The Leafs and Matthew Knies have some important business to address

The Toronto Maple Leafs have been burned by contract extensions over the last few seasons and a big part of that is because they've chosen to wait things out, let the chips fall as they may, and allow the player to gain a little more leverage after they've over-performed during a contract season.

Now, it might not be the same exact situation because Mitch Marner tore through his entry-level contract after scoring 67 goals and 224 points in 242 games, including a 94-point season in his contract year in 2018-19. That allowed Marner to push his negotiations all the way into September before signing a 6-year deal with an AAV of $10.9 million.

Matthews, on the other hand, signed his contract extension in February of 2019 - past the midway point of his contract year - after he had already put up 97 goals and 178 points in his first 182 games through that date. He earned a heftier $11.634 million AAV for the following 5 seasons but the Maple Leafs believed they were positioned well moving forward.

William Nylander's contract negotiations that took place during most of this past season before he finally inked an 8-year deal worth $92 million. Instead of trying to get the deal done in the summer and before the 2023-24 regular season kicked off, the Maple Leafs played a wait-and-see approach which more than likely blew up in their face, adding an extra million to Nylander's ask.

Knies is definitely the top prospect within the Maple Leafs' organization and with him being eligible to sign a contract extension this summer, it might make more sense financially to iron out the details sooner rather than later.

After completing his first full season in the NHL, Knies scored 15 goals and 35 points in 80 games played this year. He added 2 goals and 3 points in 7 post-season contests after scoring 1 goal and 4 points in 7 playoff games last year. With a much larger role expected in 2024-25 and with the salary cap rising exponentially over the next few seasons, Knies will want to cash in.

There aren't too many comparable players to set the stage for what Knies could sign for, but a good example could be forward Matthew Boldy from Minnesota after the Wild got ahead of the curve and signed him to a 7-year deal worth $49 million after he enjoyed a breakout sophomore season that saw him ultimately score 31 goals and 63 points.

It would be a big leap from the Maple Leafs if they signed Knies to an 8-year contract extension with an AAV anywhere between $5.5M and $7 million, but they would be banking on a consistent upward trajectory for the budding young star coming out of his ELC and continuing over the course of the better part of the next decade, all of which are very plausible.

Ottawa, Buffalo, and Minnesota took the leap of faith and it may save them cap space over the long-term. Will the Maple Leafs follow suit? Should they follow suit? We'll find out this summer.