Everyone is talking about Matthews' next extension; but what does Nylander's look like?

Nylander is eligible to sign an extension at the same time as Matthews and he is due for a fairly large raise as well. In the midst of his 6-year, $45M deal that pays him $6.9M per season, Nylander is coming off of a career best 34 goals and 80 points. This season, through 28 games, he already has 15 goals and 27 points and is on pace for 44 goals. He is well on his way to eclipsing both career highs from last season.

If Nylander continues on that pace, what exactly does his next contract look like? Since June 1, 2020, there have only been 3 right wingers that have signed lengthy extensions which are Kevin Fiala, Matthew Tkachuk and Jordan Kyrou with AAV's ranging from $7.8M to $9.5M. there have also only been 4 left wingers in Nylander's age range that have signed 5+ year deals with those being Johnny Gaudreau, Krill Kaprizov, Gabriel Landeskog and Filip Forsberg with AAV's ranging from $7M to $9.75M.

Although Nylander can play center when needed, he is primarily a winger and if you compare his production to the players mentioned above, Nylander projects to be somewhere between $9.4M and $9.8M per season. To Nylander, that could be a bit low, considering he held out and was almost forced to sign for less than he wanted to back in December of 2018. He may feel like he is owed more money and could say he doesn't want anything that starts below $10M. Completely fair on his end, given his level of production, but it's a matter of; does he want to chase the money, or does he want to win?

With the salary cap expected to rise almost $10M over the next 4 years, the Leafs should have no issue fitting his new deal, Matthews' new deal and an extension for Mitch Marner all under the cap - especially once John Tavares' contract expires in a couple of years. In feels somewhat inevitable that he will almost certainly take a "hometown" discount to remain a Leaf as an age 35+ player.