No July 1 Deal Means Madhouse with Matthews & Maple Leafs

The Toronto Maple Leafs find themselves in a precarious position as they navigate contract negotiations with their star player, Auston Matthews. Recent developments and rumors suggest that the team’s management, led by Brendan Shanahan and MLSE, is preparing for challenging times and tough negotiations. The departure of former general manager Kyle Dubas and the search for a new manager has added an additional layer of uncertainty to the situation. And, with news that Matthews isn’t willing to sign an extension before July 1 — because he wants to see how everything plays out first — things just went from unclear to potentially explosive.

It was suggested that the Maple Leafs (at least Kyle Dubas) were mildly comfortable letting Matthews go past the July 1 deadline and ultimately come to a decision to remain with the team. Others noted that even though this was a risk, they felt it was similar to David Pastrnak’s situation in Boston, where the Bruins weren’t thrilled he was waiting, but remained confident an extension would eventually get done.

Friedman noted in Monday’s 32 Thoughts podcast: “If Matthews hadn’t signed with Dubas there they would have kept him and they believe they would have gotten it done. Now, nobody is really sure, so that’s obviously the biggest story.” The alternative was checking the market for a trade, even thought Dubas was prepared to make Matthews the highest-paid player in the league. Now, with Dubas no longer in charge, the organization’s stance and Matthews’ perception of the team’s direction remain uncertain.

Convincing Matthews to Stay

At this point, it’s not clear what Matthews is thinking. It’s one thing to offer him a lucrative contract, but now the Maple Leafs must convince him of their long-term vision and their ability to compete for championships. Matthews is undoubtedly a talented player, but where is this team going? Who will be in charge and will the new general manager demonstrate a clear plan for success and provide Matthews with the confidence to commit his future to the team before July 1? That’s a tall ask.

One reported challenge in any future negotiations is Matthews’ preference for a shorter-term contract, potentially limited to four or five years. This would be the second time in his career he’s gone this route and a new general manager may not be so keen to oblige. Balancing Matthews’ desires with the team’s interests will be a delicate task.

For that reason, it shouldn’t come as a surprise that hockey insider Elliotte Friedman notes the Maple Leafs are actively seeking a new general manager with a tenacious and assertive approach. More specifically, they want someone with “some bite”, which suggests a departure from Dubas’ management style. Friedman adds that the Leafs want someone in place who can make bold decisions and not shy away from difficult choices.

Navigating the Matthews July 1 Contract Deadline

One of the significant challenges facing the Maple Leafs is the looming contract deadline of July 1. The Leafs can negotiate prior or trade the player prior, but once that date kicks in, so does Matthews’ no-move clause. Losing leverage in any future trade makes a decision on Matthews one of the most critical decisions the team will face all season. In no uncertain terms, their choice will have a significant impact on the team’s direction and long-term success.

Related: Turmoil in Toronto: Shanahan Prevented Multiple Dubas Decisions

Friedman added, “I did have one player reach out to me and say that they weren’t even sure if Matthews would have signed by July 1 with Dubas, cause if they made big changes around the draft, the question became how would Matthews feel about it?” There are changes inevitably coming and it makes sense that Matthews would want to sit back and watch things unfold before committing.

Anything Can Happen at This Point with Matthews and the Maple Leafs

According to Jeff Marek, allowing Matthews to go past July 1 unsigned would be potentially disastrous for the organization. For such a scenario to unfold would be unthinkable for the Maple Leafs. The potential of losing Matthews without any return is a franchise-altering nightmare. Previous managers may have taken risks, but this situation goes beyond anything experienced before, and granting Matthews the power to walk away for nothing would be a catastrophic mistake.

Friedman’s report implies that Matthews has already made up his mind on that front, thus the situation becomes even more complicated. If Matthews is not willing to meet the organization where they’re at with all of these mega franchise changes, the Leafs may have no choice but to explore the possibility of a trade. And, if he’s traded, what other dominos fall?