Early Life
McCaskill was born in Kapuskasing, Ontario, while his father, Ted McCaskill, was playing for the Kapuskasing GM's. McCaskill spent his childhood in several cities, including Nashville, Memphis, Vancouver, Phoenix, Newport Beach and Los Angeles, while father played professional hockey. McCaskill's father retired from hockey in 1975 and his family settled in Paradise Valley, Arizona
McCaskill attended Trinity-Pawling School in Pawling, New York. During his senior year, McCaskill had an 8–0 record with an 0.97 ERA and 97 strikeouts, scored 26 goals and 22 assists in 17 hockey games, and was the varsity soccer team's leading goal-scorer. He turned down a baseball scholarship to Arizona State University so that he could pursue both hockey and baseball at Vermont.
He also played for the Fiorentina Baseball team, in Florence, Italy.
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