4. Max Bentley
Max Bentley was a slick centre from Delisle, Saskatchewan who was known as the “Dispy Doodle Dandy from Delisle” for his tremendous skating and puck handling abilities.
Bentley and his brother Doug became stars for the Chicago Blackhawks in the early 1940s. Max, in particular, stood out for his exceptional stickhandling skills which he could employ at top speed. For the Hawks, he was sort of a 1940s version of Denis Savard. Bentley was a legitimate superstar in the NHL, so it’s a wonder that he was available for acquisition in the first place.
Bentley join the Toronto Maple Leafs on November 2nd, 1947, along with Cy Thomas in a massive seven-player swap that saw Gus Bodnar, Bud Poile, Bob Goldham, Ernie Dickens, and Gaye Stewart head off to the Windy City.
With the exception of Bodnar, a former Calder Trophy winner, the Buds managed to land Bentley for a package of relative pluggers. The trade that brought Bentley to the Leafs was much like the one that brought Doug Gilmour to the team 45 years later. The Toronto Maple Leafs were able to secure a premier pivot who was a game-breaker and difference maker while maintaining the core of their roster.
In Toronto, Bentley reinforced a roster that was already stacked at centre with the likes of Syl Apps and Teeder Kennedy. Bentley’s presence helped to transform the Maple Leafs into the NHL’s first true dynasty as they continued to win cups with him in 1948, 1949, and 1951.
Max Bentley was elected to the Hockey Hall of Fame in 1966. He is considered widely as one of the greatest Maple Leafs of all-time.