The Maple Leafs and William Nylander are taking longer than they should to come to a negotiated settlement on his new contract. They each want different things, primarily in dollars or Average Annual Value (AAV), but somewhere in the middle where neither side is happy is what we expect of a compromise deal.

There are eight possible contract terms the Kyle Dubas and Nylander could settle on. One thing that has been reported with direct quotes from primary sources is that both parties want a long-term deal. Neither side has defined “long” for us, but it’s safe to assume that it’s five years or more they’d both prefer.

A shorter, bridge deal is seen as the second choice for both parties, but they might both settle on that choice to get this done. There are reasons why opting for the compromise might be more difficult to bring off than the original long-term deal, however, and that could be why this is taking so long.

I’m going to use Matt Cane’s model for projected AAVs at each term. It compares past player value and contracts awarded and estimates what a contract is likely to be, not what is “should” be. Several PPP commenters have done similar exercises, ranging from back of the envelope estimates to more systematic approaches and come up with nearly identical numbers. These numbers won’t suit the “he’s overrated” and “if he loved us, he’d take a discount” crowd, but then nothing will.

Eight year deals are status symbols for franchise players, and that’s reserved for Auston Matthews.

Seven Years

  • Expires in 2025 and buys two UFA years.
  • Cane’s projected AAV: $6,965,044 /

Leafs

This is the ideal deal for the Leafs. It buys two UFA years, which pushes the AAV up because you have to actually pay for that, but they could conceivably offset that increase with a no-move clause in the final years.  It locks a core player up to the maximum term they would want to give him. This was likely the term on the earliest offers, but it’s obvious they couldn’t get an agreement on the AAV.

Nylander

This is the perfect term for Nylander. It’s got maximum security, the highest AAV he’s likely to get, and he has the potential to dictate his future now by getting a no-move and/or no-trade clause in the final years. I assume this was the term on his initial ask, and it seems the reports that they’re too far apart on the AAV to make this work have to be true.

Six Years

  • Expires in 2024, Nylander is UFA, but the deal has bought one UFA year.
  • Cane’s projected AAV: $6,955,003 /

Leafs

I think the model is off on this AAV. It should be a little lower than the seven-year option. But that said, this deal is really not much different, and the Leafs would be happy with it for the same reason they’d like a seven-year contract. If the team could push for a much lower AAV than the seven-year option, they would be really happy, and this may have been their early preference.

Nylander

Taking a six-year deal instead of a seven leaves Nylander a little younger when it ends, but that’s about all the benefit of it to him over the seven, particularly if the Leafs pushed for an even lower AAV.

Five Years

  • Expires in 2023, and Nylander is UFA.
  • Cane’s projected AAV: $7,010,668/

Leafs

A five-year deal does not give the Leafs any advantages. It buys no UFA years; it’s very expensive; they can’t buy some AAV back with any no-trade or no-move clauses (those can only be included in years the player would be a UFA). While a five-year deal is fairly common for high-end players who aren’t franchise stars, it has never looked like a smart deal for the Leafs in this situation.

Nylander

This is a good option for Nylander because it expires with him at the youngest possible age for UFA riches. But it’s not buying any UFA years and it can’t have any no-move or no-trade protection. Nylander is giving up two years of security for what the model forecasts as a slightly higher AAV, but are the Leafs really going to offer him more for five years when it’s not really any advantage to them?

Four Years

  • Expires in 2022
  • Cane’s projected AAV: $6,741,261/

Leafs

The cons to this deal for the team are a little worse to those for the five-year deal. It’s still expensive, solves no cap issues, buys no UFA years, and it ends with an RFA one year from UFA who has arbitration rights. If that sounds familiar, that’s the situation the Ottawa Senators put themselves in with Mark Stone.  Stone opted for an arbitration award of a lucrative one-year deal that puts all the power in his hands for his next contract as a pending UFA.

Nylander

The NHL owners have an option to terminate the CBA early next September. The NHLPA has one the following September, with 2020-2021 the first year that could be lost to labour strife. If neither the owners nor the players opt out of the CBA, it expires at the end of the 2021-2022 season.

So with the second most likely year of labour disruption to occur just as this deal would end, Nylander should stay well away from this term, even though the chance to run the Stone gambit is a big positive. He’s also at high risk of not being allowed to sign anything more than a five-year deal when he re-signs. The next CBA might contain contract term limits of less than the seven and eight years in the current agreement. The owners had to concede on this last time, but the appetite for a five-year limit is very high with both the league and the owners.

