Can Sam Yoon win?

By DAVID S. BERNSTEIN  |  February 11, 2009

If they're wrong, of course, Menino will win re-election without breaking a sweat. But even if there is a kernel of truth to the theory, candidates will still need to do more than just talk about it to turn it into a ballot-box revolt.

For challengers to oust the incumbent, some political observers speculate, they will need to lay the seeds of doubt about Menino, and then have external events furnish the proof of his failings.

A good place for Yoon and Flaherty to start sharpening their knives will be during the upcoming budget process, which will see Menino proposing cuts to services that affect pretty much everybody, giving him very little cover for political attack.

But what really could hurt Menino is the kind of scandalous news story that puts faces and stories to city problems, rather than just dollars and cents.

Perhaps new revelations will come from the ongoing examination of pension abuse — triggered by reports of Boston Fire Department employees gaming the system. Or investigations into the Boston Police Department — one involving "Boom-Boom Room" partiers, and another involving drugs stolen from evidence lockers — could finally explode. Or, the federal corruption inquiry that has led to the arrests of former state senator Dianne Wilkerson and City Councilor Chuck Turner could expand to tarnish Menino appointees or friends. (Them's the breaks when you've ruled the city for a decade and a half.)

But events that snap a city to attention are often entirely unpredictable. A stunning quadruple-homicide in December 2005 made the city aware of its rising violence — and made Menino appear out-of-touch for having dismissed the problem throughout that year's mayoral campaign. And the tragic deaths of two firefighters in 2007 exposed the city's failure to administer drug and alcohol tests — and made Menino appear weak in his dealings with the city's unions.

5) MENINO'S AURA OF INVINCIBILITY MUST CRACK As long as people assume that Menino is unbeatable, he is unbeatable. Potential contributors, volunteers, and endorsers will stay huddled with the once and future mayor. News media, seeing no race, will not hype it.

In past elections, Menino has been able to remain in his bunker, safe with a large lead in the polls. He avoided almost all joint appearances with his 2005 challenger Maura Hennigan, for instance, and rarely responded to her criticisms.

In fact, Menino has not been forced to actually engage publicly in a campaign since 1993 — when, after replacing Ray Flynn as acting mayor, he beat a crowded field to capture his first full term.

This time, most observers believe, the challengers will be credible enough, and sufficiently funded, to draw attention and support. And some think that if his opponents' support reaches a certain "tipping point," to use Malcolm Gladwell's phrase, others will feel safe expressing their own support for the challengers. That's also when ordinary voters will start paying attention to the other candidates, and begin to seriously consider a post-Menino Boston.

6) FLAHERTY MUST TURN HIS SUPPORTERS AGAINST MENINO, NOT YOON In September, the three candidates (along with businessman Kevin McCrea, and anyone else who throws their hat into the ring) will square off in a preliminary election, with the top two vote-getters — presumably Menino and one challenger — going on to a head-to-head showdown in November.

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