Craigwell was born in Toronto, Ontario. As a youth, he played in the 1984 Quebec International Pee-Wee Hockey Tournament with a minor ice hockey team from Oshawa.\n', '

Craigwell was drafted by the Sharks in the 10th round, 199th overall in the 1991 NHL Entry Draft. He was the 11th player ever drafted by the Sharks. Prior to being drafted he played in the Ontario Hockey League with the Oshawa Generals for 3 years, scoring 95 points in 56 games his final year there.[citation needed]\n', '

During the 1991–1992 NHL season, the first for the Sharks, Craigwell was called up in the middle of the season and skated in 32 games, scoring 16 points. The 1993–1994 season was the first for Craigwell to play full-time for the Sharks, but the results were dismal, as he was regulated to a defensive role and scored only 9 points the whole year. The following year he suffered an ankle injury and missed the entire 1994–1995 season.[citation needed] \n', '

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