T-Minus 5 Days

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View From The stands Vol 3.

As I sit to write this article we are 5 days away from the deadline for William Nylander to agree to a contract with the Toronto Maple Leafs or any of the other 30 NHL teams. At this point it’s hard to imagine that any of the other 30 teams are willing to offer Nylander a contract that would cost them draft pick compensation, the time for that has come and gone. Now we are left with four scenarios, all of which I will breakdown below, but first let’s look at the player. 

William Nylander is a 22 year old former 8th overall pick, who represented the shift in philosophy for a Maple Leafs team who were churning their tires trapped in a stretch of mediocrity that started with the implementation of the NHL salary cap. Nylander was a player whose game was based around his skill and talent; a stark contrast compared to the days of truculence and tenacity that had cursed the Leafs for years. 

When Nylander transitioned to the North American game he continued to shine scoring 77 points in just 75 games. Willy made the jump to the NHL in the spring of 2016 and managed 13 points in 22 games. That marked the end of Nylander’s stay in the minors. This was a kid whose skill shined through at every level and after the Leafs were lucky enough to draft Auston Matthews 1st overall, Nylander was one of the biggest beneficiaries. Riding shotgun alongside Matthews on the Maple Leafs’ topline, Nylander managed to put up matching 61 point seasons. 

Now the Leafs find themselves in a tricky situation, with both Matthews and Marner needing new contracts this summer and having signed John Tavares to a 7 year $77 million contract. Fans everywhere immediately began to chime in claiming the Leafs certainly wouldn’t be able to keep all four of these major pieces. The Leafs’ rookie General Manager though immediately tried to remove some fuel from the fire when he stated, “We can and we will” when he was asked about signing all three players coming off their rookie deals. 

“We can and we will.” 

Those five words seem to have been easier said than done. As we roll closer to the December 1st deadline we find ourselves with four possible scenarios. 

Let Him Sit

No Restricted Free Agent has missed an entire season since Michael Peca who held out the entire 2000-2001 season for the Buffalo Sabres. Peca was later traded to the New York Islanders for Tim Connolly and Taylor Pyatt. Out of the three scenarios I’ll outline this as the scenario I find least likely. 

How Does This Benefit Player: Flat out, it doesn’t. Sure, William could sit the season and find himself a job playing in the KHL, but this doesn’t help him progress with his NHL career and playing overseas isn’t going to do anything to increase his value to NHL teams. The Leafs will retain his rights in this situation and he’s no closer to unrestricted free agency than he was two months ago. The best case scenario for Nylander in this situation would be a team with expiring cap space MIGHT be willing to part ways with some additional assets and sign him to an offer sheet, but there is no guarantee that the Leafs wouldn’t match this deal to prove a point. 

How Does This Benefit the Team: This might take some spotlight off the team and could potentially provide Kyle Dubas some additional credibility in the future, but this doesn’t make his team better. This move simply pushes the situation to the offseason when Kyle and the Leafs will be looking to put pen to paper for their two other Restricted Free Agents. This isn’t a win for either party and should be the last resort if the team and player can’t find a reasonable resolution or receive proper compensation on the trade front. 

Bridge Deal 

Sometimes betting on yourself is the safest bet a player can make or sometimes it blows up in your face. This is a situation where you need to sit back and really think about what’s best for both the team and the player. If you’re the player, can you outperform your contract and prove that you deserve the long term high dollar contract? Or do you end up coming up short, and costing yourself millions? For a player like Nylander you’d have to imagine there is more reward than risk, but what if he were to end up like Conor Sheary? After scoring 53 points in 61 games, he signed a 3 year $9 million deal only to watch his numbers decrease to 30 points in 79 games last season.


How Does This Benefit the Player: A bridge deal simply put is the “SHOW ME THE MONEY!” contract, it’s a players chance to show the team that he’s worth every penny he was asking for and more. This contract might be the perfect compromise for both player and team. Two years at around $5 million would give Nylander two more years to showcase his talents on Matthews’ wing and proving to management that he is worth his so-called asking price of $8 million per season. 

How Does This Benefit the Team: A two-year deal puts the Leafs into a much more advantageous position with the salary cap. The cap is likely to rise over the next two seasons and with the possible addition of a team in Seattle, you can only expect it to continue to climb and at that point the Leafs would also be out from under the $6.25 million owed to Patrick Marleau. A bridge deal on a cap friendly term might be the best case scenario for the Leafs. As they’d then have the ability to have a larger sample size of the player, while also having the option to move the player while having the upper hand over other teams looking to acquire him. 

Trade Him 

Sometimes a relationship sours and there is no coming back from it, especially when money is involved. There is a reason that teams and players both hate going to arbitration and that’s because sometimes when you open the door you don’t like what’s standing on the other side. That is also true when it comes to contract negotiations. There are plenty of examples of players who’ve been dealt after some difficult contract negotiations including Ryan O’Reilly, most recently, who found his way out of Colorado a couple seasons after signing an offer sheet with the Calgary Flames. 

How Does This Benefit the Player: A trade would offer William the opportunity to go to the market where he could be regarded as the star player and might even offer him the opportunity to become the star center which he has longed to be. With the depth down the middle in Toronto it’s obvious Nylander won’t get the chance to play center or be the star of the team as he’s overshadowed by Matthews, Marner and Tavares. Going to another market would allow Nylander to be “the guy” and possibly capitalize on all those endorsement offers that go along with being the star in the market. 

How Does This Benefit the Team: The Leafs are considered by many the team to beat in the Eastern Conference, but the team still has some glaring errors. Although the Leafs’ defense has outperformed most expectations, there still seems to be a hole on the right side of their defense and the lack of some physicality on their 4th line. Dealing Nylander might be the best chance the Leafs have to find the missing piece of the puzzle to try and end their Stanley Cup drought. As a team, they’ve managed to have proven that Nylander is a complimentary piece of their puzzle and they’ve managed to excel without him. Combined with the emergence of Kasperi Kapanen, you’d have to imagine Kyle Dubas is more than willing to pull the trigger if the right deal becomes available. 

Long Term Contract

It’s hard to imagine that both team and player could have come this far and still might end up agreeing on a deal that they should have been able to hash out earlier in the offseason, but it still might happen. If the rumours circling the internet are true, that deal could end up being in the six year type window and with so many comparables you’d have to imagine it would end up in the $6-7 million range. 

How Does This Benefit the Player: In a lot of ways this probably doesn’t benefit Nylander, because its hard to imagine that Kyle Dubas is willing to cave after holding out all these months. If Nylander walks away from these negotiations with a deal under $7 million iit would be hard to consider that a success for he and his agent. This offer does provide Nylander stability and puts him on a roster that should contend for a Stanley Cup for years to come, but might not offer him the control he’d like as he won’t be entitled to any no trade or no movement clauses for the first few years of his contract. 

How Does This Benefit the Team: If the Leafs are able to lock Nylander into a long-term contract that is under $6.5 million per season this could be considered a resounding success for the Maple Leafs and doing so closer to the December 1st deadline offers the Leafs cap savings in years 2 and beyond. This negotiation would also prove that Kyle Dubas is the right man for the job and Toronto, and would set a precedent for the other young RFA on the team. 

My Guess 

A week ago if you’d have asked me I would have told you I’d expect Nylander to be traded, but as the deadline comes closer I have shifted my mentality slightly. I still believe there is a chance Willy has played his last game in Toronto, but I am leaning more and more towards Kyle Dubas signing William Nylander to a long term deal that sets the Leafs up offensively for at least the next 5 seasons. 

All I know is hopefully by Saturday at 5 pm we don’t have more questions than answers.