New Jail Oversight Members Bring Firsthand Experience to Sheriff Accountability

The San Francisco Rules Committee moved quickly through a brief but substantive Monday session, seating two new civilian watchdogs over the county jail system and greenlighting entertainment zone expansions designed to keep momentum going in the Yerba Buena neighborhood's commercial revival.

• Jail educator and court interpreter appointed to Sheriff's Department Oversight Board, filling two vacant seats with people who work inside the system daily

• Downtown entertainment zones expanded to connect Yerba Buena alleys, add Market Street businesses, and widen Second Street event footprint

• Both items advance to the full Board of Supervisors, expected on the March 24 agenda

Inside Eyes: Two Women Who Work in SF Jails Will Now Oversee Them

The Rules Committee unanimously appointed Gail Rossborough and Carla Cuevas to the Sheriff's Department Oversight Board — the civilian body charged with monitoring jail operations and deputy conduct. Both women bring something unusual to an oversight role: years of daily, on-the-ground experience inside San Francisco's county jails.

Why it matters: The Oversight Board has had vacant seats, limiting its capacity to hold the Sheriff's Department accountable. Filling them with people who already navigate the jail system — one running college programs, the other interpreting in courtrooms and lockups — gives the board members who have witnessed conditions firsthand rather than learning about them secondhand through reports.

Where things stand: Rossborough, who serves as Director of In-Custody College Pathways at Five Keys Schools and Programs, told the committee she has spent 11 years running post-secondary education inside County Jails 2 and 3 through partnerships with City College of San Francisco. She was pointed about her independence from the department she'll now help oversee.

"I don't have any commitment to them. My commitment when I work in the jails are with my students," said Rossborough.

She outlined priorities that included expanding access to the education corridor and pushing for healthier food options in jail meals, specifically reducing reliance on high-salt, soy-based diets.

Supervisor Rafael Mandelman, who represents District 8, pressed Rossborough on whether the consolidation of jail facilities — including the closure of the downtown jail — had made it harder for inmates to access education programs. He noted that deputies at the San Bruno site appear stretched thin.

"The consolidation meant that there's just more work for the deputies to be doing at the San Bruno site. And so they are not as available to make the corridor available," Mandelman said. Rossborough confirmed the pandemic reduced the number of classes held in the education corridor at County Jail 3, but said the Sheriff's Department has since made reopening it a priority.

Cuevas, a SOMA resident and certified court interpreter with 15 years working inside county jails and courtrooms, presented her candidacy through three lenses: as a labor leader, a legal professional, and a community member shaped by personal hardship.

"For 15 years I have worked inside our county jails and courtrooms. As a certified court interpreter, I see the other side of the Sheriff's Department daily," Cuevas said.

She described witnessing lockdowns, overcrowding, understaffing, and critical gaps in language access — issues she said she could bring to the board from direct observation. Cuevas also shared her personal story as a Mexican immigrant, a survivor of domestic violence, and a mother who once navigated homelessness. She holds leadership roles with the California Federation of Interpreters and the California Alliance of Legal Interpreters, satisfying the labor-seat requirement for Seat 4.

Decisions: Committee Chair Shamann Walton, Supervisor for District 10, moved to appoint Rossborough to Seat 1 (term ending March 1, 2027) and Cuevas to Seat 4 (term ending March 1, 2029). The vote was 3-0 (For: Supervisors Sherrill, Mandelman, Walton; Against: none; Absent: none).

"The Sheriff's Department Oversight Board is an important body and we have a lot of work to do to make sure" it has the resources and membership it needs, Chair Walton said before calling the vote.

What's next: The appointments head to the full Board of Supervisors, expected on the March 24 agenda.

Yerba Buena Entertainment Zones Get a Boundary Tune-Up

The committee also advanced an ordinance making technical fixes to several downtown entertainment zones in the Yerba Buena and SOMA area — modest map changes designed to let a successful neighborhood activation program reach more businesses and foot traffic.

Why it matters: San Francisco's downtown activation program has turned alleys and side streets into event spaces with food, music, and retail pop-ups. The Yerba Buena neighborhood has been a standout, but the original zone boundaries left gaps that prevented some businesses from participating and disconnected adjacent event areas from each other.

Where things stand: Ben Van Houten, staff with the Office of Economic and Workforce Development (OEWD), walked the committee through three specific fixes:

1. Jesse Alley connection: The two Jesse Alleys — Jesse East and Jesse West — currently have separate entertainment zones with no connection between them via Mission Street. "You could have entertainment zone activity in both alleys but not walk between them," Van Houten explained. The ordinance links them.

2. Yerba Buena Lane expansion: Successful activations on Yerba Buena Lane have excluded businesses that front on Market Street. "Some of the businesses adjacent to Yerba Buena Lane that actually front on Market Street have not been able to participate. This would enable them to do that," Van Houten said.

3. Second Street side streets: Entertainment zone footprints on side streets near Second Street — including Mena Alley, Natomi Street, New Montgomery Street, and Shaw Alley — would be expanded so activations can spill over during Second Street events.

Jill Linwood of the Yerba Buena Partnership offered the only public comment, calling the program a clear success story. "The entertainment zone activations in the neighborhood have been extraordinarily successful. So much so that we see the benefit of fine tuning the lines to allow more businesses to participate," Linwood said.

Decisions: The ordinance passed 3-0 as a committee report (For: Supervisors Sherrill, Mandelman, Walton; Against: none; Absent: none).

What's next: The legislation heads to the full Board of Supervisors, expected on the March 24 agenda. If approved, the expanded zones could be operational for spring and summer programming in the Yerba Buena corridor.