Contracts for the Big-3

[sickbeast]

That happens, the Leafs match, use Nylander this year and trade him in the summer for a better haul because he has a contract and you know how his cost going forward

I had actually thought about that scenario and it actually makes a lot of sense.  The Leafs have enough cap space where they could easily pay Nylander even $9 million this season.  It's next season and beyond where they would have a problem.  But it would make perfect sense for them to sign Nylander, use him for this season, and then trade him after they (hopefully) win the cup.

 

[Kin]

I'm saying you don't know what the compensation would be in a trade. Given that we never see offer sheets it's far more likely a team would work out a deal for Nylander rather than attempt to sign him to an offer sheet. That's just reality.

No, that's just an argument. But you ducked the larger question. Even if hypothetically the Leafs should match a 5 year/40 million dollar offer sheet rather than take a 1st, 2nd and 3rd and trade him later when more teams will have cap room and be able to be in on the process, why not sign him to the 8 year deal now? Why would Nylander ever be more valuable at 8 million until he's 27 but not 8 million until he's 30?

Signing Nylander to the sort of deal he wants doesn't guarantee you never move on from him, just that if you trade him and he is worth what he wants(and if he isn't then teams aren't going to want him at that price) you have him locked up for as long as possible so it's a more valuable asset.

As to "why would they ever give up more than a first second and third?" , the deal could be contingent on Nylander signing a 7 year deal with the new team so they'll offer players + picks.

Again, why? Why wouldn't that team rather have Nylander at a much cheaper cost? Even if they don't have the cap room, you're arguing that they'd be willing to trade a valuable asset for him but why not trade that asset separately for its best return and spend as little as you can on Nylander?

The reason we wouldn't see a five year/8 million AAV offer sheet is because the Leafs would just match it because the compensation would suck. So if you'd match that offer sheet and look to trade him, the smarter course of action is to lock him in at that AAV but for the longest possible term.

Again, no crystal ball on hand but I think I've seen enough NHL trades to know that teams in the Leafs position don't tend to do well in trades.

 

[Zee]

I'm saying you don't know what the compensation would be in a trade. Given that we never see offer sheets it's far more likely a team would work out a deal for Nylander rather than attempt to sign him to an offer sheet. That's just reality.

No, that's just an argument. But you ducked the larger question. Even if hypothetically the Leafs should match a 5 year/40 million dollar offer sheet rather than take a 1st, 2nd and 3rd and trade him later when more teams will have cap room and be able to be in on the process, why not sign him to the 8 year deal now? Why would Nylander ever be more valuable at 8 million until he's 27 but not 8 million until he's 30?

Signing Nylander to the sort of deal he wants doesn't guarantee you never move on from him, just that if you trade him and he is worth what he wants(and if he isn't then teams aren't going to want him at that price) you have him locked up for as long as possible so it's a more valuable asset.

As to "why would they ever give up more than a first second and third?" , the deal could be contingent on Nylander signing a 7 year deal with the new team so they'll offer players + picks.

Again, why? Why wouldn't that team rather have Nylander at a much cheaper cost? Even if they don't have the cap room, you're arguing that they'd be willing to trade a valuable asset for him but why not trade that asset separately for its best return and spend as little as you can on Nylander?

The reason we wouldn't see a five year/8 million AAV offer sheet is because the Leafs would just match it because the compensation would suck. So if you'd match that offer sheet and look to trade him, the smarter course of action is to lock him in at that AAV but for the longest possible term.

Again, no crystal ball on hand but I think I've seen enough NHL trades to know that teams in the Leafs position don't tend to do well in trades.

Because Nylander at 6 years under $7M is far more valuable than him at 8x8. Leafs could use him as a trade chip if they felt they needed to and he'd bring back far more if his cap hit was lower.  That and the fact it's easier to fit Matthews and Marner in long term if Nylander is under $7M. Would 8x8 be the end of the world? No but it's not optimal.

The fact they'd match 5x$8M is only because it would be stupid to let him walk for that so it would be better to match and see what happens. Once the player has agreed to sign with another team though he's indicated he doesn't care about being here long term so Leafs might be more inclined to trade him at that point. 5 years would also bring him to UFA status which isn't ideal.

