If the Boston mayoral race were a poker game, Mayor Thomas M. Menino would be holding all the aces—an approval rating around 85 percent, the incumbency, major endorsements, and a war chest of more than a million dollars—while challenger Peggy Davis-Mullen not only lacks good cards, but also faces a plethora of embarrassing accusations of having cheated her way into the game.

While there still remain a few wild cards-including a couple of lawsuits the City Council recently filed against Menino, Davis-Mullen’s potentially strong support from Boston parents and teachers, and the councillor’s widely-recognized ability to show up the mayor in public speaking-chances are slim that the challenger can actually win.

The two-term City Councillor is the first opposition to challenge the mayor in eight years, and is a longshot to be the first female mayor in Boston’s history.

But even Bruce C. Bolling, the man who was defeated by Menino back in 1993, is lining up behind Boston’s current mayor.

“I think he’s done a very credible job,” says Bolling of his former opponent.

The Power of Incumbency

Statistically speaking, the odds are against Davis-Mullen.

“I don’t think any incumbent mayor has ever lost in the history of Boston,” says longtime City Councillor Francis “Mickey” Roache.

Menino’s predecessor—a then-popular Raymond Flynn—only left his office to become ambassador to the Vatican in 1993. Menino, who then became acting mayor, has since solidified his power with victories in the 1993 and 1997 elections.

Since her entry into the race April 17, Davis-Mullen has sought to increase her name recognition-relatively small compared to the mayor’s.

And now, after a rash of stories in The Boston Globe and The Boston Herald investigating various allegations of wrongdoing—ranging from sitting for the bar exam too early to not filing state income taxes in 1998 and 1999—Davis-Mullen’s name recognition has increased, but her public image has taken a beating.

In early April, Davis-Mullen turned up on a list of Massachusetts public officials who hadn’t paid state income taxes.

Due to privacy laws, officers of the Department of Revenue (DOR) cannot classify a filing as “late.” But in a technical quirk, Timothy Connelly, the DOR’s director of communication, was able to say that Davis-Mullen’s papers weren’t filed two weeks ago, but now are.

“We are very confident in our record-keeping,” Connelly says.

Davis-Mullen’s campaign, however, denies that the returns were late.

“She filed her 1998 and 1999 tax forms on time,” said Karen E. Sharma, a campaign spokesperson, yesterday.

Then there’s the matter of Davis-Mullen’s bar application, where the candidate was found to have sat for the bar exam without the necessary prerequisite of completing her studies in law school. Sharma said that Davis-Mullen’s alma mater, The New England School of Law, misinformed Davis-Mullen about her readiness to graduate.

“Our records show that we did everything correctly,” says Dean of the Law School John F. O’Brien, declining to explicitly place the blame on Davis-Mullen.

While no new legal proceedings are scheduled on either of these matters, they have led to a deluge of negative press soon after her candidacy and a more general inquiry into her character and private life.

Local media are digging to such an extent into the councilor’s history that the Globe recently reported on Davis-Mullen’s overdue water and sewer payment-from 1991.

Searching for Support

While Menino has a very high approval rating, he is not without critics.

Perhaps the most contentious issue of the mayor’s tenure has been development and planning in Boston, ranging from City Hall Plaza to the municipal harbor.

The development-oriented Alliance of Boston Neighborhoods (ABN) takes a strong stance that the power structure is askew.

“The BRA [the state-appointed Boston Redevelopment Authority, which is autonomous from the city] has usurped the planning power of the city and we have no real recourse,” says Shirley Kressel, the president of the ABN. “This is the time to look at the mayor and his relation to this development.”

But despite its disapproval of the current development, the ABN will not endorse Davis-Mullen.

“We don’t have a position in the Boston mayoral race,” Kressel says.

Aside from those angry over development, speculation has it that a challenger could win important votes from the mayor among unions and city employees.

Boston teachers had a long and difficult negotiation this past October, while its firefighters are in the midst of a protracted effort to hammer out a contract with the city.

