I have always been a fan of Shanahan, both as a player and the chief executive of the Leafs hockey operation, however, imo he's made two major decisions that I think will go down as big mistakes when we look back a few years from now :
1) drafting Nylander (8th) when he was acting as gm in June 2014 when he could have drafted David Pastrnak who went to the Bruins at the 26th spot;
2) choosing Dubas over Lamoriello and Hunter.
Dubas was hired in July 2014 as an assistant gm before Hunter and Lamoriello came on board, I would venture to guess that he had given his input to Shanahan in the drafting of Nylander in June. No wonder he would bend backwards to resign Nylander.
I believe Dubas was the correct choice.
The Nylander contractl, it's a 6 year deal, a bit of a rush to judgment, calling it a mistake after 1 abbreviated season.
The Maple Leafs braintrust weren't the only ones who missed out on Pastrnak.
Florida, Buffalo, Edmonton, Calgary, NYI, Carolina, Winnipeg, Anaheim, Nashville, Arizona, Washington, Dallas, Detroit, Columbus, Philadelphia, Minnesota, Tampa, Chicago, St. Louis, Pittsburgh, Colorado, and Vancouver all selected before Boston took Pastrnak with the 25th (not 26th) pick.
With the possible exceptions of Florida, Edmonton and Detroit, you could point a finger at any of those teams and say they "blew it" by not selecting Pastrnak.
William Nylander is a fine NHL player, who has performed well for the Maple Leafs over his 1st 4 seasons.
Would he like another swing at the 2018-19 season? Sure, and so would Evgeni Malkin.
Players have up and down years.
A better question could be how all those idiots missed Brayden Point, not selected until the 79th pick of the same draft as Pastrnak and Nylander?