The worry is beginning to mount in Leafs Nation; is it justified?

Now, this isn't your typical "the sky is falling" piece. This is more just a question as to when the fanbase is justified in showing outward concern over the lack of traction on the Matthews and Nylander extensions. We knew we wouldn't likely see a Matthews deal within a week of the start of free agency, but many had assumed that we might see a Nylander deal done. Now, almost two weeks into the free agency period, there still seems to be almost no movement whatsoever on either front.

Yes, there may still be over two months remaining until training camp and both players are still under contract through next season, so their contract statuses won't prevent the Leafs from icing a killer lineup again next season, but the question that everyone wanted to ask last season was where Auston Matthews would sign as a UFA in 2024. Despite the fact that Matthews has stated on a number of occasions that he wants to be in Toronto, the fact of the matter is that with every single day that goes by with Matthews not being signed, the less likely people are to believe him.

Insiders continue to express their confidence in Matthews re-signing in Toronto at some point this summer and we know that his deal, if/when he does sign, will not be an 8-year term, but rather in that 3-5 year range, which will allow Matthews to sign one last mega deal at the end of his next contract. However, if the term is decided and if we have an approximate AAV lined up, why isn't the deal signed?

Do I personally believe that Matthews will sign an extension in Toronto? Yes, I do. Am I beginning to consider the fact that the longer Matthews remains unsigned, the opportunity that he could have a change of heart and pivot towards testing free agency may increase? I'm getting there.

Nylander is a bit of a different case. His issue seems to be mostly about the money. We know how he feels about playing in Toronto and we know, from various reports, that he's the most likely to sign a full 8-year extension. If the Leafs were willing to offer him $10M per season, he would have likely signed already. The bigger concern with Nylander here is that he won't budge on his ask. He won't sign a new contract this summer and in doing so, he'll only further delay a Matthews signing. The other issue here is that the Leafs will almost certainly lose a trade involving Nylander. We saw what deals for Timo Meier and Alex DeBrincat brought back to their respective clubs. Is there an appetite for the Leafs losing a Nylander trade?

The Leafs are in a pretty tough spot right now and the fans are getting restless. If these players truly do want to win, raking the Leafs' feet over the coals isn't going to get them any closer to that goal. Holding out isn't going to get them any closer to that goal. It's also not going to cause the fanbase to begin to resent the players. This whole thing is a no-win situation for anyone. So, again, I ask; when is the appropriate time for fans to begin to air their grievances with the team? Because it feels like we're getting pretty close.