With respect to the William Nylander situation, it’s imperative that Brad Treliving learns from some of the mistakes of his predecessor.

Yes, hindsight may be 20/20 and John Tavares’ don’t normally fall into your lap in free agency but there’s no question Kyle Dubas developed a quick reputation for his generosity with respect to contract negotiations. Hell, he was pretty much Santa Claus.

Bottom line: This mindless philosophy that everyone needs to get exactly what they want needs to stop. The Leafs screwed themselves royally the first time around, and needless to say, they’re still paying for it now, and likely will continue to do so for several years to come.

It’s time for a course correction.

Simply put, it’s important for a pecking order to be established. Everywhere you look around the NHL, the good teams seem to have one in place —not the Maple Leafs. Auston Matthews was always going to write his own cheque, and as anticipated, he pretty much did. The real work was always going to start with Nylander, and unquestionably, the way his situation is handled will set the tone for everything to come.

Through 17 games this season, Nylander has performed like a Hart Trophy candidate. He’s been downright tremendous. That said, this widespread notion through the majority of the fanbase and media that the team should give the 28-year-old whatever he wants is downright ridiculous. In fact, it’s the definition of insanity. They need to be smart with this.

Getting back to the initial point, the current structure of the team is the problem here, specifically Mitch Marner. He’s going to want a raise on his next contract, which once again, could be in the same ballpark as Matthews’ new deal. Furthermore, if you’re the Nylander camp, why wouldn’t you use Marner’s current contract as a starting point – or at the very least – a comparable?

I don’t envy the job ahead for Brad Treliving and company —that’s for sure.