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Jailen is a talented soccer player.
He started at the age of 7 and quickly demonstrated he was a natural at the sport, showcasing his skills as an ambidextrous footballer. After one season of u8 Fall soccer, Jailen played up on the u10 Boys Spring Travel team. Although he was the youngest on the team, he validated his ability to play at that level. Jailen has since played for FCUSA Boston 2008 Boys Elite Team and is now a member of GPS South Shore 2008 Boys Elite Team.