By Savannah Blackwell and Tim Redmond

ON A BLAZINGLY hot Saturday afternoon at the corner of Market and Castro Streets, volunteers for two San Francisco mayoral candidates vie for the attention of voters wandering the crowded sidewalks. It's not an uncommon scene – but this year it has a different edge.

On the east side of the intersection, longtime members of the Harvey Milk Lesbian, Gay, Bisexual, Transgender Democratic Club, including a shirtless Michael Goldstein, cannabis activist Dennis Peron, and housing activist Tommy Avicolli Mecca, hand out flyers promoting Sup. Tom Ammiano. They are all political veterans, survivors of decades of battles against the local political power structure, and for the vast majority of that time, Ammiano has been with them. So they're working for him today, even if they have to struggle to stir up the energy that four years ago made Ammiano synonymous with the battle to take back San Francisco.

Across the street several tattooed and pierced twentysomethings hold signs urging voters to support Sup. Matt Gonzalez, the upstart president of the San Francisco Board of Supervisors and Green Party leader. Inbal, 24, and her 25-year-old partner, Jen, tell us they both got involved in Ammiano's electrifying write-in effort in 1999. But this time around they just couldn't get enthused about his campaign.

"I haven't seen [Ammiano] doing a whole lot lately," Inbal said. "It doesn't seem like he's made the big stands he used to make. And it seems like Gonzalez is more firm about his beliefs."

The political heart of the city's queer community showcases some of the tension that underlies this local political season. The mayoral race this year is unusual even by San Francisco standards: three credible progressive candidates are in contention and, despite their best efforts to keep the campaign on the high ground, are ultimately fighting each other for votes, money, and energy as they try to concentrate on the shared goal of defeating front-runner Sup. Gavin Newsom. It's left in a fair amount of disarray the coalition of neighborhood activists, community organizers, labor unions, tenants, and environmentalists that only two years ago seemed to have broken the back of the Brown-Burton machine. More significant, perhaps, it's left a good number of political leaders, as well as part-time activists – the foot soldiers who provide energy and money to political campaigns – struggling to figure out where to put their time. Some are just sitting it out, denying any of the candidates the cash and clout that could help them define themselves as they head into a tough runoff.

The San Francisco Labor Council hasn't been able to settle on a single candidate, so the group's Labor Neighbor field operation remains in mothballs for this race. The San Francisco Tenants Union is deeply divided, as is the local chapter of the Sierra Club. State Board of Equalization member Carole Migden and San Francisco district attorney Terence Hallinan are both staying neutral – in part, they told us, because they don't see one obvious leader among the candidates, and they want to maintain good relations with all three.

Public Defender Jeff Adachi held a fundraiser for Ammiano Sept. 12 – even though he has also endorsed Gonzalez.

So, through a perfect storm of political ambition, weak leadership, and yes, a touch of real, old-fashioned democracy, the San Francisco independent and progressive movement has three champions – and just a month before Election Day, none of them has broken out of the pack as a clear front-runner who actually stands a chance of beating Newsom in a December runoff.

For anything resembling a close parallel, you have to go back to 1991, when then-supervisor Angela Alioto and then-assessor Richard Hongisto challenged incumbent Art Agnos, who had been elected with strong progressive support but then quickly alienated much of his base. Neither Alioto nor Hongisto picked up much traction, and former police chief Frank Jordan, running from a fairly united right, slipped into the Mayor's Office.

This time around, of course, is very different: there's no incumbent, and all three progressive are campaigning hard, mobilizing voters and demonstrating they have at least the potential to make it to a runoff.

But it's a complex and tricky situation that illustrates the dilemma the city's left, long marginalized and fighting a powerful downtown-backed machine, faces as Mayor Willie Brown's career in local politics comes to a close and the machine he runs starts to dissolve into oblivion.

On the one hand, the fact that there are three strong candidates – and no powerful kingpin deciding who is allowed to carry the progressive banner – bodes well for the sort of robust democracy San Francisco has too often lacked under the thumb of the machine.

