|1) MICHAEL FLAHERTY | 38 | CITY COUNCILOR | SOUTH BOSTON|
If nothing else, Flaherty deserves the top spot because he’s one of the select few seriously considering running. Flaherty has built a formidable city-wide organization, and topped the ticket in each of the past three at-large elections. He’s smart, disciplined, and photogenic. It’s a sign of Flaherty’s strength that Menino seems intent on squashing his nascent candidacy — but it’s also a sign of how difficult it will be for Flaherty to win.
|2) RALPH MARTIN | 54 | CHAIRMAN, GREATER BOSTON CHAMBER OF COMMERCE | JAMAICA PLAIN|
Former Suffolk DA Martin, an African-American one-time Republican who has re-registered as an Independent, can appeal across the city, his advocates say. He is openly interested in running, but those who have spoken to him about it say he comes across as someone who wants to be talked into running. And that makes them doubt that he has the fire in his belly to leave his cushy life, as partner at Bingham McCutcheon, to launch the necessary 24/7 campaign. “He’s never proven he’s willing to do anything risky,” says one longtime political observer.
|3) JOHN TOBIN | 38 | CITY COUNCILOR | WEST ROXBURY|
Another pol who’s not shy about his mayoral ambition, Tobin starts with a strong base in one of the highest-voting districts in the city, centered on the West Roxbury Parkway. Good-looking and likable, Tobin is a natural on the stump, and has allies throughout city political circles. But he’s far from a household name, and doesn’t seem to have a single issue or trait to distinguish himself in people’s minds. If he uses the coming year to stand out on an issue on which Menino is thought to have failed— such as education or housing — he could be a formidable candidate, say several sources.
|4) CHRIS GABRIELI | 47 | CHAIRMAN, MASSACHUSETTS 2020 FOUNDATION | BACK BAY|
The multi-millionaire venture capitalist has the money, the experience as a candidate (albeit an unsuccessful one), and the name recognition to run. Plus, his foundation’s focus on fixing education provides a ready-made campaign theme. “He would be instantly credible as a candidate,” says one source. Those who have spoken with him about his plans, however, say that Gabrieli isn’t convinced that mayoralty is a good fit for him — or that he could win. Nevertheless, some think he’s itching to be talked into running.
|5) STEVE LYNCH | 52 | US REPRESENTATIVE | SOUTH BOSTON|
Life’s pretty good as a congressman, now that his party is in the majority. But some say that, ever since John Kerry decided to run again in 2008, Lynch now sees a US Senate seat as unattainable. And with his two daughters growing up, he could be thinking of ending the Boston-Washington split life. He’d have the money and the backing of the trade unions, but Lynch’s conservative social views — on abortion and gay rights in particular — might preclude him from winning in today’s Boston.
|6) PETER MEADE | 61 | EXECUTIVE VICE-PRESIDENT, BLUE CROSS BLUE SHIELD OF MASSACHUSETTS | BRIGHTON|
“He knows the issues, and he has the ambition,” says one local elected official. “He’s done all the right things.” That includes holding positions with the city (public-safety coordinator, parks and recreation commissioner), the media (WBZ radio host), private sector (Blue Cross Blue Shield of Massachusetts, Warner Amex Cable), and nonprofits (The New England Council, Catholic Charities, MassINC). He’s retiring from BC/BS in February, and more than one pol thinks he’s pondering a run for mayor.
|7) SAM YOON | 37 | CITY COUNCILOR | DORCHESTER|
A disappointing third-place finish in the November 6 city council election didn’t help, but some close observers see signs that Yoon is giving serious thought to a mayoral challenge in ‘09. He has proven fundraising prowess and crossover appeal among minorities, progressives, white-collar professionals, and social-services advocates. On the other hand, many inside City Hall remain unimpressed with Yoon, to say the least, and dismiss the notion of him posing a challenge to Menino.
|8) ROB CONSALVO | 37 | CITY COUNCILOR | HYDE PARK|
The biggest asset for Consalvo has long been the patronage of Tom Menino, who would love to see his Hyde Park protégé follow him into office, sources say. In fact, the one way Menino might actually leave his office is “if Robbie Consalvo was council president and Tommy could hand it off to him,” says one close city observer. Of course, that’s exactly the reason Consalvo’s fellow councilors will never vote him in. Many doubt Consalvo’s citywide appeal — it’ll “never happen,” one City Hall insider says — but others warn to take him seriously.
|9) CHARLOTTE GOLAR RICHIE | 48 | SENIOR ADVISOR TO GOVERNOR DEVAL PATRICK | DORCHESTER|
Richie, who finally split with Menino this year to work for the governor, has built a considerable network of political alliances in the city during her years heading its Department of Neighborhood Development. “She’s been able to transcend issues of race and class,” says one well-connected African-American activist. “She can work with minority communities, corporate communities, and faith communities. She’s a player.” Her name recognition and personal charisma may be lacking, as many point out, but she is perhaps the one candidate who can embody both a message of change and a continuation of Menino’s neighborhood-services focus.
