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Caleb, who was nicknamed PlayStation by the Puerto Rico Islanders supporters for his tireless work rate, grew up playing youth soccer for the Capital Area Soccer League and was North Carolina High School player of the year in 1996 when he helped lead Sanderson High School to the North Carolina State title.
The team was coached by Jay Howell, Director of Coaching at the Capital Area Soccer League in Raleigh, North Carolina, and features many players with local amateur or collegiate affiliations from Triangle area high schools and universities such as the University of North Carolina at Chapel Hill, Duke University, and North Carolina State University.