On the other hand, the fact that there are three strong candidates demonstrates that the machine's opponents are still unable to find – or perhaps, to accept – strong, respected leadership.

As Green Party activist Ross Mirkarimi, who is working for Gonzalez, told us, "It's both sobering and empowering. We're emerging from one generation and political climate into a new one, and we're in an awkward adolescence.

"It's a free-for-all, but I think it's somewhat healthy."

The Ammiano days

How did this happen? It's a long and not always happy story.

In November 2000 there was absolutely no doubt about who was the ranking player in the San Francisco left. Ammiano, coming off a mayoral write-in campaign that, while unsuccessful, generated a level of grassroots energy that has reached almost mythical proportions, lead a rebellion that tossed almost all of Brown's allies off the Board of Supervisors. Gonzalez, Aaron Peskin, Jake McGoldrick, Gerardo Sandoval, and Chris Daly were all elected either with Ammiano's strong support or with the backing of his army. He was elected board president almost by acclamation.

But over the next two years, some of the shine on Ammiano's armor began to tarnish. He started squabbling with some of the newcomers over both substantive and relatively minor issues. After a public power measure he authored lost by only a few hundred votes in 2001, he angered activists by dragging his feet drafting a new measure, then pushing one that was far more moderate. The board, over his opposition, adopted amendments by Gonzalez that made the new measure stronger (although it, too, was unable to overcome a multimillion-dollar Pacific Gas and Electric Co. campaign and lost at the polls).

In 2002, Ammiano's handpicked candidate for state assembly, Harry Britt, lost to a one-time Brown ally, Mark Leno. Then Eileen Hansen, his candidate for supervisor in the heavily queer District Eight, lost to a former Brown staffer, Bevan Dufty. And early this year, his choice for board president, Aaron Peskin, lost to Gonzalez.

Part of what happened, of course, was that Ammiano was no longer the lone progressive voice holding down the left flank of the board.

"You have to look at the whole picture here," Peskin told us. "When you had a board that was a wholly owned subsidiary of a supremely powerful mayor that was essentially a rubber stamp, Tom was the lone voice of dissent. But he woke up one day and had to retool himself to be a different kind of leader."

But part of it was also a calculated strategy to move Ammiano just a tad to the center to help attract a broader base of support for the mayoral race. That was bound to leave him open to criticism from the city's left, which has a long history of eating its own.

"That's the trick," David Novogrodsky, executive director of International Federation of Professional and Technical Engineers Local 21 told us at the time. "He needs to broaden his base. But how does he do that and remain himself?"

Between 2001 and 2003, on tough issues such as the business-tax repeal and the contract giving Clear Channel Communications control over newspaper distribution in parts of the city, Ammiano shifted from the go-to progressive – the one whom activists could always count on – to a politician more willing to compromise, to search for what he could portray as a reasonable deal.

That was, in part, a reflection of reality: the 2000 victories were the result of a broad group of voters, across the political spectrum, rebelling against Brown's corruption, and the next mayor would have to be able to reach out beyond the traditional "progressive" groups to win over voters in the center. But while they angered his core constituents, Ammiano's moves didn't seem to be winning over a lot of moderate voters to his camp.

He was also visibly tired. He told us last December he was "exhausted" after the 1999 and 2000 campaigns. On some issues, like homelessness, he never demonstrated a strong leadership role, leaving less-experienced supervisors to carry the ball against Newsom's antihomeless juggernaut.

Still, Ammiano had his defenders – plenty of them. After all, his political career hardly began in 2000. For much of the 1990s, Ammiano was the only one at city hall whom activists could turn to for help, and he had a long list of accomplishments. Benefits for domestic partners, district elections, tenant protections, living-wage laws, and clean-government reforms – all those were Ammiano victories, and without him, they might never have happened. He made some mistakes, supporters said, but on balance he was the only one with the experience and consistent history.

But by the spring of 2003, with Newsom gearing up for a multimillion-dollar mayoral blitz, Ammiano's campaign was almost nowhere. He had little money, and it wasn't clear who, if anyone, was actually handling strategy or day-to-day operations. And worse – much, much worse – a lot of Ammiano's army was AWOL. With the disappointment of some hardcore activists and the seeming lack of campaign direction, Ammiano for Mayor 2003 wasn't generating anything close to the excitement the 1999 write-in had.

