Insider confirms Leafs prepared to take extreme measures in Nylander negotiations.

The Toronto Maple Leafs now appear to have less than two weeks to either reach a deal with restricted free agent forward William Nylander or to find Nylander a new home via a trade that will bring back equal or greater value than Nylander would provide to the Maple Leafs line up at this time. At least that appears to be the case from those on the outside looking in, but that may not actually match the reality of the situation.

For the first time last week we began to hear reports that the Leafs could potentially consider the option of actually letting Nylander sit out a full year of his young National Hockey League career. It is of course a tactic that would hurt the Maple Leafs considerably as well as obviously being a less than ideal situation for Nylander, but it is one that would send quite the message regarding just how serious newly appointed Maple Leafs general manager Kyle Dubas is going to be as a negotiator. The move would not only set a tone for future negotiations with the Nylander camp but it would do so for potential future negotiations with Auston Matthews and Mitch Marner as well. 

On Saturday during the Hockey Night in Canada broadcast of the NHL's games NHL insider Chris Johnston of Sportsnet confirmed that Dubas and the Maple Leafs are in fact willing to go to these extreme measures if necessary.

“If there isn’t a trade that presents itself — and we spoke last week about the fact that they are gauging the market on William Nylander, and William Nylander’s demands don’t come to the range that they’re comfortable paying — they’re comfortable letting this player sit and I think that’s significant with the fact that it’s 13-plus days remaining and tensions only to get a little higher as we get closer to Dec. 1,” said Johnston as per Sportsnet.

It's been nearly two decades since a team has used this measure in negotiations with a restricted free agent, an indication that both sides usually come to terms before the final hour, even in the most tense of negotiations. Recently defenseman Jacob Trouba and the Winnipeg Jets were locked in a similar battle and even in spite of the bad blood in those negotiations they got the deal done before time expired. 

The Leafs however are in a rather unique situation with Marner and Matthews to also think of, players who are almost certainly ahead of Nylander in terms of importance to the organization at this stage. On top of that they have found tremendous success this season, even while Auston Matthews has been out the last 3 weeks with a serious injury, without Nylander in the line up and that has undoubtedly shifted a ton of pressure off the shoulders of Kyle Dubas and placed it firmly on the shoulders of Nylander's management.  In fact you could argue that every win the Leafs have picked up while facing all of this adversity has chipped away at the value that Nylander has, at least as far as the Leafs are concerned internally.

Perhaps worst of all for Nylander is that fan sentiment appears to have shifted strongly towards the Leafs in these negotiations, and I don't think there would be a great deal of outrage if the Leafs did indeed hold out a full season to secure a better long term deal for the organization.