 Bentley was one of six hockey @-@ playing brothers , and at one point played with four of his brothers with the Drumheller Miners of the Alberta Senior Hockey League . In 1942 – 43 , he made NHL history when he played on the league 's first all @-@ brother line with Doug and Reg . He played five seasons in Chicago with Doug before a 1947 trade sent him to the Maple Leafs in one of the most significant transactions in NHL history to that point . Bentley won three Stanley Cup championships with the Maple Leafs before spending a final NHL season with the Rangers in 1953 – 54 . He then returned to his home in Saskatoon to finish his playing career . Considered one of the best players of his era , Bentley was inducted into the Hockey Hall of Fame in 1966 . 
