 He played two years of senior hockey in Drumheller, and one more with the Saskatoon Quakers in the Saskatchewan Senior Hockey League (SSHL) before playing his first professional games with the Providence Reds of the American Hockey League (AHL) in 1940 – 41. He caught the attention of the Chicago Black Hawks, and while the team was impressed with his play, they wanted him to start with their American Hockey Association (AHA) affiliate in Kansas City. Bentley initially refused, and considered retiring. He was convinced to report by Kansas City's coach, Johnny Gottselig, and played only five games before injuries in Chicago led the Black Hawks to request a call-up. Gottselig sent Bentley up, reuniting him with brother Doug who had joined Chicago in 1939. Max played his first NHL game on November 21, 1940, against the Bruins. He scored his first goal on December 1 against the New York Rangers.
