San Francisco — Whoever came up with San Franciso Mayor Willie Brown’s re-election slogan — “He‘s One of a Kind” — has a definite eye for turning lemons into lemonade. What other American big-city mayor would have the gall to make such statements as “Democracy is best served if I am unopposed [for re-election]” (a Brownism of a couple of years back), or “People shouldn’t live here if they don‘t make $50,000 a year” (Brown’s solution to the city‘s gentrification woes)? Or to muse about turning the old Treasure Island naval base in the middle of San Francisco Bay into a site for a casino? Or to proclaim “Exotic Erotic Ball Day” and “Marilyn Chambers Day” (“in the Barbary Coast tradition”), as Brown did earlier this year?

More seriously, the problems Brown had promised to address during his initial campaign for mayor four years ago — the bloated and extraordinarily inefficient public-transit system known as the Muni (for Municipal Railway), and the burgeoning numbers and aggressive conduct of homeless people — have only worsened during Brown’s first term. New problems have emerged as well. San Francisco has become an increasingly pricey place to live. Gentrification‘s set in; affordable housing has all but vanished; big chain outlets have displaced neighborhood stores.

In the midst of which Mayor Brown embarked on a gentrification campaign of his own: a massive drive to refurbish the city’s once elegant City Hall, displacing some city departments in favor of statuary. Longtime Brown associates like Jack Davis, his campaign manager, cashed in on the boom, making hundreds of thousands of dollars from corporations seeking to take advantage of the new commercialism. The city‘s housing and minority contracting operations became the focus of FBI probes, and some Brown associates were implicated in the allegations.

Still, it came as a surprise to many that Brown had to campaign so hard for re-election. The legendary political mastermind, speaker of the California Assembly for a record-setting 15 years, a sensationally popular mayor during his first year in office, saw his popularity plummet and an unexpectedly dramatic challenge to his re-election take hold.

Brown had to scramble hard to stave off the insurgency of his populist challenger from the left, San Francisco supervisor and self-styled “Queen of Gay Comedy” Tom Ammiano. The president of the Board of Supervisors, whose late-breaking write-in campaign swept him past former Mayor Frank Jordan and multimillionaire ex–political consultant Clint Reilly in the November 3 primary, forced Brown into a December 14 runoff.

But scramble hard Brown did. Turning the squeaker of six weeks ago into a landslide, he crushed Ammiano Tuesday night by a TK percent to TK percent margin. At his victory party at the Longshoremens’ Hall on Fisherman‘s Wharf, Brown was surrounded by a throng of liberal activists and a parade of pols, including Assembly Speaker Antonio Villaraigosa, who called Brown, “my big brother.”

“I didn’t win this,” Brown exulted to the crowd. “You all did!” But absent from view and mention were most of those who had provided Brown with the avalance of soft money that powered his landslide. Ammiano‘s energetic campaign registered 14,000 new voters in the past month, but they weren’t enough to overcome the big lead Brown and his free-spending business allies built up among the usual voters.

It wasn‘t supposed to have been this way.

Willie Brown’s election four years ago seemed to signal both the renewed ascendancy of San Francisco‘s fabled liberallabor political machine and the political flowering of the City by the Bay’s fascination with superstardom. Initially, Brown seemed perfectly attuned to the new San Francisco. A city entranced by its athletic superstars and status as the world‘s favorite tourist destination saw in the stylish Brown someone who would represent it well in the national media. First elected to the state Assembly in 1964, Brown had become a spellbinding speechifier, an elegant dresser and the master of backroom intrigue. Leaving his hardscrabble Texas upbringing behind him, Brown arrived in San Francisco at the end of the ’50s, educated himself in the public universities, and embarked on a career in politics through the patronage of the late Congressman Phil Burton, a towering figure in American liberalism. He moved to the pinnacle of power in California 19 years ago, when he took advantage of a split between Democratic factions to seize the speakership with Republican votes. From there, he went on to become a master of legislative logrolling and big-money politics, as well as the most powerful African-American elected official in America.

For all his mastery of the inside game, though, Brown became a symbol of a corrupt, entrenched political system in California. Though he escaped the fate of several associates swept away by scandal, he was powerless to stop — indeed, was the poster boy for — the initiative campaign for term limits, which state voters enacted in 1990. Forced by this constitutional amendment to give up his Assembly seat of 31 years, Brown decamped in 1995 to San Francisco, where he unseated the incumbent conservative mayor, Frank Jordan, an ex–police chief and a nostalgic throwback to the old San Francisco of Irish pols and cops, who had himself defeated a member of the Burton-oriented liberal machine four years previous.

