the net. Playing career Senior hockey Bentley's early career was spent with several senior teams throughout Saskatchewan. He first played in his hometown of Delisle for the Tigers hockey team in 1932–33 before playing a year in Saskatoon, then another in Regina before settling in Moose Jaw for three seasons beginning in 1935–36. He led the South-Saskatchewan Senior Hockey League in scoring in 1936–37 with 37 points and added another 14 in the playoffs, also leading the league. In 1937, Bentley, along with future Hall of Famer Elmer Lach attended the Toronto Maple Leafs training camp; both were rejected as too small for the National Hockey League. According to Lach, Conn Smythe, manager of the Leafs, saw Bentley and Lach and said "They were sending me big guys from the West, but instead they’ve sent me peanuts." He moved to Alberta with brother Reg, and joined elder brothers Max, Wyatt and Roy with the Drumheller Miners of the Alberta Senior Hockey League (ASHL) for the 1938–39 season. When not playing hockey, Doug helped run a gas station that the family purchased in Drumheller. Chicago Black Hawks The Chicago Black Hawks signed Bentley to a contract in the fall of 1939. He had previously been placed on the protected list of the Montreal Canadiens, meaning they were the only NHL team eligible to sign him to a contract. They subsequently dealt his NHL rights to the Boston Bruins for Vic Myles. When he and brother Max went to Boston for a tryout camp, Bruins' owner Art Ross declared them "among the worst amateurs to come to my camp". However, by the time Chicago signed him, Bentley had established himself as one of the top forwards on the prairies. Bentley appeared in 39 games in his rookie campaign with Chicago, scoring 12 goals and 19 points. His brother Max joined him early in the 1941–42 season, and the pair were placed on a line together. After two years of development with the Black Hawks, Bentley emerged as the NHL's scoring leader in 1942–43 with 73 points, a total that tied Cooney Weiland's NHL record for points in a season. He was the first Black Hawks player to finish as the scoring leader, and finished second in voting for the Hart Trophy as most valuable player. World War II had decimated the rosters of all NHL teams, and with the Black Hawks searching