Chief Middlebrook has devoted his career to law enforcement and the courts. Most recently he served as Director of Court Operations. Before coming to CCSO he was the Division Manager for the United States District Court – Middle District of Florida. He previously spent 16 years as the Collier County Court Administrator.  Chief Middlebrook began his career with the Naples Police Department, where his assignments included detective in Vice-Intelligence-Narcotics, road and investigations Sergeant, and Commander of Special Operations. 

Chief Middlebrook has previously served with the Domestic Security Task Force, has served on the board of directors for the David Lawrence Center, and the Florida Association of Community Corrections. Chief Middlebrook is a member of the American Jail Association, the American Corrections Association, the National Sheriff’s Association, and the Florida Sheriff’s Association.  Chief Middlebrook was a founding member of the United States Custom’s Service Blue Lightning Strike Force.   

Chief Middlebrook earned his degree from Edison College and was awarded the Certified Court Manager designation from the National Center for State Courts. He is a graduate of the United States Department of Justice- Drug Enforcement Administration Drug School. His training emphasis is in Homeland Security.