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The Toronto Maple Leafs and new GM Brad Treliving have a number of hoops to jump through over the next month, including adding an assistant coach to Sheldon Keefe’s staff and filling some of the holes vacated by 10 unrestricted free agents, but the biggest priority is plotting the future of a pair of core-four forwards in Auston Matthews and William Nylander.
Treliving met with Matthews in Arizona earlier this month and preliminary indications are that the Leafs and the Hart Trophy winner are on the same page in terms of wanting to get a new deal done soon after he is eligible to sign an extension on July 1. Nylander on the other hand, is where the Leafs have some uncertainty and have different paths they can go down.
The 27-year-old set career-highs in goals (40), assists (47), and points (87) in his eighth NHL season with Toronto and has a year left on his six-year deal at just under $7 million per season. Like Matthews and Mitch Marner, Nylander has a clause in his contract that kicks in on July 1, but it is a modified no-trade clause in which he has to submit a 10-team no-trade list and not a more restrictive no-movement clause.
Because of that, Treliving can afford to be more patient in terms of negotiating with agent Lewis Gross to see if a deal can be reached. The Leafs GM and Team President Brendan Shanahan have publicly pronounced their desire to keep the core four together, but the reality is that might only be possible if Matthews and Nylander are prepared to take a haircut on salary in exchange for security.
Both players indicated last month that they want to stay in Toronto, but as with anyone in their position, they also want to get paid. Matthews will likely become the highest-paid player in the league, coming up from $11.634 million to in excess of Nathan MacKinnon’s $12.6 million AAV. Where the give and take will occur is if Matthews will accept slightly more than MacKinnon in exchange for Toronto succumbing to his demand for a shorter-term (four or five-year) deal or whether he wants $13.5 to $14 million on an extension.
The same goes for Nylander. Based on his improving numbers each season and just entering his prime that he would want as big a number as possible on an eight-year extension, but how big is where the problem is. Using a comparable like Nashville’s Filip Forsberg (who like Nylander had a pair of 30-goal years and hit the 40-goal plateau just prior to his new contract), he signed an eight-year, $68 million deal ($8.5 million AAV). That is a number that Treliving could live with.
If the number is in Mikko Rantanen/Johnny Gaudreau territory ($9.5 to $9.75 million), then Toronto will likely explore trade options, and based on Nylander’s representative being Lewis Gross (the same agent as Gaudreau), they will have to know how close or far apart the two sides are before the draft when a number of teams will be shopping a lot of players in similar contractual circumstances.
Based on what happened in 2018, it is very unlikely that Nylander will be reasonable and take a more friendly deal from the Leafs, and will look to get as much as possible on his new deal or test the open market next summer when the cap is going up. With that being the case, and Toronto needs to reconstitute their club to be more successful when it counts the most in the postseason.
That does not mean giving up Nylander for nothing or for the sake of change. It means trading Nylander to reallocate their cap dollars toward players with more physicality and/or upgrades on defense.
If the Leafs bring back the core group and the same head coach again…..how can anyone logically expect a different result???
Toronto Maple Leafs Blogger • 
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