Simon was born in Rosehill, East Dry River, Port of Spain, Trinidad. He is credited with the invention of the Ping Pong Steel Pan instrument. Simon also was part of TASPO, the Trinidad All Steel Percussion Orchestra and visited Great Britain in 1951.
Winston "Spree" Simon worked closely with Anthony Williams who later on invented the fourth and fifth Soprano Pan. Simon also gave Bertie Marshall significant impulses for his work in developing harmonical tuning.
The American musician and composer Van Dyke Parks celebrated the life of Winston Simon in the song Tribute to Spree on his album Clang of the Yankee Reaper written and first recorded by Lord Kitchener. He loved pan music.
- Felix I. R. Blake: The Trinidad and Tobago Steel Pan. History and Evolution. ISBN 0-9525528-0-9
- The Steelband Movement: The Forging of a National Art in Trinidad and Tobago. By Stephen Stuempfle. (Philadelphia: University of Pennsylvania Press, 1995)
- Ring of Steel: Pan Sound and Symbol by Cy Grant, MacMillan 1999