He won the Stanley Cup with the Black Hawks in the 1937–38 NHL season. During the playoffs, he broke his toe before the start of the Stanley Cup final against the Toronto Maple Leafs. The Black Hawks substituted Alfie Moore in the first game. After the first game, Moore was ruled ineligible, and the Black Hawks lost the next game. Karakas returned with a steel-toed boot and he won the next two games which lead to the Black Hawks winning their second Stanley Cup win.