Ten Maple Leafs contracts expire the same year as Auston Matthews

All of John Chayka's signings and moves made this offseason point to the team accepting it has only two years to win with Auston Matthews.

Matthews' directive to the front office this offseason was to add some bite to the lineup and they did so by adding Nick Paul, Colton Sissons, Teddy Blueger, Jack Roslovic, and Brandon Duhaime while also adding insurance behind Anthony Stolarz by signing Sergei Bobrovsky.

It was clear from the start that Chayka had a gameplan in mind, and while there are still questions about how it'll play out on the ice; on paper it's solid. But looking into the moves made it's clear that they were made solely to help Auston Matthews win - with no known plan beyond that.

John Chayka's bottom-six signings have an expiration date that matches Matthews' window

Obviously there's a reason why Chayka is banking so heavily on these next two years, and it's because Matthews' deal is up in 2028. If you're going to try and win you may as well do so with the limited time you have, and if it doesn't work then back to square one.

Toronto added the following players for their win-now window:

- Nick Paul ($3.15M AAV, Exp. 2029)
- Jack Roslovic ($4M AAV, Exp. 2028)
- Teddy Blueger ($2.5M AAV, Exp. 2028)
- Colton Sissons ($4.25M AAV, Exp. 2028)
- Brandon Duhaime ($2.6M AAV, Exp. 2029)
- Sergei Bobrovsky ($7M AAV, Exp. 2029)

Toronto also has Max Domi, Steven Lorentz, Dakota Joshua, and Zack MacEwen's deals all expiring in 2028 as well so there could be a serious turnover in two years. That's 10 players total (8 in 2028) the team will need to figure out up front alone - basically three entire lines.

Luckily for him, if Matthews does decide to move onto another team, the Maple Leafs have Gavin McKenna to build around not to mention a solid core of William Nylander, Easton Cowan, and Matthew Knies.

The only deal that doesn't really fit that two-year window is the one for Darren Raddysh, which sees him here for the next eight years at $8.5-million AAV. But that wasn't done with just Matthews in mind, it was meant to transform a blueline offence that was stagnating for years and is one of the last eight-year pacts a player can make thanks to the new CBA.

We previously talked about how important this season was for Chayka and how he can set the standard for what to expect going forward, and if he wants the best chance at keeping his captain he'll need his signings to do exactly what they were brought here to do.

What Matthews' future looks like if Toronto fails for two years

If Toronto doesn't end up getting themselves figured out by 2028, then it's more likely that Matthews leaves. It's not just a matter of getting into the playoffs, but it's making it to a Conference or Cup Final to give him some confidence in the process.

But history isn't on their side, and what comes next is pretty simple - Matthews walks.

Now it's not guaranteed, but at this point he will have been the Maple Leafs' greatest player with nothing to show for it. All the records in the world won't matter if he can't win the Cup before his career is done.

2028 is shaping to be one of the most elite free agent classes ever, with not only Matthews but Connor McDavid and Zach Werenski potentially also available. Edmonton or Columbus could go after Matthews to replace their stars and we know that Los Angeles is prepping for a big signing, so there's also a potential new team as well.

Matthews has always given his time, dedication and loyalty. But that's come at a cost of winning, and if he can't do it in the next two years, it might be the end of his time in blue and white.

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