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One of the NHL’s legendary “tough guys” has died. 45-year-old Bob Probert was on a boating trip Monday in his Canadian hometown when he collapsed with severe chest pains. Probert’s father-in-law, a police officer, tried to revive him with CPR, but that was not successful. His wife and children were also no the boat.

Probert played for the Detroit Red Wings and the Chicago Blackhawks during his 16-year NHL career. He ranks fifth in career penalty minutes.

Probert also made headlines off the ice. In 1989, he was arrested for trying to carry cocaine into the U-S from Canada, and he served three months in a U-S prison. After retiring, Probert worked briefly as a hockey broadcaster, but he soon left that job, due to a substance abuse issue.

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