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Insider on Leafs: Matthews contract extension isn't even the most complicated situation for the team this summer

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Mike Armenti
June 26, 2023  (11:14)
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The 2023 NHL Entry Draft and the opening of free agency are now just days away, so this week is expected to be a very busy one for all 32 teams, but perhaps none more so than the Toronto Maple Leafs.

The Leafs not only have a total of 20 UFAs and RFAs to make decisions on, but they also have two very important contract extensions to negotiate with Auston Matthews and William Nylander. Believe it or not, one NHL insider says that while most might anticipate Matthews being the biggest hurdle for the Leafs this summer, it's actually the Nylander deal.

TSN's Darren Dreger made an appearance on TSN 1050's First Up this morning, joining hosts Aaron Korolnek and Carlo Colaiacovo to discuss the happenings around the league this weekend, with all of the trade talk. He also revealed why he believes the Nylander negotiations are potentially the most problematic scenario that the Leafs will face.

"I think the Nylander situation is maybe is a bit more complicated. With Matthews, when you get the term, you know what the money is going to be. It's going to be, essentially, whatever Auston Matthews says it's going to be. So, is that $13M? Is it $13.5M? Is it $14M? Like, what is that number? What if William Nylander and his agent come back and say, 'well, we need $10M' or 'we need $10.5M', you know, the Marner, the Tavares-type money. What do you do in that scenario? So, a lot of work for the Maple Leafs general manager this week." - Dreger on Nylander being the biggest hurdle for the Leafs this summer, rather than Matthews

Nylander's agent, Lewis Gross, is notorious for lengthy, grinding contract negotiations. We saw it last time around with Nylander, we saw it with Rasmus Sandin, and we saw it with another one of his clients, Johnny Gaudreau. If Gross intends to make this a rough ride for the Leafs this summer, there's a good chance that Brad Treliving learns from his past mistakes and simply cuts ties with Gross' client and trades William Nylander to the highest bidder.

Obviously, with Matthews and Nylander not eligible to sign extensions until Saturday, we won't have any answers this week on those potential deals and the hurdles that may come with them, so we'll just have to wait out the next 5 days to see how things develop.

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Insider on Leafs: Matthews contract extension isn't even the most complicated situation for the team this summer

Who gets done first; Nylander or Matthews?

Matthews34078.7 %
Nylander9221.3 %
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