E-Mail This Article to a Friend Is it Menino forever? The odds on mayoral candidates four years from now BY ADAM REILLY

How long will Tom Menino keep going?

For most of the recent mayoral campaign, the answer seemed clear: four more years. Menino, it was widely assumed, would easily be re-elected on November 8. Then he would serve out his fourth term, thereby surpassing Kevin White as Boston’s longest-serving mayor, and retire to general acclaim in 2009. But shortly before the election — which, as expected, he won handily — Menino complicated the picture, telling the Globe that he wouldn’t reject the thought of seeking a fifth term. "I’m not ruling anything out," he said.

This comment could have been a warning aimed at silencing potential critics, especially on the Boston City Council. It could have been a strategic move aimed at preventing a staff exodus immediately following the election, although his ensuing promise to request resignations from every city-department head makes this less likely. (We’ll see if he follows through on his pledge.) Or it could have reflected Menino’s realization, in the run-up to yet another mayoral win, that he simply doesn’t have many other attractive options.

After leaving City Hall, White moved into academia at Boston University; his successor, Ray Flynn, became ambassador to the Vatican. Given Menino’s unique mix of skills and limitations, it’s difficult to imagine him following in Flynn’s or White’s footsteps — or, for that matter, doing anything whatsoever once he steps down. The mayor has no law degree to fall back on, no insurance or real-estate business to tend to. Government has been his business and he’s worked hard at it. And judging from his recent landslide win over tenacious challenger Maura Hennigan, the job is Menino’s for as long as he wants it.

All that said, there’s a strong chance that Menino’s upcoming term will, in fact, be his last. When the next election rolls around in 2009, Menino will be 66 years old and eligible for a pension of well over $100,000. Furthermore, as a cancer survivor, the mayor knows firsthand that his time isn’t finite — there will be only so many hours left for traveling, golfing, and doting on his six grandchildren.

The key to this decision may be his wife, Angela. Friends and associates say she’ll have the most influence on his future plans. But because theirs is a strong and old-fashioned marriage, it’s unlikely that anyone other than the mayor and his children will know what she thinks or advises.

If Menino decides to step down in four years, Boston’s moribund political culture could get the jolt it so desperately needs. If we’re lucky, the mayoral race of 2009 will be a wide-open affair full of drama and intrigue, with a half-dozen or more strong candidates vying for an open seat.

With that in mind, the Phoenix recently spoke with some of Boston’s sharpest political minds about who will be in the mix four years from now. On the basis of these conversations, we assembled the following list of contenders. The accompanying odds are based on current circumstances, and factor in both the person’s desire to run and his or her chances of actually landing the job. Some yearn to be mayor with every fiber of their being — this means you, Michael Flaherty! — while others’ intentions are harder to gauge. But everyone mentioned below has one thing in common: in an eight- or nine-way mayoral preliminary, they could pull in 16 or 17 percent of the vote, enough to advance to the two-candidate final — and at that point, anything’s possible.

MICHAEL FLAHERTY

Odds: 2-1.

Flaherty’s mayoral dreams are no secret — and judging from the November 8 election, they might actually come true. Heading into Election Day, Flaherty’s position atop Boston’s at-large city council ticket was supposedly threatened by progressive favorite Felix Arroyo. Instead, the 5600-vote margin separating Flaherty from Arroyo (who finished second) was the biggest gap between the at-large winner and runner-up in more than two decades. Even better, Flaherty’s numbers improved in neighborhoods across the city.

Come 2009, Flaherty should be the best-financed, best-organized candidate in the mayoral field. Still, it wouldn’t be a cakewalk. Despite Flaherty’s potent campaign machine and liberal bona fides (among other things, he’s a long-time supporter of gay rights), he’s still an Irish guy from South Boston — and in the inescapable New Boston narrative of city politics, that’s not necessarily a good thing. Also, Flaherty painted a big fat target on his back with his strong showing last week, and his rivals on the council may well try to unseat him as council president come January.

MARIE ST. FLEUR

Odds: 5-2.

Pick your first: St. Fleur, the state representative from Dorchester, would be Boston’s first female mayor, first Haitian-American mayor, first mayor of color. Nothing energizes like a chance to make history, and St. Fleur could expect plenty of deep-pocketed donors, eager volunteers, and effusive press coverage. Remember, too, that St. Fleur is a skilled political insider who’s risen to vice-chair of the powerful House Ways and Means Committee. (She also does a mean version of "Danny Boy.") Right now, she doesn’t have a broad political base or a ton of money. But with her skills, her symbolic potential, and the help of legislative allies like House Speaker Sal DiMasi, that base could coalesce fairly quickly. In the meantime, her key leadership position should keep the campaign donations flowing in over the next four years. Just one question: is this really the job St. Fleur wants? Or are her sights set on federal office?

JOHN TOBIN

Odds: 3-1.

The councilor for West Roxbury and Jamaica Plain is an ambitious politician bound for bigger and better things. But what? And when? In reality, Tobin’s next move is anybody’s guess, including his own.

In a mayoral race, Tobin would be helped by his media savvy and quick wit — not to mention strong support in West Roxbury, which remains Boston’s most politically potent neighborhood. Unlike his council colleague Michael Flaherty, though, Tobin’s been slow to cultivate connections outside of his home base. This is partly due to Tobin’s job description — he’s a district councilor, not a citywide one — but there may be some parochialism involved as well. Tobin’s lack of empathy as he led the charge for neighborhood schools last year wouldn’t help him nab mayoral votes in Boston’s neighborhoods of color. Neither would the fact that, after four years in office, Tobin — whose district includes a Latino population that’s big and getting bigger — still hasn’t learned Spanish or hired a Spanish-speaking aide. Then again, Tobin has a strong following among gay and lesbian voters thanks to his long-time support (as a West Roxbury Irishman, no less) of gay rights. And he’s got the natural poise of a big-time politician — not to mention a bunch of generic "Vote John Tobin" signs stored in an undisclosed location.