What are we even doing with William Nylander right now? We've seen how this plays out before

During the summer of 2018, Leafs Nation patiently awaited a Nylander contract that never came. When the season shifted from summer to fall and training camp began, Nylander was nowhere to be found. The holdout would last several more months, into December, when, just 5 minutes before the deadline to sign would pass, Nylander finally put pen to paper on a 6-year deal, worth a little over $6.9M per season.

At the time, Nylander's rumoured ask was in the $8M range, while the Leafs were holding firm to something in the $5.5M-$6.5M range. Obviously, Nylander's deal eventually grew to become a very good contract for the team, with the player outperforming his AAV in the final two years of the deal. However, at the time, Nylander was paid what he was worth - perhaps even a bit more than what he was worth at the time. The young Swede was coming off of back-to-back 61-point seasons. Those would remain his two best seasons until 2021-22 and 2022-23, when he posted 80 and 87 points, respectively.

Now, as we consider where things are at between the Leafs and Nylander currently, we should also acknowledge that things are headed down a very similar path. That simply can't happen. Brad Treliving wasn't around when Nylander and his agent, Lewis Gross, raked Kyle Dubas' feet over the coals in his last negotiations, but he does know what Gross is all about. Gross also represents Johnny Gaudreau, who strung the Flames along right up until the night before free agency opened in 2022. Gaudreau, of course, left Calgary to pursue an opportunity in Columbus.

Nylander has already shown us that he's completely fine with sitting out until December 1st. If he's willing to miss two months of playing time, he's certainly willing to play a full season without a contract extension in place. If that happens, he'll be a UFA next summer and the Leafs will risk losing him for nothing. That simply can't happen.

Brad Treliving having a grasp on what Lewis Gross is like will help him in these negotiations with William Nylander. The fact that Nylander wants to be a Leaf will also help him. However, the Leafs should avoid a few things:

1) Caving in and giving Nylander $10M per season
2) Allowing Nylander to make it to training camp without an extension in place
3) Allowing the Nylander negotiations to interfere with getting an Auston Matthews extension done

If any or all of these is a legitimate concern, the team may need to simply acknowledge that the situation is potentially too costly to have it play out and just look to move Nylander to the highest bidder as quickly as possible before training camp begins.

As unfortunate as it is, this scenario may come down to trading the player and losing the trade or hanging onto the player and losing him for nothing next summer. It's a no-win scenario unless Nylander decides that he really wants to be in Toronto and that he's willing to take a fair deal for both sides to make that happen, even if it means moving off of his $10M ask. With Lewis Gross calling the shots, I wouldn't hold my breath on Nylander taking less than what Gross has convinced him he's worth.