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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.

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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.

Later that night, at his own election-night party, where the casual style of the late ’70s predominated and there was scarcely a suit in sight, Ammiano insisted that he wasn‘t that clever. Indeed, he seemed somewhat apprehensive about the prospect of being in the runoff, protesting that he wasn’t even all that sure that he had made it.

Perhaps he knew that he and his campaign weren‘t quite ready for their new heights. In a San Francisco Examiner poll just a week after the first round of voting, Brown regained the edge over Ammiano by a 43-percent-to-33-percent margin. Tellingly, Brown’s numbers hadn‘t really gone up from the tracking poll, but Ammiano had dropped nine points.

It seemed that Ammiano’s new media exposure actually worked to his detriment. Though he was actually viewed more favorably by likely voters, he was not coming across as a strong executive. As one Democratic consultant put it after an Ammiano television appearance, “He comes off distractingly effeminate, even for San Francisco” — in contradistinction, he might have added, to such onetime leading local gay elected officials as Supervisors Harvey Milk and Harry Britt. Campaign focus groups soon confirmed the consultant‘s observation: The candidate lacked what many participants considered a proper “executive presence.”

Ammiano had a further problem: Though he was running to Brown’s left, most of the large number of undecided voters, a quarter of the likely electorate, were moderates and conservatives. While Brown‘s more conservative challengers, Jordan and Reilly, were loath to support Brown (Reilly actually endorsed Ammiano), the wily mayor moved to lock up the right, adding the endorsement of the local Republican Party to that of the Democrats.

The failure of Ammiano to broaden his base of support enabled Brown to reclaim the lead. Insurgents often prove to be temperamentally unsuited to the task of taking ultimate advantage of the cracks in the political system that they have helped create, and Ammiano proved no exception to this rule. Brown was free to feint to the right, moaning to columnist George Will about the “heavy left” (which would presumably make him the light left), and promising to support a review of rent control. But he was also free to revert to old form.

He began, on primary night, by, in essence, apologizing to the city for his arrogance and inability to solve the high-profile problems of the homeless and the blundering public-transit system. Right after that, he went to Las Vegas for a few days to relax and to attend a fund-raiser on his behalf hosted by that city’s new mayor, former mob lawyer Oscar Goodman. Upon his return, Brown complained that Ammiano‘s write-in candidacy had played havoc with democracy — depriving him of victory in the primary and costing the city money to hold a runoff election.

Despite Ammiano’s grassroots appeal, virtually every major left-liberal organization stuck with Brown. The venerable Alice B. Toklas Lesbian and Gay Democratic Club placed an ad on TV, featuring a gay couple fretting over Ammiano‘s “far-out tax proposals.” And even though Ammiano champions labor’s cause on the San Francisco Board of Supervisors, 103 of the city Labor Council‘s 104 affiliates have backed Brown — an amazing figure that neatly matched the near unanimity of Brown’s backing from financial interests.

In the primary, Brown, who mustered $2.5 million for his campaign, was also aided by over $600,000 in “independent expenditures” on his behalf from major business and labor interests and the state Democratic Party. For the runoff, both Brown and Ammiano were limited to $400,000 by the city‘s campaign-finance-reform law, a total that Brown reached easily but Ammiano was unable to achieve. But that law does nothing about independent expenditures, and Brown’s allies acknowledge spending another $1.3 million on his behalf.

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Thanks to a ruling from the state‘s compliant Fair Political Practices Commission, the source of most of these funds won’t be disclosed until next month. It was veteran political lawyer Joe Remcho who successfully argued before the FPPC that such “independent expenditure” committees shouldn‘t have to disclose their contributors in a timely fashion, and who won another ruling that allowed these committees to escape the city’s limits on contributions to candidate committees. Remcho works for Willie Brown and for San Franciscans for Sensible Government, a group that spent massively on Brown‘s behalf, controlled by super-rich San Francisco developer Walter Shorenstein.

Willie Brown’s victory doesn‘t make his core Democratic and liberal supporters all that happy. The mayor had to move rightward to win. Worse, he had to further indebt himself to big-money interests.

Though Ammiano’s challenge fell short, the power of his write-in insurgency was another reminder that big-money machine politics, even big-money liberal machine politics, is turning off voters in the Bay Area, California‘s liberal heartland. The defeat of longtime Brown ally and former Oakland Mayor Elihu Harris by a little-known Green candidate in a special election for the Assembly early this year was the first wake-up call for the Bay Area’s Democratic establishment. Brown‘s tribulations and Ammiano’s rise should be the second. But is anybody listening?

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