Campaigns hit overdrive

In the final days of an already fierce campaign for four at-large seats on the City Council, a battle has emerged to top the ticket. Council President Michael Flaherty and Councilor Felix Arroyo, once briefly allies, are now locked in an intense fight to finish first, spending and raising money at a furious pace as they seek the bragging rights and clout of the top vote-getter.

Each is looking for the kind of citywide support that could propel a mayoral campaign in 2009, when Mayor Thomas M. Menino is expected to leave the city's highest office. Flaherty, who has made no secret of his mayoral aspirations, had stockpiled campaign funds for a decisive victory this fall.

But then Arroyo, the city's first Hispanic councilor and a native of Puerto Rico, emerged as a serious threat. Thought of by many as a standard-bearer for the so-called New Boston of minority and immigrant residents, whose numbers and levels of political activism have grown in recent years, he has garnered broad support. After finishing second in the September preliminary election and winning more wards than any other candidate, Arroyo set his sights on first place in the final and suggested he would consider a run for mayor in 2009.

''Absolutely, we want to finish first," Arroyo's campaign manager, Patrick Keaney, said last week. ''Anything else, finishing second or lower, we would consider a failure for this campaign."

Though Keaney added that he did not look at the challenge as ''knocking off Michael Flaherty," the sitting council president, a first-place finish for Arroyo would amount to exactly that. Flaherty has surpassed all his opponents in the last three elections, and he is intent on doing it again tomorrow.

Both men know, however, that nothing is guaranteed. The race for four citywide seats on the council is crowded and fiercely competitive this year, partly because Councilor at Large Maura Hennigan is leaving her seat to run for mayor. First-time candidates John Connolly of West Roxbury and Sam Yoon of Dorchester are trying to capitalize on momentum generated by their respective third- and fifth-place finishes in the preliminary; Councilor at Large Steven Murphy of Hyde Park, who finished fourth in September, is working hard to keep his seat. Patricia White of Roslindale, the only woman in the race and the daughter of a former mayor, finished only a few hundred votes behind Yoon in the preliminary. Matt O'Malley of Roslindale, who has the backing of the most vocal city workers' unions, is campaigning around the clock today, and Ed Flynn of South Boston, son of another former mayor, is hoping to get out the veterans' vote.

Still, the race for first place could have important implications for the city's political future.

''I think what we're looking at here, although nobody will say it until after Tuesday, is those who are 'papabile,' those guys in Rome who are on the short list to be pope," said Larry DiCara, a former city councilor and an amateur historian of city politics. ''For better or for worse, anybody who tops the next ticket is thought of as being 'papabile' -- could be the next mayor."

DiCara noted, however, that winning the most votes in the at-large race has historically been a poor predictor of mayoral victory. DiCara himself finished first in the 1979 council race, only to come in fourth in the mayoral run-off four years later. Menino, a former district councilor, never ran at large.

Arroyo is known as a poor fund-raiser; he waited until the last minute to raise money for his campaign this year, allowing his war chest to bottom out at $1,344 by the end of September. But he raked in about $65,000 last month, roughly a third of it from three fund-raisers he held in his native Puerto Rico. He also hired a professional fund-raiser at the beginning of last month, a move that brought in most of the rest, Keaney said.

Arroyo has also been spending fast on mailers targeted toward his base -- Latinos, African-Americans, working-class tenants -- and relying on union support to penetrate heavily Hispanic neighborhoods like Jamaica Plain and East Boston. He has also been working to expand his following across the city, putting out a glossy mailer citywide and launching a round of automated phone calls.

Under pressure from Arroyo and the ambitious first-timers, Flaherty has tried to replenish his campaign account in the last few weeks, raising more than $43,000 since mid-October, much of it from downtown lawyers and developers. He has burned through more than $180,000 since the preliminary, spending on consultants, glossy brochures, and radio and cable TV ads.

Steve Crawford, Flaherty's campaign manager, said that volunteers have made some 12,000 personal phone calls since the preliminary, including 5,000 in Vietnamese and Chinese. The campaign has also advertised in Spanish newspapers and run radio ads featuring the Rev. William Dickerson of Greater Love Tabernacle, a largely African-American church in Dorchester.

''He'd be very disappointed if he didn't top it again," said Councilor John Tobin of West Roxbury, who backed Flaherty for council president four years running. ''When you've been there, and you've won it, you want to keep on doing that. There's a real possibility that [Arroyo] could contend."

The Flaherty-Arroyo rivalry is a dramatic reversal of the candidates' cautious cooperation in 2003, when Flaherty endorsed Arroyo, who was then seen as in danger of losing his seat. After finishing a close second to Flaherty that year, Arroyo tried to wrest the council presidency from him two months later. It didn't work, but it cost the upstart Arroyo an endorsement from Flaherty this year. After finishing second again in this year's preliminary, Arroyo declared that ''there's no improvement except to go to first place."

Last week, Arroyo demurred when asked about that comment, insisting he would be happy as long as he won reelection. He called a question about his mayoral ambitions premature. ''I never have raised that possibility," he said.

Arroyo has also been campaigning hard for Yoon, a political newcomer from Dorchester who is the first Asian-American to run for City Council. Arroyo has recorded automated phone calls for Yoon, held joint events with him, and even put out joint mailings. Some observers called that a risky strategy in a city where ''bullet voting" -- voting for one candidate instead of four in order to improve a single candidate's chances -- is a common strategy. The potential concern for Arroyo is that voters who support both men might see Yoon as the underdog and give him a bullet vote because they see Arroyo as safe.

Then again, if Yoon and another newcomer win seats on the council, Flaherty's hold on the council presidency may be less certain.