|10) PAUL GROGAN | 56 | CEO, BOSTON FOUNDATION | JAMAICA PLAIN|
Grogan is hellbent on making sure that everyone thinks of him as a potential mayoral candidate, say sources — but skeptics don’t believe he actually intends to run. A former staffer for past mayors Kevin White and Ray Flynn, Grogan now doles out some $10 million in grants every year. That has helped him accumulate a fair number of friends, including those in philanthropist circles who are capable of helping him raise money for a campaign. But he’s too obscure and not dynamic enough to win, say detractors, who suspect Grogan’s real interest is in being the subject of conversation, not the recipient of votes.
|11) STEVE TOLMAN | 53 | STATE SENATOR | BRIGHTON|
He’s a champion of the trade unions, and his base is bigger than some realize: more than half his Senate district is in the city, and his wife’s family is well-connected in West Roxbury and Roslindale. His kid brother, Warren, has a strong following among the progressive crowd, which would be helpful to his campaign.
|12) JOE KENNEDY | 55 | CHAIRMAN, CITIZENS ENERGY | BRIGHTON|
Money is obviously not an issue for the former congressman — heck, he’s still got more than $2 million sitting in his old congressional account. Charming, popular, and 10 years out of politics, everyone agrees that Robert Kennedy’s son would immediately become a top-tier candidate if he jumped in. He could lose voters over his oil-based friendship with Hugo Chavez and the recent resurfacing of his untidy divorce/annulment proceedings. More important, some close to him insist he’s done with politics.
|13) LINDA DORCENA FORRY | 33 | STATE REPRESENTATIVE | DORCHESTER|
Forry, a Haitian-American who married into a politically connected Irish family, is a rising star in Boston politics and can appeal to many demographics. One elected official says she has “genuine star power” reminiscent of Deval Patrick. Groomed by Charlotte Golar Ritchie, Forry is a sharp political player, insiders say, and perhaps the most viable female candidate in a city dominated by male officeholders. Still, with just two years in elected office, many observers think Forry needs to prove herself before taking on a mayoral run.
|14) MARTIN WALSH | 40 | STATE REPRESENTATIVE | DORCHESTER|
A surprising number of political insiders point to Marty Walsh as the prototype for a new style of Boston Irish pol that could go far. He’s beloved by trade unions, solidly progressive (including his support for gay marriage), and a dogged, talented campaigner — he’s the only person to ever beat Martha Coakley at the ballot box. Walsh was ready to run for US Congress when speculation had Lynch graduating to the Senate upon John Kerry’s 2008 retirement — a scenario that never came to pass. Still, he’s not exactly a household name or a flashy new face, so not many would put him in their top five.
|15) TOM FINNERAN | 57 | RADIO HOST, WRKO | MATTAPAN|
Yes, he’s a convicted felon and the statewide symbol of all that’s wrong with Beacon Hill politics. So that’s two strikes against him. But he once had mayoral ambitions, still has lots of allies, and now has a daily megaphone to promote himself. If he’s ever going to re-enter the political arena, sources agree, it would be through a “comeback kid” campaign for mayor.
|16) WILLIAM DICKERSON | 45 | PASTOR, GREATER LOVE TABERNACLE CHURCH | DORCHESTER|
Politically wired, eloquent, good looking, and smart, people agree that Dickerson is destined for elected office. He has even backed down some on his anti-gay-marriage stance, making him more viable than vocal homophobes, such as Ray Hammond of Bethel AME Church. Several sources think Dickerson’s the minority figure with the best chance to catch fire as a fresh-voice candidate; on the other hand, rifts within and around the Black Ministerial Alliance would prevent Dickerson from gaining full support in black neighborhoods, let alone in the rest of the city.
|17) MARIE ST. FLEUR | 45 | STATE REPRESENTATIVE | DORCHESTER|
Several observers say that St. Fleur could go much higher on this list. She was good enough, after all, to be Tom Reilly’s hand-picked lieutenant governor. But that candidacy unraveled amid revelations of St. Fleur’s personal financial debts. While the money problems are relatively minor and largely in the past — and her constituents have forgiven her to the tune of an 84 percent re-election vote — the lingering tarnish of her public image is unknown.
|18) WILLIAM GALVIN | 57 | SECRETARY OF STATE | BRIGHTON|
He’s a little old for a city that may be looking for new blood, but he’s sitting on a war chest of well more than a half-million dollars. Don’t forget that Kevin White was secretary of the state prior to becoming mayor.
|19) MICHAEL ROSS | 35 | CITY COUNCILOR | MISSION HILL|
Some see Ross, a Jewish progressive popular in the Back Bay and in black communities, as a perfect New Boston candidate. Others say that he’ll never get beyond his unpaid-parking-tickets scandal, in which he was fined $2000 by the State Ethics Commission for improperly using his office to have tickets dismissed.
20) MAUREEN FEENEY | 59 | CITY COUNCIL PRESIDENT | DORCHESTER
Up until this year, everyone knew that Feeney was just biding time before seizing the city clerk position upon Rosaria Salerno’s retirement. Then a splintered council, full of mayoral wannabes hoping to deny the presidency to their imagined rivals, left an opening through which Feeney maneuvered to take the gavel. Next thing you know, she’s telling people she’d consider running for mayor herself. If she keeps the presidency, she’s in line to become acting mayor if Menino leaves — exactly how Menino himself got the job in 1993.