Maple Leafs Might Take Calculated Risk with Nylander’s Contract

In the ever-changing landscape of the NHL’s barely-increasing salary cap era, teams and agents are constantly seeking contract comparables to gauge fair valuations in the current challenging environment. One such comparable when it comes to the Toronto Maple Leafs and William Nylander is Alex DeBrincat’s recent contract extension with the Detroit Red Wings.

Because there are similarities between these two players, I recently took a look at what DeBrincat’s deal might mean for Nylander’s contract expectations or what the Maple Leafs could potentially acquire in a trade. But, another writer for The Athletic, Eric Duhastchek went a step further and noted that the concern over a deal might lead to the Maple Leafs taking a calculated risk with their dynamic star.

Nylander’s History of Negotiation Complicates Matters

Duhatschek was asked in a mailbag article the following: “What is the impact of Ottawa’s relatively weak return for Alex DeBrincat on the market for players such as William Nylander and Travis Konecny? — Matthew D.” The response was that, while the situations might be different, there is certainly something there to be aware of if you’re Maple Leafs’ GM Brad Treliving.

He noted that Nylander’s personality might play a pivotal role in all of this. He explained:

If Nylander were more of a go-with-the-flow sort of personality, then the answer might be yes: that DeBrincat’s deal roughly sets a term and a dollar figure that might apply to Nylander as well. But Nylander’s history is anything but go-with-the-flow. He’s been determined in the past to go a lot further than most players to get what he thinks is contractually a fair deal.

source – ‘Alex DeBrincat’s impact, William Nylander’s future and who’ll play in net for the Devils?’ – Eric Duhatschek – The Athletic – 07/14/2023

Nylander has shown determination in the past to push for what he believes is a fair deal beyond the norm. Meanwhile, DeBrincat understood that to get what he wanted, he had to take a deal. He needed to accept less money and less term to wind up in Detroit. That affected the trade in a major way because the Red Wings held the leverage.

Maple Leafs Want To Keep Control Over All Of This

The situation with Nylander is slightly different than DeBrincat’s and the Ottawa Senators. While the Sens are pushing for a playoff spot, they’re not in contention for the Stanley Cup like the Maple Leafs are. Toronto has a lot more to lose this coming season if they screw up a Nylander deal.

Duhatschek points out that Toronto’s desire to win is paramount in all of this and the need for 2023-24 season playoff success must take priority over a potential return for the player if a trade is inevitable. He points out that Nylander has been one of the team’s better performers in underwhelming postseasons of the past, creating a sense of urgency to reach an agreement with him. If trade offers and the return associated with a deal do not make the club better for this season, the Leafs are not likely to make the move. The Leafs won’t trade him and take less than he’s worth because teams feel they’ve got Treliving over a barrel.

Is a Calculated Risk More Likely?

The scribe notes that all of this may lead to the Maple Leafs taking a calculated risk and allowing Nylander to play out the year at his current compensation before reassessing the situation after the season. That’s a gamble because it opens the door to Nylander walking away in the summer for nothing, or leaving the Maple Leafs in a situation where the best they can do is trade his rights for an underwhelming return around next year’s NHL Draft.

The question in Toronto becomes, how likely is it that the team can convince Nylander to stay after a winning season? Or, how much more likely are they to offer him the deal he wants than what they’re willing to offer right now? Finally, is it better for the Leafs to keep him and try to win, than to trade him for whatever they can when that trade time comes? They’ll get pennies on the dollar (unless he has a monster season), but they’ll hopefully have a long playoff run on their resume or a Stanley Cup parade to lessen the sting of an underwhelming return.