 

[Kin]

Because Nylander at 6 years under $7M is far more valuable than him at 8x8. Leafs could use him as a trade chip if they felt they needed to and he'd bring back far more if his cap hit was lower.  That and the fact it's easier to fit Matthews and Marner in long term if Nylander is under $7M. Would 8x8 be the end of the world? No but it's not optimal.

I'm not entirely sure you're getting the point here. I'm not asking why the Leafs would want him to sign for less than he wants, that's obvious. I'm asking why the Leafs think signing him and trading him would be better at 5/8 AAV but not 8/8.

Because whoever you trade Nylander to, if he's holding firm at 8, is going to have to be someone who is ok with paying him 8. If they're willing to sign him to 5 years/8 million, clearly they'd rather have him for the same salary but longer term. He's more valuable as a trade chip at 8/8 than he is at 5/8. That's what the hypothetical is about. If they can sign him for less, great, but this is a hypothetical where they can't.

The fact they'd match 5x$8M is only because it would be stupid to let him walk for that so it would be better to match and see what happens. Once the player has agreed to sign with another team though he's indicated he doesn't care about being here long term so Leafs might be more inclined to trade him at that point. 5 years would also bring him to UFA status which isn't ideal.

No, it's not ideal. That's the whole point. If a team is willing to sign him for 5/8, which incidentally means they think he's worth 8 million a year, then he's more valuable to them at 8/8. So if the Leafs are willing to pay him 8 million this year before shopping him next summer, he's a more valuable trade chip with a longer term contract.

In which case the Leafs should just sign him to 8/8, let him play this year and then trade him in the summer when more teams can bid on him.

 

[Zee]

Because Nylander at 6 years under $7M is far more valuable than him at 8x8. Leafs could use him as a trade chip if they felt they needed to and he'd bring back far more if his cap hit was lower.  That and the fact it's easier to fit Matthews and Marner in long term if Nylander is under $7M. Would 8x8 be the end of the world? No but it's not optimal.

I'm not entirely sure you're getting the point here. I'm not asking why the Leafs would want him to sign for less than he wants, that's obvious. I'm asking why the Leafs think signing him and trading him would be better at 5/8 AAV but not 8/8.

Because whoever you trade Nylander to, if he's holding firm at 8, is going to have to be someone who is ok with paying him 8. If they're willing to sign him to 5 years/8 million, clearly they'd rather have him for the same salary but longer term. He's more valuable as a trade chip at 8/8 than he is at 5/8. That's what the hypothetical is about. If they can sign him for less, great, but this is a hypothetical where they can't.

The fact they'd match 5x$8M is only because it would be stupid to let him walk for that so it would be better to match and see what happens. Once the player has agreed to sign with another team though he's indicated he doesn't care about being here long term so Leafs might be more inclined to trade him at that point. 5 years would also bring him to UFA status which isn't ideal.

No, it's not ideal. That's the whole point. If a team is willing to sign him for 5/8, which incidentally means they think he's worth 8 million a year, then he's more valuable to them at 8/8. So if the Leafs are willing to pay him 8 million this year before shopping him next summer, he's a more valuable trade chip with a longer term contract.

In which case the Leafs should just sign him to 8/8, let him play this year and then trade him in the summer when more teams can bid on him.

Well if this mythical team that thinks he's worth $8M exists, they haven't shown themselves so far. It's all hypothetical at this point. Nylander thinks he's worth > $8M/season, it remains to be seen if anyone else in hockey agrees.

 

[Kin]

Well if this mythical team that thinks he's worth $8M exists, they haven't shown themselves so far. It's all hypothetical at this point. Nylander thinks he's worth > $8M/season, it remains to be seen if anyone else in hockey agrees.

Well, we don't know what Nylander may or may not have been offered by other teams but more to the point if Nylander thinks he's worth 8 and he's not budging and, like you suggest, no other team thinks he's worth that then why would a team trade for Nylander just to be confronted with his salary demands at 8? If the mythical team you're suggesting that just can't wait to give the Leafs a great dynamic young defenseman mid-season for Nylander but would balk at signing him to the contract he wants, why would they think they can strike a better deal than Dubas?

Again, this is why trading a player without a contract, or on an expiring contract, isn't usually a good thing. Teams either want to pay a guy what he wants or they don't. They certainly aren't going to be lining up to give away great returns just to find themselves in the same quagmire the Leafs are in with him.

 

[princedpw]

Besides, if you were a team who really wanted Nylander why in the world would you offer the Leafs more than whatever the compensation would be for signing Nylander to a five year deal at the money he wanted?

