Born in Palm Beach County, Reagan moved to Gifford, Florida, in 1944 and graduated from Gifford High School. He was a running back for Florida A & M University, where he received a B. A. in Art Education. He worked as a teacher in the Indian River County school system. A friend of the Buckners and “Poncho” Moran, Reagan gave up painting, but returned to it following the rediscovery of the Highwaymen.