2. Lou Lamoriello (July 23, 2015 – April 30, 2018)
Best Trade: Anaheim Ducks trade Frederik Andersento Toronto for 2016 1st Round Draft pick and 2017 2nd Round Draft pick.
Worst Trade: Chicago trades Jeremy Morin to Toronto for Richard Panik
Best FA Signing: Patrick Marleau signs a three year $18.75 million contract
Worst FA Signing: Matt Martin signs a four year $10 million contract
Best Draft Pick: Auston Matthews (2016 NHL Entry Draft, 1st overall)
Worst Draft Pick: Jack Walker (2016 NHL Entry Draft, 152nd overall)
Grade: A
Final Thoughts: There is no GM that did more with less. Lamoriello evaluated a team in a terrible situation, hit the refresh button and executed a perfect rebuild to help the Leafs make the playoffs for the first time since 2004.
1. Conn Smythe (February 14, 1927 – September 1, 1957)
Best Trade: Detroit trades Turk Broda to Toronto for $8K cash
Worst Trade: Detroit trades future considerations (cash)to Toronto for Charlie Conacher
Grade: A +
Final Thoughts: In 30 years as the architect of the Toronto Maple Leafs, Smythe made the playoffs 25 times, with 13 Stanley Cup Final appearances, including 7 championships.