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 and Los Angeles, while father played professional hockey. McCaskill's father retired from hockey in 1975 and his family settled in Paradise Valley, Arizona.
Hockey career highlightsEdit
McCaskill played center and right wing for the University of Vermont from 1979-1983. In 1982, McCaskill won the Cunningham Award as the Most Valuable Player on the Catamounts. He was also a finalist for the Hobey Baker Award and named to that season's NCAA East All-America First Team and the ECAC All-Star First Team. He was the team captain during the 1982-83 season.
McCaskill was drafted in the fourth round (64th overall) by the Winnipeg Jets in the 1981 NHL Entry Draft. He played only one season of professional hockey for the Sherbrooke Jets, a Jets farm team. During the 1983-84 season, he scored 10 goals and added 12 assists for 22 points. He retired from professional hockey after the one season to focus on his professional baseball career. McCaskill failed to impress Winnipeg coach Barry Long, who commented, "McCaskill plays hockey the way he plays baseball - once every four days."