Latest update July 2nd, 2026 12:35 AM
Oct 24, 2018 News
By Sean Devers in Trinidad
The legendary Mighty Shadow passed away yesterday morning after suffering a stroke on Sunday. The Trinidad and Tobago Calypso icon was 77
Born on October 2, 1941, in Belmont, Port of Spain, Winston Bailey better known as the Mighty Shadow, grew up in Tobago, the smaller of two islands which constitute the Twin Island Republic
Shadow, along with four others, including former Guyana and West Indies Cricketer, Shivnarine Chanderpaul, was due to receive an honorary doctorate from the St Augustine campus of the University of the West Indies (UWI) this weekend
Shadow and Chanderpaul were to be conferred with an Honorary Doctor of Letters and an Honorary Doctor of Laws, respectively, at the University’s 2018 graduation ceremonies on October 25.
Shadow was a former Calypso Monarch and Road March winner in 1974 and 2001, making him the competition’s oldest winner.
The Calypsonian was the second person to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with his song “Stranger”.
Shadow was also awarded the Humming Bird Silver Medal in 2003 for his contribution to culture.
Shadow had several hits including ‘Dingo lay’ and ‘You Looking for horn Boy’. Funeral arrangements will be known shortly.
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