E-Mail This Article to a Friend Key to the city Tom Menino’s grip on Boston seems unshakable. But with the mayor’s health problems mounting, a challenge from City Councilor Maura Hennigan could threaten his reign. BY ADAM REILLY

WHEN BOSTON MAYOR Tom Menino announced a bevy of high-level staffing changes last Tuesday, he came perilously close to kicking off his re-election campaign. With his newly appointed staffers looking on, Menino stood at a podium in City Hall’s Eagle Room and basically served notice that he wasn’t going anywhere. "We need to keep Boston moving forward, and the way we do that is by bringing new ideas, new energy to city government," the mayor declared. "I can tell you that we made some real good choices here, and I think the people of Boston will be really happy here with the choices we’ve made in our administration over the next several years."

No surprise there. Despite ongoing speculation that, if John Kerry wins the presidential election, Menino could be tapped for a post in the new administration, such a move seems as unlikely today as it did a month and a half ago (see "Succeeding Kerry," News and Features, July 9). More important, although Menino’s political ascent was serendipitous — as City Council president, he became acting mayor when Ray Flynn left to become ambassador to the Vatican, in 1993 — he’s now entrenched enough, and popular enough, that it’s hard to imagine anyone else as mayor of Boston.

But then — one day after his forward-looking City Hall press conference — Menino was hospitalized for a flare-up of Crohn’s disease, a gastrointestinal disorder that can cause inflammation and ulceration of the digestive tract. The Menino camp quickly reassured the public that the mayor’s case of Crohn’s is mild and won’t affect his ability to do his job, an argument that was generally echoed by the Boston Globe. (The Boston Herald didn’t consider the question.) Even with this medical setback, most knowledgeable observers of city politics still expect Menino, 61, to seek and win re-election next fall. But the Crohn’s announcement served as a reminder that the course of the mayor’s career could still be altered by unforeseen events. Menino may well be in office in 2009, when he would surpass Kevin White as Boston’s consecutively longest-serving mayor. (White served from 1968 to 1983, while James Michael Curley served four non-consecutive terms over the first half of the 20th century.) Then again, Menino may not be the city’s top elected official five years from now — or even, as improbable as it sounds today, in January 2006, when Boston’s mayor is next sworn in.

FOR JOHN NUCCI, the clerk magistrate of Suffolk Superior Court, the idea that Menino might not seek a fourth term is nearly as absurd as the notion that someone would be foolish enough to challenge him. "I’d be willing to bet everything I own that he’s running for re-election," says Nucci, a former City Council president who made his own mayoral bid in 1993. "I think for any potential opponent, looking at this realistically, it’s clearly a kamikaze run. It’s not winnable under any scenario."

The numbers back up Nucci’s argument. According to a Boston Globe poll released this week, Menino’s overall favorability rating among Bostonians is 70 percent — enviable for any politician, but especially impressive given the Democratic National Convention–related disruptions and the city’s recent uptick in violent crime. "His numbers were actually higher a year or two ago — they have dipped a bit — but they’re still really strong," says Suffolk University pollster David Paleologos. "His favorability would have to drop into the 50s before we would see him as vulnerable."

Even though challenging Menino currently seems tantamount to political self-immolation, at least one person — at-large city councilor Maura Hennigan — appears inclined to give it a try. Hennigan is a veteran Menino critic, but she’s been especially vocal over the past year or so. Anytime something goes wrong in the city, it seems, Hennigan has rushed to draw attention to it. When a toddler was burned by a faulty manhole cover in the South End last week, Hennigan held a press conference on the spot. When the media reported that small businesses were suffering during the DNC, Hennigan sent out an empathetic e-mail urging constituents to grab a meal at a mom-and-pop restaurant. When Zoning Board of Appeal chair Joseph Feaster, who was instrumental in Menino’s 1996 campaign to retain an appointed School Committee, was ousted after doing legal work for a city developer, Hennigan called for more stringent municipal conflict-of-interest regulations.

