Every two years, a new crop of would-be city councilors get their chance to make a mark on Boston politics. Some serve notice that, win or lose, they’re forces to be reckoned with — take John Connolly and Sam Yoon in the current at-large city-council race. Others make some early noise, only to fade away after Election Day.

And Gibrán Rivera? With the election three months away, it’s still unclear what his legacy will be. Rivera, a 30-year-old community organizer, is challenging City Councilor John Tobin in Boston’s sixth district, which includes West Roxbury, Jamaica Plain, and parts of Roxbury and Roslindale. His campaign has inherent demographic interest: while the political clout of Boston’s Latinos is growing, no Spanish-speaking candidate has won election to the council outright. (Felix Arroyo finished fifth in the at-large race in 2001, but joined the council when fourth-place finisher Francis "Mickey" Roache became Suffolk County register of deeds.)

Rivera may be at the forefront of a new generation of Latino candidates, win or lose. The 2000 Census put Boston’s Latino population at more than 85,000, compared to 62,000 in 1990. Moreover, given this year’s tough at-large council race, Arroyo will be working to get out the Spanish-speaking vote — and considering the sizable Latino population in District Six, Rivera should be a beneficiary.

There’s just one problem: except for Rivera and his committed supporters, most people rate him as, at best, an extreme long shot.

Why the pessimism? Flash back to 2003, when Tobin beat Francesca Fordiani, a Jamaica Plain activist who ran a vigorous campaign. By focusing on Tobin’s opposition to the Community Stabilization Act, which would have limited the ability of bigger landlords to hike rents around the city, Fordiani pushed the incumbent in Wards 10 and 11 (northern Roxbury) and ran well in Ward 19 (Jamaica Plain and Roslindale). But in high-voting Ward 20 (West Roxbury), which delivered more than half the votes cast in the final District Six election, Tobin crushed his challenger, 5507 votes to 521. The final count: 74 percent for Tobin, 26 percent for Fordiani.

Several seasoned City Hall observers expect a similar result come November. "You may see a replay of two years ago," one warns. "How do you beat somebody when you have part of the constituency in one community, but no base in the other, larger community?"

Rivera, however, treats such skepticism with a kind of Muhammad Ali–esque, I’ll-shock-the-world swagger. Last week, sitting in Rivera’s Egleston Square headquarters, I suggested his candidacy might be a glorified organizing campaign, with winning the race a secondary goal. He smiled indulgently. "We are running to win, and we’re going to win," Rivera promised. "You can quote me on that. And you can check in with me on the evening of November 8 to talk about that."

THE END OF IDEOLOGY

Rivera has several gripes with Tobin. He condemns the councilor’s plan for a return to neighborhood schools, which Tobin floated during last year’s student-assignment review process (see "Late Assignment," News and Features, July 16, 2004). (Tobin, who chairs the council’s education committee, proposed giving top priority at all schools to families living within a one-mile radius, an idea widely reviled in Boston’s minority communities.) "Most neighborhoods in Boston said very clearly that they prefer choice and accountability, not neighborhood schools," Rivera argues. "It just seems like, as chair of the education committee, he was making an argument that doesn’t serve the vast majority of children and families in the public schools." Rivera also pans Tobin’s continued opposition to the Community Stabilization Act, which the council rejected again last year. As Rivera sees it, market forces aside, the council’s failure even to try to mitigate skyrocketing rents is unconscionable.

Ultimately, though, Rivera’s beef with Tobin seems to be philosophical. According to Rivera, Tobin represents a bankrupt political paradigm — one in which politicians act as a distant elite, rather than collaborating and cooperating with the people they represent. "This campaign sets out to build community — to build political power," Rivera says. "We’re going to win in a way that brings people into the fold, and in a way that allows people to envision a different kind of system."

On this subject — the council’s place in the broader political landscape — it’s hard to overstate the difference between Tobin and his challenger. During a recent interview at Anna’s Donuts, the mom-and-pop West Roxbury establishment where Tobin holds his office hours, the councilor reluctantly identified himself as a "centrist moderate." But he also emphasized that he sees the council as a non-ideological body. "I think when you get into ideology in city-council races, it tends to be a bit overblown," he says. "I don’t put much stock into that."

The left-leaning voters of his district may disagree. West Roxbury may be heavily Irish and politically conservative, but Jamaica Plain remains a progressive hotbed. And as Tobin courts JP’s lefty contingent, his centrist approach — and support for neighborhood schools — could become a liability.

On this particular issue, though, Tobin is unrepentant. In fact, he takes credit for several recent changes in the Boston Public Schools, claiming they were inspired by the work his office did last year. (One example: students in grades K-8 now get priority at all schools within a mile of their home, even if some of the schools lie in a different school zone.) And he rejects the argument that the student-assignment debate breaks down along racial lines.

Tobin has defied easy characterization throughout his council tenure. For example, he’s been the council’s strongest supporter of the arts, a subject often linked to the political left. Another Tobin priority — bringing free wireless Internet access to all of Boston — is non-ideological, but has progressive overtones, as did his campaign to televise the once-mysterious proceedings of the Boston School Committee. Furthermore, Tobin has long been a staunch supporter of full civil-marriage rights for gays and lesbians, something he’s quick to note.

This eclecticism could work in Tobin’s favor if he runs for higher office. Earlier this year, there was speculation he might seek one of the council’s four at-large seats this fall. This would have strengthened his citywide base, and paved the way for a mayoral run if and when Tom Menino rides off into the sunset. Tobin is also mentioned as a possible successor to State Senator Marian Walsh, if Walsh seeks higher office herself; as a state senator, Tobin could run for mayor without jeopardizing his job. "I think he’ll be a candidate for higher office," one City Hall insider says of Tobin. "He’s clearly ambitious."

Tobin’s mastery of the press, too, is a strength worth noting. He’s adept at the quick quip, but can also offer serious, thoughtful observations when necessary — and he always calls reporters back. As a result, Tobin gets plenty of free publicity; in the last six months, he’s been mentioned a collective 29 times in the Boston Globe and the Boston Herald. (Arroyo, another councilor thought to be interested in higher office, has been mentioned eight times in the same period.) If Tobin uses his council seat as a political springboard — or if this year’s re-election fight proves tougher than expected — this media savvy could prove invaluable.