However, some of the organization's blunders over the years are too laughable to ignore. Trading Tuukka Rask to the Boston Bruins for Andrew Raycroft. 19 years without a playoff series win, 56 without a Stanley Cup. Trading Tyler Seguin-plus for Phil Kessel (although, Kessel balled out in Toronto, so I cannot call that an outright blunder). The Leafs have some bad ones over the years.
Well, you can add one more tactical blunder onto the list: goaltender Jeremy Swayman of the Boston Bruins.

Swayman's recent appearance on Dropping the Gloves revealed that the Leafs had serious interest in him after the two sides had heavy dialogue leading up to the draft.
Just 23, Swayman already has 51 NHL games under his belt, sporting a 2.23 GAA and .920 SV% with a 30-17-3 record. Goalies tend to hit their prime around age 26, so Swayman's future looks very bright at this point.
What makes this pick so detrimental for Toronto is not so much that they did not take Swayman. Rather, it is the player they did take; goaltender Ian Scott, who recently announced his retirement from professional hockey.
As the Maple Leafs charge into 2022-23 with a Matt Murray-Ilya Samsonov tandem, they could have a 23-year old, cost-controlled Jeremy Swayman. Instead, they do not have Swayman and their division rivals will deploy him against the Leafs yet again.
Classic Leafs.
|
HIER
16 MAI 2026
| ||||
| B | P | PTS | ||
| Rasmus Dahlin | 1 | 4 | 5 | |
| Tage Thompson | 1 | 3 | 4 | |
| Jack Quinn | 2 | 1 | 3 | |
| Zach Benson | 1 | 1 | 2 | |
| Jake Evans | 1 | 1 | 2 | |
| Jason Zucker | 1 | 1 | 2 | |
| Ivan Demidov | 1 | - | 1 | |
| Konsta Helenius | 1 | - | 1 | |
| Zach Metsa | 1 | - | 1 | |
| Arber Xhekaj | 1 | - | 1 | |
| Bowen Byram | - | 1 | 1 | |
| Cole Caufield | - | 1 | 1 | |
| Lane Hutson | - | 1 | 1 | |
| Michael Matheson | - | 1 | 1 | |
| Ryan McLeod | - | 1 | 1 | |
| Josh Norris | - | 1 | 1 | |
| Mattias Samuelsson | - | 1 | 1 | |
| Josh Anderson | - | - | - | |
| Zachary Bolduc | - | - | - | |
| Alexandre Carrier | - | - | - | |
| STATS COMPLÈTES | ||||