Sheriff Vicki L. Hennessy

Vicki L. Hennessy

Vicki Hennessy served her first shift as a San Francisco Deputy Sheriff on Christmas Eve in 1975 at the old San Bruno women’s jail. A member of the first recruit class, which included women, communities of color and LGBT Deputies, Hennessy bought her own uniform -- a white blouse and navy blue pants. She was not issued any equipment or provided any formal training. In fact, the Deputy on the previous shift simply handed her the keys, turned over the jail and told the rookie Deputy to cover the swing shift.

Fast forward 40 plus years. Deputy Hennessy is now Sheriff Hennessy, San Francisco’s 35th Sheriff since 1850 and the first female to lead the Department. She is also the first San Francisco Sheriff to rise through the ranks and win election from city voters to the Department’s highest position.

First impressions can last a lifetime. Since being sworn in on January 8, 2016, Sheriff Hennessy has reinvigorated and expanded training for Deputy Sheriffs, Supervisors and Command Staff -- training she never received that long ago Christmas Eve.


Taking nothing for granted, Sheriff Hennessy has recommitted her Department to focus on safety and respect by reaffirming fundamental jail operations while expanding the breadth and depth of training classes. This includes gender awareness for understanding, protection and privacy of transgender prisoners; crisis intervention to teach staff members how to identify and work with mentally ill offenders; and management classes for newly promoted supervisors on how to set expectations for Deputies and create and maintain a culture of accountability.

She has accelerated Department hiring, bringing 168 new Deputies on board over the last two years with plans for more new law enforcement hires in the coming years to counteract previous staffing shortages.

Having served in every division while part of the San Francisco Sheriff’s Department executive management team from 1983 through 2008, Sheriff Hennessy has been at the center of San Francisco’s national leadership in criminal justice policies, which emphasize rehabilitation, restorative justice and successful reentry. In County Jail #5 alone, the Sheriff’s Department offers inmates 77 different classes and services -- from addiction support to strategies for avoiding criminal behavior and parenting skills. This is in addition to operating the first charter high school for incarcerated adults and offering in-custody college courses taught by City College of San Francisco professors.

Sheriff Hennessy’s initiatives are informed by one overarching goal: safety for all staff, visitors, inmates and service providers.

In safe jails, she explains, deputies and inmates have regular, positive interactions. With their basic needs met, inmates can concentrate on their cases and participate in educational, vocational, recovery and life skills classes without feeling threatened by others. This supports the incarcerated person’s successful reintegration into the community which, in turn, boosts public safety.

Sheriff Hennessy co-chaired the Work Group to Re-envision the Jail Replacement Project in 2016. The Work Group identified and is implementing a series of strategies to release people from jail as early as possible. These include individuals who have been arrested and are awaiting a court date, but are not considered a public safety threat as well as those arrestees whom the District Attorney will not file charges against. This effort has helped reduce the daily jail population and created new opportunities for collaboration and cooperation among San Francisco city departments involved in the criminal justice system.

A native San Franciscan, Sheriff Hennessy also serves on the board of Five Keys Schools & Programs, which operates San Francisco County Jail’s award-winning, in-custody charter school. Sheriff Hennessy works every day to balance public safety with social justice.

Undersheriff Matthew Freeman

Undersheriff Matthew Freeman

Matthew Freeman joined the Sheriff’s Department in January 1991. He has served in a multitude of department assignments, including Custody, the Courts, the Institutional Patrol Unit and Field Operations.

A member of the Emergency Services Unit for 24 years, Undersheriff Freeman has served as the Incident Commander and Mobile Field Force Platoon Leader in many emergency operation deployments in San Francisco, and in mutual aid response to other jurisdictions. He has received extensive training in emergency response planning and all-hazards events from member agencies of the National Domestic Preparedness Consortium. He enjoys serving the Department as an instructor, and teaches advanced officer, supervisor and Emergency Services Unit training. Freeman has held each rank in the Sheriff’s Department. As Chief Deputy, he served as the Custody Operations Division Commander for five years. Freeman was promoted to Undersheriff in May of 2017.

Undersheriff Freeman was born, raised and attended school in San Francisco. He is married and has two daughters.