The Toronto Maple Leafs Have Till 2028 to Win a Stanley Cup

The Toronto Maple Leafs have a competitive window till 2028.

If the club can’t win a Stanley Cup, or multiple ones, by then Toronto Maple Leafs fans could be looking at a long, cold rebuild.

But why 2028 specifically?

I recently read a piece by Jonas Siegel of The Athletic. In the article, Siegel discussed the tasks GM Brad Treliving had before him this summer. Siegel wrote his thoughts in mid-June, roughly two weeks before the opening of free agency.

Now, Siegel’s line of thought was the Toronto Maple Leafs needed to address the blue line, goaltending, and forward depth. That’s nothing new to anyone familiar with the team. However, Siegel made this comment about the term Toronto would commit to Chris Tanev:

“It’s believed a four-year deal will be the ticket again for Tanev. Which raises the question for Treliving of whether to commit to the 34-year-old for as long — until 2028 — the Leafs have Auston Matthews under contract.”

This insight provides a crucial look into where the Leafs, as an organization, are heading. The club will remain competitive as long as Auston Matthews is on the team. After that, who knows?

What Happens If the Toronto Maple Leafs Don’t Win Anything with Matthews?

Let’s get the easy part of the discussion out of the way. The Leafs win at least one Cup from now till 2028. If that’s the case, Matthews will have established himself as one of the all-time greats while making a dream come true for Leafs Nation.

But what happens if the Toronto Maple Leafs can’t win anything while Matthews is still under contract? The likelihood that Matthews re-signs in 2028 is slim. Matthews would be about 30 years old and looking at his last shot at a long-term contract.

Assuming Matthews is still an elite goal scorer at 30, he should be in high demand. He would surely bolt Toronto for a team that has a clear shot at winning a Cup.

While William Nylander would still be under contract, knowing Nylander, he won’t want to stick around without Matthews. So, he might turn around and demand a trade.

Furthermore, there’s no telling what the Leafs’ roster would look like in four or five years.

The bottom line is that Leafs fans are looking at the beginning of a long winter in 2028. Matthews will go the same way Steven Stamkos did this offseason. Stamkos left after two Stanley Cups. So, there’s no guarantee Matthews will stay even if the Leafs win multiple Cups.

When Matthews eventually leaves, the Leafs will undergo a painful rebuild. If the last one is any indication, Leafs Nation could be looking at multiple seasons of tanking before quietly building from the ground up.