One of the would-be candidates is meeting with small groups of Boston residents around their kitchen tables. Another is trying to broaden his appeal to neighborhoods where he is not currently well known. A third has quietly conducted a poll that he refuses to discuss.
The three Boston political figures, Councilor at Large Michael F. Flaherty, Councilor John M. Tobin Jr., and former Suffolk district attorney Ralph C. Martin II, are all exploring campaigns for the 2009 mayor's race - on tiptoe. They are seeking to generate buzz, but not too much. Stepping out too strongly could provoke the wrath of the city's famously hardball mayor, Thomas M. Menino.
Menino - who has never, as an incumbent, faced a significant challenger - sounds intent on seeking an unprecedented fifth term. His longtime friend and campaign treasurer, David Passafaro, says the mayor is unlikely to spell out his plans until 2009, but Menino talks as if he won't be able to stop himself from running again.
"I'm declaring I have a lot of work to do," Menino said in an interview with the Globe after a speech before city and town officials from across the state. "I have a great job here, and I've still got a lot of things I want to accomplish."
If he does run again, history is on Menino's side. Only once in the past century has a sitting Boston mayor lost a reelection campaign, and that was James Michael Curley who, at 75, had already served a prison term for mail fraud. Next year will mark 30 years since a challenger even gave a mayor a run for his money.
All of which means that any potential candidate needs an early start raising funds and building an organization.
So the stealth phase of the 2009 campaign has begun.
Take, for example, Flaherty, who is visiting residents in their homes in what he calls a "kitchen table" tour. He wants it known that he is out there, but he won't say if he is running.
"Our city needs to be run by its people, not stats," Flaherty said in an interview, launching into what could count as a full-fledged stump speech. "Our schools need to be led by parents, not politics. Our neighborhoods need to be fueled by opportunity, not fear."
But on the subject of whether he is running, the tone of his words is different. "My decision will be reached by listening to residents, not rumors," he said.
Some who know him well believe that he is in. Flaherty is only 38, but has been angling for the mayor's office for years, and those who have spoken with him say that he feels he missed his moment to run in the last mayoral election.
"He's doing it," a fellow city councilor said of Flaherty. "He's up or out. The time is now."
Elected in 1999, the citywide councilor from politically potent South Boston became the top vote-getter in council elections, but last year lost the presidency that he used to build a larger profile. Still a strong fund-raiser with a broad base, he retains $428,414 in campaign funds. Since his reelection in November, he has not stopped campaigning. His once-close relationship with Menino has frayed considerably, as the two find themselves constantly sparring inside City Hall.
Reticent as he may be on the subject, Flaherty looks outright chatty compared with fellow potential candidate Ralph Martin.
Martin was the first black district attorney for Suffolk County, appointed to fill a vacancy by Governor William F. Weld and later elected to the post. He held onto the position for a decade, sharing the national limelight for the Boston Miracle, the drop in violent crime that resulted from the partnership between law enforcement, community, and church leaders. Long considered a rising star, Martin receded from the political arena in 2002 for a lucrative partnership at a private law firm, Bingham McCutchen. He retains $105,996 in a campaign fund.
Now 55 and chairman of the Greater Boston Chamber of Commerce, Martin is being encouraged to run by business and institutional leaders, said one Martin ally. Whether those leaders would be willing to buck the mayor by publicly supporting a Martin candidacy is another matter.
Massachusetts pollster Tom Kiley conducted a survey for Martin aimed at assessing his viability and weighing the mayor's vulnerabilities, said the Martin ally, who would not share the results. Martin would not discuss the issue. Skeptics say the Jamaica Plain resident would have to do substantial work to rebuild an organization of his own to do battle with the mayor's formidable machine.
Tobin, the least known of the potential candidates, is the most willing to discuss his interest.
"If the mayor decides not to run, I see very little that would stop me from being a candidate for mayor in 2009," Tobin said. "We're preparing for that."
And if the mayor does run?
"If a free-for-all develops, I'm not going to sit idly by," Tobin said. "I'd have to take a look at it."
Tobin, 38, was elected in 2001 and has a limited but powerful base, representing Jamaica Plain and West Roxbury and the highest-voting precincts in the city. In the past year, he has established a youth council and begun reaching out to those beyond his district to get better versed on the broader issues he might confront in a mayoral contest, including public safety, education, the environment, and the arts. He started the year with about $118,205 in his campaign account.
While Flaherty, Martin, and Tobin are taking the most serious steps to position themselves for a possible candidacy, others would undoubtedly come out of the woodwork if the mayor bows out of the 2009 campaign. Among those considered mayoral material are Peter Meade, a vice president at Blue Cross Blue Shield; US Representative Stephen Lynch; former US representative Joseph P. Kennedy II; and from the City Council, President Maureen Feeney, Sam Yoon of Dorchester, Mike Ross of Mission Hill, and Rob Consalvo of Hyde Park. Paul Grogan, the oft-mentioned head of the Boston Foundation, told the Globe he will not be running in 2009.
If Menino wants to cling to the office, political observers say, he could be nearly impossible to dislodge.
Boston's system of government gives him enormous authority; he seldom needs the approval of a weak City Council. He enjoys free, public advertising: his name adorns signs affixed to buildings and fences citywide.
Over the last 40 years only three men have sat in the mayor's chair. Mayor Kevin White holds the 16-year record, which Menino is poised to surpass this summer. Raymond L. Flynn served for more than nine years.
Despite his long tenure, Menino remains scandal-free and is lauded even by foes as a doggedly hard worker. He is involved in city neighborhoods, including Roxbury and Dorchester, where ballot results show he maintains a strong voter base.
Last year, after the Globe reported on Flaherty's fund-raising efforts and his possible ambitions to become mayor, Menino swung back with a flurry of campaign events. He ended the year with $973,502 in his campaign warchest. "I'm not stale," he said in his recent interview.
Raising money for a campaign against him would be daunting, since Menino inevitably takes challenge personally, holds grudges, and controls the levers of city government. The lawyers and developers who traditionally fund city campaigns are reluctant to stray from the mayor; even those who are not his biggest fans rely on his administration's support for quotidian items from liquor licenses to building permits.
When Maura Hennigan challenged Menino in 2005, she said, the mayor's allies tried to discourage people from attending her fund-raisers; contacted a supporter who had a pending permit in City Hall; and even kept track of who attended her house parties.
"The problem is that people continue to be afraid, because people need permits, they need to conduct their business, feed their families, educate their kids," said Hennigan.
Hennigan borrowed most of the money to fund her campaign, $525,000 of the $663,299 she spent, only to lose by more than a 2-to-1 margin. Now a Suffolk Superior Court clerk of criminal courts earning $110,000 a year, she's still raising money to pay off $10,000 monthly mortgages.
To next year's crop of contenders, Hennigan advised, "They have to raise a lot of money, and they have to be prepared to recognize there may be people who want to be with you but for whatever reason, they might not be. . . . It comes with a cost."
Stephanie Ebbert can be reached at ebbert@globe.com.
