Known as the "Dipsy-Doodle Dandy from Delisle" because of his fancy skating and superb stickhandling, Max was the youngest of the three NHL Bentleys (the other two were Doug and Reggie). Max grew up on a farm, one of 13 children, six of whom were boys. All of the kids played sports, and at one time five of the boys played on the same hockey team, the Drumheller Miners.
Max originally had a tryout with Boston as a 16-year-old, but he looked so small the Bruins sent him packing. On his way home, he stopped off in Montreal to try out with the Habs, and there the Canadiens' manager said Max looked so sick he should see a doctor. Incredibly, the doctor told Max he had a heart condition. If he didn't go home and forget about hockey, the doctor said, Max wouldn't live a year.
Max always looked gaunt and pale, and throughout his career he was plagued by minor injuries, pains, aches, dry throat, burning eyes, upset stomach, ulcers, diabetes and kidney trouble. He was often called "a walking drug store" because of his pharmacological tendencies, and for 155 pounds he was also quite resilient.
Although the Hawks liked Max, they wanted him to develop in Kansas City, the team's farm club. At first Max balked at reporting and decided to retire at 18 years of age. But Johnny Gottselig, a former great Max admired who was the current coach in K.C., promised to look after him and make sure he got to the NHL. Max reported the next day. Just a week later, injuries forced Chicago to call a forward up from the farm and Gottselig pointed to Max. He never saw the minors again.
In his first year Max played on a line with brother Doug and Mush March, but the following season the coach put Bill Thoms on the line as a policeman for the two high scorers. That was the turning point of the season, as Max finished third in the NHL's scoring race--Doug was first--and won the Lady Byng Trophy.
Max became famous for his drive to the net, his aggressive play to score and the fact that he was constantly in motion. He never stopped skating and had as many moves in his day, contemporaries would later say, as Wayne Gretzky did during his era.
Max won the 1946-47 scoring championship on the last day of the season--his second consecutive scoring title. Going into the game against New York, he was one point ahead of Rocket Richard, whose Canadiens were playing Boston. The game itself didn't matter for the Hawks, who were so far down in last place they couldn't see up at all. Max was getting reports about the Montreal game, and in the first two periods Richard had two points, and moved ahead. But in the third period, Max had an early assist to tie Richard. Then, midway through the period, he took a Mosienko pass at center and returned the favor at the blue line and cut to the net. Mosienko fed a perfect pass to the slot and Max's quick shot to the corner slid past the sprawling glove hand of Charlie Rayner. The Rocket was held off the score sheet and Max won the scoring title by one point.
While his years with his brother in Chicago were rewarding, the turning point of his career came on November 2, 1947, when he and Cy Thomas were traded to Toronto for an unprecedented five players--Bud Poile, Bob Goldham, Gaye Stewart, Gus Bodnar and Ernie Dickens. While many thought Conn Smythe was crazy to make the trade, the Leafs won the Stanley Cup three times in the next four years with Max. He assisted on the game-tying goal in game five of the 1951 finals that saw Bill Barilko score the Cup winner in overtime.
Bentley himself was at first saddened by the trade and the loss of playing with his brother. But he immediately became a star on a star team and helped the Leafs to victory, and his popularity in Chicago was never as great as it was almost instantly in Toronto. One night at the Gardens, the Leafs needed a goal. Charlie Hempstead, a racehorse owner and season ticket subscriber who sat right by the Leafs bench, petitioned Max. "Score a goal and I'll give you a horse," he proposed. Max did and Charlie obliged.
During the 1952-53 season, Max was hampered by a genuine back injury and played only 36 games before retiring. The Leafs sold his rights to the Rangers, and he was reunited briefly with brother Doug for part of the 1953-54 season in New York. When he retired, he had scored 245 goals and was second among active players only to Maurice Richard.