Boston mayoral contest '09

Flaherty has his work cut out for him
by Kevin John Sowyrda
MySouthEnd.com Contributor
Thursday Jan 29, 2009

The race for mayor of Boston may not be a "show me the money" contest as much as it will be a "show me some new ideas" race. In that vein, Councilor Michael Flaherty’s novel, YouTube baptism as a contender for the city’s highest office is best taken seriously by the incumbent potentially seeking an unprecedented fifth term at a time when recession beleaguered voters have few reasons to embrace the status quo.

But first, a reality check for the at-large City Councilor, who has enjoyed broad support in the South End, which can be attributed to his progressive stance on key social issues. Menino will hardly go down in history like that Marlin Brando "could-ah been a contendah" film character. Menino has been the de jure contender for many years, beating a crowded field of articulate political pros in a special election in 1993, garnering more than 60 percent of the vote. He’s kept a bullet train pace since then, building a massive, urban political machine envied by other state politicos. To be perfectly blunt, Menino’s the George Patton of Massachusetts politics: brash, highly aggressive, savvy and armed with a legion of loyalists and an intimidating war chest of $1.4 million; in comparison, Flaherty has only $590,000 at his disposal.

"Flaherty’s an articulate candidate, but in a business where money can be the king maker Mayor Menino remains a formidable and respected incumbent," said Boston media consultant Jan Saragoni.

But this is not to say Councilor Flaherty need storm Pork Chop Hill to take the mayor’s office. What he may lack in political cash the young Flaherty compensates for with political cache, an unquestionably superior ability to communicate, and the physical appearance of youth and vitality which plays to the desire for change - presuming you subscribe to the theory of Menino Fatigue, as do I.

True, you can bet the job you might still have that the councilor from South Boston will not out raise His Honor anytime before November. Keeping pace with Menino’s money machine is a marathon no one’s going to win. This is business as usual, and should you doubt it just call former Menino opponents Maura Hennigan and Peggy Davis Mullen.

Hence, Menino Fatigue. Many in the city grow tired of a chief executive at times perceived as temperamental and thin-skinned and whose vision for the Hub seems limited to a nearsighted view of a posh, harbor side City Hall - an architectural plan now thankfully mothballed. And the potential fodder for a Menino challenger is actually quite fresh, coming from recent criticism in the news regarding the Mayor spending more than a cool million on political activities just as one member of his family is revealed for enjoying a special job arrangement with a major city developer.

Flaherty’s chances rest on the possibility that there’s a silent majority of Bostonians who are feeling intense pains in the pocketbook, which might trigger less than the normal level of tolerance for an incumbent issuing disjointed pronouncements and utilizing backroom political tactics from an already scandal-weary electorate.

But a coin flip reveals two factors that may make Menino his usual, formidable self. First, Flaherty, for all his oratorical skills, will have to overcome the political fact that Menino is a municipal version of Barack Obama, which is to say the mayor has consistently proven that he can raise huge sums of money to overwhelm any political opposition. And then there’s this: the mayor is a workaholic. I recall a conversation I once had with former mayoral communications director and South Ender Carol Brennan, who told me that no matter how early she rose for work, the mayor was already awake and 10 steps ahead of the rest of the staff. For Flaherty to outwork the mayor, he best prepare for 18-hour campaign days.

Those long campaign days will be consumed by a needed discussion on the economy, and on this front Flaherty has already outmaneuvered the Mayor by publicly opposing an increase in the city meals tax. While Menino is fighting for state approval to raise the meals tax by two percent, Flaherty has just come out swinging on the issue, arguing that making a night out on the town even more expensive in this economy is hardly a prodigious move. Flaherty’s right on this issue, and proves that he’s more in touch with the hurting local business owners who are already facing empty tables at Boston eateries.

So the race is on. The incumbent who’s everywhere, hardly articulate but hardly unapproachable, versus the renegade councilor who hails from a different generation with better prose but an inferior political machine to propel his candidacy. Sure, the odds-on favorite is the same mayor we’ve had for nearly 15 years. And yes, the era we have chronicled in Boston for so long is one where entrenched incumbents reign without question and are challenged only at the peril of the challengers.

But like many things in American politics of late, that glass ceiling may not be long for this world.