The Mighty Shadow aka Shadow (Winston McGarland Bailey, Belmont, Trinidad and Tobago, October 4, 1941 - October 23, 2018) was a Trinidadian calypsonian. Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents. He began to sing at a very early age and he wanted to be a singer. He won the Road March in 1974 with "Bassman"(where he also placed second with "I come out to play") and 2001 "Stranger" making him the competition's oldest winner.