Way back in July, Kyle Dubas did the unthinkable and signed John Tavares as a free agent to his seven-year, $11M AAV contract. Two things happened immediately after this massive coup for Dubas and the Leafs: first, it turned the Leafs’ top offense into something even more scary and arguably a Stanley Cup contender; second, people immediately started worrying that it was impossible for the Leafs to afford Nylander, Marner and Matthews under their cap in addition to having Tavares’ contract.

Kyle Dubas, however, did not see it that way when he was asked about it soon after the Tavares signing was announced:

Tavares. Nylander. Marner. Matthews. Can the Maple Leafs really keep all four?

“We can, and we will,” Dubas told Sportsnet’s Elliotte Friedman and Jeff Marek on this week’s episode of 31 Thoughts: The Podcast, which will be released Thursday morning.

For what it’s worth, we have this Bob McKenzie piece as of Monday about the situation that seems to back that up: Dubas has no interest in trading Nylander even with the situation as it is.

For those of you who don’t have time to read the many words that are about to follow, you can scroll down to the TL;DR section at the bottom.

Let’s clearly spell out the 2019/20 cap situation

According to the Leafs’ Cap Friendly page the Leafs will have a projected cap hit of $49,313,333, which if the salary cap ceiling stays the same would leave the Leafs with $30,186,667 in projected cap space. However, that cap hit includes having Horton’s contract count against the cap, which would be removed when he gets put on LTIR. So, really, they’d have $35,498,667 in cap space.

They may have to do some contract/CBA finagling in order to start the season with a certain cap hit, then put Horton on LTIR to remove his cap hit, and then bring back some players to the roster to make use of that room. In order to do that, they’ll have to have a bunch of guys who they can move to the AHL until the right time that they can call them up without having to expose them on waivers. Thankfully, the Leafs are very smart about this sort of thing so we shouldn’t expect any problems with that.

Now, the Leafs will also have a whole lot of RFAs and UFAs to re-sign, including the likes of Auston Matthews, Mitch Marner, and Jake Gardiner. I don’t want to get into trying to painstakingly project each new contract and cap hit because that’s not really the point I want to make here.

Instead, I’m going to make my point by making up some numbers that a lot of people won’t like because they represent the Doomsday Scenario they’re worrying about. I’m focusing on the Big 3 since that’s what we’re all worried about. So let’s say the Big 3 wind up with the following contracts/cap hits:

  • Nylander: $8.5 million AAV
  • Marner: $10 million AAV
  • Matthews: $12.5 million AAV/

That comes to a cap hit of $31 million, which would eat up pretty much all of that projected cap space of around $35.5 million. We know that the cap will not stay the same as it is this year, but we don’t know by how much. Last year the cap ceiling rose from $75 million to $79.5 million, thanks in large part to the Vegas Golden Knights joining the league. There won’t be another new team in the league again this year, and the season before that the cap only rose by $2 million, from $73 to $75 million. That was the lowest amount the cap has risen since the cap was instituted.

So let’s be conservative, because again this is about the Doomsday Scenario, and say the cap only increases by $2 million again, bringing it to $81.5 million. That would leave the Leafs with around $6.5 million in cap space going into the 2019/20 season assuming the Big 3 have those cap hits.

That seems bad considering all of the other roster spots they would need to fill, including three wingers, two defense, a backup goalie, and any bench/pressbox filler. Even if you filled each spot with someone making the absolute league minimum, and had no pressbox filler, that would still put you really close to the cap ceiling.


Marleau - Matthews - Nylander

Hyman - Tavares - Marner

??? - Kadri - Brown

??? - Gauthier - ???


Rielly - Zaitsev

Dermott - Holl

??? - ???




All that said, while having six roster holes with little cap space to fill them seems bad, take a look at the holes that need filling. They’re not the most important spots, and you can fill them with depth. You can sign cheap UFAs like Nick Shore, Drew Stafford, or Tyler Ennis at forward. You can also call up your own AHL depth like Trevor Moore, Pierre Engvall, Calle Rosen, or Andreas Borgman that make closet to league minimum as well.

It’s not ideal, but it would only need to be for a year or two while the cap goes up, other contracts expire, and the Leafs get more cap space to work with. Alternatively, they could make a move now (as in, heading into the 2019/20 season) to create that space. Let’s talk about some of the options are available to them that don’t include trading any of their star players.

Sign one of the Big 3 to a bridge deal

Remember, the big problem for the Leafs salary cap does not really extend beyond the 2019/20 season. If their cap problems are more short term, one way of fitting everyone under the cap is by kicking the big contracts down the line with a bridge deal for Nylander, Marner, and/or Matthews. Now... of those three, the one that makes the most sense is Nylander.

