For more than a decade, the local AFL-CIO has backed D.C. Council member Harold Brazil. But this year, the city's preeminent labor organization bypassed the veteran Democrat and instead threw its support to his chief opponent, 33-year-old political newcomer Kwame Brown.

Brown also is outshining the at-large council member among local Democratic activists, winning endorsements in Wards 1 and 5 and a straw vote in Ward 4. Brown is even giving Brazil trouble on his home turf: In a vote last month, the challenger drew sufficient support among Ward 6 Democrats to deny Brazil an endorsement.

"I think this city has reached a point where it has Harold Brazil fatigue," Joslyn N. Williams, president of the Metropolitan Washington Council of the AFL-CIO, said of the incumbent, who first won office in 1990. "There comes a time when you need new blood, new faces, new ideas. We just thought it was time for a change."

Change could be in the air. With less than a month until the District's Sept. 14 primary election, half of the six council members seeking reelection are facing serious opposition. In all three races, the challengers stand a fighting chance to win the Democratic nomination and effectively boot the incumbents out of office, according to political analysts.

In addition to Brazil, Ward 7 council member Kevin P. Chavous is battling a slew of challengers led by Vincent C. Gray, a former human services official who has raised more than $50,000 and won key endorsements. And Ward 8 council member Sandy Allen is trying to hold off a challenge from former mayor Marion Barry, among others.

The incumbents are, in general, dismissive of the threat.

"Every time I've run, there's been at least five or six people in the race. So this is not new to me," Allen said in an interview.

Said Brazil: "The voters are smart. They'll flirt around at the dance, but they're going to 'leave with the one that brung them.' "

But others sense the first rumblings of what could be a major shake-up on the 13-member council. As much of the city experiences an economic renaissance, some voters east of the Anacostia River, in Wards 7 and 8, are feeling left behind by the current leadership. Brazil, meanwhile, seems to have lost some luster after nearly 14 years in office. He also may be suffering from revelations this year that he used council staff members to assist in his private law practice and that a woman with whom he had a personal relationship was given a new city job and a raise.

"There's a great sense of restlessness with the D.C. electorate," said A. Scott Bolden, chairman of the D.C. Democratic State Committee. "They are very interested in better leadership, whether from the incumbent or the challenger. And that means every candidate will have to work harder for their votes."

This year's races are even more "spirited," Bolden said, because voters see legitimate challengers whose campaigns are better organized and financed than in years past.

"There are viable alternative candidates," Bolden said. "It will be interesting to see [what happens] because if there are changes with those three, it's going to represent a major paradigm shift on the D.C. Council."

Brazil, Chavous and Allen have raised more money than their opponents. But over the past decade, energetic challengers have repeatedly defeated better-known and better-funded incumbents. In 2000, for example, Adrian M. Fenty outcampaigned 21-year-veteran Charlene Drew Jarvis for her seat in Ward 4. This year, Fenty (D) did not draw a challenger.

When they first ran for office, Brazil, Chavous and Allen also danced onto the political stage as feisty underdogs. Chavous narrowly beat incumbent H.R. Crawford in 1992. Brazil ousted Nadine P. Winter from her Ward 6 seat in 1990. And Allen beat incumbent Eydie D. Whittington in 1996 after losing by a single vote in a special election in 1995.

With long service comes a long record, and each is campaigning on a laundry list of accomplishments ranging from better police service to more affordable housing and a revitalized downtown. But long records also provide ammunition, and challengers are accusing Chavous and Brazil, in particular, of losing touch with voters.

In Ward 7, Chavous, 48, has drawn fire for frequent trips out of town and for not checking in regularly with constituents. Gray, 61, director of the city's Human Services Department under former mayor Sharon Pratt and current director of Covenant House, has hammered the incumbent's commitment to the ward, charging that Chavous too often sends staff members to meet with residents rather than going himself.

Chavous replies that he is often busy working on legislation and can't attend community meetings. He cites a list of achievements, including his effort as head of the council's education committee to create charter schools and a school voucher program.

But Sam Bost, president of the influential Far Northeast/Southeast Council, said Chavous has lost his vote.

"I truly understand that a council member's main job is legislation," Bost said, "but you cannot forget those people who elected you."

Chavous leads in overall fundraising with $88,514, compared with Gray's $52,389. But Chavous has collected $16,259 over the past two months, while Gray has raised $38,531 in that time.

In Ward 8, Allen, 60, also faces complaints from residents who say her office has failed to respond to their concerns. Barry, 68, is trying to capitalize on dissatisfaction with Allen, arguing that he is "a fighter" who can bring the spoils of economic development to the city's poorest ward.

Allen argues that she has funneled new housing and city services to the ward. She has raised nearly $100,000 and garnered a public endorsement from her council colleagues.

Barry, meanwhile, has not filed a campaign finance report -- after receiving an extension, his first report is due tomorrow. But political analysts say the impact of cash is negligible in the race because Barry's name alone may be worth thousands of votes.

"That's a race where money is not a factor," said Jamie Kendrick, executive director of the Service Employees International Union Maryland and District of Columbia State Council. "We know Barry has raised at least $500 because we gave it to him. That's enough to print some signs and T-shirts."

The contest for Brazil's seat may be the most closely watched. Though he is chairman of the Economic Development Committee and considered a friend to both business and labor, Brazil, 55, is widely criticized for spending more time on his law practice than on civic service. He also has tested the patience of many City Hall insiders with his quirky legislative maneuvers.

"You see Harold on the dais and, on any one issue, he probably will go three ways," said Williams, the local AFL-CIO president. "On his own bills, you look up, and Harold may be voting against his own amendments."

Earlier this year, council member Jim Graham (D-Ward 1) considered taking on Brazil. Graham abandoned the quest, but others popped up to take his place, including Sam Brooks, 24, a native Washingtonian who has impressed many observers with his intelligence and understanding of city issues.

But Brown is considered to be Brazil's stiffest opposition. The son of longtime D.C. Democratic activist Marshall Brown, Kwame Brown has knocked on 15,000 doors and scooped up a load of impressive endorsements.

The Greater Washington Board of Trade members were impressed with Brown, said Ted Trabue, chairman of the board's political action committee, but never considered abandoning Brazil.

And Brazil has raised vastly more money, collecting $458,836 vs. Brown's $103,456, according to the most recent campaign finance reports. But political analysts nonetheless consider the race to be competitive, in large part because of Brown's fresh appeal.

Williams noted that Brazil beat an incumbent who was "tired, not in touch. It was time for a new generation and a new breed of leaders." Chavous, he said, ran the same kind of campaign his first time out.

"So at what point do these guys say it's time for a new generation to also have their shot at leading this city?" Williams said. "That's the question before us."

Staff writer David Nakamura and staff researchers Bobbye Pratt and Madonna Lebling contributed to this report.

Council member Harold Brazil has lost out on some endorsements.