Dick Duff began his career with the Maple Leafs in 1954, where he showed his gritty two-way play quickly as an asset.

Duff would be one of the players around whom Toronto was rebuilt.  While he was not a scoring machine, he was a glue guy who was capable of digging his skates in where necessary and doing the grinding necessary to win games.  The Left Wing had three straight seasons (1956-57 to 1958-59) where he had at least 26 Goals, and he would play a large part in Toronto’s 1962 and 1963 Stanley Cup wins.

Duff was traded late in the 1963-64 Season to New York in a deal that sent over Andy Bathgate.  Duff missed out on the Maple Leafs’ Stanley Cup that year, but he won four more with Montreal.  As a Leaf, Duff scored 342 Points.

Duff entered the Hockey Hall of Fame in 2006.

Ken Randall was an original member of the Toronto Arenas when the National Hockey League formed, and we will make the case that he was one of the most underrated players of the era.

Randall played mostly on the blueline but would occasionally play at Right Wing when needed.  A Stanley Cup champion immediately when the Arenas won it all, he was also a champion in 1922, when the then-named St. Pats won it again.  Except for his first year, Randall was in the top ten in Defensive Point Shares each season he was in Toronto, which ended when he was traded to Hamilton.

With Toronto, Randall had a good run with 86 Points in 128 Games.

The Toronto Maple Leafs have had their share of titles and snipers, but it is a surprise to some to learn that Rick Vaive was the first player in franchise history to score 50 Goals in a season.

Arriving from Vancouver in early 1980, Vaive blossomed into one of Toronto’s top goal scorers of the 1980s, who not only had that aforementioned 50-Goal year (1981-82) with 54, but he also eclipsed the 50-Goal mark the next two seasons.  The Right Wing was also an All-Star in all of those seasons.  Vaive’s lamp-lighting production dipped after that, but in those three years, 30-Goal outputs were perfectly respectable.  

Vaive was traded to Chicago right before the 1987-88 season began, and as a Maple Leaf, he had 299 Goals, and was a point-per-game player.

Max Bentley’s best years might have been with Chicago, where he won the Hart Trophy in 1946, but at age 27, he was traded to Toronto, where the two-time scoring champion had a lot left to offer.

The Maple Leafs had a lot more talent than Chicago, but Bentley was still a good scorer, posting five consecutive 40-point years with the Buds.  Bentley helped Toronto win three Stanley Cups (1948, 1949 & 1951) and was the leading playoff scorer in 1951.

Bentley was traded to the Rangers before the 1953-54 Season, where he was reunited with his brother Doug, but he only played in half the season and refused to report to New York the following year.  His rights were given back to Toronto, but they never agreed on terms, and Bentley never played in the NHL again.  As a Maple Leaf, Bentley scored 256 Points, the same amount he did in Chicago.

Bentley was chosen for the Hockey Hall of Fame in 1966.