Before former San Diego police officer Anthony Arevalos’ arrest in 2011, his supervisors knew he had made sexually charged comments to a woman with mental disabilities while transporting her to a hospital. They knew he looked at pornography at work on his department-issued computer. And they knew he had been accused of behaving inappropriately toward a 16-year-old girl during a traffic stop.

Supervisors had also cleared Arevalos of sexually assaulting a 28-year-old woman while taking her to jail a year before his arrest. They had sent him back out on the streets to patrol downtown alone. In that case, the sergeant in charge of the criminal investigation was convinced of Arevalos’ guilt, and a district attorney who later reviewed the case found problems with the department’s investigation (though still declined to prosecute him for it).

One of Arevalos’ colleagues described him this way: “Teflon.”

“I felt he believed no matter what he did, that he would not get in trouble,” said Henry Castro, who worked in traffic division with Arevalos and said in court filings he’d used the word.

The depth to which high-ranking police officials knew about Arevalos’ behavior prior to his 2011 arrest for soliciting a sexual bribe from a 32-year-old women in a convenience store bathroom is revealed in a trove of interviews and documents from a civil lawsuit filed by Arevalos’ final victim.

With new accusations surfacing against two more SDPD officers this month, the court documents raise fresh concerns about the department’s ability to stop potential predators before they strike. Lawyers in the case are arguing SDPD has a pattern of covering up serious misconduct and are seeking a court-ordered independent monitor to oversee the department.

In the almost three years since Arevalos’ arrest, Police Chief William Lansdowne has admitted the department missed red flags about Arevalos’ behavior. The chief, who retired abruptly Tuesday, has promised numerous reforms to prevent further officer problems, and recently ordered an external audit of SDPD. Shelley Zimmerman, an assistant chief, was nominated Wednesday to be Lansdowne’s replacement. She promised to reinstate an internal anticorruption unit, which Lansdowne had disbanded, to proactively monitor officer conduct.

Arevalos’ final victim is known in court papers as Jane Doe. Among the revelations from her case:

• In the late 1990s Arevalos told his supervisor he’d flirted with a woman with mental disabilities in the back of his patrol car. Officer Francisco Torres, who was on the call with Arevalos, said his partner’s conduct went far past flirting. Torres said in a deposition that Arevalos had also taken naked photos of the woman and the woman had put Arevalos’ baton in her vagina while Arevalos watched.

Arevalos’ supervisor at the time, Rudy Tai, who now leads the department’s criminal intelligence unit, gave Arevalos a verbal warning after the incident. Tai said in his deposition he doesn’t recall being told of the more serious allegations. If he had, he said, he would have acted on them.

• In 2007, department officials found Arevalos repeatedly visited a pornographic website on his work computer while on duty. Arevalos was transferred to the traffic division as a result.

In a deposition, Arevalos’ supervisor in the traffic division said it’s department policy to advise new supervisors of any disciplinary transfers. She said she had no idea Arevalos had been transferred because of pornography on his computer.

• Later in 2007, the father of a 16-year-old girl complained to two of Arevalos’ supervisors about a traffic stop in La Jolla. He alleged Arevalos made his daughter, who was driving alone, get out of her car and bend over in front of him, ostensibly to check her registration tags.

Arevalos again was issued a verbal warning by his supervisors, who determined he had no reason to be in La Jolla because he was assigned to patrol downtown.

• In 2010, Arevalos was transporting a DUI suspect to jail when the arrestee alleged he pulled over and forced his hand inside her vagina.

At the jail, she immediately complained about being sexually assaulted. Two investigations were launched as a result of the complaint. An Internal Affairs investigation cleared Arevalos of wrongdoing. A criminal investigation was more controversial.

Sgt. Dan Cerar, who oversaw that investigation, concluded that Arevalos was guilty. He said in a deposition that his investigation was hampered by shoddy evidence gathering. A prosecutor, Sherry Thompson, agreed.

“I thought that the case was troubled in the way the police department handled it,” Thompson said.

Cerar said he wanted to bring in experienced detectives to work the case. His supervisor told him he couldn’t. Cerar also wanted to interview Arevalos’ colleagues in the traffic division. His supervisor denied that request, too.

“I was told this is as far as we’re going to go,” Cerar said.

The district attorney’s office decided not to bring charges against Arevalos. A year later, he was arrested in the convenience store bathroom incident. During that time, Arevalos solicited sexual bribes from at least three other women.

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When San Diego police officers are punished, Lansdowne said in his deposition, everyone’s aware of it.

“There are no secrets in this police department as it relates to discipline in this organization,” Lansdowne said. “It’s almost always common knowledge.”

In its legal filings, the city argued SDPD acted appropriately against Arevalos at all times, given the information available. The city says each incident either wasn’t sexual misconduct, didn’t happen or was properly investigated.

Still, the department’s failure to fully document problems with Arevalos’ behavior left him with a record that looked better than it should have.

Arevalos’ supervisor in the traffic division didn’t know about Arevalos’ previous discipline when he was accused of acting inappropriately toward a 16-year-old girl. Cerar, the sergeant who supervised the 2010 sexual assault investigation, didn’t know Arevalos had been punished before, either.

Had Cerar been allowed to interview Arevalos’ colleagues, he might have learned about the officer’s reputation. Arevalos’ fellow officers knew that he passed around the driver’s license photos of good-looking women he had pulled over, and they believed he profiled attractive women for traffic stops.

Tai, who was Arevalos’ supervisor in the 1990s, led the sex-crimes unit when Arevalos was arrested in 2011. Tai didn’t tell his own investigators Arevalos had admitted to flirting with a woman with mental disabilities in the late 1990s. He said in his deposition he didn’t think the incident was relevant to the case.