It was minutes before the Dec. 1 deadline for William Nylander's eligibility to play this season. Toronto Maple Leafs fans were counting down to the deadline. Would the standout 22-year-old forward re-sign with the Leafs? Would he sit out for a season? Would this restricted-free-agent contract stalemate necessitate them trading away their top-line winger?
"At the end, it becomes a bit frantic as it gets down the deadline," said Toronto GM Kyle Dubas, "but in the end, no real emotions. We just to stuck to our process."
The process paid off for both sides: Nylander's new deal pays him $41.77 million over six seasons and carries an annual average value of $6.9 million against the salary cap. The first season carries a prorated $10 million salary that comes out to $6.77 million, including a $2 million signing bonus. That means it has a current season average annual value of $10,277,778. The "out years" of the contract after this season carry a cap hit of $6,962,366.
It's a creative deal, and the end of a stressful process. Rare is the restricted free agent who pushes his team to the brink; Dubas joked that the team was "making history, but not the kind we wanted" by having it go so long.
But in the end, Nylander likely did better than he would have had he inked a deal at the start of the season.
There are repercussions both in Toronto and around the league. Here's a look at how the dominoes fall after the Nylander deal.
What does this mean for William Nylander with the Toronto Maple Leafs?
On a micro level, it means that forward Josh Leivo is no longer a Maple Leaf. A third-round pick in 2011, he became a fan favorite having split time between the Leafs, where he played 84 games in six seasons, and the AHL Toronto Marlies, where he played the rest of the time. The 25-year-old center was traded to Vancouver on Monday for Michael Carcone, a 22-year-old AHL forward, which opens up a roster spot for Nylander.
In the big picture, it's a win for the two sides at the bargaining table: Nylander got more money by pushing this thing to the limit than he would have earlier this year, and Dubas gets a contract that fits the Leafs' financial plans, gets under the $7 million-per-year cap number the Leafs were loath to hand out, and has a deal that makes Nylander imminently moveable if Toronto decides to ship him out.
The Leafs are a better team with Nylander on the ice. He has 135 points in 185 career games with the Leafs, and has proved himself to be a top-line player. Auston Matthews, when skating with Nylander at 5-on-5 last season, had an on-ice shooting percentage of 13.44, compared to 10.48 without him during the last two seasons. Matthews also had a goals-for percentage of 67.53, compared to 56.41 without Nylander. Matthews is a ridiculous offensive talent who becomes preposterous when Nylander's on his wing.
Obviously, at 22 years old and on a six-year term that ends with him hitting unrestricted free agency, this stats-padding partnership could end up being rather lucrative on Nylander's next contract. But hey, this one isn't all that bad, either: $24.3 million of his contract is paid out in guaranteed bonus money, including $8.3 million of it in 2018-19.
As we said, the Leafs are a better team with Nylander than without him, but let's be real: They could be an even better team if Nylander ended up netting them a key piece to a still-forming championship puzzle. And while Nylander's contract stalemate may have netted him more money, it's still a very portable contract for Dubas: Nylander isn't eligible for any trade protection on his deal until the final year, and then it's only a 10-team no-trade clause.
So if the Leafs don't find their playoff success with Nylander, and Dubas diagnoses a need like a top-four defenseman, teams would line up for the chance to get a young offensive standout locked into a reasonable cap hit ($6,962,366 after this season) until 2024, given his comparables. (The Carolina Hurricanes, who were sniffing around Nylander before this deal was done, leap to mind.)
What does this mean for Auston Matthews and Mitch Marner?
The Leafs were in a unique position with Nylander's contract talks extending into the season, in that they could load up in Year 1 with a hefty cap number ($10,277,778) on a $12 million salary, and then have that contract be much more manageable ($6,962,366) in the "out years" of the deal.
Which really, really helps when Matthews and Marner are restricted free agents next summer and need new deals.
What are they going to end up getting? That probably has less to do with Nylander and more to do with the benchmark that Tavares set when he signed as a free agent last summer, with an $11 million average annual salary. At least that's what the Leafs hope, because if the benchmark is the $12.5 million cap hit that Connor McDavid received from the Edmonton Oilers, things could get hairy with Matthews. But the smart money is that he'll end up between $11.5 million and $12 million per year, to become the second-highest-paid player annually in the NHL.
