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.
Roy Conacher was already a two-time Stanley Cup Champion (with Boston) and a World War II veteran before he arrived at the Blackhawks in his early 30s, and while it would have been a reasonable assumption for most fans and pundits to think that his best seasons were behind him. That wasn’t the case as he would still be a productive player and would put forth his best season in the 1948/49 campaign, where he was a First Team All Star, the Art Ross Trophy winner, and the leader in Power Play and Game-Winning Goals. He would follow that up with two more 50 Point seasons.