October 23, 2018

Winston Bailey’s Shadow Leaves The Nation in Mourning

He was “Mighty” and had a personality larger than life, but succumbed to a debilitating stroke that he suffered over the weekend.

“The Mighty Shadow” passed away early this morning at the age of 77 while at Mt. Hope Hospital.

Winston McGarland Bailey, better known by his stage name, “Shadow”, was born in Belmont, Port of Spain. He spent his early childhood years growing up with his grandparents in Les Coteaux, Tobago.

The legendary calypsonian and songwriter captured his first Road March in 1974 with the hit song “Bassman”. He won again 27 years later in 2001 with “Stranger”, becoming the oldest artiste to win the competition. In the process, Shadow completed the prestigious double, as his performance of “Stranger” in the International Soca Monarch won the veteran entertainer top honours. In 2000, the year previous to his last Road March victory, Shadow was crowned the Calypso Monarch king with “What’s Wrong With Me?” and “Scratch Meh Back.”

Shadow was awarded the Trinidad and Tobago Hummingbird Medal (Silver) for his contributions to music in 2003.

Shadow’s achievements in the field of music will undoubtedly leave an indelible footprint on the twin-island Republic of Trinidad and Tobago, the Caribbean and beyond.

His unique style and charm will remain embedded on the minds of Calypso and Soca fans who had the pleasure to meet and see him perform on stage.

Always in touch with the pulse on the streets, Shadow produced timeless classics for decades. I am sure these will be listened to and treasured for decades more.

Phillip Lashley



Mighty Shadow in Hospital

Calypsonian, the Mighty Shadow, has been hospitalised. The 74-year-old has been at the Eric Williams Medical Sciences Complex where he is being treated for an undisclosed illness. CEO of the NCRHS Kumar Boodram confirmed that t...
by Phillip Lashley



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