With his career spanning 50 years, he has assisted with the creation of many dive operations and initiatives throughout his time. Winston has made approximately 6,000 - 7,000 dives and was played an integral part in establishing the first permanent dive moorings in Little Cayman and Cayman Brae. In addition, he was a pioneer for encouraging the government to declare Bloody Bay and the Jackson Point as the first marine parks in Little Cayman. His favorite dive sites are the Anchor Wall, Bloody Bay and Jackson Point in Little Cayman. His love for diving also accompanies his love for boats he is well known for the many live-aboard dive boats he has crafted from scratch over the years.