O\'Callahan graduated from Boston Latin School in 1975 and then attended Boston University from 1975–1979, where he was a team captain during the 1977–78 and 1978–79 seasons and was named All-East twice, All-New England and All-America, team MVP twice, Beanpot MVP, NCAA tournament MVP, and Cochrane award winner twice. He also played for Team USA at the 1979 Ice Hockey World Championship tournament in Moscow.\n', '

The year after he graduated, O\'Callahan was selected to represent the US in the 1980 Winter Olympics. Three days before the Olympics, in an exhibition match against the Soviet Union, O\'Callahan injured his left knee. This forced him out of the opening game against Sweden at the Olympics. He returned for the famous "Miracle on Ice" game against the Soviet Union in the first game of the medal round.\n', '

O\'Callahan was drafted 96th overall in the 1977 NHL Entry Draft by the Chicago Blackhawks. He joined the Hawks after the Olympics, initially playing for two seasons in the minors for the American Hockey League New Brunswick Hawks. He finally made the Blackhawks roster in 1982 and played there until 1987 when the Hawks left him unprotected. He was claimed off waivers by the New Jersey Devils and played a further two seasons before retiring 1989. He also made a final appearance for the United States national team at the 1989 Ice Hockey World Championship tournament.\n', '

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