Ammiano was urging patience. With the recall dominating the news, he and his advisers pointed out (with some justification), the mayoral race wouldn't begin in earnest until October. With Ammiano's record, history, and name recognition, his advisers said (again, with some justification), there was a good chance he'd make it into a runoff even without much money – and once that happened, the donations would almost certainly pour in. But patience has never been a virtue of the local left, and even some of Ammiano's allies were starting to get nervous.

Alioto, meanwhile, was loudly mounting her own mayoral run. Buoyed by millions of dollars she'd earned as a private lawyer handling civil rights cases, the former supervisor had hired a team of high-priced consultants (including Duane Baughman and Doug Schoen, who had helped engineer the election of Mayor Michael Bloomberg in New York City) and was aggressively seeking endorsements, arguing she was the only one capable of beating Newsom head to head.

Alioto had strong progressive credentials: she was a staunch public power advocate, a strong supporter of public health and social welfare programs, and a vocal critic of Brown's corruption. Her platform, however, was a good bit to the right of Ammiano's in some areas: she didn't support higher taxes on businesses, for example, and wasn't a big fan of district elections. By late summer Alioto had lined up a fair amount of labor support (including the huge local Service Employees International Union) and had the endorsements of some onetime Ammiano allies, like Supervisor Sandoval.

Two weeks before the deadline to file as a candidate for mayor, the polls generally showed Newsom strongly in the lead, with between 32 and 38 percent of the likely vote, followed by Ammiano at around 18 percent and Alioto a few notches behind that. But neither Newsom nor Ammiano had moved up at all since early spring, suggesting to some observers that the front-runner could be beaten – but that Ammiano wasn't showing the political strength to pull it off. And since Alioto wasn't exactly bursting out ahead of the pack either, some progressive leaders (particularly Peskin and Gonzalez) started scrambling around looking for another candidate.

Peskin commissioned a poll that showed (to nobody's surprise) Migden and state senator John Burton had strong name recognition and would be popular candidates. But it also showed surprisingly high numbers for Gonzalez – and when it became clear there was no deus ex machina ready to fly in from above, Gonzalez – who had less than three years' experience in elected office – decided to jump into the race.

Up against Gavin

Two months later, with the furor over the gubernatorial recall sucking up much of the media's time and energy, the results look like this: Ammiano has apparently dropped a few points in most polls, to around 15 or 16 percent, and Alioto is nearly even with him. Gonzalez's own poll shows him just a few points behind the two – leaving the three candidates in what amounts to a statistical tie, splitting the 45 percent or so of the anti-Newsom vote. (That same poll shows Gonzalez tied with Newsom in a head-to-head contest; Alioto's polls, not surprisingly, show her running strongly against Newsom also.) There was little doubt Gonzalez's entry had damaged his onetime mentor, that the young political newcomer was taking votes away from the longtime progressive icon whom many hoped would become the city's first openly gay mayor.

Obviously, if the person who emerges at the head of that pack gets the backing of the two other candidates' supporters, he or she could still mount a formidable challenge to Newsom. But it's going to be tough: while Newsom is running a high-powered campaign that will send him into the runoff with clear momentum, the three top challengers are arguing over who best represents the opposition and using up precious time and money trying to win what amounts to a "progressive primary."

Instant-runoff voting was supposed to ensure that scenario never happened again. Under the proposal, passed in March 2002, voters would rank their top three choices, and the second- and third-place votes for candidates who finished out of the running would be distributed to the top two. That way, if the three progressives together managed to inspire a strong voter turnout, one of them would have had an excellent chance to finish in first place.

But the city's Department of Elections, through a combination of intentional delays, foot dragging, and incompetence, never managed to implement the system.

Some, like Migden, say the scenario is a disturbing sign of a lack of political coherence. "There's no large, authoritative, convening force to step in and say, 'We need some discipline here,' " Migden told us. "We have the entry of candidates who are not coming from an organized, committed union of the left that's implementing a strategy."

