San Francisco's District 5 has been considered one of the City's most progressive, or to quote John Burton, "What we used to @#%$&*! call liberal." "D5" has gone through some tumultuous times these past 10 months; its previous and popular supervisor was elected Sheriff and became embroiled in a domestic incident which led to his arrest, suspension and a controversial reinstatement which has pitted neighbor against neighbor and the members of the "City Family" against each other. In its wake, a new supervisor was appointed, and a new crop of challengers and controversy ensued. Frankly, I've never seen anything like this in a D5 election. There have been so many twists, turns and "October Surprises", that I'm almost afraid to open my mailbox. On Tuesday, the voters of District 5 will have to sort through the drama, the politics, the anger and the angst, to pick either the embattled incumbent, or one of the challengers, each with an interesting history of their own. On Wednesday, I'll analyze the early results of ranked choice voting, but first, a brief look at the individuals, their challenges and chances to win the race.

The Incumbent

The incumbent is Supervisor Christina Olague, a recent emigre to D5 from D2, a progressive veteran, a former Planning Commissioner, and the first bisexual Latina to hold the office. Hand picked by the more moderate Mayor Ed Lee, Olague seemed to be in the driver's seat, as incumbents rarely lose these races. However, after her controversial vote for the 8 Washington development project, Olague drew fire from her fellow progressives and seemed to be vulnerable from the new challengers. Next, in a move seen by many as more political than pragmatic, Olague was the first of 4 Supervisors to reinstate the suspended Sheriff, Ross Mirkarimi, once an extremely popular, former D5 Supervisor until his highly public, and tragic domestic troubles with his wife and neighbors overtook him. The backlash for that vote has recently seen the Mayor disappointed in his appointee; the triggering of thousands of dollars being spent in a campaign to unseat her; viral anti-Olague YouTube videos, emails and a drop-mail blitz. Olague may yet still win, but only if the last minute efforts by a variety of domestic violence advocates and other monied interests fail to persuade the D5 voters. Olague will also need the second and third place votes of her competitors to put her over the top to win. One thing not mentioned very often in District elections, is that voters like to elect one of their own, a native or someone with deep neighborhood roots. That may work against Olague here in D5.

The Challengers

The challengers are many, although only 4 have been deemed by the pundits to have a legitimate chance at unseating Olague. London Breed, an African American D5 native, is also a former Redevelopment Commissioner, head of the African American Art & Cultural Complex and seen by many to be one of Olague's biggest challengers. Like Olague, Breed has raised a lot of funds, has plenty of endorsements, but has also courted controversy. Breed's outspoken comments cost her an endorsement from Senator Diane Feinstein, but remains in good stead with CA Attorney General Kamala Harris. Several years ago, I watched Breed and Rebecca Prozan work and win to become Obama delegates in 2008; she is no stranger to campaigning. Many believe however, that Breed's base in D5 is small and despite her pleadings, her ties to former Mayor Willie Brown and her votes as a Redevelopment Commissioner may come back to haunt her. Breed will also need to get a lot of the second and third place votes, and if she survives deep into the ranked choice rounds, she may have a shot. Both Breed and Thea Selby have recently appeared on two-sided door hangers, urging voters to vote for one or the other; an odd pairing which, like the Olague/Rizzo co-endorsements, may end up helping or hurting them both. I also have to ask the question: Can an African American actually win in D5? Do Breed, Davis, (and Daniel Everett) actually have a chance in a District that now has fewer African Americans than Bayview or the Tenderloin? History says no; Malia Cohen barely defeated Tony Kelly in the D10 race of 2010, and only because all of the other African American votes ultimately went her way in the ranked choice voting rounds. Breed doesn't have that option in D5.

