Simon was born in Laventille, Trinidad. He is credited with the invention of the Ping Pong steelpan 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 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.
- Felix I. R. Blake, The Trinidad and Tobago Steel Pan. History and Evolution. ISBN 0-9525528-0-9
- Stephen Stuempfle, The Steelband Movement: The Forging of a National Art in Trinidad and Tobago, Philadelphia: University of Pennsylvania Press, 1995
- Cy Grant, Ring of Steel: Pan Sound and Symbol, Macmillan Caribbean, 1999, ISBN 978-0333661284
- Terry Joseph, "Remembering 'Spree' Simon", TriniSoca.com, 18 April 2001