The Toronto Maple Leafs aren't exactly at a crossroads. Yet they are close enough to this proverbial intersection that what they do now will matter in the very near future, and will have a massive impact on the organization's financial situation for a decade-plus.
With that in mind, it's tough to blame Maple Leafs general manager Kyle Dubas for perhaps taking a bit too much time making sure William Nylander's deal is in a preferred sweet spot.
A quick glance at CapFriendly.com indicates that Toronto has more cap room than all but three teams in the NHL. They have around $12.5 million to play with, but that will all quickly vaporize as they lock down their exciting young forward core.
Negotiations Are Bigger Than Just Nylander
Nylander needs a new deal and is in the midst of a somewhat lengthy holdout at this stage of the year, but both Auston Matthews and Mitch Marner are also scheduled to become restricted free agents this summer. The Maple Leafs' entire future up front will be negotiating—and presumably settling on—new deals over the next 12 months, which makes this a critical juncture for Dubas.
It's evident when looking at the caliber of players here that this was never going to be an easy process, but if Nylander's negotiations are any indication, the Maple Leafs are in tough to keep this particular group intact moving forward.
Instead of opening the season with Toronto this week, Nylander is still at home in Sweden, waiting for his agent and Dubas to settle on a new extension. Further complicating matters is that his negotiations aren't happening in a vacuum.
If he gets max dollars, then there's absolutely nothing to prevent Matthews and Marner from asking for as much money as possible in the coming weeks and months. Which is why you saw Brendan Shanahan starting to accumulate the dirt that could eventually make up the hill that management will die on while trying to squeeze these three elite talents in.
John Tavares, Model Maple Leaf?
Shanahan waived free agent signee John Tavares around as a model who should be followed—a player who accumulated some worth, sure, but also left some cash on the table to make room for more talent on the team.
“And at the end of the day, we see a great example with a John Tavares," Shanahan told gathered members of the media earlier this week. "We were able to attract a player like that who could have made more money elsewhere, who is still doing very, very well financially. But it wasn’t his responsibility to set a new bar or please other people with other interests. He’s a hockey player. He wanted to come here and win hockey games."
Tavares signed a seven-year contract worth $77 million this summer, leaving the New York Islanders to achieve the goal of winning a trophy with his hometown Maple Leafs.
Now the onus is on these three prolific forwards to do the same, apparently.
To this point, Nylander hasn't wanted any part of the hometown discount plan. Sportnet's Nick Kypreos touched on this on Saturday and indicated that the two camps aren't really even looking at bridge deals. It's long-term commitment or, perhaps, bust.
"Nylander’s certainly holding firm on his demands on a long-term deal," Kypreos said. "Many people believe that the answer to this is a bridge deal, but I can tell you that it hasn’t been seriously contemplated at all to the point where they aren’t even discussing anything on a three, four, five-year deal."
What if Auston Matthews Signs In-Season?
While Nylander and Dubas continue to go to the mat, looking for the right fit, things could get interesting if Matthews ends up signing in-season. What happens if Toronto's leading point producer over the last three seasons does end up taking a small discount to help the Maple Leafs keep Marner and Nylander?
Suddenly the public's view of the situation could shift, and again the pressure could end up on Nylander to take fewer dollars to remain a part of Toronto's growing juggernaut.
While Marner reportedly doesn't have much interest negotiating as 2018-19 unfolds, during the same SportsNet segment referenced earlier, Chris Johnston noted that Matthews could.
"There were discussions throughout the summer with both Auston Matthews’ camp Mitch Marner’s camp with their extensions. They could’ve done that July 1, but some of those discussions are off. Mitch Marner and his camp have called a moratorium on talks throughout the season. They don’t want to see that distraction. I get the sense that Auston Matthews would be willing to work on his extension throughout this season."
Things are getting remarkably interesting in Toronto, which is essentially the center of the Hockey Universe (please don't tell them I said that, though). It's only October, though, so buckle up.