Born in 1944, Jesse Brown graduated from Chicago City College, studying also at Roosevelt University and Catholic University. After serving as a U.S. Marine during the Vietnam War, Brown worked for a quarter century with the charitable organization Disabled American Veterans (DAV).

He was executive director of DAV when President Bill Clinton selected him to lead the Department of Veterans Affairs. Brown returned to DAV in 1997, where he worked as executive director of the Disabled Veterans' LIFE Memorial Foundation.