Lee Massie has served in Law Enforcement in the Central Florida area for 41 years. He started his career with the Winter Garden Police Department in 1984 where he served until May of 1986. From there he was hired by the Orange County Sheriff’s Office where he had the opportunity to work in numerous assignments to include Patrol, Undercover Narcotics, Metropolitan Bureau of Investigations, School Resource, Tactical Patrol and the Intelligence Unit. Lee was also selected to serve as an Interim Police Chief for the Town of Windermere. During his time in Intel and as a result of the tragic events of 9-11 Lee was part of a team that was tasked with the creation of the Central Florida Intelligence Exchange, which was the first regional fusion center in the State.
Lee finished his career with the Orange County S.O. as a Captain, serving as Sector Commander for patrol on the east side of Orange County. In October of 2012, after almost 27 years of service, Lee retired from the Orange County Sheriff’s Office and immediately accepted the position of Chief of Police for the Kissimmee Police Dept. where he served for 4 years.
In 2016 Lee left Kissimmee and was hired as the Managing Director for Valencia College’s Criminal Justice Academy.
In 2019 Lee was offered the position of Special Agent in Charge for the Orlando Region with the Florida Department of Law Enforcement, where he oversaw the responsibilities for FDLE covering a nine county region.
In 2023 Lee was promoted to Assistant Commissioner overseeing the Orlando, Tampa, Ft. Meyers and Miami Regional Operation Centers.
Currently, Lee is serving as the Undersheriff of the Osceola County Sheriff’s Office.
Lee has a Bachelor’s Degree in Criminal Justice and is a graduate of the Southern Police Institute’s Command Officer Development Course and the Senior Management Institutes of Policing through the Police Executive Research Forum.
Lee has been married to his wife Kim for 27 years and is the proud father of two daughters.
