It wasn't just any Monday for Maple Leafs fans yesterday as William Nylander agreed to sign an eight-year 92-million-dollar extension. This gives Nylander the largest value of any deal signed in Leafs history. It’s hard to say the new deal is undeserved, especially when you consider Nylander, who is coming off back-to-back 80-point seasons and a career-high 40 goals in 2022-23, is on pace for another 40-goal season and could hit the 100-point mark for the first time in his career. Through 37 games this season, Nylander has 21 goals and 33 assists for 54 points. Despite being on a team with the league leader in goals (Auston Matthews), there’s a case to be made that Nylander is the team’s most valuable player this season.

The real question to me is this deal worth it for the Leafs.? In evaluating I think it's good to look at the salary cap rankings for next season, Nylander will be tied for the fifth-highest salary cap with $11.5 million. The Leafs now have four guys in the top 10 (Matthews, Marner, Nylandr, Tavares). If you were to draft the players in the NHL, where would Nylander go? I am not sure about you, but I didn't find him in my top 10. While I surely get the desire to keep Nylander especially given his current play there is always more risk signing a player when their market value seems to be at or near its peak. Despite his recent play one must note Nylander entered this season having never finished higher than 20th in league scoring. Since his emergence in 2021-22, he ranks 14th in points.

When a player signs a big deal like this I often try to find a comparison, for Nylander it seems the best recent comparison is David Pastrnak. The Czech Dynamo and Nylander are the same age and play the same position. Signed 10 months ago, Pastrnak's deal with the Boston Bruins was also for eight years but with an $11.25-million cap hit. However, Pastrnak already has a 48-goal, 95-point campaign under his belt and was amid a season in which he finished as the Hart Trophy runner-up. Pastrnak's pact was worth 13.64% of the cap ceiling when he signed the contract (13.5% of 2023-24's cap). Nylander's deal is worth 13.77% of this season's cap ceiling and 13.1% of 2024-25's projected cap. In a nutshell, the contracts are mighty close despite Pastrnak's longer track record of elite production. I think Nylander will need to maintain or improve the pace he is currently playing at for at least the first half of the deal for it to be worth it; this isn't the tallest of tasks but has its obstacles. Overall, while I see the value in Nylander and am a big fan of his game, it seems there is a solid risk for the Leafs to look back upon this deal with regret.