The Tavares contract probably affects Marner more, as it's hard to fathom him getting more than the $11 million annually that his center is receiving. One assumes that Matthews and Marner combined land in the neighborhood of $20 million together. This is a better neighborhood than the $18 million combined for Steven Stamkos and Nikita Kucherov from the Lightning (McMansions) but not like the $21 million neighborhood McDavid and Leon Draisaitl live in with Edmonton (those Italian villa knockoffs that you can't see from the road, situated behind their iron gates).
The only way Nylander's deal might have affected Matthews and Marner is if he held out for Draisaitl money, in which case it would have affected them because he (a) wouldn't have played this season and (b) would be on another team.
What does this mean for next summer's other key restricted free agents?
Dubas said the "looming number" of restricted free agents was an influence on the Nylander talks going so long.
Along with Matthews and Marner, there's an all-star team of restricted free agents next summer: Colorado Avalanche forward Mikko Rantanen, leading the NHL in points; Winnipeg Jets star Patrik Laine, leading the NHL in goals; Lightning forward Brayden Point, leading his team in goals; Hurricanes forward Sebastian Aho; Calgary Flames forward Matthew Tkachuk; Vegas Golden Knights forward William Karlsson; Boston Bruins defenseman Charlie McAvoy; and Columbus Blue Jackets defenseman Zach Werenski.
Oh, if only the NHL were a place where rival general managers attempted to poach each other's young stars. Whether it's the old-boys' club mentality or the fact that offer sheets are treated like that standoff at the end of "Reservoir Dogs," with no one willing to pull the trigger first, the poaching never occurs.
What's interesting here, however, is how this group of restricted free agents acts in a post-Nylander negotiation world. Has he blazed a new trail where some of these names are willing to press their team up until that Dec. 1 deadline in order to maximize their value, especially in the first season? Or was the Nylander negotiation the outlier, and specific to the Leafs?
The bonus structure of the contract might be the template for some of these RFA contracts: a ton of money up front, getting the player a bunch of guaranteed dough and getting the team a cap number that makes the player rather enticing in a trade, or gets him into the salary structure better.
One player to watch is Rantanen, who is on pace to threaten the Avalanche record of 120 points (set by Joe Sakic in 1995-96). He's going to get a massive raise, and has professed a desire to get something done with the Avs. But how much more could he earn than the $6.3 million annual value of his linemate Nathan MacKinnon, who should be the team's highest-paid player in theory?
Has this changed the game for young players' second contracts?
"I hope not. I hope for the sake of everybody -- for the players, the teams, the game in general -- that teams and players are able to work things out and get every player into training camp," said Dubas.
But seeing Nylander push the Leafs to the brink, and end up with a better deal than he would have otherwise earned, is certainly emboldening to other young players. Frankly, other teams were dissatisfied the Leafs didn't hold the line here.
"They waited to sign him because they could afford to wait to sign him. Other teams aren't in that position. It was disappointing," one Eastern Conference governor told ESPN at the NHL Board of Governors meeting.
There is always the chance that the Leafs turn around and deal him a few months from now, citing the contract stalemate as an act of insubordination, and send a chill through the rest of the RFA world. But Dubas has publicly said he intends to keep his young core together.
The real issue here, to be honest? That RFAs like Nylander don't have arbitration rights to force a resolution before having to sit out the first two months of the season.
"Being that the league is trending younger and younger, and players are making an impact at an earlier stage of their careers, I'd like for young players to have arbitration rights immediately after their entry-level contract," agent Michael Deutsch told me during the summer.
Agent Allan Walsh agreed. "All of the RFAs that end up going towards camp and holding out, you would do away with them if you had mutual arbitration kick in after the entry-level contract," he told me. "By having this one dark year, you're putting some of the top restricted free agents into a Faustian bargain where they either take a deal with no leverage at below-market value or are being forced to hold out. Why?"
The Nylander situation was nearly the nightmare result of this lack of rights. It could be a matter worth discussing for the next collective bargaining agreement. Alas, it's also one that would require players to have some semblance of leverage to get changed ... and they don't.