Councilmember Rebecca Kaplan and Jean Quan with A’s co-owner Lew Wolff last summer.

MEET THE CANDIDATES This time four years ago, Jean Quan was viewed as the underdog to Don Perata. She erased a nine-point margin after the first round of the ranked choice voting race to upend the former State Senate pro tem. Mayor Quan had a rough early going–a bad economy, worsening crime and a response to Occupy Oakland that angered both protesters and the business community all at once. That she went through numerous city administrators and police chief like pairs of socks did nothing to quell lingering doubt about her leadership, but over the past year she has somehow begun to pull it all together. Crime is down, her guidance in cleaning up the city’s police department has been lauded, Oakland’s city finances are on the upswing and large development is flowing to Oakland. Theoretically, ranked choice voting attracts more candidates to races. In this case, 14 candidates entered the race because their early calculations found Quan vulnerable. In addition, they all viewed public safety as the singular issue of this race.

Port of Oakalnd Commissioner Bryan Parker was appointed by Quan in 2013. He quickly threw his hat into the ring by appealing to the city’s business groups and African American voters. The chamber of commerce and the San Francisco Chronicle endorsed Parker. Joe Tuman was the surprise fourth place vote-getter in 2010. He returns as the race’s toughest talker when it comes to fighting crime. Following the progressive renaissance in the New York City mayoral race, civil rights attorney Dan Siegel entered the race in January vowing to restore social justice and raise the city’s minimum wage to $15 an hour. Councilmember Libby Schaaf then entered the race and called for fresh leadership even though she has served on the City Council since 2010. However, Schaaf highlights a string of legislative successes involving government transparency, raising the minimum wage and slowing down Oakland’s rush toward surveillance cameras in public places. Her council colleague, Councilmember Rebecca Kaplan, hopes to parlay her appeal following two successful citywide victories into the mayor’s office. Kaplan finished third in the 2010 mayor’s race and is credited with helping Quan overtake Perata. Polls have shown Kaplan consistently leading as the first choice among voters. City Auditor Courtney Ruby opted against running for sure re-election this year to run for mayor. Her candidacy is predicated on being the only reform candidate with a record of cleaning up Oakland city government. These seven make up the first and second tier of candidates. Meanwhile, the third tier consists of eight political newcomers.

Jason “Shake” Anderson, a community organizer and member of the Occupy Oakland movement leads this group. In one poll last September Anderson had more support than Ruby, despite having significantly less financing. Ken Houston is a contractor for one of the city’s leading construction companies who vows to literally cleaning up Oakland’s streets. Saied Karamooz is a tech executive and frequent critic of campaign finance. Nancy Sidebotham is a well-known community leader who has previously run for the City Council. Other candidates include Patrick McCullough, Charles Williams and Eric Wilson. But, perhaps the most famous candidate in this race, at least nationally, is insurance broker and reputed multi-millionaire Peter Liu. Late night talk show host Jimmy Kimmel featured the off-beat and gun-totting Liu’s views on masturbation last week in his monologue.

Mayor Jean Quan

WHAT’S THE BEEF Many of the main competitors to Quan entered the race over a year ago or had their sights set on running against her for some time. Oakland in 2013 was being described in post-apocalyptic terms. Crime and death littered its streets, they said. Public safety was indeed Issue #1 and most figured it would in 2014, too. Well, crime, or the perception of an unsafe city, still permeates Oakland, the numbers say differently, though. In addition, years of dwindling numbers on the police force have reversed–over 712 are on the streets today. Since the summer, the rhetoric on crime has been somewhat subdued for fear of giving Quan a political football to spike in her own end zone. The line of attack by many has now moved to questioning Quan’s overall leadership. Tuman and Schaaf routinely seed their arguments with subtle messages that the mayor doesn’t “speak” right and therefore her leadership is suspect. However, candidates like Quan, Kaplan and Schaaf also find difficulty when their insider status is questioned by the likes of Tuman, Parker, Ruby and a few other third tier candidates. What began as a referendum on crime and Quan’s stewardship during those times has morphed into a very general argument against her re-election.

PAST RESULTS 2010 General Election (First Round): 1. Don Perata 40,342 (33.7%) 2. Jean Quan 29,266 (24.8%) 3. Rebecca Kaplan 25,813 (21.6%) 4. Joe Tuman 14,347 (12.0%) 5. Marcie Hodge 2,994 (2.5%) 6. Terence Candell 2,315 (1.9%) 7. Don Macleay 1,630 (1.4%) 8. Greg Harland 966 (0.8%) 9. Larry Lionel Young, Jr. 933 (0.8%) 10. Arnie Field 733 (0.6%); (RCV Final Round): 1. Quan 53,897 (50.96%) 2. Perata 51,872 (49.04%).

Rebecca Kaplan announcing her candidacy
for mayor last June.

OUTLOOK Kaplan has steadily held a lead in this race, according to the polls. The consensus is Oakland voters recognize the name, but they may also sense her positive attitude when it comes to the city. If the polls are correct, there may also be concern that Kaplan’s campaign has been playing it safe over the past month while challengers like Schaaf, Parker, Tuman and even Quan have stepped up their games. Hoping to run out the clock on this race is a dangerous strategy. The late charge by Schaaf got everybody’s attention among the law and order moderates in this race, which may help Kaplan. Schaaf is definitely on a hard charge at the right time, but which candidates will push her over the top now that the Three Musketeers—Tuman, Parker and Ruby—are calling for outsiders, not insiders like Schaaf in the mayor’s office. The stragglers at the bottom of the field in total represent a small percentage of the vote, but in a tight race, everything counts and those candidates don’t seem to be likely pairs for supporting Schaaf. By some accounts, Quan and Kaplan made some sort of blood pact to band together and put one of them in the mayor’s office. In 2010, Quan was the beneficiary of this grand bargain, four years later, its Kaplan’s turn.

PREDICTION 1. Kaplan 2. Schaaf 3. Quan 4. Tuman 5. Siegel 6. Parker 7. Ruby 8. Anderson 9. Liu 10. Houston 11. Williams 12. Sidebotham 13. McCullough 14. Karamooz 15. Wilson

RCV Final Round: 1. Kaplan 2. Schaaf