Prior to his arrival in the Windy City, Jim Pappin helped the Toronto Maple Leafs win the 1967 Stanley Cup, where he was the leading scorer in the playoffs, but it was in Chicago where he put up his best individual numbers.
Chico Maki played all fourteen of his NHL seasons with the Chicago Blackhawks. However, since he suited up for Games 1 and 2 of the 1961 Stanley Cup Finals (he didn’t play in them), he actually had his name etched on the Cup before he began any of those fourteen campaigns.