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Born to an immigrant West Indian family, there was no shortage of land athletes for Skyler to follow as a boy. His grandfather played soccer for club and country in St. Lucia, while his mother and uncles all played basketball and ran track. Skyler, however, discovered his was flat-footed and could not endure the physical pain of constant running. After moving to South Florida at 11, he began swimming and everything came naturally once he was in the water. Skyler competed in the sprint freestyle, backstroke, and the relays, swimming for the cities of North Lauderdale and Coral Springs as an age-grouper. Following his competitive days, he started to lifeguard and began teaching soon after, and joined Imagine in the spring of 2017.