It’s been dubbed the “queer celebrity death match.” The race to succeed Supervisor Bevan Dufty is the most competitive local election of 2010, with four openly gay and well-connected candidates running to represent a district that boasts the highest voter turnout in the City. Land use attorney Rafael Mandelman, Assistant District Attorney Rebecca Prozan, PUC assistant manager Laura Spanjian and Deputy City Attorney Scott Wiener have been campaigning for a year, raising money and endorsements – even though the election is not until November. Can progressives win a seat that has eluded them for years? While the two gay political clubs have taken sides in this race, how will the SF Democratic Party endorsement play out? And with two candidates aligned in the “moderate” and “progressive” camps, what’s the path to victory for the other two – who are formidable in their own right? And probably the most intriguing question of all – how will Ranked Choice Voting affect the outcome? Join me below the fold ...

District 8 is commonly known as the “gay seat,” because it includes the Castro and Noe Valley neighborhoods. Despite being ranked the third most progressive district in the City (according to the Progressive Voter Index), in the past ten years District 8 voters have not picked the “progressive” candidate for Supervisor when offered that choice. Eileen Hansen lost to Mark Leno in 2000 and to Bevan Dufty in 2002, and Dufty was re-elected in 2006 over Alix Rosenthal. It’s also been suggested that with gentrification, the district has become more moderate.

But District 8 Supervisors have also not marched in unison with moderates – playing the “swing vote” on key issues. Leno, for example, cast the eighth vote in 2001 to override Willie Brown’s veto of TIC legislation – and in Sacramento has proven to be one of our most progressive state legislators. Dufty has been less pro-tenant than his predecessor, but has increasingly voted with the Left – such as on David Campos’ ordinance to protect immigrant youth.

In other words, it’s a district where a progressive “should” win – and Rafael Mandelman is clearly auditioning for that role. The President of the Harvey Milk LGBT Democratic Club already has the endorsements of Assemblyman Tom Ammiano; Supervisors John Avalos, Eric Mar, Chris Daly and Ross Mirkarimi; School Board members Jane Kim and Mark Sanchez, and the Milk Club. Expect more similar endorsements – but if history is any guide to how District 8 voters think, Mandelman will need to expand his support.

The other three candidates – Scott Wiener, Laura Spanjian and Rebecca Prozan – are all past co-chairs of the more moderate Alice B. Toklas LGBT Democratic Club. The Club recently made an early endorsement of Wiener and Prozan because, according to current co-chair Bentrish Satarzadeh, “they most emulate what Alice stands for and its values.” When asked to explain the Club’s values, she said: “being in touch with the community and loyalty.” Loyalty, said Satarzadeh, is “not going where the political winds blow.”

Spanjian had a different theory for not getting the Alice endorsement, despite also having been co-chair. “I’ve worked closely with both the Alice and Milk Clubs,” she said. “I work with people of all sides of the ideological spectrum. Certain groups don’t like that, but I think voters do.” Spanjian is endorsed by former Supervisors Leslie Katz and Susan Leal, and has the support of moderates in this race like Assemblywoman Fiona Ma and Roberta Achtenberg. But she also ran for the Democratic Central Committee on the progressive hope slate and her campaign manager – Jim Stearns – has worked for Aaron Peskin.

Scott Wiener is an early front-runner among moderates – with endorsements from Mayor Gavin Newsom, Supervisor Sean Elsbernd and the Firefighters Union. His complete list of endorsers deftly organized by neighborhood include landlords Kim Stryker and David Fix (from Small Property Owners of SF) and Plan C Chair Mike Sullivan. Wiener’s association with Plan C has been raised in the past, and it appears that the group has now rallied to his support.

But Rebecca Prozan has cut into support from moderate small business owners, with her past in the Office of Neighborhood Services under Mayor Willie Brown. She also has the support of Supervisor Michela Alioto-Pier, School Board members Steve Ngo and Rachel Norton and her boss – D.A. Kamala Harris. Practically everyone I’ve talked to has said the same thing: Prozan will outwork everybody. She generated a lot of goodwill from the Obama campaign, and people will come out of the woodwork to walk precincts for her.

What are the Candidates’ Relative Chances?

The dynamics will be far more evident after June 8th. Mandelman, Spanjian and Wiener are all on the SF Democratic County Central Committee – and are running for re-election concurrent with their Supervisor races. Expect them to have lots of volunteers in June, hoping to yield a strong showing that impresses insiders going into the November 2nd election. That David Campos was the top vote-getter for DCCC in June 2008 (compared with his District 9 rival, Eric Quezada) had an impact in shaping perceptions for that race.

And the June DCCC results will also affect who gets the Democratic Party endorsement. If progressives keep control, it will help Mandelman and (to a lesser extent) Spanjian. But if the moderates – who will not let themselves get caught flat-footed like they did in 2008 carry the day, Scott Wiener will be the biggest beneficiary. Expect more “slates” to emerge.

Of course, there’s also the impact of Ranked Choice Voting. Right now, Wiener and Mandelman are the two favorites in the District 8 race – because they are the top choices of the moderate and progressive camps, respectively. At this early stage of the game, the few people following this race are intense partisans – and both Wiener and Mandelman are benefiting from the institutional support that a “machine” brings. But it also means they have the highest number of people who dislike them, which can hurt them later on.

In the District 4 race to replace Fiona Ma, political observers assumed that the winner would either be Newsom’s candidate Doug Chan – or progressive favorite Jaynry Mak. Instead, they both lost – because the two factions got negative with each other. Ed Jew was everyone else’s “second choice” – which allowed him to quietly finish in first and get elected.

Spanjian and Prozan pride themselves on being unaffiliated with either political faction, a smart strategy in the long run. But it also means they must work harder now at building a campaign infrastructure. Spanjian says that it’s forcing her to “run a more grassroots campaign” – and she’s replicating Bevan Dufty’s strategy of a self-imposed contribution limit of $150 per donor. And of course, Prozan has a reputation for being a hard worker.

Voters are still getting used to Ranked Choice Voting, which is relatively new. In the 2008 Supervisor races, very few cast strategic votes for their “second-choice.” A candidate still needs a large base of people who will pick them as a “first-choice” – so they can emerge as one of the top two contenders. So Spanjian and Prozan will have their work cut out for them.

But a candidate with high name-recognition is also likely to get a lot of “sloppy seconds,” which gives Wiener, Mandelman, Spanjian and Prozan an incentive to campaign hard to get their name out there. And like in the District 4 race, “going negative” also creates the risk that voters will go with anyone but one candidate – who can finish last.