This would be a good question for Brian Burke.

 

[sickbeast]

Well if this mythical team that thinks he's worth $8M exists, they haven't shown themselves so far. It's all hypothetical at this point. Nylander thinks he's worth > $8M/season, it remains to be seen if anyone else in hockey agrees.

Well, we don't know what Nylander may or may not have been offered by other teams but more to the point if Nylander thinks he's worth 8 and he's not budging and, like you suggest, no other team thinks he's worth that then why would a team trade for Nylander just to be confronted with his salary demands at 8? If the mythical team you're suggesting that just can't wait to give the Leafs a great dynamic young defenseman mid-season for Nylander but would balk at signing him to the contract he wants, why would they think they can strike a better deal than Dubas?

Again, this is why trading a player without a contract, or on an expiring contract, isn't usually a good thing. Teams either want to pay a guy what he wants or they don't. They certainly aren't going to be lining up to give away great returns just to find themselves in the same quagmire the Leafs are in with him.

No one is going to trade for Nylander without negotiating a contract with him first.  Or else they will wait for Toronto to sign him and then trade from him as a known commodity.

I have a feeling the Leafs might sign Nylander long term and then trade him at the end of the season.

 

[Zee]

Well if this mythical team that thinks he's worth $8M exists, they haven't shown themselves so far. It's all hypothetical at this point. Nylander thinks he's worth > $8M/season, it remains to be seen if anyone else in hockey agrees.

Well, we don't know what Nylander may or may not have been offered by other teams but more to the point if Nylander thinks he's worth 8 and he's not budging and, like you suggest, no other team thinks he's worth that then why would a team trade for Nylander just to be confronted with his salary demands at 8? If the mythical team you're suggesting that just can't wait to give the Leafs a great dynamic young defenseman mid-season for Nylander but would balk at signing him to the contract he wants, why would they think they can strike a better deal than Dubas?

Again, this is why trading a player without a contract, or on an expiring contract, isn't usually a good thing. Teams either want to pay a guy what he wants or they don't. They certainly aren't going to be lining up to give away great returns just to find themselves in the same quagmire the Leafs are in with him.

A team that would offer sheet Nylander would have to have the room to do so, and those types of teams are most likely not considered cup contenders at the moment. A viable offer sheet would have to be 7 years not 5, cause what GM would sign a guy to a 5 year deal so it brings the player to UFA status immediately?  Your idea of a 5x8 offer from a team is unrealistic unless the offering team is doing it soley to spite the Leafs.

So, let's say non playoff team thinks Nylander is good value at 7 years, $56M because they believe he can be their #1 center.  They either work out a deal with Nylander with the Leafs permission and trade prospects + picks or they outright offer sheet him and risk losing 4 first round picks.  If the offering team is a current non playoff team I say take the 4 first rounders as you're playing the odds of getting a top 10 pick.

As to why team would offer prospects + picks, they would fear that even with Nylander they're not good enough yet and don't want to risk losing out on a top 10 pick.

 

[Kin]

A team that would offer sheet Nylander would have to have the room to do so, and those types of teams are most likely not considered cup contenders at the moment. A viable offer sheet would have to be 7 years not 5, cause what GM would sign a guy to a 5 year deal so it brings the player to UFA status immediately?  Your idea of a 5x8 offer from a team is unrealistic unless the offering team is doing it soley to spite the Leafs.

No. There's a massive advantage to a team signing a five year offer sheet instead of a 7 year one. We've gone over it at length.

Basically, this is the calculation for the other team. Let's say that they figure that, at best, Nylander will want 14 million a year in five years. Then their math is this.

Option A:

Nylander signs five year/40 million offer sheet.
Sign him to new 14 million AAV deal in five years
Amount you pay Nylander over 7 years: 68 million
Cost to acquire Nylander in assets: 1st, 2nd and 3rd round picks

Option B:

Nylander signs 7 year, 56 million dollar deal
Amount you pay Nylander over 7 years: 56 million
Cost to acquire Nylander in assets: 4 first round picks

So you're saying there isn't any team that would rather not give up 4 first round picks and only end up paying him 12 million dollars more over the course of 7 years? And again, that's in a scenario where Nylander is a 14 million dollar player in five years. If he's just at 10 or 11 or 12 the difference is marginal but the asset cost is still much, much less.

