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Bobby Gilliland began his career at the Jackson Police Department on December 1, 1959.  He was hired as a patrol officer and assigned to the Patrol Division.  

Some nine years an three months later, Officer Gilliland was promoted to the rank of  Sergeant on March 1, 1969.  Then somewhere between April, 1975 and November 1976, Sgt. Gilliland was transferred from the Patrol Division to Booking as the Booking Sergeant.  

Later, Sgt. Gilliland was  promoted to Lieutenant on June 8, 1983 and was reassigned to the Patrol Division.  Then on January 16, 1985, Lt. Gilliland was promoted to Captain over the Patrol Division where he remained until he retired.  During his service, Captain Gilliland received several letters of appreciation and commendation for his service to the community.

Captain Bobby Gerald Gilliland retired from the Jackson Police Department on July 11, 1989 after serving over 29 years with the department.