Comparing Offseason Strategies: Oilers vs. Maple Leafs

The NHL offseason is a critical period where teams reshape their rosters, adjust coaching staffs, and refine strategies for the upcoming season. That’s certainly the case in Edmonton and Toronto, where two of the league’s most scrutinized Canadian franchises are once again under the microscope.

Both teams entered the 2025–26 season with Stanley Cup aspirations but fell well short of expectations. That has prompted talk of significant change in Edmonton and provided the motivation to make it in Toronto.

Oilers and Maple Leafs: Key Differences in Their Offseason Strategies

There are similarities between the Oilers and Maple Leafs, given their somewhat unique and respective situations.

Toronto flopped badly this season, and started by making management changes, sending out Brad Treliving and bringing in John Chayka and Mats Sundin. Head coach Craig Berube looks to be getting another shot next season, and there will be a focus on building a roster that Auston Matthews believes can win.

Meanwhile, Edmonton looked tired, and their roster was downgraded. They appear focused on complementary roster-building, leaving GM Stan Bowman safe (for now), but reports on Tuesday suggest that head coach Kris Knoblauch is on the hot seat, with the Oilers having sought permission to speak with Bruce Cassidy. The Oilers need to improve the core around Connor McDavid and Leon Draisaitl, and after years of contending, they took a big step backward in 2025-26.

Toronto had long been criticized for a “core four” (Auston Matthews, Mitch Marner, William Nylander, John Tavares) that delivered regular-season success but struggled in the postseason. This offseason, the organization is exploring major changes because it didn’t even make the playoffs. The Leafs appear willing to move on from more core pieces, but that’s easier said than done, given some of their contracts.

The Oilers also have players that they’ll struggle to move on from, not because they are unwilling, but because the contracts aren’t going to be attractive to other teams and the players have clauses protecting them.

Similar Challenges Faced by Both Teams

Salary cap constraints and contract clauses remain the most significant hurdle for both teams. Each is consistently building their rosters up against the upper limit, limiting their ability to make splashy free-agent signings. Each GM would have to get creative through trades or buyouts, which are much easier in theory than in practice.