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. He won the Calypso Monarch in 2000 with &quo… read more
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 si… read more
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 Mar… read more