If you ask analysts and insiders in the media, or bloggers that use analytical models to predict contracts, or just compare Nylander’s quality as a player with others that accepted bridge deals, you’ll see a number in the $4M to $5.5M AAV range over two to four years. If you think that still seems high, you’re missing the point — which is that even at $5.5M that’s still $2.5 million less than the $8(ish) million that Nylander is asking for, which goes a long way to helping sort out their cap next season.

Nylander reportedly doesn’t want a bridge deal, but in the end it might just make the most sense for both sides of the contract dispute.

Don’t re-sign Jake Gardiner or Ron Hainsey

Let’s start with the Leafs’ two pending UFAs that make more than $1 million per year: the Leafs could just let Jake Gardiner ($4.05M AAV) and Ron Hainsey ($3M AAV) both walk as free agents. They would not be affordable with only $6.5~ million in cap space available to fill 6 to 9 roster spots. Combined they already have over $7 million in a combined cap hit, and while given Hainsey’s age and performance we wouldn’t expect him to make more than $3 million, we absolutely would expect Gardiner to get more than his $4.05M cap hit.

That would leave some big holes on their defense, at least for the 2019/20 season. The choice you have there is filling the holes internally with cheap young defencemen like Liljegren or Sandin (if they’re ready) or like Holl, Rosen, Borgman or anyone else who is older but making less than $1 million and can bridge the gap. Or you sign cheap veteran guys for less than $1 million.

This is not ideal, at least for the one year, and by itself this would not make the Leafs fit under the cap. But it’s a start, and can be combined with something like....

Get rid of Patrick Marleau’s Contract

In 2019/20, Patrick Marleau will have just turned 40 years old and will carry a $6.25 million cap hit. Now, it’s worth noting that his actual salary for the year would be $4.25 million and $3 million of that is from a signing bonus. While he’s had a great career and did score 27 goals for the Leafs last season, the quality of his overall play has been slipping. Getting rid of that cap hit would almost by itself solve the Leafs’ cap issues even in this Doomsday Scenario.

But there are two problems with that. First, Marleau has a full No Movement Clause, so he cannot be traded, waived, or sent to the minors without his permission. Second, because he’s a 35+ aged contract, the Leafs would carry his full $6.25 million cap hit even if he retires or gets bought out. So that leaves some creative skullduggery to get out of his contract somehow, which has been a possibility that people have speculated will happen when Leafs first signed Marleau.

Either he develops a career ending injury before the start of the season and joins the Robidas Island Club as an informal Marlies’ coach, or he develops a sudden allergic reaction to his hockey equipment, or the Leafs trade him on July 2nd after they pay his signing bonus to a team who wants to clear the cap floor without having to pay him much, and so on and so forth. There also may be a chance that after getting his signing bonus, he agrees to mutually terminate his contract with the Leafs instead of ‘retiring’.

Any number of those would have to involve some type of handshake agreement with Marleau, where he has to consent to any of that happening. It’s also toeing the edge of cap circumvention pretty hard, and while this is a league where that kind of thing is not that uncommon it’s not normally that blatant. Still, it could happen.

If they do find a way to shed his contract, that gives the Leafs more than $8 million in cap space to work with.

Trade Nikita Zaitsev

Tied for next highest cap hit, and a player that Leafs fans don’t really like is Nikita Zaitsev with his $4.5 million cap hit over the next five seasons. Trading him to another team that wants some help on defense would give the Leafs over $10 million in cap space to work with, which would be enough to fit in the Big Three and fill out the remaining roster spots. Still not ideal, as it would create ANOTHER hole on defense, but you start seriously considering the possibility of being able to re-sign Gardiner instead.

Trade Nazem Kadri for that upgrade on defense

The other guy who has a $4.5 million is Nazem Kadri, whose contract runs until the 2022/23 season. As much as we might not like to trade a guy who is still young, is capable of scoring 30+ goals and 60+ points while breaking even in possession against other top lines, he might be one of the easier guys to trade precisely because he has a lot of value.

People who want to trade Nylander for an upgrade on defense should look long and hard at Nazem Kadri. Next season he will be 29. He will still be close to his peak value and performance, but he might not have the potential to make use of that value as a 3C. His role is not quite as important now that the Leafs have Matthews and Tavares playing ahead of him, and if you want a replacement 3C, well, have you heard of this Nylander kid? He’s pretty good.

