If the kickoff to Shelley Zimmerman’s police career sounds like a Hollywood plot, that’s because it was.

Zimmerman, named San Diego’s chief last week, spent three months undercover in fall 1983 at Patrick Henry High in Del Cerro. Passing herself off as a Midwestern transfer named Shelley Rogoff, a 24-year-old Zimmerman infiltrated groups of students and targeted those she believed to be drug sellers. At the end, her work netted more than 70 arrests, the San Diego Union reported at the time.

Zimmerman’s assignment may now sound like a cop cliché, but consider this was four years before fictional police officers – including Johnny Depp! – posed as high school students in the “21 Jump Street” TV series. Nothing like it had ever happened in San Diego before, and no one had any idea how widespread the drug problem was in schools at the time, remembered Bill Holman, the prosecutor on the case. The arrests were a nightly news staple, he said.

“You’d have thought we’d have busted the Arellano-Felix gang,” Holman said, referring to a Mexican drug cartel.

It helped, Holman said, that Zimmerman looked like she was 12 years old at the time. The Midwestern transfer part was an easy sell, too. To this day, you can hear the Ohio in her voice. And police officials worked hard on a cover story, Holman said. The department got an apartment where Zimmerman could debrief her colleagues that doubled as a fake residence for her to tell her classmates where she lived.

But beyond that, Holman said he was impressed by Zimmerman’s professionalism while undercover. Most rookie cops, he said, are overeager and talk over suspects rather than trying to get them to incriminate themselves. Zimmerman let the kids talk.

“It was so easy for her to buy dope from these people,” Holman said.

Zimmerman told family members that after the bust, one student was shocked to learn she was a cop because he voted for her for homecoming queen. Through an SDPD spokesman, Zimmerman confirmed some facts about the situation, but declined an interview with VOSD.

Zimmerman’s involvement didn’t end when she left Patrick Henry. Cases trickled through the court system over the next 18 months and Zimmerman had to testify. Despite allegations from the students, Zimmerman told the court she didn’t use any pot. (Zimmerman and Holman reiterated that last week.) Zimmerman also attended student expulsion hearings, like this one the Union detailed in 1984 involving a student with the pseudonym “Mike”:

The door opened. And Mike and his mother entered. So did Zimmerman.

After the half-hour session, Mike turned to his police accuser, the first of 10 students facing the possibility of expulsion to do so.

“I hate you,” he told the 24-year-old officer. “But I respect you. I realize what I’ve done.”

Since the bust, he added, he has stayed away from drugs.

“Good. Congratulations,” said Zimmerman. She smiled.

Clarification: This post has been clarified to reflect that Zimmerman targeted student drug sellers.

Liam Dillon was formerly a senior reporter and assistant editor for Voice of San Diego. He led VOSD’s investigations and wrote about how regular people...

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