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Jessie Massey began his career with the Jackson Police Department on September 16, 1960.  He was hired as a Patrol Officer in the Patrol Division.  He was later transferred to the Juvenile Division as a Detective.  Then Detective Massey was later promoted to the rank of Sergeant on March 1, 1969 and was eventually promoted to Lieutenant on March 1, 1974.  During his career Lt. Massey acquired several letter of appreciation and commendation for his service to the community.

Lieutenant Jesse L. Massey retired November 1, 1977 with 17 years of service with the Jackson Police Department.