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With 3043 career penalty minutes – good enough for 9th all-time – they don’t come much tougher than Chris Nilan. In 1978, the Boston native was drafted 231st overall by Montreal and was considered a long shot to make the league. Nilan spent his first season in the minors but that was the last he would see of the American Hockey League. He was called up in the spring of 1980 and went with Montreal into the playoffs. He would spend seven-and-a-half seasons with the Habs, scoring a career-high 21 goals in 1985 playing on a checking line with Guy Carbonneau and Bob Gainey. Winning a Stanley Cup ring in 1986, Nilan played on Team U.S.A. in the 1987 Canada Cup. In January 1988, he was traded to the New York Rangers; in 1990, he went to his hometown Boston Bruins. Midway through the 1991-1992 season, he was traded back to Montreal where he retired.