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.