Calzadilla attended Metuchen High School where he was an All-N.J. State selection in soccer. Coming into his freshman year, Calzadilla was considered one of the top newcomers to the Mountaineer squad. He was considered a talented player who, upon entering his sophomore year, was going to be counted on due to the experience he gained his freshman year. That year, it was believed that he was going to use his talents to assist on goals and score some from the wing position.