Some old Chesa Boudin-era drama is rearing its head again, as DA Jenkins’s former assistant chief of investigations is hauling her to court, saying she lied when dropping the charges against a police officer who shot and killed someone.

Back in 2020, when Chesa Boudin was still SF District Attorney, Boudin brought the first-ever homicide charge against an on-duty SF police officer, for the 2017 shooting of unarmed Keita O’Neil. The officer in question, now-former SFPD officer Chris Samayoa, had his charges dropped once Boudin was recalled and new DA Brooke Jenkins was appointed.

When Jenkins dropped those charges against Samayoa, she accused Boudin and his office of misconduct that would leave her unable to prosecute the case. Specifically, she claimed Boudin had improperly pressured then-assistant chief of investigations Jack Friedman into signing an arrest warrant he was not comfortable signing. Friedman has come forward to say this is hogwash, and now Mission Local reports Friedman has sued DA Jenkins for defamation and doing damage to his career in a civil suit filed Monday.

Jenkins fired Friedman in May of this year, by the way.

“Jenkins falsely and publicly blamed her decision to drop the charges against Samayoa on Friedman, former San Francisco District Attorney Chesa Boudin, and others, claiming that the charges were politically motivated and not legally justified, and that Friedman had lied when he attempted to respond to her,” Friedman says is his lawsuit, which Mission Local has published online.

The lawsuit also cites the letter Jenkins wrote to state AG Rob Bonta when she decided to dismiss Samayoa’s charges, in which Jenkins characterizes Friedman pretty unflatteringly.

“Friedman told me he agreed to draft the (arrest) warrant, but that he was not sure if he would sign it due to concerns about whether sufficient probable cause existed,” Jenkins' office wrote in their letter to Bonta. “Friedman was crying during this portion of the discussion so I tried to console him and told him I could understand the pressure he was under.”

Again, Friedman says this is bullshit. “District Attorney Jenkins publicly and gratuitously blamed plaintiff Friedman for alleged misconduct in preparing an inadequate arrest warrant, made untrue, public statements about him, and terminated his employment for allegedly lying during her office's investigation of the process that led to the issuance of the warrant,” his lawsuit says.

The suit does not mention a dollar amount for damages, but Friedman is clearly looking for a dollar amount for damages. The suit asks for relief from “physical and emotional distress,” and says Friedman “has suffered extreme harm to his reputation as an attorney and sworn peace officer by being publicly accused of misconduct and dishonesty.”

This case looks like a “he said/she said” situation right now, so we’ll see how it plays out in court. But this is not the first ethical issue (or accusation thereof) to arise during Brooke Jenkins's 15-month tenure as DA. She was disqualified from a murder case over a family connection, found guilty of prosecutorial misconduct by an appeals court, hit with ethics violation allegations over the sharing of sensitive documents, and was the subject of a state bar complaint that said she lied during a debate. And of course, there was the whole secret $153,000 payment she took from a Recall Boudin-affiliated PAC when she claimed was volunteering for them.

Some of those complaints are allegations, some are proven, others are actions that are legal but ethically iffy. But the dropping of the charges in the Samayoa case seemed to be part of a pattern in which Jenkins drops charges against police officers, perhaps to curry favor politically.

Related: DA Jenkins’s Office Disqualified From Murder Case, and Boy Is She Upset at the Chronicle’s Coverage [SFist]

Top image: San Francisco district attorney Brooke Jenkins (L) speaks as San Francisco police chief William Scott (L) looks on during a press conference at San Francisco Police headquarters on April 13, 2023 in San Francisco, California. San Francisco police arrested 38 year-old tech tech entrepreneur Nima Momeni at his home in Emeryville, California in connection with the stabbing murder of Cash App founder Bob Lee. Momeni was taken into custody without incident. (Photo by Justin Sullivan/Getty Images)