Left and Lefter

With his mastery of the levers of influence in Sacramento and proven national reach, Brown promised to end the seesaw of power in San Francisco and take the liberal Democratic machine of the ‘60s into the new century.

For a while, it seemed to work. Brown was extremely popular during his first year, as San Franciscans noted his skill in garnering state and federal funding, and his stylish and witty manner. His Borsalino hats even enjoyed a brief vogue, though the Brioni suits were too pricey to become a trend. (No mere Armani for Willie.) The economy was strong, and capital flowed to San Francisco, one of the key financial and cultural hubs of the Pacific basin.

But as Brown’s term wore on, as homelessness, transit, affordable-housing and city-corruption woes grew more serious, Brown‘s trademark egotism -- “My body would reject anything less than Brioni” -- became far less endearing. With his once stratospheric approval rating down to 35 percent, two major candidates challenged him for re-election. Former Mayor Jordan, who could count on a solid base among conservative voters, figured that his own rather hapless tenure looked squeaky-clean in retrospect. But it was Clint Reilly who most worried the Brown campaign, if for no reason other than the one they best understood: money. Reilly had made a fortune by running winning local and losing statewide campaigns. Reviled by state Democrats for steering Kathleen Brown’s 1994 gubernatorial campaign into the ground, he also had managed Jordan‘s losing 1995 re-election campaign against Willie Brown -- thereupon opting to leave politics and devote his time to a burgeoning real estate portfolio.

In the tong-war fashion of San Francisco politics, Reilly hated Willie Brown and his political consultant Jack Davis, who had once been Reilly’s protege. The feeling was mutual. Reilly, they felt, would spend whatever it took from his personal fortune to take down Willie Brown.

In the end, Jordan proved an inert, blast-from-the-past candidate. And Reilly did spend whatever it took. But his $4 million -- a record $185 per vote -- availed him very little, for he was destroyed before he had the opportunity to destroy Brown. By his ex-partner Davis, who revealed an ugly 1980 incident -- long discussed in state political circles -- in which, he said, Reilly had beaten a woman into unconsciousness, breaking her jaw.

Reilly, who was running second and beginning to move up until the revelation, saw his support plummet. In a debate against Brown and Jordan, Reilly offered an account of his conduct that differed in one detail from Davis‘. “No bones were broken,” Reilly insisted. With that, his campaign was over, and so was the election -- at least between the three main candidates whose names appeared on the ballot.

But Reilly’s massively funded campaign against Brown had taken a toll on the incumbent. As well, the swirl of negative campaigning from the three major candidates disgusted many San Franciscans. The way was clear for an alternative.

Just three weeks before the November 3 election, that alternative presented himself. Board of Supervisors President Tom Ammiano, who had flirted with a mayoral candidacy for months before taking himself out of contention during the summer, reversed field and declared himself a write-in candidate. Almost instantly, volunteer workers were spilling out of Josie‘s Juice Joint and Cabaret, a nightspot turned impromptu campaign headquarters at the edge of the Castro district.

The effect was electrifying. The media and much of the public found the idea of this last-minute, low-budget, write-in insurgency both exciting and refreshing amid the sordid and morbid spectacle that the mayoral campaign had become. With no major endorsements save that of the Bay Guardian, the city’s longtime alternative weekly, with a campaign treasury of about $20,000, Ammiano shot past Jordan and Reilly, pulling down 25 percent of the vote and forcing Brown, who was held to less than 40 percent, into Tuesday‘s runoff.

Ammiano’s candidacy may have come out of nowhere, but he was certainly an established, if not establishment, San Francisco pol. A onetime schoolteacher and comedian, Ammiano served on the city‘s school board, then won election to the Board of Supervisors in 19TK. There, he spearheaded a campaign to raise the city’s hourly living wage to $11, championed more affordable housing, and opposed the coming of big chain outlets into the city and the city subsidies that have funded their arrival. Like a number of urban progressives across the country, Ammiano argued for a commuter tax into the city, and had also expressed interest in a stock-transfer tax. He was not, in short, the favorite of San Francisco business.

The mayor was furious that Ammiano had forced him into a second round. And apprehensive. One private tracking poll, taken just before the November 3 primary, showed Brown leading Ammiano by a statistically insignificant margin of 44 percent to 42 percent when the two were pitted against each other. Early on election night, ever the Machiavellian, Brown insisted that “Mr. Ammiano planned all along to launch an 11th-hour write-in bid.” Brown saw Ammiano‘s last-minute bid as a way to escape sustained media scrutiny, duck out of the sometimes ugly debates, and avoid months of attacks from the other candidates.