Yoon or Flaherty

By DAVID S. BERNSTEIN  |  August 20, 2009

That effort may get a boost from a nonpartisan effort, taking place through a coalition of community groups in the city. They are targeting voter-education efforts to a list of 55,000 Bostonians who voted for the first time last November (and who have never before voted in a Boston city election). Although this coalition won't be promoting one candidate over another, the list is heavy with young adults, new citizens, and recent Boston transplants — all likely Yoon voters.

Yoon himself has improved as a candidate, too. Once a skinny wonk lost in his suit, he now rolls up his sleeves and loosens his collar, and speaks engagingly and with humor and animation.

Ride the lightning
Flaherty has done a fine job promoting the notion that Boston needs to make a major systems upgrade from the once-useful but now-obsolete model installed back in 1993, say neutral observers. Particularly effective was Flaherty's "Good — Better" ad campaign, which compared the Menino-Flaherty choice with old and new pairings, like a Walkman and an iPod.

But, those observers caution, his hard work and money may in the end serve as advertising for Yoon.

After all, Flaherty — with his prematurely gray hair and his undeniable similarity to Irish-heritage pols like District Attorney Dan Conley of West Roxbury and State Senator Jack Hart of Dorchester — looks almost equally outdated next to Yoon. As one veteran political consultant puts it, one "change candidate" looks like New Boston and one looks like James Michael Curley.

Of course, none of that will matter if voters don't pay enough attention to Yoon to make that comparison. His fundraising has not gone well, which has hurt his visibility. He has spent little of his meager funds over the spring and summer, doing no significant advertising or mailings, and paying only a handful of staffers — and still his campaign heads into August with only about $200,000 in the bank. Yoon says he will spend every penny in the stretch run to the preliminary — gladly starting at zero on September 23.

Flaherty has closer to $500,000, even after outspending Yoon all year. But he might try to hold much of that in reserve, say local politicos, because his core supporters have already given the maximum and he would have a tougher time replenishing for the general-election campaign — when he'll be facing Menino, who has $1.5 million on hand after already spending more than $800,000 this year.

In that difference lies one important piece of this Flaherty-Yoon clash. Flaherty has a steady appeal, but little chance of catching Patrick/Obama-type lightning. Yoon demonstrated that quality in his out-of-nowhere 2005 citywide victory, and could do it against Menino — particularly if Yoon captures the imagination of the city's racial minorities, which have been Menino's safety net. A Boston-based political consultant harkens back to how Southern black voters, thought to have been in Clinton's pocket, seemed to switch their allegiance to Obama overnight when his campaign cracked the sense of Clinton's inevitability.

That possibility is why, almost unanimously, seasoned political observers argue that Yoon is the greater threat to Menino — true, Yoon may get trounced, but he also might excite the electorate enough to pull off a surprising win.

The conventional — and historically very true — wisdom is that Boston political campaigns begin after Labor Day. That will leave only two weeks for Flaherty and Yoon to woo the city before the preliminary vote. With so much on the line in such a short time, things may yet get heated. ^

To read the "Talking Politics" blog, go to thePhoenix.com/talkingpolitics. David S. Bernstein can be reached atdbernstein@phx.com.

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