Will he run or won't he?
That is one of the questions floating in the backrooms of City Hall, even as the presidential race drags on and the mayoral election - in November 2009 - stands months away. Political horse race fans say the clock is ticking for Councillor at-Large Michael Flaherty as summer draws near, as does a major milestone for Mayor Thomas Menino, his potential rival.
July 12 will mark 15 years at the top slot in City Hall for Menino, who likes to play it coy when asked if he's running for an unprecedented fifth term.
But the focus appears to be not on Menino, and another potential mayoral challenger, Councillor John Tobin, but on whether Flaherty, who was elected to the City Council in 1999, will challenge the city's chief executive.
"Everybody's waiting to see what he's going to do," says one City Hall insider, speaking on condition of anonymity.
The press releases coming out of Flaherty's office taking Menino's administration to task have dropped off in recent weeks. Flaherty continues to hammer away at the administration at council hearings, but has made little public mention of it. And Flaherty, a former council president, was the only councillor not to put in an appearance at current Council President Maureen Feeney's civic summit earlier this month.
"It speaks to an overall hesitation," the insider says.
Others are less doubtful, saying Flaherty is still plugging away.
Flaherty continues to hold his "kitchen table" tour, where he has been sitting down with residents in their homes and listening to them raise concerns about cleaner streets and lower crime rates, as he pushes for the city to use new technology to maximize local services and cut wasteful spending, according to aides. He has also been chairing the education budget hearings.
"Unless something happens with the [Suffolk County District Attorney] seat, he's running for mayor," another insider says.
Some chafe as such talk so early, noting that the presidential race is still underway. At this time last year, U.S. Sen. Hillary Clinton was expected to win the nomination. In politics, anything can change over the course of 24 hours, never mind over a year.
"Not even going there," said Feeney, an ardent Clinton supporter who is running for re-election to her district seat, when asked about the mayoral race.
"It's a good 18 months away, 17 months away," adds Councillor at-Large Stephen Murphy, a Menino supporter, while attending Memorial Day services at Cedar Grove Cemetery on Monday. "I know we have one active candidate. I see him here, and that's the mayor. I'm aware that he's running and I think he's done an admirable job as mayor, so it'd be difficult for anybody to make a case as to why to replace him, you know, if there is a challenger out there.
But the difficulty of running a race against Menino was made more apparent in April when the Boston Globe released a poll showing Menino with a 72 percent approval rating. But the more eye-popping figure was this: Fifty-four percent of Boston adults said they had personally met Menino, who keeps a busy scheduled packed with local events. The poll also showed concerns over crime and the economy.
"He's just everywhere," said a Beacon Hill observer. "If someone is going to beat him, they better start showing up to things. You gotta be out there, you gotta be working it."
"People are for the most part satisfied," Murphy says of Menino. "People see him, they can feel him, reach out to him, tell him their concerns."
That was evident in 2005, when Menino clobbered challenger Maura Hennigan, garnering 67 percent of the vote to her 32 percent, and spending $1.7 million to her $700,000. In 2001, Menino spent $1.6 million to beat Peggy Davis-Mullen.
The notoriously thin-skinned mayor was also recently ranked by a local magazine as the most powerful man in Boston, ahead of House Speaker Salvatore DiMasi, who represents the North End, and Gov. Deval Patrick.
Menino has been fundraising at a rapid clip, picking up tens of thousands of dollars in the last few months, while Flaherty has deposited about $16,000 in his campaign account.
At the end of 2007, Flaherty had $428,414 in the bank. Menino, on the other hand, had $973,502.
"Every day he's not [running for mayor], it's a wasted day," said the first insider.
Even as Flaherty continues to contemplate a run, others are beginning to eye his at-large seat. Former Nantucket selectman Doug Bennett and local Haitian-American activist Jean Claude Sanon have recently announced campaigns. Both are widely considered long shots.