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Robert Wiley Dailey, Jr. began his law enforcement career at the Jackson Police Department on September 1, 1952 when he was hired as a war time appointee.  Dailey was assigned to the Patrol Division until May 1, 1959 when he was promoted to the rank of Sergeant and transferred to the Traffic Division.  

Later Sgt. Dailey was tranferred to the Criminal Investigations Division and promoted to the rank of Detective Sergeant and on August 1, 1967 Sgt. Dailey was promoted to Detective Lieutenant.  Then on September 1, 1974 Lt. Dailey was promoted to the rank of Detective Captain and Division Commander over C.I.D. where he remained until December 17, 1986 when Captain Dailey was promoted to Assistant Chief of Police.  

As Asst. Chief Dailey progressed through the department he was honored to have the opprotunity to represent the Jackson Police Department as a guest Instructor for the Tennessee Law Enforcement Training Academy providing instruction in the area of Criminal Investigations.  He also was selected to attend the F.B.I. National Academy and received numerous letters of commendation.