It’s October 12^th. It’s October 12^th and William Nylander isn’t signed. It’s October 12^th, William Nylander isn’t signed and it hasn’t really impacted the Leafs too much. It’s October 12^th, William Nylander isn’t signed, but it hasn’t really impacted the Leafs too much, yet we continue to produce fresh takes on this issue despite no real developments.

Today’s different side of the same coin post focuses on how badly Peter Chiarelli has fucked the Leafs in this situation. It’s comical.

Peter Chiarelli’s $8.5M AAV contract for Leon Draisaitl gave the Nylander camp the comparable contract that they refuse to move past. It’s the reason that Nylander is stuck at $8M a season (well that and uncertainty of what Marner will get despite being similar players.)

If Draisaitl had anything resembling a sane contract, (i.e. something in the $7M-$8M) range, we’d probably have Nylander back by now.

The thing with the Draisaitl comparison that gets overlooked because the contract is so bloody ridiculous, is that Draisaitl had a 77 point season prior to getting that contract, and last time I checked, 77 is more than 61. Granted, Draisaitl was playing on McDavid’s wing, but Nylander was playing on Matthews, and you could argue that’s the next best thing.

There was also a plan in place that Draisaitl would be moving to center the following season, and generally teams are willing to pay more for a center. While I have no doubt that Nylander could play center and on most teams he would get that opportunity, with Matthews, Tavares, and Kadri up the middle for the foreseeable future, it seems unnecessary to move Willie off the wing. Even if you don’t agree with paying centers more (for the record, I do.) Draisaitl lived up to his billing more or less in that role by putting up 70 points in the first year of his mega contract. He still saw sometime on McDavid’s wing, and that inflated those numbers a little, but it seems like Nylander needs to give up on this comparison because it’s not reasonable.

As bad as Chiarelli did here, it’s more on the Nylander camp for digging their heels in on this. If $8M/yr is something that Nylander wants, the Leafs should reasonably be looking at shipping him elsewhere, but that brings us to the second way that Chiarelli has fucked the Leafs.

Hall for Larsson, the deal is one for one.

I admit to having the following hierarchy when it comes to valuing players (at least when it comes to trades/contracts/etc)

But even though I firmly place wingers below defensemen, I can’t fathom a world where Taylor Hall is traded one for one for Adam Larsson. It was a franchise crippling deal that should have led to the immediate dismissal of Peter Chiarelli, but instead it seems to be a cautionary tale of trying to deal top line wingers.

It seems pretty likely that if the Leafs were to come to terms with the fact they’ll need to move on from Nylander, they aren’t going to want draft picks or prospects. It seems unlikely that a team is going to be giving up another top line winger in exchange for Nylander, I’m not sure you can make any kind of case for the Leafs adding a center. We’re looking at defense, and while the deal doesn’t need to be 1 for 1, the comparisons since the Hall trade are no existent, and any deals involving a winger being traded has been one for prospects or picks as the primary return.

So now that we’ve blamed Chiarelli for all of our problems we can go back to dealing with the problem. It’s that Nylander, Marner, and Matthews are going to be damned expensive. Not so expensive that the Leafs can’t reasonably have all three in their lineup, but not without a few of the following things happening.

 

So, that’s definitely a positive. The Leafs would have almost $2M at minimum more to work with than they do today. If the NHLPA goes with full inflator (doubtful), they’ve probably enabled the Leafs ability to keep a lot of their roster intact, maybe even bring back Jake Gardiner too, if that’s your sort of thing.

This was probably the plan all along, to let Marleau return to San Jose to retire, but really, do we think San Jose wants that at this point? I’m willing to bet that if they sign Erik Karlsson long term and they find themselves dealing with the cap implications of that, adding Marleau’s $6.25M cap hit isn’t very realistic, even if they are excited about the smaller salary, and the fact that there still isn’t any reason to believe that Marleau can’t be effective in the 2019-20 season.

Marleau + the minimum cap increase probably covers off what Mitch Marner is going to cost for salary, and getting Marleau out the door will be important. Potentially the Leafs could have options besides the Sharks, but with his No Movement Clause, the ball is completely in Marleau’s court, and leaving the Leafs probably isn’t something he’s particularly keen on doing.

The other option is that he considers this his last season. He waits to collect his bonus on July 1^st from the Leafs, and they deal him a team willing to carry his cap hit, and then he retires. Cap circumvention at its finest, folks, but it relies on a player who is still capable of playing deciding that he’s done.

This is just a good idea regardless. I can’t imagine that there are too many teams interested in Zaitsev, but I honestly wonder what would happen if the Leafs dumped Zaitsev on the Marlies this year. Would he eventually agree to a mutual termination of the contract once a KHL team threw some money at him? I dunno. I’m just done with Zaitsev, and that cap space is a lot more valuable than anything he’ll be doing on the blueline.

This is a loaded one, but one that definitely resolves not only getting Matthews, Marner, and Nylander back, but comfortably bringing back Kapanen and Johnsson too, assuming they’ve earned raises.

Gardiner has some appeal to a certain price, and I’d argue that’s the case for all of the Leafs free agents. That’s why I’ve put together my own means for assessing what I’m willing to see the Leafs pay on their top free agents…

Basically, what I’m happiest with the Leafs paying is at the top of the chart, once we wind up in the grey, I think they’ve moved into I’d consider trading them territory and the blue represents values that I wouldn’t be able to get over.

For Jake Gardiner, I’m happy with him up until $5.5M a year, but if he the Leafs give him $5.5-$6M, I’d consider him potential trade bait. If Gardiner somehow reached $7M/yr in his next deal I would be disgusted with the Leafs.

There are a lot of bigger issues that will come into play in 2019-20, and I’m certain no one has any interest in reliving the Nylander situation again next year with Matthews and Marner, but the issue right now is getting Nylander signed.

The idea of bringing in Nylander at $8M is pretty ridiculous and unnecessary, well, unnecessary as long as the Leafs keep on winning, but the $8M number is never going to feel good. The upside to that is that it seems very unlikely that Nylander will get that, or at least not get that as his annual cap hit.

At the same time a contract with Nylander is more feasible than we think, it’s not a bad idea for the Leafs to explore what can be done via trade. While a return of futures might be somewhat of a disappointment, the fun thing about futures is that they can used to acquire the defenseman the Leafs need somewhere down the line. Much more on the nose is the rumour of the Predators showing interest in Nylander. The wealth of talented defensemen they have in stock should show tremendous appeal for the Leafs, and the Ryan Johansen for Seth Jones deal makes it seem like something we shouldn’t dismiss.

As for the long term. The rising salary cap washes away a wealth of issues, but that’s not to say that the Leafs won’t have tough decisions on the horizon no matter how this plays out. The Leafs have no shortage of talent that have been labelled “the core” of the team, but in reality the Leafs will need to identify a much more specific core of who is truly sticking with the Leafs no matter what. That’s likely Tavares, Matthews, Rielly, and only one of Nylander or Marner. Everyone else will become a tough decision at some point.