The pros to this deal rest largely in Nylander’s ability to negotiate for term and a high AAV on his next deal, and he could end up with a very high career salary by going with a shorter term now, but the risk that something ruins that well-laid plan is real.

Three Years

  • Expires in 2021
  • Cane’s projected AAV: $6,302,581/

Leafs

If they have to settle on a bridge deal, three years might work for the Leafs. But just getting past 2020-2021 doesn’t guarantee labour certainty. The big negative for a three-year deal for the team is that Nylander is an RFA at expiry and yet the AAV is going to creep up to something close to what they’d be paying to buy UFA years. It’s not a beneficial compromise for the team unless they really force Nylander to a lower number on the AAV than the model forecasts.

Nylander

If Nylander has good luck, or even just no bad luck, a three-year deal now followed by a seven-year deal could make him the maximum amount of money over his career, more even than if he starts with four years now. He would be 25 when the deal ends in 2021, and would have multiple seasons of results to draw on as an RFA with arbitration rights. Players and their agents don’t like to play poker against the gods of luck, however. One ill-timed injury and this scenario all goes up in smoke and the Leafs could have the arbitration advantage. He would also have to be very concerned at all the trade deadlines that would be sliding by, with the temptation for the Leafs to trade him.

The best you can say about this deal is that it’s better than all the other short-term options, but given the risks he’s taking on a bridge deal, he’s not going to want to give out discounts on the AAV.

Two Years

  • Expires in 2020
  • Cane’s projected AAV: $5,440,360/

Leafs

Many teams would prefer a two-year deal that expires in the summer of 2020, since they’d have one expensive player they wouldn’t have to pay until the season actually started, and for all anyone knows now, that might be never. But the Leafs don’t care about cash payouts.

Two years allows the Leafs to solve their mild cap problems and then lock Nylander down for his peak performance years with a long-term extension. They’d want him for much less than $5 million, however.

Nylander

He would never take this deal, not unless he really believes expansion plans will stop a lockout in its tracks. The potential of losing all or part of a year’s salary wipes away any benefit he might gain by getting tough on the AAV either now or in an extension. Without the lockout potential, a two-year deal might be his ideal second choice, since it gives him time to lay down two good years and then go to arbitration. The lockout has made this compromise impossible, and that might be why we’re where we are right now.

One Year

  • Expires in 2019
  • Cane’s projected AAV: $5,167,787/

Leafs

A one-year deal gets Nylander on the ice, but the idea of doing this all again next summer cannot have much appeal. An extension on a one-year contract cannot be signed until January 1, 2019, and that would mean the Auston Matthews and Mitch Marner deals would either have to be done first or they’d have to be put on hold.

All decision making would be complicated by the fact that next year’s cap hit would be sitting as an estimate. While I think the Leafs know how they will fit all four of their expensive players under the cap next year, they would want to kick this can farther down the road than one year to avoid last-minute surprises.

Nylander

One-year deals are very high risk for any player. One of the risks is that he’ll be traded at the deadline if the Leafs suffer a setback. He also runs the risk of an injury-shortened season killing his ability to get a better deal next summer, particularly via arbitration. He’s almost as unlikely to go for this as he is a two-year option.

I don’t think William Nylander thinks he’s getting an $8 million AAV long-term deal. I don’t think the Leafs think they’re getting Nylander for $6 million for any term more than three years. The obvious solution has always seemed to be seven years at some token amount over or under $7 million.

If that’s unachievable, then the whole mess of the uncertain CBA expiry is making a bridge deal negotiation really complex. Nylander will want more years than the Leafs will want to give him, and suddenly the negotiation is about two things: AAV and term.

My hope is that at some point they come back to the table on a six- or seven-year deal, compromise on the AAV, and just get the best possible Leafs roster on the ice every night for years to come.

If the Leafs really push for three years and a low AAV, banking on their greater power in the negotiation, then they’re playing poker with the luck gods, and they might just end up paying him a hell of a lot more long term than they would have with 7 by 7. If the cap keeps going up, his contract three years from now might be bigger than we can even imagine now, particularly since a term deal then is buying even more expensive UFA years.

The bridge deal isn’t all that good for either side in this case, and they were both right to be thinking term at the start of this process.

It worked out for Tampa and Nikita Kucherov, it might work out for the Leafs and Nylander too. But first they have to get him to buy into a deep discount now or there is no benefit to the team to not just do a long-term contract. What’s in it for Nylander to give up AAV now? I hope Dubas had a really good answer to that in Switzerland, or they might stay mired in the mud for a lot longer.