Last year, Oakland Mayor Jean Quan suffered through an somewhat embarrassing few days when, in a matter of roughly 48 hours, the city saw two police chiefs abruptly resign. The third police chief, Sean Whent, still awaits word whether the interim tag will be removed or a permanent, and fourth chief, will soon be named. Was this exodus an isolated event at City Hall? Apparently not.

Last month, when Deanna Santana was pushed out by Quan as her city administrator, the story seemed different. Santana, too, was unhappy with leading the city for some time. She made public overtures for jobs in Dallas and Phoenix and was passed over for both. The damage was done and Quan made the move. Santana’s assistant Fred Blackwell, a well-liked and capable technocrat, was elevated and the city’s progressive community appeared content. But, now the story has come full circle to evoke the stunning merry-go-round at the police department a year ago. On Wednesday, Blackwell said he was leaving his dream job in Oakland for greener pastures at a San Francisco non-profit. It only took Blackwell three weeks to determine his dream may have been more of a nightmare. The news may also be a tipping point for Quan’s tenuous political future.

Going into April, just seven months before Election Day, Quan’s re-election is anything but a sure bet, but her chances have been vastly understated by many. Quan still maintains the power of the incumbency and ,thereby, she controls and solely benefits from anything remotely positive that occurs from here to Election Day. You might say, conversely, anything negative only sticks to Quan, too, but the city’s negatives are already ingrained in voter’s mind. Say, a murder spree inflicts Oakland this summer, that’s not necessarily a fresh narrative as it relates to Quan’s administration.

However, the imagery of the rats jumping ship at City Hall is a narrative that may begin to coalesce after Blackwell’s departures this week. Does anybody want to work with Quan? Is she incapable of leading her own administration? Most striking, her opponents can now respond rhetorically, and with ominous wonder, what exactly is going on at City Hall? Any one of 15 potential challengers to Quan’s could easily label her the “Worst Boss in America,” both in serious and wildly comic tones.

Another way Blackwell’s departure could severely hurt Quan’s re-election is with the Raiders and Coliseum City. Since last December, Quan has frequently mentioned her goal of signing a stadium deal with the football team sometime this summer. Fairly or not, the statement is ostensibly a promise to voters and fans the team will remain in Oakland. However, Blackwell is the city’s most knowledgeable mind on Coliseum City, along with deflecting the Warriors potential move to San Francisco. Now that he’s gone there exists an enormous dark cloud over 66th Avenue and Hegenberger Road. And it’s not clear who at City Hall possesses even a small percentage of his expertise on the complicated land deal that may have to occur before even one stadium is built at the current Coliseum complex.In addition, if Blackwell’s reported ability to ring a conciliatory tone in negotiations is lost, how will he cajole the Raiders to make the concessions needed? Who, for instance, will facilitate selling a portion of the team to potential stadium investors, along with working with some of the most combative members of the Alameda County Board of Supervisors to swing a deal to sell the Coliseum property to those same investors?

If the Raiders leave, then voters can just add them to a list of important people and entities who have bailed on Quan starting with former police chief Howard Jordan and followed by Capt. Anthony Toribio, Deanna Santana, Fred Blackwell and maybe a debilitating portion of Quan’s coalition of supporters needed for another four years in office.

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Originally posted at East Bay Citizen.