Not long ago I wrote something that looked at how viable it is to trade Nylander for a star defenseman, along the lines of a straight up Johansen-for-Jones type deal. Not every defenseman that I mentioned was really good enough for Nylander on their own, but some of them would be good enough in a trade for Kadri. Brett Pesce is someone that Pierre LeBrun speculated on that would make more sense in a swap involving Kadri.

At the same time, you can use Kadri to get an emerging young defenseman who is ready to break into the NHL and has the potential of at least a good second-pairing guy. Someone like Rasmus Andersson, Adam Boqvist, Cal Foote, Nicolas Hague, Juuso Valimaki, Connor Timmins, and so on. This wouldn’t help the Leafs be a better team right now, but would buy them time and shore up their system with quality defense prospects along with Liljegren, Sandin and Durzi.

Trade Connor Brown and/or Zach Hyman

Let’s say you do any of the above. That would help the Leafs fit the Big 3 contracts under their cap next season but wouldn’t give them a lot of spending to fill the remaining holes in the roster. Let’s say they try to re-sign Gardiner but need a couple of million in cap hit to fit him in at whatever he’s asking for.

Well, there we have Connor Brown ($2.1M AAV) or Zach Hyman ($2.25M AAV). Both are capable NHL wingers who are still relatively young, and have RFA/UFA contracts coming up in the next 2-3 years. Both would probably get at least a bit of a raise on what they are making right now, and both are not so good as NHLers that the Leafs couldn’t afford to replace them with someone else in their system.

Actually, that’s not fair to either of them. Let’s put it this way... the difference between Hyman/Brown and a hypothetically cheaper replacement is much smaller than the difference between Nylander/Gardiner and their replacement. And that’s why you don’t trade Nylander, or any of the Big 3, or any other legit top pair/top line, star players. You trade your depth, you trade your middle players. You especially trade the non-star players when they start to become too expensive, and ideally you trade them a couple of years before their contracts run out when they still have value in a hypothetical deal.

About those hypothetical contract numbers...

So remember those cap hits I threw out for the Big Three? Remember how I said I purposefully assigned bigger numbers to each one to represent the Doomsday Scenario we all feared? My point was that even if all three get that much, you still should want the Leafs to trade other players, shed other contracts, and find other ways to make their salary cap work.

You do NOT trade any of the Big 3 — including Nylander — in the name of making their salary cap work. The only reason you trade any of them is if someone comes to you and offers you a trade that makes the Leafs better.

Realistically, let’s take the high numbers that each player is reportedly asking for (or WILL ask for next year) and take what most people say are reasonable middle grounds relative to their comparables:

  • Nylander: $7.5 million AAV
  • Marner: $8.5 million AAV
  • Matthews: $11.5 million AAV/

Suddenly the Leafs go from having a $31 million cap hit between the three of them to only a $27.5 million cap hit. Again, the precise numbers here do not matter as much as the fact that what they will likely get in a contract will be less than what they ask for, even if they’re still more than what we’d hope for. That’s still an extra $3.5 million in cap space to add onto all of the figures mentioned above.

And the cap ceiling? With 31 teams instead of 30, the cap is likely to increase more than $2 million. Even if it’s only by another $1 million or so, that still creates yet more cap space to work with. Instead of having around $6.5 million in cap space left to sign 6 to 9 players, you could have around $11 million. That’s a major difference.

Now don’t get me wrong, the Leafs are still going to have to walk away from someone on their roster that is a good NHL player, whether it’s Gardiner, Zaitsev, Marleau, Kadri, Brown, and/or Hyman. That’s just the nature of the salary cap, and having a roster of mostly younger players who are getting to their first RFA/UFA contracts. I’m sure Chicago would have loved to have held onto Byfuglien, Ladd, Versteeg, Saad, Panarin, Hjalmarsson, Campbell, and others after they won their first Stanley Cup.

But what Chicago did is trade them, or let them walk, and replace them with others in their system or through various trades to shore up their roster depth around their core of star players. They did NOT trade Kane, Toews, Hossa or Keith. The Penguins did NOT trade one of Crosby, Malkin, Letang, or Kessel. The Kings did NOT trade one of Doughty, Carter, Kopitar, Quick or Richards (for Richards, see the Marleau section above on skullduggery). The Tampa Bay Lightning will NOT trade one of Stamkos, Kucherov, Hedman, Point or Vasilevskiy.

Ultimately, you have to ask whether the Leafs are better off hanging onto Nylander, or hanging onto any of the six other current roster players who aren’t stars? In my opinion, and likely in Dubas’ opinion, they’d rather hang onto Nylander.