Although he was puny at just 5' 8" and 155 pounds, Bentley quickly learned to use his superior skating abilities to survive the rough and tough NHL. He was also brilliant with the puck. He could stickhandle through a maze of players at top speed - a true rarity in any era. He was a deft passer and had a laser like wrist shot.
Bentley credited his incredible wrist shot to his farm chores back home in Delisle, Saskatchewan. His father would tell him that milking cows would make his wrists strong, and in turn would provide him with an excellent shot.
The Bentleys, like most western Canadian farming families, worked hard to earn their living but relished athletics almost as much. Bill, the father better known as "Boss," was a blazing speedskater in his day, and taught all of thirteen his children to skate expertly. All 6 of his sons went on to star at various levels of hockey, including Max, Doug and briefly Reg in the NHL. Even the seven daughters formed a team that would often beat any local teams looking for a scrimmage, including the brothers.
In 1938 Max and Doug headed to Montreal to try out for the Canadiens. But Max became ill and upon further examination was diagnosed with a severe heart condition. He was told to never play hockey again in order to maintain a normal and long life.
Max returned to the farm and initially followed the doctor's orders, which left him miserable as could be. Eventually, with the encouragement of his wife Betty, he returned to the rinks and joined 5 of his brothers with the Drumheller Miners of the Alberta Senior Hockey League.
Doug got another training camp invite, this time with the Chicago Black Hawks. Doug stuck with the Hawks and impressed immediately. The following season, 1940-41, Max got an invite and also made the team.
Almost from the get-go the Bentley brothers took the Windy City by storm. Originally paired with Bill Thoms, the dynamic duo became the terrific trio once Bill Mosienko joined the Bentleys on the top line. Using their great speed and intricate passing plays, they became known as "The Pony Line." They patterned themselves after their heroes Frank Boucher and Bill and Bun Cook. Both the Pony Line and the Rangers "A Line" have been compared in modern terms to the great Soviet Red Army teams of the 1970s and 1980s.
Not including the two years he missed for military duty, Max enjoyed 5 seasons in Chicago. However it was his two year stint following WWII duties (1945-1947) that Max really asserted himself as one of the game's elite. Nicknamed the "Dipsy Doodle Dandy from Delisle," Max won the Hart Trophy (1945-46), the Art Ross Trophy (1945-46 and 1946-47) and was voted to the first All-Star team (1945-46) and second All Star team (1946-47).
Despite the Pony Line's success, the Black Hawks were never able to acquire enough depth to become true contenders in the competitive 6 team NHL. So on November 4, 1947, they went looking for depth, and sacrificed Max Bentley to get it. In one of the biggest trades in all of hockey history the Hawks sent Bentley to the Toronto Maple Leafs for 5 players - an entire forward unit consisting of Gaye Stewart, Gus Bodnar and Bud Poile, plus defensive pairing Ernie Dickens and Bob Goldham.
Max was initially heartbroken about the trade, and NHL insiders didn't understand why the Leafs gave up such a big part of their team to get just the one player - even if it was the great Max Bentley. The trade would quickly backfire on the Hawks instead and stands as one of the most lopsided trades in NHL history. The Hawks floundered without Max, missing the playoffs for the next several years.
Meanwhile in Toronto, Max was a key player in three Stanley Cup championships (1948, 1949 and 1951). Playing on a much deeper team (Max had to share ice time with fellow centers Syl Apps - who retired in 1948 - and Teeder Kennedy), Max never posted the same offensive statistics during the regular season in Toronto. However come playoff time he was unstoppable - twice leading all scorers in assists and once in points.
Max, who often played with Joe Klukay and Nick Metz (then Ray Timgren after Metz's retirement), was a fan favorite in Toronto. Perhaps his greatest moment as a Maple Leaf came final game of the 1951 Cup finals against Montreal. With the Canadiens up 2-1 in the dying seconds, the Leafs pulled their goaltender for an extra attacker. Bentley managed to manoeuvre his way right into the slot and set up Sid Smith who in turn hit the goal post. Tod Sloan was there to make sure the game headed into overtime. The Leafs won the game - and the Cup - in the extra frame, thanks to the heroics of Bill Barilko.
Bentley's career was winding down by 1953, but he wanted to end his career by once again playing with his brother Doug. The two reunited briefly with the New York Rangers before both waved good bye to the NHL, and returned to Saskatchewan until his death in 1984.
Fittingly, both Max and Doug Bentley are members of the Hockey Hall of Fame.
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