 

[Kin]

This would be a good question for Brian Burke.

Leaving aside that "Maybe we'll get lucky and another team will be as dumb as Brian Burke" isn't a great plan the actual answer to your question would be a simple one. Burke either gave Boston what they wanted for Kessel because he worried that Boston would match or because he worried that Kessel might sign with Nashville.

So the analogy here comes back to the reality of it. Either multiple teams are willing to give Nylander what he wants salary wise, in which case the Leafs are better giving Nylander that salary and then trading him to whichever of those teams they want or the Leafs would match at 5/8 at which point they should just sign him to 8/8.

 

[Zee]

A team that would offer sheet Nylander would have to have the room to do so, and those types of teams are most likely not considered cup contenders at the moment. A viable offer sheet would have to be 7 years not 5, cause what GM would sign a guy to a 5 year deal so it brings the player to UFA status immediately?  Your idea of a 5x8 offer from a team is unrealistic unless the offering team is doing it soley to spite the Leafs.

No. There's a massive advantage to a team signing a five year offer sheet instead of a 7 year one. We've gone over it at length.

Basically, this is the calculation for the other team. Let's say that they figure that, at best, Nylander will want 14 million a year in five years. Then their math is this.

Option A:

Nylander signs five year/40 million offer sheet.
Sign him to new 14 million AAV deal in five years
Amount you pay Nylander over 7 years: 68 million
Cost to acquire Nylander in assets: 1st, 2nd and 3rd round picks

Option B:

Nylander signs 7 year, 56 million dollar deal
Amount you pay Nylander over 7 years: 56 million
Cost to acquire Nylander in assets: 4 first round picks

So you're saying there isn't any team that would rather not give up 4 first round picks and only end up paying him 12 million dollars more over the course of 7 years? And again, that's in a scenario where Nylander is a 14 million dollar player in five years. If he's just at 10 or 11 or 12 the difference is marginal but the asset cost is still much, much less.

Your Option A is missing, sign Nylander for 5 years and Nylander walks as a UFA at end of 5 years.

 

[Kin]

Your Option A is missing, sign Nylander for 5 years and Nylander walks as a UFA at end of 5 years.

I don't think there's a massive difference in risk for Nylander walking in 5 years vs. Nylander walking in 7 years. Especially when, in the former scenario, you also have 3 extra first round picks.

 

[dappleganger]

I think it wholly depends on where the picks are.

So, in other words, whether or not it's a good trade depends entirely on something the Leafs can't possibly know when they make the trade? That doesn't sound like a terrific strategy for prudent decision making.

The Leafs will have to do their due diligence here.

If it's top 7, there's some benefit to that. This team is going to need young assets going forward to offset the larger contracts coming up soon.

How much of a detriment is it overpaying a player worth $6.5m at current market rates?

Well, for starters, I don't think that's true in terms of Nylander's value.

But more to the point what's the real end game there? Even if you hit on the pick and get someone as good as Nylander then in 3-4 years, when Tavares is probably reaching the end of his peak, the Leafs might be as good as they'd be now if they just signed Nylander? And that's better than maybe giving Nylander a million or so more than you might like?

Willy's situation isn't very dissimilar to Kessel's departure from Boston.

The team didn't want to pay what the player wanted and dealt him. Even if it was just a 1st and 2nd Boston got back, that trade worked out pretty good for them. You gotta be lucky to be good.

All I'm really saying is although not ideal, getting picks back for Willy wouldn't be the worse thing in the world because this team is going to need young, good players on entry level deals to fill out the roster in the near future.

 

[Kin]

I mean, there's a pretty glaring problem with the internal consistency of your argument. On the one hand, you're saying that the Leafs should match a 5 year/40 million dollar offer sheet because getting a 1st, 2nd and 3rd for Nylander is a bad trade. On the other hand, you're saying that if Nylander got a 7 year/56 million dollar offer sheet, the Leafs should take the four firsts because that would be a good trade.

Then, you're saying that no GM of another team would want to do the first, which is a bad trade for the Leafs but would rather do the second, which is a good trade for the Leafs.

Personally, I tend to think NHL GMs want to make trades that are good for their team.

 

[Kin]

All I'm really saying is although not ideal, getting picks back for Willy wouldn't be the worse thing in the world because this team is going to need young, good players on entry level deals to fill out the roster in the near future.

