Maple Leafs' Two-Year Plan Could Be Setting Up a Connor McDavid Pursuit

Photo credit: Sergei Belski-USA TODAY Sports

The Toronto Maple Leafs have entered the 2026 offseason needing a retool after missing the Stanley Cup Playoffs for the first time since 2016.

Since taking over as general manager, John Chayka and senior executive advisor Mats Sundin have wasted little time reshaping the roster to get the organization back into contention with seven major acquisitions on July 1st or before, including the likes of Sergei Bobrovsky, Nick Paul, Colton Sissons, Emil Andrae, Jack Roslovic, Brandon Duhaime, and Teddy Blueger.

However, one trend that is hard to ignore is the number of contracts the Maple Leafs have expiring following the 2028 campaign. The number currently sits at 12 and includes one very important name to the Maple Leafs organization: Auston Matthews.

With Matthews' contract expiring in 2028, it could very well end the Maple Leafs' "championship window," as the Maple Leafs captain's future is currently up in the air. Heading into the summer, reports from NHL insiders included that the Scottsdale native was unable to commit to the Maple Leafs heading into next season, with Matthews needing major improvements to the roster if he was willing to stick around.

Since then, those rumours have quickly shifted as the relationship between Matthews and the Maple Leafs appears to be on good terms because of all the trades and signings they have made heading into next season. If the Maple Leafs fail to miss the postseason for a second consecutive season, then Matthews' tenure with the Maple Leafs will likely come to an end, whether or not he sticks around for the 2028 season.

When you look ahead at who can become available to replace Auston Matthews in 2028, or if things go well within the organization, all fingers point to Connor McDavid. The superstar forward signed a short-term two-year $12.5 million deal with the Oilers just one season ago, and if the Oilers continue on the path they are on, McDavid could very well be on the move, similar to the Maple Leafs captain.

Regardless of whether John Chayka's signings are because of Matthews' contract situation, they are smart. Many NHL teams have decided to take the route of signing players to long-term contracts for less money per season, and while that is a great way of adding talent to your lineup, if they don't work out as you envisioned, they are tough players to move. Look at players like Calle Jarnkrok with the Maple Leafs or Pierre Engvall with the New York Islanders; they are nearly impossible to move.

Connor McDavid has been a player that many have speculated that several teams, including Toronto, would position themselves to make an aggressive pitch should the opportunity ever arise for the Maple Leafs. Whether John Chayka is planning the Maple Leafs roster around this seems unlikely at this moment; however, it could be a logical reason for the current construction of the roster.

The Maple Leafs' ultimate goal will always be to extend Matthews. However, pursuing another franchise player, or simply preserving financial flexibility, could be part of the plan. Chayka's approach has been noticeably different from other general managers around the NHL or previous Maple Leafs management groups.

What many fans need to be aware of is that the next two years will likely define the direction of the franchise for the near future. If the Maple Leafs return to contention, Matthews could choose to remain the face of the organization for years to come. If things don't go as planned, Toronto would enter the summer of 2028 with significant salary-cap flexibility and the ability to reshape its roster around whichever opportunities become available.

Whether that eventually includes a pursuit of Connor McDavid remains purely speculative today. What isn't speculation is that Chayka has positioned the Maple Leafs to have options when one of the most important summers in franchise history arrives.