E-Mail This Article to a Friend No man’s land Matt O’Malley confronts Boston’s hidden political divide BY ADAM REILLY

Matt O’Malley should be a contender. From a progressive point of view, the at-large candidate for Boston City Council is strong on most issues: staunchly pro-choice and pro-gay-marriage; in favor of restructuring the all-powerful Boston Redevelopment Authority and giving its planning functions to a separate agency; against the controversial biolab slated for construction at Boston University Medical Center; willing to tackle big-picture matters like the Patriot Act and the war in Iraq at council meetings. Some lefties might frown at his opposition to the Community Stabilization Act, which would limit the ability of bigger landlords to jack up rents. But O’Malley’s push to ratchet up production of co-op and rent-to-own housing could nudge Boston’s brutal housing market in the right direction.

Moreover, unlike some of his rivals, O’Malley can discuss complex policy issues in a manner that’s both detailed and accessible. And as far as temperament goes, his self-deprecating nerd-politician shtick is at least as compelling as any other persona in the at-large race.

O’Malley does, in fact, have a chance of winning election to one of the council’s four at-large seats when Boston voters go to the polls on November 8. But given his track record, that chance is slimmer than one might have expected. Back in 2003, O’Malley managed a sixth-place finish in the at-large race, one spot behind Patricia White, whose family ties (her father, Kevin White, was mayor of Boston from 1968 to 1983) gave her major advantages in terms of money and name recognition.

Soon after, O’Malley signed on to manage the campaign of acting Suffolk County sheriff Andrea Cabral, who faced a tough challenge from at-large city councilor Steve Murphy. Cabral’s unexpected trouncing of Murphy in the September 2004 Democratic primary was hailed as a seminal moment in city politics. (See "Winner’s Circle," News and Features, September 24, 2004.) And O’Malley — the redheaded Irish kid who helped a black woman trounce an old-school politician — looked to be a major beneficiary. "Matt O’Malley will ride the new political wind to office," predicted then–Herald columnist Howard Manly, who is African-American. "More than anyone else, he is the rightful heir to that rainbow coalition."

Fast forward to this fall. In September’s preliminary election, O’Malley dropped to seventh place. White beat him again. So did Sam Yoon, Boston’s first Asian-American council candidate, and John Connolly, the son of former secretary of state Michael Connolly. Since then, it’s become a political commonplace that Connolly, Yoon, and Murphy — and possibly White — are fighting for the third and fourth at-large seats. O’Malley, however, is supposed to be finished. "It looks like O’Malley’s not going to make it," one City Hall observer said after the preliminary. "Which is too bad, because he’s a nice kid."

If O’Malley doesn’t make it, students of city politics will note his inability to parlay the Andrea Cabral connection into votes. They’ll also cite the strong candidacies of Connolly and Yoon. And they’ll be right on both counts. But there’s a bigger problem here as well — namely, that in today’s Boston, there may simply not be a place for a candidate with O’Malley’s particular profile.

A NEW BOSTON

Last week, during a candidate forum at UMass Boston, O’Malley took up the question of whether the oft-discussed "New Boston" actually exists. "Is there a New Boston?" he asked. "You’re damn right there is — and I helped create it." Given O’Malley’s humble amiability, this pointed reference to the Cabral campaign was a bit jarring. The candidate, it seemed, was getting frustrated.

But two days later, during an interview at a Jamaica Plain coffeehouse, O’Malley struck a decidedly optimistic note. "I feel great where we are," he told the Phoenix. "If we had picked up less than 10 votes per precinct in the preliminary, we’d be in the top four, maybe even the top three. It’s absolutely doable."

This makes O’Malley’s situation sound better than it is. There are 254 precincts in the city of Boston; adding 10 votes in each would increase O’Malley’s preliminary total by more than 20 percent. But O’Malley has other arguments for his continued viability. Given the mayoral election pitting incumbent Tom Menino against at-large councilor Maura Hennigan, the low turnout in the preliminary (when just 15 percent of Boston voters came to the polls) should double or triple; this, in turn, should bring more liberal voters to the polls, which would presumably help O’Malley. Furthermore, O’Malley notes, his preliminary total jumped from 7000 in 2003 to 12,000 this year. And — as he’s fond of mentioning on the stump — he was the only candidate to win precincts in heavily African-American Roxbury (Ward Eight, Precinct Six) and heavily Irish-American West Roxbury (Ward 20, Precinct One, which also includes part of Roslindale).