SF Police Oversight Department Could Use Some Oversight

Since 1983, San Francisco has had a civilian Department of Police Accountability which is responsible for oversight of the city’s police. In practice this means investigating claims of bias or excessive force and looking into every shooting by a police officer.

A lawsuit filed last week suggests that the DPA might need some oversight of its own. According to Janelle Caywood, a former lawyer who worked with the department from seven years, the person who ran the department, Paul Henderson, created a hostile work environment, misspent funds and engaged in workplace retaliation. This is taken directly from the lawsuit.

Within the first few days of Ms. Caywood’s employment, he jokingly gifted hemorrhoid medication to a receptionist during an office holiday party. In 2019,he discussed with Ms. Caywood a “sex party” his ex-partner had participated in, showing her a photograph of a dildo. In 2023, he presided over an in-office drag queen strip-show, to which the staff and interns were encouraged to bring $1 bills. In other words, he made it clear to his staff that he would practice and tolerate unprofessional conduct that ignored norms for avoiding a hostile work environment on the basis of protected categories.

But the bulk of the complaint involves Caywood’s supervisor Diana Rosenstein who was apparently close with top boss Paul Henderson.

Diana Rosenstein, a Caucasian woman, had recently been appointed manager over the legal teams, and she became Ms. Caywood’s supervisor. Ms. Caywood began to hear complaints that Ms. Rosenstein had singled out her team for negative treatment that other investigators, many of whom were not minorities, were not experiencing. Senior investigator Candace Carpenter, who is Black, confided to Ms. Caywood that she believed Ms. Rosenstein had unfairly targeted her and other women on the team with unjust criticisms, which was consistent with Ms. Caywood’s observations…

Ms. Caywood decided to inform Mr. Henderson of Ms. Rosenstein’s behavior…Mr. Henderson replied words to the effect that Ms. Rosenstein (with whom he was close) just needed to work on her “bedside manner” and that he would talk to her…

Within a few days, Ms. Caywood was shocked to hear that Ms. Rosenstein was telling their co-workers that she hoped Ms. Caywood would quit. Ms. Caywood approached Ms. Rosenstein about this, and Ms. Rosenstein said words to the effect of “Paul [Henderson] tells me everything you say,” and “don’t bother going to Paul about me – he doesn’t care, and I’m not going anywhere.”

Eventually Caywood says she learned that Rosenstein was rewriting reporters under her name.

In October 2024, Ms. Caywood realized that Ms. Rosenstein had written and submitted “sustain” reports, i.e., reports recommending discipline of police officers, that purported to have been authored by Ms. Caywood despite the fact that Ms. Caywood had never seen them. Ms. Caywood learned from co-workers that Ms. Rosenstein had altered reports and findings written under another attorney’s name without that attorney’s knowledge, as well. Ms. Caywood believed writing reports under other attorneys’ names was unlawful.

Caywood raised the issue internally but nothing was done about it. Her supervisor, Rosenstein, also called a black judge an “Uncle Tom” after he disagreed with her during a hearing.

On November 5, 2024, Ms. Caywood and Ms. Rosenstein attended a settlement conference via Microsoft Teams in a police misconduct case. The other attendees were then-Police Chief Bill Scott, deputy City Attorney Kate Kimberlin, attorney for the accused officer Scott Burrell, the Police Commissioner, and retired superior court judge and Police Commissioner C. Don Clay. During the conference, Judge Clay (who is Black) disagreed with Ms. Rosenstein about the DPA’s position as to one of the charges, leading Ms. Rosenstein to send texts messages to Ms. Caywood calling him an “Uncle Tom,” and saying “He and Clarence Thomas can go to hell,” and “So disappointing to see a black man act like this. He should be ashamed.”

Caywood reported those comments and an investigation was launched. In December 2024, Rosenstein resigned. Caywood was blamed for having helped launch the investigation. Eventually, Caywood filed an EEOC complaint in August 2025. Two days later she was fired. Henderson, the boss who fired her, has denied doing anything wrong.

“I categorically deny the allegations made against me and the department and find them offensive to our reputation and proven history,” DPA Director Paul Henderson said. “The city will respond vigorously to this lawsuit in court.”

So we’ll have to wait a while to see if the city decides to settle this case or if it winds up going to trial. If the complaint holds up in court then the office responsible for police accountability wasn’t being run very professionally.

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