Actually, if the team trades Nylander, a far more glaring issue is going to be adding an elite player. Keeping the team intact around Marner, Matthews and Tavares isn't going to be a problem cap-wise. The problem is that team isn't going to be good enough without significant upgrades elsewhere. Like I said earlier, it's probably worse than last year's team.

Taking a gamble on where first round picks might be isn't a good way to add that kind of player.

 

[Zee]

I mean, there's a pretty glaring problem with the internal consistency of your argument. On the one hand, you're saying that the Leafs should match a 5 year/40 million dollar offer sheet because getting a 1st, 2nd and 3rd for Nylander is a bad trade. On the other hand, you're saying that if Nylander got a 7 year/56 million dollar offer sheet, the Leafs should take the four firsts because that would be a good trade.

Then, you're saying that no GM of another team would want to do the first, which is a bad trade for the Leafs but would rather do the second, which is a good trade for the Leafs.

Personally, I tend to think NHL GMs want to make trades that are good for their team.

No I'm saying a team would rather sign a player to 7 years than 5 and in that case would try to work a trade out with the Leafs so instead of 4 first round picks maybe it's 2 prospects + 2 picks. In any event offer sheets are so rare that it doesn't matter what hypotheticals we come up with, it won't happen and Nylander will either play for the Leafs or he'll sit

 

[Kin]

No I'm saying a team would rather sign a player to 7 years than 5.

Not always. Certainly not always if the asset cost is much, much higher at 7 years.

Regardless though, this is where we get back to the point of even if that's true, that's why it's to the Leafs benefit to sign Nylander for as long as they can and then trade him in the summer where they're likely to have more offers and when Nylander is signed for 7 full years and not now when it would be more like 6 and 3 quarters.

 

[sickbeast]

All I'm really saying is although not ideal, getting picks back for Willy wouldn't be the worse thing in the world because this team is going to need young, good players on entry level deals to fill out the roster in the near future.

The problem with that is, getting an elite player with an eighth overall pick is pretty rare.  The chances of the Leafs ever getting another Nylander out of a first, second, and third round pick are quite remote.  I also doubt they would get a top ten pick out of it.  The four first rounders would be a lot more interesting but I don't think there is any meaningful chance of that happening.

IMO Nylander puts the Leafs over the top this season.  They should find a way to sign him any way they can.  And then trade him in the off season.  It doesn't look like they will be able to get him on a team friendly deal.  And quite frankly Mitch Marner makes Nylander look like a mediocre player by comparison.  This might sound crazy but I actually think Marner could turn out to be just as good a player as Auston Matthews, if not better.  Yes, Matthews has the elite skill set, but I've never seen a player with wheels and hockey sense like Mitch Marner.  Not on the Leafs anyhow.  I love the way he backchecks.  He never seems to run out of gas.  100% if it comes down to keeping Nylander or Marner, the team has got to go with Marner hands down.  And IMO he needs to get paid.  Matthews is going to get his $12.5 million.  That much is a given.  But IMO they should pay Marner big time, even if it means they can't keep Nylander.

 

[dappleganger]

I mean, there's a pretty glaring problem with the internal consistency of your argument. On the one hand, you're saying that the Leafs should match a 5 year/40 million dollar offer sheet because getting a 1st, 2nd and 3rd for Nylander is a bad trade. On the other hand, you're saying that if Nylander got a 7 year/56 million dollar offer sheet, the Leafs should take the four firsts because that would be a good trade.

Then, you're saying that no GM of another team would want to do the first, which is a bad trade for the Leafs but would rather do the second, which is a good trade for the Leafs.

Personally, I tend to think NHL GMs want to make trades that are good for their team.

No I'm saying a team would rather sign a player to 7 years than 5 and in that case would try to work a trade out with the Leafs so instead of 4 first round picks maybe it's 2 prospects + 2 picks. In any event offer sheets are so rare that it doesn't matter what hypotheticals we come up with, it won't happen and Nylander will either play for the Leafs or he'll sit

Where are you guys getting the 4 1st round picks from? If Willy signs at anything between $6,088,981 to $8,118,641 AAV, it's a 1st, 2nd, and a 3rd.

He'd have to sign at $10,148,303 AAV and above to return 4 1st round picks in compensation.

($8,118,642 to $10,148,302 would be 2 1st round picks,  a 2nd, and a 3rd)