Do the Maple Leafs Have a 2-Year Window With This Roster?

The Toronto Maple Leafs enter the 2026-27 season at the start of a new era. New GM, new coaches, new backroom staff, even a whole host of new players. But while most eras begin with the potential to run for many years, the way the Leafs are currently positioned suggests things could change again in two years.

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The Leafs are desperate for success after the disappointment of last season, which snapped a nine-year run of reaching the playoffs, and the need to get over the hump grows ever more important with each passing year. Yes, the Maple Leafs have managed to reach the second round a couple of times, but that is not good enough.

John Chayka came into the organization with a clear mandate not to rebuild, but rather to retool. This has happened, with the team bringing in players that fit certain roles effectively, including landing future Hall of Famer Sergei Bobrovsky in net, and landing the top prospect in the 2026 NHL Draft, Gavin McKenna.

While McKenna may not truly break out until his second season, unless he proves to truly be a phenom in his rookie campaign, it still lines up with the theory that the Leafs need to show progress and be more successful over the next two years before another potential reset is in the offing.

Auston Matthews‘ Future

One of the main reasons the two-year theory appears to exist is because of Auston Matthews’ contract situation. The Toronto Maple Leafs captain enters the final two years of his contract, and it will take a lot of improvements to convince him to stick around beyond that.

If the Leafs are still perpetually struggling in the early rounds of the playoffs, Matthews will likely walk to another team viewed as more of a genuine Stanley Cup contender. If, however, the Leafs show enough progress, perhaps start showing they can progress deeper in the post-season, then Matthews may be convinced that the team is close to getting over the edge and finally living up to expectations.

Much will hinge on Matthews in terms of the Leafs’ success, and there is still the possibility that the team has to part ways with him even before his contract is up, as it would be a travesty to lose a player of his caliber for nothing if there’s a clear indication that he does not view his long-term future in Toronto.

If Matthews is gone by the end of his contract, it would send shockwaves through Toronto, and the Leafs would have to seriously reconfigure and work to build a different type of roster without the star power that the captain has brought throughout his career.

The Current Roster and the Cap

What also gives more credence to the two-year theory is how many of the Toronto Maple Leafs’ contracts are currently structured. When considering just the current, expected NHL roster, the team has no expiring contracts next summer.

Every off-season signing or acquisition is under contract beyond the 2026-27 season, with the Leafs having 12 players across the offense and defense seeing their deals expire in 2028. This includes ten UFAs, such as Matthews, Jack Roslovic, Colton Sissons, and Oliver Ekman-Larsson. Emil Andrae and Easton Cowan are the two RFAs and, depending on performances and potential, they could stick around even longer.

But with so many players’ deals coming to an end in two years, it opens up a plethora of possibilities for the Leafs in a way that is not normally possible. The current cap projection for the team sees them having around $6.7 million in cap available next summer, meaning the team could add a significant contributor to the established group; then the following year, this opens up to $56.7 million at present.

With nearly $60 million to play with in the summer of 2028, this could see a whole new roster constructed, with some interesting names potentially hitting the open market.

The McDavid Hope

Of course, the big possible free agent of the 2028 class is Connor McDavid. There have long been hopes that one day McDavid would come home to Toronto and lace up for the team he grew up supporting. With $56.7 million in cap space, the Toronto Maple Leafs could easily offer McDavid enough to make him at least consider the move.

If McDavid can’t win in Edmonton and is interested in joining the Leafs, the team could use a lot of the available cap space to bring in more big-name players to fill out the roster. By that point, McKenna should have settled into the league and be a top player on the team, and there’s even the possibility that Matthews could return if McDavid joins, with the pair forming one of the greatest center groups in the league.

This would naturally be contingent on the Leafs showing enough improvements to show McDavid that things are serious. This could lead to another GM and coaching change, or it could simply be a complete rewrite in terms of player personnel. If there’s any genuine possibility that McDavid does not stick around in Edmonton and has interest in trying to be the guy who brings the Stanley Cup back to Toronto, then that fits into the two-year window with the current roster also.

It may just be a pipedream, but if in two years the Leafs have that chance and can rework the roster to fit around McDavid, it could usher in another era for the team and one that fans of the team may be even more excited for.

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