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Port of Spain, Trinidad, Tuesday October 24, 2018 – Legendary Trinidadian calypsonian Winston ‘Mighty Shadow’ Bailey passed away at the age of 77.
Bailey, who had been ailing for some time, suffered a stroke last weekend and his family confirmed that he died in hospital in the early hours of this morning, days before he was set to receive an honorary doctorate from the University of the West Indies for his contributions as a composer.

Among his hits were “Bassman”, “Pay the Devil”, “Poverty is Hell”, “What’s Wrong With Me”, “Feeling the Feeling” and “Yuh Lookin’ For Horn”.

Tributes have been pouring in since the news of his death broke.

Prime Minister Dr. Keith Rowley said Bailey had “revolutionized the calypso world with his haunting sound and unique delivery which he crafted and perfected in an impressive catalogue of work spanning several decades”.

“He was an original in all his various musical creations. His music told us stories about ourselves through poignant social commentary which was often fused with wry humor. Over the years his contribution to the development of our local music earned him regional and international acclaim,” he added.

Bailey was awarded the prestigious Hummingbird Silver Medal in 2003 for his contribution to music in Trinidad and Tobago, and also won the Road March title twice, as well as the Calypso Monarch.

“We are honored to have witnessed the life of this great musician and to have experienced his outpourings of the best of our calypso culture. We are grateful for the music he gave us and proud of his legacy which will remain undiminished for all time,” Rowley added.

Minister of Communications Stuart Young added that Bailey brought “something different” to the calypso/soca genre.

“From the way he dressed and danced to the layered lyrics he sang. Shadow’s songs were in many ways a commentary on us as a people but also a rallying call for us to reflect and perhaps change those characteristics he felt didn’t work for us,” he said.

“His contribution to the cultural landscape is remarkable and immeasurable. Trinidad and Tobago has lost a unique voice.”

The Trinidad and Tobago Promoters Association also remembered Bailey as “a true patriot and friend”.
“And we are saddened by this loss to our culture scape, we know his relatives and friends will be grappling with this loss in the coming days, the TTPA extends its arms to offer any assistance that they may need.

Once again we are saddened by this loss and we give the assurance that we will do all we can to celebrate his powerful contribution to us all and keep his legacy alive. Many of us will stand in our homes and sit in our cars today and dance to the music he made, we want to remember him with joy. Thank you Shadow,” the association said in a statement. 

The West Indian American Labor Day Carnival 2018 attracts the usual 2 million revelers representing the Caribbean culture and colors with music, dance, costumes, food, flags, powder, oil, steel pan, iron and beautiful people.

Eastern Parkway Brooklyn was the place to be on Labor Day September 3 . 2018 along with the other 2 million people to experience Carnival Caribbean styleee. From 11 am to 6 pm the parade of music and costumes was a peaceful day enjoyable for families and friends representing with flags from every Caribbean island and South America. 

​The 5-day festival begins at the Brooklyn Museum grounds from Thursday before Labor Day through the weekend and culminates in a spectacular New York Carnival Parade on Eastern Parkway in Brooklyn, New York.