Voters here have ushered in a new generation of political leadership, setting the stage for a mayoral runoff next month between a millionaire entrepreneur who promises to crack down on the homeless and an unapologetically left-wing Green Party member who won an upset over his political mentors.
The winners in Tuesday's first round of voting were restaurant owner and Supervisor Gavin Newsom, 36, and Board of Supervisors President Matt Gonzalez, 38.
Each represents a new beginning to voters in a city hammered by job loss and overrun by panhandlers. Whichever one is elected will become the city's youngest mayor.
As much as is possible in a place as liberal as San Francisco, the mayoral showdown five weeks from now will offer a clear choice:
Newsom, a liberal Democrat by the standards of most other cities, has been cast by opponents here as a socialite "Republocrat." He is allied with billionaire Gordon Getty and lives in a multimillion-dollar mansion in Pacific Heights, one of the city's most expensive neighborhoods, with his wife, a prosecutor and CNN commentator who is a former lingerie model.
By contrast, Gonzalez, an arts aficionado and poetry buff, doesn't own a car and rents an apartment in the considerably less fashionable Western Addition neighborhood. Newsom's supporters portray Gonzalez as an ultra-left "cafe brat" whose support won't extend beyond the city's young hipsters.
Newsom first captured the attention of voters with a ballot initiative last fall that he called "Care, Not Cash." Overwhelmingly approved by voters, but now hung up in the courts, it would drastically slash General Assistance payments to the homeless and give them vouchers for services instead. Opponents say those services are already stretched too thin.
This year, Newsom followed up with a ballot initiative to ban begging in many parts of the city -- near any bank ATM, for example -- and outlaw aggressive panhandling everywhere.
Gonzalez promoted his own initiative -- to boost the minimum wage citywide to $8.50. That would add San Francisco to a short list of cities that have imposed their own minimum wage laws and raise the wage to the highest in the nation, matched only by Santa Fe, N.M. The statewide minimum wage is $6.75.
Newsom's measure was backed by many business groups. The same people opposed Gonzalez's measure. But voters approved them both with nearly identical majorities -- 59% on the panhandling measure; 60% on the minimum wage.
"There's no logic or nothing," said state Senate leader John Burton (D-San Francisco) of his city's voting habits.
Regardless of who wins -- and Newsom has a large edge -- the city's old guard is moving over, or being pushed aside.
Newsom and Gonzalez will battle for a seat being vacated by Willie Brown, who leaves public life after decades of flamboyant service. Brown, who launched Newsom's political career by naming him to the Parking and Traffic Commission in 1996, will step aside because of term limits. He plans to found a public policy institute.
Burton may also soon pass from the scene. His Senate term runs out next year, and he rejected repeated appeals by leading Democrats to run for mayor.
Voters also signaled that several other prominent liberals have passed their prime, casting aside Tom Ammiano, a longtime gay rights activist and San Francisco supervisor, and former Supervisor Angela Alioto. Both have made failed attempts at the city's top job before.
San Francisco pollster David Binder said Gonzalez will face an uphill battle against Newsom, who has pulled support from across the moderate middle.
Gonzalez won 20% of Tuesday's vote to Newsom's 41%. And many of those who backed Alioto -- regarded fondly by Italian Americans for being the daughter of former Mayor Joseph Alioto -- may throw their support to the more conservative Newsom.
Still, Gonzalez surprised many by making the runoff, and his supporters say they have momentum on their side.
Gonzalez did not announce his candidacy until August and, like his opponents, had trouble capturing the attention of voters amid the hoopla of the gubernatorial recall race.
But a grass-roots movement on his behalf flourished, as volunteers strapped Gonzalez signs to their bikes and vans, and musicians and artists all over town held last-minute fund-raisers for him.
"The wild card got in," San Francisco State political science professor Richard DeLeon said of Gonzalez. The Newsom camp "didn't even prepare for that."
"It's going to be very interesting," he added. "I think there's great potential, especially on the college campuses, and Gonzalez really seems to be tapping that source of energy. That can make a huge difference."
A strong showing by Gonzalez could startle San Francisco's long-entrenched Democratic Party structure, DeLeon said. "They want to smother this little baby in its cradle -- this insurgent Green Party," he said.
Indeed, Newsom has the backing of the Democratic Party's leading figures. In addition to Brown, U.S. Sen. Dianne Feinstein, who is a former San Francisco mayor, and Rep. Nancy Pelosi have endorsed him. Wednesday morning, Brown appeared next to the lanky Newsom to rally more support for the coming weeks.
"San Francisco is a strong Democratic town. Gavin Newsom is a lifelong Democrat. Matt Gonzalez abandoned the Democratic Party," Newsom spokesman John Shanley said. "I can't think of a reason we won't do well if we work hard."
On the other side, some Ammiano backers are already scrambling to ensure that left-leaning voters go for Gonzalez.
Robert Haaland, president of the Harvey Milk Lesbian, Gay, Bisexual, Transgender Democratic Club and a longtime Ammiano supporter, appealed to backers to come together at a "Little City, Big Tent" fund-raiser scheduled for Sunday to back Newsom's opponent.
"In our passion and commitment for each of our candidates, we sometimes lose sight of the values that unite us," he wrote in an invitation sent out before the election. "We must come together to fight Newsom's politics of mean."
Newsom's core message -- that he will tackle the homeless issue -- struck a nerve with many voters. His pledge to make the city more business-friendly also earned him backing among downtown interests and immigrant entrepreneurs.
But his opponents accuse him of seeking to punish the homeless. They note his expressed intent to direct homeless people to sources of help, such as mental health clinics and programs for drug addicts, but say he has done nothing to come up with money for expanding those services.
Gonzalez's foes say the candidate's proposals would drive businesses out of a city that has already been hit hard by the collapse of the dot-com bubble. Among other things, he has proposed a gross receipts tax on business and an increase in the real estate transfer tax on property worth $2 million or more.
Gonzalez, who would become the first Green Party mayor of a major U.S. city, said Wednesday that characterizing him as too far left because of his party affiliation is meaningless.
When it comes to governing a city, his goals to reduce patronage in City Hall, help small business and improve financing of public works projects are in line with the San Francisco mainstream, he said.
Other Green Party positions -- support for gay marriage and opposition to the death penalty -- are shared by any viable candidate in San Francisco, Newsom included.
"At the end of the day, people are going to look at Gavin Newsom and say, 'Hey, this looks a lot like a continuation of the Willie Brown experience,' " he said.