Raymond Winters

Raymond Winters joined the San Francisco Sheriff’s Office in October 2001, following in the footsteps of his father and sister. He was promoted to captain in 2025.

Captain Winters rose through the ranks, first as a sergeant in 2008, then to lieutenant in 2016. Throughout his career, he has served in nearly every major area of the Department, including the Custody Operations Division, City Hall Administration, the Training Unit, and Field Operations Division.

He currently manages County Jail #3 in San Bruno, the Sheriff’s Office’s dedicated program and education facility.

Captain Winters grew up in Pacifica and San Francisco, and attended Saint Ignatius College Preparatory.  He earned a bachelor’s degree in History at California Polytechnic State University, San Luis Obispo, and later graduated from the San Francisco Police Academy as a member of the 26th Regional Class.

In his spare time, Captain Winters enjoys hiking, camping, traveling, and cheering on the San Francisco 49ers and Los Angeles Dodgers. He is an active supporter of the Special Olympics of Northern California, serving as Race Director for events such as the 5K & Polar Plunge, and sitting on the Law Enforcement Torch Run Executive Committee.  He also supports Mothers Against Drunk Driving (MADD), planning and participating in Move Like MADD.

 He is married with two children.