That’s not all. Hennigan urged that the DNC be relocated to the new convention center in South Boston, a move recommended by Governor Mitt Romney and rejected by Menino; criticized the city’s handling of the Hayward Place development in the Theater District; pushed for the investigation that led to the corruption-related ouster of Inspectional Services head Kevin Joyce; questioned Boston’s school-assignment-plan review process; and panned Menino’s 2004 State of the City address as a compendium of stale ideas. Oh, yeah — Hennigan, who broke her foot in a much-discussed run-in with a pothole last year, has also directed her outrage at the mayor whenever other Bostonians have similar accidents. (This, it should be noted, is just a partial list.)

Hennigan hasn’t actually announced that she’s running for mayor. But during a recent interview, she trotted out what sounded like a nascent stump speech. She stressed that a desire to serve all Boston’s citizens prompted her to give up her District Six seat in 1998 to run citywide, recalled Menino’s willingness to give away city land to the Red Sox for a new stadium in the Fenway, and hinted that heightened demands on Boston police during the DNC, followed by post-convention vacations, contributed to the city’s recent spike in violent crime. "When you’ve had all this experience and you’ve been able to acquire all this knowledge, it can be a little frustrating when you think there’s a better way to do it, and you try to put it forward," Hennigan said. "You only get so far, and you have the chief executive, who is the policymaker, go off in another direction." She even unveiled what could become the 2005 campaign’s nastiest insult. Asked how the Menino years will be remembered, Hennigan seemingly implied that Boston’s current mayor will be a lasting source of inspiration to mediocre people everywhere: "He came in, he hadn’t even a college degree, [but he] went back to school and got that. I think for an average person, they can look back at Mayor Menino when he decides to leave, or when he leaves, and say, ‘Hey, I could do it, too. Mayor Menino did it.’"

In the Menino-dominated Boston of today, Hennigan’s jabs at the mayor make for good copy. And some observers of city politics speculate that’s all she’s after — that Hennigan is simply using the heightened profile accorded a prospective mayoral challenger to pave the way for another at-large council run. But Menino insiders are anticipating a challenge from Hennigan next year. "Right now, much like Peggy Davis-Mullen in 2001, Maura Hennigan appears to be positioning herself as the anti-mayor and presumptive opposing candidate to Mayor Menino," says a source close to the mayor. "Everyone in town is acting as if that’s the case. She’s appearing in the local newspaper. She’s getting on TV. She’s doing the things a credible candidate has to do."

Would Hennigan have a prayer? At this point, it seems doubtful. For starters, there’s the small matter of money. As of July 31, Menino had about $392,000 in the bank; Hennigan had just over $8700. What’s more, unlike her ambitious City Council colleagues Michael Flaherty and Steve Murphy, Hennigan isn’t regarded as having an especially strong campaign organization. By contrast, Menino controls a potent political machine — and during his decade-plus in office, he’s forged strong ties with neighborhood leaders and local nonprofits that depend on the city’s largesse and would almost certainly support his re-election.

Then there’s Hennigan’s message deficit. Menino has long styled himself Boston’s "Urban Mechanic," a self-deprecating label that isn’t inspiring (unlike Kevin White’s "Loner in Love with the City" self-description), but has a kind of Everyman-ish appeal. But rather than embracing the eminently achievable goal of outdoing Menino in the vision department, Hennigan, with her fixation on potholes and faulty manhole covers, seems instead to be trying to out-urban-mechanic the Urban Mechanic. Despite Menino’s high approval ratings, the constituencies are there for would-be mayoral challengers — union members irked by this year’s bitter collective-bargaining negotiations; black, Latino, and Asian parents dissatisfied with conditions in the schools; and opponents of the biosafety laboratory slated for construction at Boston University Medical Center, to name a few. But Hennigan’s approach seems unlikely to cobble together these disparate groups into a cohesive force.