John Rizzo, is another longtime D5 resident; a software expert & family man, a Trustee of the SF Community College Board and has also garnished a ton of endorsements from both environmental and political groups. Like Olague, Mirkarimi, Matt Gonzales and Supervisor Jane Kim, Rizzo is another former Green Party member who made the switch to the Democrats. And like Olague and Breed, Rizzo's tenure with the Community College Board has also been at the center of some well documented controversy. Nevertheless, Rizzo has raised money, and has seemingly stayed out of the way of the heated exchanges between the camps of Olague, Breed and Julian Davis. To win, Rizzo will need the majority of the second and third place votes of the other progressive candidates, (Davis, Selby, Johnson, Resignato), if they are eliminated before he is, to beat or come within in striking distance of Olague, and only if the voters turn on her and pick Rizzo as their first or second choice. Olague and Rizzo recently co-endorsed each other, a strategy that could benefit Olague, or Rizzo, or backfire on both.

Julian Davis was once considered the biggest, progressive threat to Olague. In the wake of the Mirkarimi affair, rumors and so-called revelations about Davis and his treatment of women appeared, however his ill advised responses to the accusations ended up costing him all but a handful of endorsements, including the SF Bay Guardian. Even before the endorsements, Davis was considered a longshot at best, and only Olague's seemingly moderate voting record on the Board of Supervisors made the progressives take a second look at Davis and Rizzo as the candidates best suited for the job. Davis' missteps and lack of funds have been deemed fatal by nearly all of the pundits and political watchers. It will take a miracle; the elimination of all of the other progressives and a massive desertion of Olague supporters for him to win.

Thea Selby has been a D5 neighborhood leader for years on the Divisadero & Lower Haight corridors, and the good natured Mom, wife and activist has endeared herself to many. Selby has also raised money, however, unlike the other major competitors in the race, Selby isn't a politico, and doesn't have the "name I.D." or recognition, (good or bad). For Selby to win, she will need the aforementioned votes and hope that the voters of D5 have become so disgusted with the controversy swirling around Olague, Breed, Davis and perhaps Rizzo, that they vote for her in such a way that ranked choice puts her over the top. I mentioned previously that Selby and Breed have recently appeared on two-sided door hangers, urging voters to vote for one on one side of the hanger, or the other on the flip side. I think the strategy has the potential of benefitting the bigger vote-getter; hard to say who that would be, but unlike Selby, Breed's literature is seemingly everywhere. Stranger things have happened, just ask the residents of District 2 and District 10.

The other competitors may be a little less known, but not any less controversial, and were never seen as real threats, due to their lack of a base and or funds. Hope Johnson sat on the City's Sunshine Task Force, an entity the City almost wishes it never created. An outspoken writer, columnist and blogger, Johnson knows the world of SF politics well, perhaps too well; she once won the SF Usual Suspects annual, "Best Political Mind" award, however neither Johnson, Andrew Resignato or the aforementioned Everett, were deemed to have had much of a chance, although Johnson & Resignato recently teemed-up for a "peoples ticket". Many suspect their presence elevated the debate and there is plenty of video evidence to support it. The earlier decision not to run by Entertainment Commissioner and Divisadero businessman Michael O'Connor, and the withdrawal of the popular Quintin Mecke due to family health reasons, may have reduced the drama and the vitriol, but would likely have split the vote among the D5 progressive base even more.

The Questions

Former D5 Supervisors Matt Gonzales and Ross Mirkarimi were extremely popular back in their day; both did a lot of good for D5 and the City, yet many folks in D5 are saddened by what has happened lately to the image of the District. Who will the voters deem to be the best candidate to address the ills, the housing and tenant issues, and everyday needs of the constituents of District 5? How will the women of D5 vote, following the Mirkarimi debacle and the latest attacks on either Olague or Breed? Are the voters of D5 so sick of the City Hall drama and the post-Mirkarimi vote, that they would be willing to unseat Olague, or are they too fearful of what Breed may do? Who did a better job at GOTV and the absentee voting? Is Breed's base larger that anyone knew and can an African American man or woman actually win in D5? Can Rizzo benefit from any Olague/Davis camp defections? Could Selby actually pull off a miracle win?  Will the negative campaigning benefit Olague, or Breed, or will it benefit Rizzo, or Selby? More questions than answers? 

We will get a clearer picture on Wednesday.

Editor's note: Eric "Doc" Smith has been a homeowner in District 5 for 10 years, was a resident of District 10 for 2 years, and a former candidate for D10 Supervisor in 2010. He has publicly endorsed the John Rizzo Campaign for District 5 Supervisor.