between the Patrick and Obama elections, Flaherty easily out-polled Yoon in the 2007 City Council election.
The reasons why that race ended so differently help explain why the vast majority of Boston's political observers believe Flaherty will defeat Yoon in this year's mayoral preliminary.
Put simply, New Bostonians — including young adults, minorities, progressive professionals, recent transplants to the city, and new citizens — historically don't vote in odd-year city elections. They came out for Obama and Patrick, but stayed home for the municipal election in between. So, in 2007, the turnout plummeted in the Yoon-friendly precincts, while staying relatively strong in Flaherty areas.
In fact, the Yoon campaign estimates there are more than 135,000 people in the city who voted in either '06 or '08, but not in '05 or '07 — a figure three times the total turnout in 2007.
Observers are highly skeptical this pattern will change. Yoon's "unreliable" voters, they say, take little interest in local politics. They watch Keith Olbermann and Jon Stewart (if anything political), not Jon Keller.
Flaherty, however, has over time built a strong base of city-election voters, and a well-oiled, far-reaching field operation to get them to the polls. He is reaching out to all crowds, and recently met with seemingly Yoon-friendly organizations Drinking Liberally and JP Progressives. He even speaks passable Spanish.
Plus, Flaherty has developed an engaging humility — with jokes about failing the Massachusetts bar three times, for instance — and a directness that makes up for a distinct lack of dynamism on the stump, where he tends to speak too softly, repeat himself too frequently, and meander rather than inspire.
Relying on political machinery, municipal-labor muscle, and disillusioned progressives strikes some as antithetical to the notion of a change-and-progress campaign. But Flaherty has impressive support in every pocket of the city: there was only a single precinct in 2007 in which he received less than 10 percent of the total at-large vote.
Case in point: Flaherty figures to have an edge with the city's Republicans and conservative independents, who are relatively small in number — fewer than 17,000 voted in the 2008 GOP presidential primary — but overwhelmingly dislike Menino (thanks in no small part to Howie Carr's relentless hammering of "Mumbles"). It's tough to imagine those conservative voters, or even Menino-hating firefighters, flocking to Yoon's side, given their general distaste for progressives and for the kind of racial politics that Yoon engaged in when he formed "Team Unity" with fellow Councilors Chuck Turner, Charles Yancey, and Felix Arroyo.
Moderates and liberals are also thought to be more open to Flaherty's "bridge between old and new" approach, thanks to the post-election experiences of Obama and Patrick, who have struggled to transform Washington and Beacon Hill, respectively.
Still, the Yoon camp believes it has a few things going for its side. One is strategist James Spencer, a highly respected veteran of campaigns in Boston and throughout the country, who, insiders warn, should never be counted out. He is zeroing in on Obama supporters, building the field team around them, and intends to get 35,000 of them to vote on September 22 — a target which, if reached, should be more than enough to finish in the top two.
Yoon's volunteers may not be as experienced or numerous as Flaherty's, but they are undeniably energetic and motivated.