January 22, 2009
For those with any lingering doubts about Councillor Michael Flaherty's intentions this election season, it is now clear he will be vying for the Mayor's chair.
It's simply a matter of when he will announce it.
The massive size of Flaherty's current campaign war chest - now topping off at over $590,000 - has been well documented, but the councillor is now actively preparing his ground operation. Sunday before last, he held a series of meetings with trusted lieutenants from past campaigns and newcomers from around the city on his home turf, the Cornerstone Pub in South Boston.
Sources who were there told the Reporter confirmations of a mayoral run were made, predicting an announcement three to five weeks out, and a mock-up of a mayoral campaign logo was shown.
"He's definitely getting in this race, it's a matter of timing," said one source, a member Flaherty's inner circle.
Flaherty has also brought in the heavy guns on strategy. On his list of expenditures for November and December is over $17,000 to Hildebrand Tewes Consulting Inc., one of the top political consulting firms nationwide.
Steve Hildebrand was deputy national campaign director for president Barack Obama's 2008 campaign. His partner Paul Tewes was the same campaign's director in Iowa - helping to engineer the surprise caucus win there that started Obama down the road to victory in the primary.
This strategic move is mirrored by Flaherty's hire of Echo Ditto, the company that formed out of the team that built Howard Dean's revolutionary Internet-savvy campaign operation. Flaherty meted out $10,000 to the firm early last month according to the Office of Campaign and Political Finance and sources inside his campaign said the company is developing a cutting edge campaign website for the councillor.
"He's building a national team to help execute one of the best campaigns in Boston history," said the same inner circle source quoted above.