Despite frustration with the mayor, the Boston Teacher’s Union (BTU) most likely will not endorse a candidate-just like the ABN.

“I don’t think we’ll get involved in the mayor’s race. I think both the mayor and Councilor Davis-Mullen have a lot of support within our union,” says BTU President Edward J. Doherty. “There’s a reluctance to go against an incumbent mayor who’s generally on the positive side of the issue.”

The firefighters are no more committal, though they say they could endorse a candidate further on in the campaign.

“Right now we’re not endorsing,” says Firefighters Local 718 President Jack McKenna.

But the ongoing negotiations will make a difference in Local 718’s choice of candidate.

“If an endorsement is sought, this will play in,” McKenna says.

And in what might be a natural constituency of voters for Davis-Mullen-women-Menino is trying to maintain his foothold.

He is aggressively courting women in his campaign, last week holding a “women’s event” with such luminaries as Vicki Kennedy, the wife of Senator Edward M. Kennedy ‘54-’56.

The Menino reelection committee seems to recognize the lack of particular constituencies falling to Davis-Mullen in naming its target demographic.

“The campaign intends on courting every constituency in the city of Boston,” says Michael S. Kelley, Menino’s campaign spokesman.

Dialogue About Debate

Seemingly everyone-from community organizations to unions to Davis-Mullen’s fellow city councilors-welcomes the chance at dialogue that a real election with two contenders creates.

“The last time the mayor ran, he had no opposition,” says Bolling, Menino’s former political rival. “With no one running against him, none of the issues came up.”

On April 23, Davis-Mullen challenged Menino to a series of six debates, but the mayor has not yet directly replied.

“If you’re the incumbent, you want to stay above the political fray,” Bolling says.

Kressel says she disapproves of Menino’s lack of expressed interest in debate.

“He doesn’t have press conferences, he doesn’t come to community meetings, and now he’s not having debates,” Kressel says.

But the Menino campaign says that debates are premature-citing the fact that the deadline for announcing candidacies has not yet been reached, and that Menino has not yet officially declared that he’s seeking reelection.

“It’s premature to talk about a debating schedule. Between now and July 10 [the deadline for nominating papers] anybody else could get into the race,” says Kelley.

Making It A Race

In the meantime, Davis-Mullen will continue to push the issues, though the differences between the candidates are small.

“The major issues of her campaign are affordable housing, public education and development,” Sharma says.

Davis-Mullen is an acknowledged policy-setter in the city’s schools, having pioneered a “neighborhood schools” initiative in the mid-`90s.

“She has been a leader on schools,” Roache says. “She’s got an issue that comes out number one all the time.”

“She’s a Southie High graduate, she’s a good strong woman, [and] she’s a viable candidate,” says Roache, who nixed planning a mayoral run of his own because preliminary studies showed that he would have to spend $2 million to give the mayor a run for his money.

Despite the school issue, the distance between Menino and Davis-Mullen is not issue-based, but personality-based.

“I think it’s more of personality clash than on any specific issue,” says James M. Kelly, one of the mayor’s strongest opponents on the city council.

“Peggy is very outgoing and opinionated and does not hesitate to offer her thoughts on an issue,” Kelly says. “The mayor, on the other hand, is extremely sensitive to any type of criticism.”

And the mayor may have overstepped his executive bounds in granting the BRA $7 million of city funds to redevelop City Hall Plaza.

The City Council is suing the mayor, something that has not happened since 1985, according to Kelly.

“The council unanimously-and bear in mind that some of the councilors are very, very fond of the mayor-voted that this matter has to be dealt with in a legal way,” Kelly says.

While the lawsuit is not unprecedented, as it is played out in court it could become embarrassing for Menino. And Davis-Mullen’s campaign is using the issue to make larger claims about the mayor’s uses of funds.

“There are students in the Boston Public School system that don’t have textbooks, there are issues on going with the firefighter’s contract,” Sharma says. “It’s a priority issue.”

—Staff writer Lauren R. Dorgan can be reached at dorgan@fas.harvard.edu.