Q&A #1: Michael Flaherty Returns?

"Jim C" asks:

Will Michael Flaherty jump back in and run for Councilor at Large? If he does will he win? Who would lose assuming all incumbents run? Political implications?

The conventional wisdom around town is that Flaherty -- former Boston City Councilor, and 2009 mayoral candidate -- is not going to run for his old seat back. He hasn't raised any real money, just enough to pay off lingering expenses and keep his campaign account from slipping into red numbers. Typically, you expect 2011 city candidates to raise money before the end of 2010, so donors can give the calendar-year contribution max of $500 in both years. Flaherty didn't do that, and has certainly done nothing to raise his profile, so most folks are now dismissing the rumor.

But I'm told that Flaherty is very serious about running for the at-large seat. And here's the logic of his 2010 silence, in my analysis: If he made any serious move toward running, that would raise the red flag for the incumbents -- particularly Ayanna Pressley, who is considered most vulnerable.

Pressley raised just a little over $20,000 in 2010, and ended the year essentially in the red -- she reported less than $10,000 cash on hand, with $16,000 of liabilities owed. That means Pressley failed to convert her donors for double-year maxes too.

Pressley will be hard-pressed to make up for that -- and the longer Flaherty waits to make a move, the harder it will be for her. Flaherty, on the other hand, has never had any trouble raising $400,000 in a single year, and even if his value has dropped (which I'm not sure it has) he should be able to scoop up a quarter-million without breaking a sweat, especially after giving his donors 2010 off. That's more than enough for him to run and win one of the four seats.

Of course, that also affects the other incumbents. But Arroyo currently has a little over $50,000 in his account. Connolly has $100,000 and a strong fundraising machine. And Murphy, while tapped out from his statewide campaign effort, has the added fundraising benefit of the council presidency.

Plus, Pressley was #4 in '09, a pretty good distance behind the others. Plus, the low-turnout non-mayoral year, combined with a presumed strong Southie showing for Flaherty, would seem to give the Irish guys an edge. So the conventional wisdom is that if Flaherty runs, Ayanna's the odd one out in November.

That might not prove true. For one thing, some have speculated to me that Flaherty's core supporters will bullet him (vote just for him, not using their other three at-large votes), actually costing votes for Murphy and Connolly, who those voters would probably otherwise toss votes to.

There is also some hope that Boston's minority communities will turn out higher than usual. That's partly because of increased political involvement and voter registration from last year's Deval Patrick campaign, and partly because it's assumed that black Bostonians would rally to save the only black at-large councilor. But it's also because there may be potentially contentious district races in Roxbury (where the upcoming special-election winner will likely be challenged again in November), Mattapan (where rumors continue of a challenge to Charles Yancey), the South End/Chinatown (where Suzanne Lee is challenging Southie's Bill Linehan), and perhaps Dorchester (where rumors are recirculating of the always-rumored impending departure of Maureen Feeney, this time perhaps to the city's open elderly-affairs vacancy).

So, maybe Murphy ends up as number five. Or maybe even Arroyo. Who knows? It could get brutal. IF it happens at all.

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