And indeed, in its heyday the machine built by U.S. representative Phil Burton was notorious for its efforts – generally successful – to keep candidates in line. One legendary example: In the early 1960s, a young Burton approached U.S. representative Jack Shelley and told him he should give up his seat in Congress and run for mayor. The way John Riordan, who was an aide to Shelley at the time, told us the story, Burton gave Shelley the facts of life: if he didn't get out of Washington, Burton would run against him. "I'll lose the first time," Burton said. "But the second time, I'll beat you."

Shelley ran for mayor and won, and Burton took over his seat in the House.

But Phil Burton has been dead a long time, and the machine he created – now in the hands of Mayor Brown and, to some extent, John Burton – is heaving and creaking as it faces its own demise. San Francisco politics in 2003 is an unruly scramble: Newsom has raised millions of dollars, much of it from the same people who have supported Brown, but he isn't entirely a machine operative (John Burton, for example, is furious over Newsom's scapegoating of homeless people). And with the advent of district elections – and the clear public revolt against Brown's top-down politics – there's no single power broker who can call the shots on any part of the political spectrum.

After all those years when a few handpicked candidates dominated elections, when democracy almost seemed like an annoyance to the cadre that ruled the city, the somewhat anarchic scene of today is refreshing. Nobody could have predicted 10 months ago that Gonzalez, a relative newcomer to electoral politics who's not even a Democrat, could get elected president of the Board of Supervisors. And when he decided at the last minute to run for mayor, nobody tried to slap him down – in fact, there was nobody in a position to do it.

Green Party activist Mirkarimi suggested the changes in the political scene are in part a reflection of the rise of the Green Party. "San Francisco has been spoon-fed the agenda of the Democratic Party for years," he explained. "Now you can see that the city is taking a new path not engineered by any one party."

That's nothing to lament; it's a wonderful development. And indeed, all three candidates have brought valuable ideas to the race, and all of them have something to offer. Ammiano's record is long and impressive – for many years, against huge odds, he was one of the only voices in city hall for the neighborhoods, labor, public power, tax reform, the homeless, and the legions of San Franciscans who were ignored or dismissed by the machine. Alioto also has a long record and speaks with unbridled passion about causes others won't touch. Gonzalez is inexperienced, but he articulates a clear progressive vision and brings tremendous energy to the race, and his campaign has generated some real grassroots excitement.

But the progressive and independent forces that united behind Ammiano four years ago are still a long way from running San Francisco – and if they want to take back the city, they'll need more than a spirit of democracy and good intentions. Politics at the level of the mayoral race is serious business. And if, as is widely predicted, Newsom becomes the city's next chief executive, it will be in part because the people who oppose his divisive and regressive politics weren't able to produce a standard-bearer to unify their broad coalition.

Three years ago that job was Ammiano's to take – and in fact, some were openly talking about the onset of an "Ammiano machine." But running a political machine wasn't in his nature – and besides, that model is anathema to San Francisco progressives, who are, after all these years, rightfully dubious about the heavy-handed exercise of political power.

But an old-fashioned machine isn't the only model for political leadership. For many years, particularly in the 1980s, Berkeley progressives organized together under a broad-based and stunningly effective group called Berkeley Citizens Action. BCA held open meetings and annual conventions and functioned like a combination community organization-political party. It provided a forum for debate, a training ground for activists – and to a remarkable extent, helped unify the left and neighborhood coalitions behind one set of candidates for city office. After the Ammiano write-in, a number of local activists started talking about the need for a real community-based political group to fill that role, but it never came together.

So now, with the election a month away, San Francisco has every indication that the progressive-independent movement is alive and well, that the old machine is dying, and even that Newsom can be beaten. But on a strategic level – the hard, cold political calculus that often wins elections – the movement is not quite on top of its game.

"If you had asked me five or six years ago if the left would have candidates in the numbers that they have now, I would have been doubtful," San Francisco State University political science professor Rich de Leon told us. "So the movement is strong. But the question is, can [the left] get its act together and unify when it has a strong chance of succeeding?"