That kinder, gentler approach may pay off in Jamaica Plain, where supporters of Maura Hennigan remember the bruising fight against Tobin in the 1999 election. Hennigan hasn’t endorsed anyone in the race. " I kind of don’t want to get in the middle of that, " she says. " I’m not looking to interject myself into that race. " But insiders see her supporters turning to Rush. Says Ward 19 Democratic Committee co-chair Howard Leibowitz, " I get the sense from some Hennigan people they’re more interested in Rush. " He cautions, however, that " that’s not universal. " Hennigan says, " It’s up to them to make that decision; I’m not giving them any direction. " But Rush is trying to capitalize on the opening. He’s received endorsements from prominent members of the Latino community, such as businessman Tony Barros and neighborhood activist Tomas Gonzalez, and he’s attended scores of community meetings.

Tobin insists, however, that the conflict with Hennigan is behind him and that he’s had success in reaching out to her supporters. " To Maura’s credit, she’s come to my times [campaign events, that is] and I’ve come to hers. We’ve moved on, " he says. Tobin has also won his share of prominent endorsements in JP, notably from Frank Jones, a respected African-American lawyer who made strong but unsuccessful showings in the 1995 and 1997 councilor-at-large races and was considered a leading candidate for the District Six seat. Says Jones, " He’s a very personable young man; I respect him enormously. He’ll be a voice of reason and thoughtfulness on the city council, and he’ll fairly represent our various communities. " Former council candidate Jose Vincenty is in Tobin’s corner, which may help win votes among Latinos. And Tobin could benefit in JP’s large gay community from the backing of Susan Tracy, an out lesbian who ran for the Eighth Congressional District seat in 1998.

Tobin is also making his case on the issues, hammering Rush for his turnaround support of the city’s Main Streets program, which provides grants for community improvement, and which was just approved last week for Centre Street in Jamaica Plain and West Roxbury. " I’m the only one until recently who advocated for a Main Streets program, " says Tobin. " To be against that is ludicrous. There are 19 in the city; they work. " (Rush says his opposition wasn’t ideological, but was simply the result of talking to neighborhood merchants who didn’t feel the program was needed. Recently, he says, the project has gained more support in the community, so he now endorses it.) Tobin has also alleged that he’s the only candidate who supports domestic-partnership benefits, though Rush insists that he backs the idea as well.

IT CAME as a surprise to most political observers that no major figures from Jamaica Plain stepped forward to run for the District Six seat. " I was shocked, " says Joe Heisler, host of the Boston Neighborhood Network’s Talk of the Neighborhoods. Jones — who commutes back and forth to Seattle for his software business — decided he didn’t have the energy for a race, and ended speculation about his possible candidacy in March. " I had anticipated that a number of people in JP would run, " he says. " There are two or three people who I think have great credibility and have made a great contribution to this community and this city, and I’m surprised that they didn’t run. " (He declines to specify who they are, though frequently mentioned names include Ward 11 Democratic Committee member Marie Turley, who also heads the Boston Women’s Commission; JP activist David Vaughn, who ran unsuccessfully for the District Six seat in 1995; former state-senate candidate Eleanor LeCain; and Hennigan’s former chief of staff, Mary Mulvey.) But Jones’s hesitation may have prevented a viable Jamaica Plain candidate from emerging. Says LeCain, " I did think about running myself, but I spoke with Frank Jones [in January] and he was interested in running. I thought that if he ran, I would support him. " When Jones finally decided against entering the race — which she recalls happening later, in April or May — it " was late to start a campaign. "

In addition to time constraints and Rush and Tobin’s high name recognition from previous races, there was another obstacle: JP turnout, which is traditionally weaker than West Roxbury’s, wouldn’t be enough to push a candidate over the top unless he or she made inroads into the other part of the district. So the only people carrying the flag for Jamaica Plain this September will be Williams and Rigas.

The 48-year-old Williams is a maintenance worker at the Mass College of Art who decided to run for office after he gave up drinking and drugs 11 years ago. He went on the ballot for the first time 1995, running for councilor-at-large (and scoring only one percent of the vote). He made a bid for the District Six seat in 1997 and 1999. (As Hennigan’s only opponent in 1997, he did better, winning 18 percent. But two years later, in a four-way primary with Hennigan, Rush, and Tobin, he was back to one percent.) Williams feels he can represent the grittier side of the district. " I think I have a better grasp of what’s going on out here than my opponents, " he says. " They’re very young and fresh and witty, but as Jimi Hendrix said, they haven’t lived the experience. A lot of people in this part of JP are on the margin. "

Williams is the only pro-choice candidate in the race, as well as the only minority (he’s part Italian, part African-American) But with his sometimes rambling diatribes and no-show campaigning, he’s not considered electorally credible by local observers. " Edgar has run a few times before, " says Smith of West Roxbury’s Ward 20 Democratic Committee. " If you want to dub a perennial candidate, he would be the perennial candidate. We invited him [to campaign debates] and he’s yet to show up. " Most insiders share the reaction of Turchinetz: " Edgar Williams? The name is familiar but I don’t know who he is. "

Elaine Rigas, on the other hand, is clearly someone to watch. The 29-year-old Wellesley graduate, with polished debutante-cum-newscaster good looks, is making her first run for office. The JP native has the signs, the literature, and even the slick spin of a seasoned campaigner, dodging questions about abortion (she finally concedes that she’s pro-life) and domestic partnership (giving the standard non-answer " I believe that everyone should be treated equally " ). Her main issue, though, is improving public schools. (Unlike her West Roxbury competitors, who were both educated at Catholic Memorial High School, Rigas stresses that she attended public school from kindergarten through her graduation from West Roxbury High.)

She’s counting on support from the Greek-American community, as well as from voters bored with Rush and Tobin: " I’ve heard from people campaigning, ‘I’m so tired of seeing the same faces run.’ " JP voters may pick her in a show of solidarity over the two front-runners from the other side of the district. And, as the only Republican in the nonpartisan preliminary election, she could gain votes from conservatives. Her gender could also help. Says LeCain, " Elaine Rigas may have an advantage because ever since it went to a district council, it’s been a woman, and people may want to keep that. "

But she didn’t start campaigning until July. " It’s tough to play catch-up when someone’s been out there six months ahead of you, " notes Smith. Rigas is a poised young woman, and she could have a future if local party operatives take notice and swoop her off to prominence, as happened to Jane Swift. But pundits believe Rush and Tobin are just too far ahead for Rigas to gain a foothold — at least in this election.

BECAUSE THERE’S a preliminary election in September, the race will be more strategic than it would be if voters got no say until the November final. " I’m guessing that the morning after the primary, Rush and Tobin will both look at where they did well, where they did poorly, and go from there, " says DiCara. Today the candidates have to do guesswork based on results from two years ago, but after September 25 Rush and Tobin will have current, hard numbers, and will be able to shift their outreach in West Roxbury and Jamaica Plain accordingly.

Maura Hennigan will be a tough act to follow: she has lived in both West Roxbury and Jamaica Plain, and her family has a storied political name. But Tobin and Rush, with their support of domestic partnership and their satellite campaign headquarters in JP’s heavily Latino Hyde Square, are both trying to reach out to the other side of the district. Of course, they can’t reach too far: " Politically, you have to go into the far left to win votes in JP, " says Greg Timilty, " but you can’t go so far left that you lose votes in West Roxbury. " Whichever candidate can pull that off — and get his or her supporters out to vote — will have earned the right to replace Hennigan.