Winston has been serious about music since his days at Kingston College where he , Howard Barrett (The Paragons), Dennis Gayle and Keith Byfield formed a group they named the Deltas. Dobby Dobson later joined the group and they performed at local dances and even recorded as Dobby and the Deltas. After Howard and Dobby left to pursue their careers the group broke up and Winston formed another group with Henry Buckley (Buck’s father) and recorded an album which unfortunately was never released.
While in Jamaica Winston was influenced by Billy’s Hometown Hi-Fi and Merritone and started collecting records. Upon migrating to New York in 1969 he hooked up with Buzz and Raphael and started collecting seriously. He soon met Spencer Tracey through his friend Andy and a great collector emerged. Winston collects across the board and is famous for his “trials” which is code for “I’m not ready to tell you about this one yet”. Winston is a recipient of a 2011 VRCA Lifetime Achievement Award.