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. He made NHL history when he played on the league's first all-brother line with Max and Reg in 1943. Injuries forced him out of the NHL in 1951, but he returned in 1953–54 to play one last season for the Rangers with Max. He spent several seasons as a player-coach for the Saskatoon Quakers, leading the team to the Pacific Coast Hockey League championship in 1952. Bentley was inducted into the Hockey Hall of Fame in 1964.