 His father taught Bentley to play hockey on their farm, where the family patriarch believed the daily chores would give his children the strength to have strong shots. Bentley's father also taught him to use his speed to elude bigger and stronger opponents as he weighed only 155 pounds fully grown. He played two years in Rosetown, Saskatchewan between 1935 and 1937 where he led the Saskatchewan Intermediate league in scoring as a 16-year-old. He moved onto the Drumheller Miners of the Alberta Senior Hockey League (ASHL) in 1937, leading that league in scoring while playing on a line with brothers Roy and Wyatt. The trio were joined in Drumheller by Doug and Reg for the 1938 – 39 season. The family operated a gas station in town when not playing hockey.
