The Ugly
Like the last category, in most cases GM’s are bound to have some real stinkers. Unfortunately for Lou, there were a few mistakes throughout his time in Toronto that stick out like a sore thumb.
Drafts
Although technically Mark Hunter was the man in charge of drafting and scouting during this time, Lou had the ultimate decision making power (aside from Brendan Shanahan/MLSE board).
The drafts under Lamoriello were, to put it nicely, awful. He was in charge of arguably the two most important drafts in 2016 and 2017, making a total of 18 selections in that time. In the first round they drafted both Auston Matthews and Timothy Liljegren, which have turned out to be great selections in both cases.
It is outside of them where the issues lie with a combined 319 NHL games played between five different players picked outside of the first round. None of those games come from the 2017 draft and the only players of consequence are Joseph Woll, who looks to be the Leafs starter going forward and Carl Grundstrom, who is a bottom-six winger for the LA Kings.
To only hit on seven out of 18 players in crucial rebuild years is nowhere near good enough, especially when two of those players are top-20 picks.
In order for these drafts to be considered successes, they did not even have to grab a Brayden Point or Jesper Bratt type steal, although it would have been nice. Had they been able to get even a decent NHL contributor like Ross Colton or Brandon Hagel it would be a much better haul.
As I have highlighted in my draft retrospective series, the Leafs draft philosophy over these years was baffling. Opting to go for many oversized defensemen and overage, low scoring players just as the former was going out of style.
Patrick Marleau signing
The Marleau contract landed on my top-5 worst free agent signings of all time and that is why it is here now. Marleau in his prime was an elite scoring winger, consistently potting 30-40 goals and hovering around point-per-game numbers.
However, he would be 38 by the time the season started and Lou signed him for three years and $6.25 million per season. There were some reasonable reservations at the time which proved to be true.
He played relatively well his first season amassing 47 points in 82 games his first season but by the end of the second season, the team was forced to package Marleau with a first round pick in order to get out from under Lou's mistake.