E-Mail This Article to a Friend No man’s land, continued

There’s something to each argument. But this optimistic gloss doesn’t fully confront the challenges facing O’Malley. Heading into this year’s race, O’Malley’s strength seemed clear. As an Irish kid who grew up near the Roslindale–West Roxbury border, he could appeal to the white, culturally conservative voters who call those neighborhoods home — but as a staunch progressive who played a key role in the Cabral race, he could also pull in support from lefties and voters of color.

So far, though, O’Malley really hasn’t benefited from anything like a Cabral Effect. If voters saw his ties to Cabral as meaningful, O’Malley should have had a strong showing in the same neighborhoods where Cabral did well during last month’s preliminary. But in Ward Five, the affluent Back Bay — where Cabral beat Murphy by a nearly four-to-one margin — O’Malley finished sixth, trailing at-large councilor and lefty favorite Felix Arroyo, Yoon, White, city-council president Michael Flaherty, and Connolly. The results in Ward 14, west Dorchester, were even grimmer for the O’Malley camp. In the September 2004 Democratic sheriff’s primary, Cabral received 1780 votes there to Murphy’s 162. In last month’s preliminary, though, O’Malley finished eighth. (For the record, Murphy managed a seventh-place finish.)

THE RACE CARD

Ethnic politics can be tricky, and parsing the contrast between Cabral’s and O’Malley’s numbers is no easy matter. It’s possible that US Attorney Michael Sullivan’s lengthy investigation of Cabral, which was recently concluded with no charges brought, diminished the efficacy of fellow Irishman O’Malley’s I’m-a-friend-of-the-sheriff’s pitch. And some voters may have found O’Malley’s clear determination to ride Cabral’s coattails off-putting. (Judging from some of O’Malley’s campaign literature, he almost considers Cabral his co-candidate.) But the bottom line is likely this: working for a black woman doesn’t automatically win a white man the loyalty of her friends.

Back to the preliminary. In Ward 20, his home ward, O’Malley fared far better, pulling in more votes than any candidate except Connolly. But he had a harder time in other white enclaves. For example, in Ward Six — the northern part of South Boston — O’Malley managed 453 votes, fewer than council president and Southie resident Michael Flaherty, Ed Flynn (the son of Southie native and former mayor Ray Flynn), Murphy, Connolly, and White. In Charlestown, meanwhile, O’Malley managed only a sixth-place finish, behind Flaherty, Murphy, Connolly, Flynn, and White.

What’s the greater lesson here? It may be this: a middle-class, unconnected, white progressive like O’Malley — who’s the son of a carpenter and a Boston public-school teacher — is going to have a hard time winning elections in today’s Boston.

It’s true that Connolly and Yoon — both of whom have seriously complicated O’Malley’s bid for office — are impressive candidates in their own right. (See "Breaths of Fresh Air," News and Features, December 31, 2004.) That said, each conforms to a specific political type. Connolly is, in many ways, a traditional Irish-American pol, with a politically well-connected family and prolific support in the largely white and conservative neighborhoods of West Roxbury and Roslindale. Yoon, meanwhile, is an ethnic progressive in the mold of Felix Arroyo, capable of drawing support both from Boston’s nonwhite populations (who, according to the 2000 Census, now comprise a majority of city residents) and from left-leaning whites who like his positions and the idea of adding a non-white face to the council.

Consider the six candidates who topped O’Malley in the at-large preliminary. Flaherty, Connolly, and White are Irish-Americans with potent family political ties. Murphy lacks those ties, but he’s built a career on appealing to white, working-class conservatives. On the other side of the equation, there are Arroyo and Yoon. Matt O’Malley entered the 2005 city-council race hoping to bridge the gap between the traditionalists and the ethnic progressives. On paper, it sounds good. But right now, it doesn’t look like a recipe for electoral success.

Adam Reilly can be reached at areilly[a]phx.com.