Drafted by the Montreal Canadiens in 1981, Chelios played with the team from 1984 to 1990. He helped the Canadiens win their 23rd Stanley Cup in franchise history in 1986. Chelios was traded to the Chicago Blackhawks in 1990 and remained there for over eight seasons without reaching ultimate playoff success. The Blackhawks traded Chelios to the Detroit Red Wings late in the 1998-99 season. Since that time, the Wings have won Stanley Cups in 2002 and 2008.
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Chris won one with Montreal Canadians, when he was a 1st or 2nd year player ( rookie?)....and he has won at least 2 Stanley Cups with the Detroit Red Wings.
Nope, though he made it to the finals twice (1977&1978) under the coaching of Don cherry.