When asked what he was most proud of during his tenure as sheriff, Bailey pointed to the various jail programs that help inmates with substance abuse and education. He won election as Berrien County Sheriff in 2000 and became the sheriff on Jan. (WNDU) - After 23 years as sheriff and nearly 45 years in law enforcement, Berrien County Sheriff Paul Bailey is retiring from the Berrien County Sheriff’s Department.īailey got his start in law enforcement at police departments in Schoolcraft and Stevensville before landing a position as a Berrien County deputy.