Around 11 p.m. Monday, Oakland Mayor Jean Quan sat inside the city's emergency command center, where she had presided over the forced eviction of Occupy Oakland.

Quan had never seemed more alone. Her police chief, Howard Jordan, had left for the night, along with the city administrator and several City Council members. Her deputy mayor, Sharon Cornu, had resigned in the wake of the police operation, along with her close friend and legal advisor, Dan Siegel.

Quan, hoarse and exhausted, was still there, hunched over a keyboard with her spokeswoman and longtime friend Sue Piper as she struggled to craft a statement explaining her actions.

The scene marked the final hours of a Shakespearean drama that found Quan, the former liberal activist, trapped between the passions of her family and closest friends and the demands of top city officials who implored her, with growing urgency, to shut down the Occupy Oakland encampment.

During weeks of intense internal debate, Quan seemed paralyzed by indecision, according to interviews with a dozen city and Alameda County officials.

As the raid approached, she tried desperately to forestall it, hoping to allow her husband, community activist Floyd Huen, and other supporters to find a nonviolent resolution. But Jordan and City Administrator Deanna Santana refused to budge; some officials believed that both would resign if the eviction was not carried out.

By 3 p.m. Sunday, hours before an operation that would involve hundreds of local law enforcement agents, Quan still seemed unsure whether to proceed, according to City Council member Ignacio De La Fuente, a Quan critic.

“The mayor has been wishy-washy, sending super mixed signals to everyone,” De La Fuente said. At a meeting with other council members that day, he said he pleaded with Quan to “take into consideration the impact on all the businesses.”

According to officials and law enforcement sources, two precipitating events persuaded Quan to act. The first was a pivotal Nov. 10 meeting of county law enforcement leaders, in which several demanded that Jordan, who was representing Oakland, end the crisis swiftly and decisively.

The second, which occurred later that afternoon, was the murder of a man who had been living at the Occupy Oakland camp a few hundreds yards from the steps of City Hall.

Piper said the mayor always knew an eviction was inevitable.

"The mayor’s responsibility was to reach out to the people in the tents and the people in the community and encourage as many people as possible to leave," she said. "We considered the action to be a success." 

The crisis was especially painful for Quan because she identified so closely with the protesters, her friends and family said. Huen had marched in support of Occupy Oakland, and their daughter, Lailan, as well as Siegel had made appearances at the encampment, at times absorbing the wrath of protesters angry with the mayor.

“The irony is that this is the city with the most supportive mayor,” Huen said in an interview. “We’ve been working on these issues for 40 years; it’s nothing new.”

After weeks of anguished vacillation, the urgency of an eviction was brought home to Quan last Wednesday, according to several participants.

Five City Council members and business and religious leaders held a press conference on Lake Merritt to demand the immediate closure of the camp. After protesters shouted down the group, some council members threatened to bring forward a no-confidence vote against Quan, giving strength to a separate recall effort that had been launched against the mayor.

For local law enforcement agencies, the camp’s time had run out. The next day, Jordan delivered a brief update on conditions at Occupy Oakland at a pre-scheduled monthly meeting with top brass from Alameda County. Over lasagna, the police chiefs and sheriffs gave Jordan an ultimatum: solve the Occupy Oakland problem quickly, because area chiefs were losing patience with repeated requests to send riot police to Frank H. Ogawa Plaza.

On Oct. 25, 17 police agencies had responded to emergency calls for mutual aid to support Oakland in what became a bloody confrontation with protesters. The Alameda County Sheriff’s Office alone spent upwards of $250,000 to provide riot police for that operation, and agencies were still tallying the costs of a mass demonstration and subsequent clashes on Nov. 3.

But because Quan had allowed protesters to resettle in the plaza — a day after she had ordered it cleared — the police chiefs no longer considered the eviction an emergency, meaning they expected to be paid.