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After helping Boston University to ECAC championships in 1976 and 1977, O'Callahan was a co-captain of the 1977-78 team and finished the season with eight goals and a team-high 47 assists. Following O'Callahan's lead, the Terriers compiled an amazing 30-2 record and took home the trophies from the Beanpot and the NCAA Championship. An All-East and All-New England selection, O'Callahan was also named MVP of the Terrier team, MVP of the Beanpot and MVP of the NCAA Tournament after tying a tournament record with six assists. He also received the first of his two Cochrane Awards as the University's top male athlete.

O'Callahan returned as team captain his senior year and helped the Terriers successfully defend their Beanpot title. The team MVP again, O'Callahan was selected first team All-America and All-East, and became the first athlete in school history to win the Cochrane Award twice.

A native of Charlestown, Massachusetts, O'Callahan continued to be successful as a player following graduation. He was a member of the 1980 Olympic team, which won the gold medal at Lake Placid, and also was a member of the Chicago Black Hawks and New Jersey Devils of the NHL.