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Deanna Santana, Oakland's City Administrator, sits in a meeting in her office at Oakland City Hall in Oakland, Calif. on Monday, Aug. 5, 2013. Santana is coming up on her two-year anniversary as City Administrator. (Laura A. Oda/Bay Area News Group)

OAKLAND -- Until recently, the only thing Oakland City Administrator Deanna Santana didn't have to worry about was her job security.

As the city careened from Occupy fiasco to redevelopment disaster to police drama du jour, Santana was hailed as a decisive leader, unafraid to stare down Occupy protesters and council members alike.

But the tables have quickly turned on Oakland's top appointed official as the city reels from a bitter labor battle and the loss of autonomy over its Police Department.

Santana is beginning her third year in Oakland despised by the city's largest union, unloved by several loyalists to Mayor Jean Quan and left to mend fences with two powerful court-appointed federal police overseers, one of whom she accused last year of sexual harassment.

Many top city staff members say Santana is the best administrator Oakland has had in a decade. But there are questions whether she'll stick around or be allowed to finish out her contract, which expires in 2015.

"I don't think it would be best for the city if she left," Councilman Noel Gallo said. "But it might be best for her."

Quan, who hired Santana and is the only person with authority to fire her, said Santana is hardworking and smart. But she wouldn't "speculate" when asked if Santana's job was safe through the mayor's first term. When asked if Santana is doing a good job, Quan replied, "Deanna is part of a very broad team that I have, and I think the team is doing a very good job."

Santana said she remains dedicated to her job and that she didn't think her situation had deteriorated. "Let's face it, the honeymoon is over," she said. "People now know me as a manager and they know my style. But it's no more or less tense or precarious than it was a year ago."

Santana got off on the wrong foot with Robert Warshaw and Thomas Frazier, the two court-appointed police officials who were instrumental in ousting former Chief Howard Jordan this year. Frazier, a former Baltimore police commissioner, is responsible for making police comply with long overdue court-mandated reforms stemming from a 1999 police brutality scandal. Warshaw, a former Rochester, N.Y., police chief, monitors the city's progress.

The federal judge who oversees the Oakland Police Department, Thelton Henderson, had Santana's sexual harassment charge against Warshaw investigated, but never released the investigator's findings and left Warshaw on the job to continue working with Santana.

"It's a very difficult and highly unusual situation," said City University of New York Law School professor Merrick Rossein, who specializes in sexual harassment cases. "I'm sure everybody is going to be very careful."

Santana's relationship with Frazier took a turn for worse last year when he was hired to produce a report on the city's botched handling of the first Occupy protest. In sworn testimony, Frazier accused Santana of trying to keep much of that highly critical report from public view.

The police officials don't speak publicly, and Judge Henderson has issued two court orders declaring their communications with city officials confidential. Several of their recent reports, however, have included complaints about obstruction from the administration, though none specifically mentioned Santana. The most ominous warning came last month from Warshaw, who wrote that he would "recommend (to the judge) appropriate remedies that hold responsible parties to account" if the administration remained uncooperative.

"There is a lot of angst about her given some of the decisions she has made," said John Burris, an attorney who has been involved with the reform process from its inception.

Quan, acting on Santana's request, talked to Warshaw after he issued his threat about administrative interference and was told that he was referring to multiple city officials, not just Santana.

"I think (Warshaw) thinks she is doing better," Quan said. "It's taken a long time for all of the parties to develop a good working relationship and right now ... the relationships are the best they've been."

Santana's relations with city unions quickly soured this year as the city began contract negotiations.

Union leaders accused Santana of purposely underestimating revenue and were furious when the city stationed a police officer at negotiating sessions after union protesters stormed the office of one Santana's deputies.

Even though the contracts were settled, relations remain raw, especially with SEIU Local 1021, which represents more than 2,500 full- and part-time city workers. Local 1021 has taken a strong stand against pension benefit reductions approved by voters in San Jose, where Santana served as deputy city manager.

"We are extremely serious that we will not go the way of San Jose," said Dwight McElroy, a 28-year Oakland city worker and SEIU chapter president. "We will insist on the removal of any administration that puts Oakland in that predicament anytime soon."

Active members from other city unions said Local 1021 has its heart set on ousting Santana. "They're feeling very emboldened and very brazen right now," said one union member who asked not to be named while discussing a different city union.

With Quan gearing up for re-election next year, both union and police reform issues have potential political ramifications. Quan won election in 2010 with Local 1021 not endorsing any candidate, but with her approval ratings low, the union's support would be helpful and its opposition could be devastating. The completion of the police reforms, now more than a decade old, could provide a boost to Quan's re-election hopes, but that depends on Frazier and Warshaw citing substantial progress over the next year.

"Deanna is caught in a nasty bind," former Councilwoman Marge Gibson-Haskell said. "She's got to protect her boss (Quan) and she's got two lousy situations: the unions and the police."

Quan already is dealing with opposition to Santana among her core progressive supporters, who are upset over the handling of several issues including redistricting and stalled police reforms.

"There looks like a lot of areas where Deanna is trying to run her own show and this isn't the place for that," longtime Quan ally Pamela Drake said.

Support for Santana appears strong inside City Hall, where several recent city managers were seen as unqualified political appointees. "She has integrity that I have not experienced in other regimes," said one longtime worker who didn't want her name used talking about Santana. "It would be my nightmare if she goes."

Contact Matthew Artz at 510-208-6435.