All-ECAC in baseball and hockey as a collegiate student-athlete, McCaskill was drafted in the fourth round of the 1982 amateur draft by the California Angels, from the University of Vermont, and would be the first baseball player from UVM to reach the major leagues since Jack Lamabe in 1962. He debuted in 1985, and his break-out season was 1986 with the American League West champion California Angels. He compiled a win-loss record of 17–10, with a 3.36 earned run average, and 202 strikeouts. He also totaled ten complete games on the season, and would go on to have six seasons of ten or more wins, throw two one-hitters, rank in the American League top ten in shutouts and earned run average three times each. On September 14, 1990, McCaskill was the pitcher of record when Ken Griffey Sr. and Ken Griffey, Jr. became the first father and son duo to hit back-to-back home runs in MLB history. At the end of his career, he played for the Fiorentina Baseball team, in Florence, Italy.
Baseball awards and honors
In 2003, McCaskill was inducted into the Canadian Baseball Hall of Fame, along with Joe Carter, Richard Bélec, and the Asahi. In response to the news of induction, McCaskill was quoted as saying, "I am stunned by this wonderful news. I can't wait to tell my family and my parents. I am very proud of my Canadian heritage, and this is going to be an honor of a lifetime."
Hockey career highlights
McCaskill played center and right wing for the University of Vermont from 1979 to 1983, and in 1982 was a finalist for the Hobey Baker Award and was 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, and won the Cunningham Award as the Most Valuable Player on the Catamounts. McCaskill was drafted in the fourth round by the Winnipeg Jets in the 1981 NHL Entry Draft, playing only one season of professional hockey for the Sherbrooke Jets, a Jets farm team, and dressed for one game with the Winnipeg Jets of the NHL but did not play in the game. During the 1983–84 season, he scored 10 goals and added 12 assists for 22 points. He retired from professional hockey after that one season to focus solely on his professional baseball career. For his achievements in hockey and baseball, McCaskill was inducted into the Vermont Sports Hall of Fame in 2015.
Hockey awards and honors
Personal
Kirk and his wife, Dana, have three sons: Riley, Reese, and Bennett, who all currently reside in Cardiff by the Sea, California. McCaskill holds both dual Canadian and U.S. citizenships. He is currently the Varsity Baseball coach at Torrey Pines High School in San Diego.