The Toronto Maple Leafs and the Edmonton Oilers are constantly compared, primarily due to the drafting of Connor McDavid by the Oilers and Auston Matthews by the Leafs in consecutive years, tying their fortunes together for a generation. Both players were heralded as the best to enter the league in years and were likened to the new Crosby and Ovechkin. McDavid nearly became a Maple Leaf through a favorable draft lottery outcome that ultimately did not go Toronto’s way.

Historically, the Leafs appeared to be a better-managed organization compared to the Oilers, who struggled with questionable signings and managerial decisions. However, things began to change when Ken Holland made significant moves, such as acquiring Mattias Ekholm and developing Evan Bouchard into a top defenseman, while Zach Hyman became a standout player alongside McDavid.

Meanwhile, the Leafs faced continued challenges and setbacks, failing to achieve comparable success. The Oilers further overshadowed the Leafs by reaching the Stanley Cup Final with several former Leafs players and threatening to break Toronto’s record of being the only team to overcome a 3-0 deficit to win the Cup, though they ultimately fell short.

This summer, the contrast between the two teams continued. The Leafs made signings like Chris Tanev and Oliver Ekman-Larsson that received little praise from NHL analysts, while the Oilers made strategic signings that were widely acclaimed. Adam Henrique, for instance, signed a team-friendly deal, Jeff Skinner joined on favorable terms, and Viktor Arvidsson added significant value without breaking the bank.

These moves bolstered the Oilers’ forward group significantly, arguably making them one of the strongest in the NHL. In contrast, the Leafs’ offseason was less impressive, with Anthony Stolarz being their standout signing, albeit in a position where they needed more decisive upgrades.

Overall, the Oilers’ decision to change GMs paid off handsomely with a highly successful summer following their Stanley Cup run. Meanwhile, the Leafs retained their GM and faced a challenging offseason, casting doubt on their playoff prospects for the upcoming season.

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