SAN FRANCISCO — Willie Brown, the savvy career politician who led this liberal city through the carnival dot-com boom and bust, will leave office later this year after completing the second of two colorful terms as "Da Mayor."
Yet many believe San Francisco's real thrill ride lies just ahead: electing a mayoral successor in a town infamous for its circus-style political theater. Already some two dozen hopefuls aim to replace Brown in the November contest, and their diverse resumes reflect the city's quirky, left-leaning political culture.
There's Gavin Newsom, 35-year-old "boy wonder," glib millionaire restaurateur and popular county supervisor who's being touted as a "West Coast Kennedy." Along with his wife, Kimberly Guilfoyle -- a successful prosecutor and former Victoria's Secret underwear model -- Newsom has amassed an army of upscale contributors and volunteers who believe the young couple can conjure a new era of Camelot in a city that thrives on social pomp and circumstance.
There's also Tom Ammiano, a gay former stand-up comedian and teacher who in 1999 forced a runoff against Brown as a last-minute write-in candidate.
There's trial lawyer Angela Alioto, daughter of former Mayor Joseph Alioto. She recently reported the theft from her law office of several computers with private polling data.
There's city Treasurer Susan Leal, who is gay.
Tony Ribera, onetime police chief and the only registered Republican, also joins the lot. So does long-shot Tahan Thomas-Daniels, a legally blind 25-year-old volunteer who says he would focus on education.
The contest remains wide open, thanks to the absence of outspoken state Senate President John Burton, a power who last year decided not to make a run at replacing Brown, a longtime friend and ally.
Election experts say the contest could hinge not only on how to bolster San Francisco's staggering economy following the high-tech bust, but on what the candidates have to say about another emotional issue: the city's homeless people.
Many residents of the compact city feel besieged by aggressive panhandlers and sunburned men who congregate not only downtown but in suburban neighborhoods from Bernal Heights to the westernmost Sunset district. Some believe elected officials have all but given up on finding a solution.
Newsom appeared to gain an early advantage with voters by pushing a controversial "Care Not Cash" initiative that was approved with overwhelming voter support last November. The plan would cut general assistance payments to the homeless to $59 a month from the current maximum of $359, with the difference to be redistributed to programs for the indigent.
A judge struck down the initiative this month, ruling that the Board of Supervisors must first approve changes in city funding. Homeless advocates are infuriated by Newsom's proposal, saying it would leave the city's neediest residents to fend for themselves.
The fourth-generation San Franciscan and son of a retired state appeals court judge also has been publicly skewered for failing to disclose $11 million in real estate and business loans, as required under state clean government laws. That included loans from billionaire philanthropist Gordon Getty -- a Newsom friend and patron.
"Gavin Newsom himself is the biggest panhandler in San Francisco, with all the money he gets from the Gettys," said Angela Alioto.
Activists have set off stink bombs in Newsom's restaurants and jammed the telephone lines with bogus reservations. Anti-corporate agitators hit Newsom in the face with a pie last year. They have picketed his office and business. One group plastered the gay Castro district with placards showing his picture, address and home phone number. "He's so hot," the poster read. "Come party with Gavin Newsom."
"This will be among the ugliest political races in city history," predicted Newsom, who has conceded his mistake in failing to report the loans. "If you're out of ideas and you're not right on issues with the people, you play the politics of personality."
Ammiano, 61, says such comments show Newsom's naivete. "Mudslinging is part of the game here," he said. "You've got to have thicker skin than that because, from what I've seen, the attacks haven't been that bad yet."
Political insiders and consultants say Newsom has built a formidable campaign machine.
"He's got a wide support base I don't see with other candidates," said San Francisco pollster David Binder. "And he seems to be pressing the right emotional buttons on the homeless issue."
Many voters see Newsom as an alternative to the outgoing mayor's often-combative style.
"Willie Brown is larger than life -- spontaneous, clever and profane," said political consultant Jim Rivaldo. "People believed he could pull the city out of its doldrums with his connections to Washington and Sacramento. But his over-the-top comments alienated and offended. His brutal honesty rubbed people wrong."