Bentley was born in Delisle, Saskatchewan. He was one of six boys, and thirteen children overall. His father Bill was a speed skating champion in North Dakota before settling in Delisle, where he became mayor and helped build the town\'s covered skating rink. All of the Bentley children were athletes, and all six brothers played hockey.\n', '

Bentley first played senior hockey in his hometown of Delisle for the Tigers hockey team in 1931–32 and 1932–33 before moving to nearby Kerrobert for two years of intermediate hockey, and then to Saskatoon and Moose Jaw for two seasons each in the North- and South-Saskatchewan Senior Hockey Leagues respectively. He moved across the border to Alberta in 1938–39, joining his brothers Doug, Max, Wyatt and Roy in playing with the Drumheller Miners of the Alberta Senior Hockey League (ASHL).\n', '

World War II had decimated the rosters of all NHL teams, and with the Black Hawks searching for players, Max and Doug Bentley convinced the team to sign Reg. Bentley played his first professional season in 1941–42 for Chicago\'s American Hockey Association (AHA) affiliate, the Kansas City Americans. Reg joined the Black Hawks midway through the 1942–43 season, and the trio made history on January 1, 1943, when they became the first all-brother line the NHL had seen. Two nights later, Max and Doug assisted on Reg\'s first, and only, NHL goal. It was the only time in league history that a trio of family members recorded the goal and assists on a scoring play. While Max and Doug were established NHL stars, Reg played only 11 games in his NHL career.\n', '

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