A former investigator at the San Francisco District Attorney’s Office is suing District Attorney Brooke Jenkins for alleging painting him as dishonest surrounding her decision to drop a criminal case against a city police officer.  

Jack Friedman filed a federal suit Tuesday against Jenkins and the city and county of San Francisco for allegedly violating his right to free speech and retaliation. 

At root was a decision by then-District Attorney Chesa Boudin to criminally charge Officer Christopher Samayoa for the fatal shooting of carjacking suspect Keita O’Neil in 2017, which was the first time a San Francisco officer had ever been charged with homicide for an on-duty killing.  

Then-San Francisco District Attorney Chesa Boudin addresses the media during a November 2021 news conference. (Daniel Montes/Bay City News)

Boudin was removed through a 2022 recall election and Jenkins was appointed by Mayor London Breed as interim district attorney, then was elected to the position.  

Once in power, Jenkins dropped the charges against Samayoa, alleging that the decision to prosecute him had been politically motivated. State Attorney General Rob Bonta also cleared Samayoa in May of this year.  

In his suit, Friedman, who was previously a Berkeley police officer, alleges that Jenkins acted maliciously when she falsely portrayed him as dishonest about the Samayoa case.  

“Jenkins publicly and gratuitously blamed plaintiff Friedman for alleged misconduct in preparing an inadequate arrest warrant,” reads the complaint.   

Jenkins mentioned Friedman by name in her lengthy February letter to Bonta about why she was dropping the case.  

California Attorney General Rob Bonta appears at a news conference in Oakland on May 10, 2023. (Attorney General Rob Bonta/Twitter)

“Friedman told me he agreed to draft the warrant, but that he was not sure if he would sign it due to concerns about whether sufficient probable cause existed for the issuance the warrant,” wrote Jenkins, who added that Friedman had been “crying” during their discussion, the implication being that he felt what he was doing was wrong.  

Friedman disputes Jenkins’ version of events in his suit, standing firm to his belief that there was probable cause to issue the warrant, and pointing out that he was not allowed to defend himself after she placed a gag order on him.  

Jenkins placed Friedman on administrative leave in January and fired him in May, a move he alleges was in retaliation.   

Jenkins barred Friedman from speaking about the case publicly, which he alleges violated his First Amendment rights. He also alleges his reputation has been damaged.  

The San Francisco City Attorney’s Office and Jenkins did not immediately respond to requests for comment about the lawsuit. 

Katy St. Clair got her start in journalism by working in the classifieds department at the East Bay Express during the height of alt weeklies, then sweet talked her way into becoming staff writer, submissions editor, and music editor. She has been a columnist in the East Bay Express, SF Weekly, and the San Francisco Examiner. Starting in 2015, she begrudgingly scaled the inverted pyramid at dailies such as the Vallejo Times-Herald, The Vacaville Reporter, and the Daily Republic. She has her own independent news site and blog that covers the delightfully dysfunctional town of Vallejo, California, where she also collaborates with the investigative team at Open Vallejo. A passionate advocate for people with developmental disabilities, she serves on both the Board of the Arc of Solano and the Arc of California. She lives in Vallejo.