Toronto Maple Leafs: How to Sign Young Superstar Trio

The Edmonton Oilers are hoping to sign Leon Draisaitl and Connor McDavid this summer to long-term deals, but it could come with a huge price tag and the end result having a direct impact on the Toronto Maple Leafs.

The obvious comparison to the Edmonton Oilers signing 2015 first overall pick, Connor McDavid, is that the 2016 first overall pick, Auston Matthews, will ask the Toronto Maple Leafs to match it. While that very well may be the case, another scenario is whether Matthews and Mitch Marner tell Lou and Shanny to match it. There is also the worst case scenario, Matthews, Marner and William Nylander all wanting to be paid like the Oiler’s captain.

The worst case scenario sees the Maple Leafs go down the Chicago Blackhawks rabbit hole and sign two players to a big percentage of the salary cap. The Blackhawks have won three playoffs games in the two years since Jonathan Toews and Patrick Kane’s $21 million combined cap hit went into effect, that included a first-round sweep at the hands of the Nashville Predators. This is after winning three Stanley Cups on more team-friendly contracts with the club. The Blackhawks offered those contracts when the salary cap looked to be increasing and the large cap hits weren’t going to be a factor.

Now, with salary cap shows no signs of increasing without players escrow being factored in, can the Maple Leafs sign Nylander, Marner, and Matthews to long-term contracts and win the Cup?

Current Cap Hit

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Before thinking about signing any of these three young superstars, you have to take into account the current and future cap hits of players already signed by the Maple Leafs.

There is only three Maple Leafs signed through the 2021/22 season. Nazem Kadri is the only forward signed until then, with a cap hit of $4.5 million, while Morgan Rielly carries a cap hit of $5 million until he is 28 and Nikita Zaitsev recently signing a contract worth a $4.5 million cap hit over the next seven years. Rounding out the Maple Leafs long-term contracts is Frederik Andersen with a cap hit of $5 million over the next four years.

While those players are signed to value contracts, based on their performance over the last season, they carry a combined cap hit of $19 million, which is a little over a quarter of the $75 million cap hit between four players for next season. That doesn’t include players like Connor Brown and Zach Hyman who need new contracts this summer, or even James van Riemsdyk and Tyler Bozak, who will need a new contract next summer. The obvious solution for Lou is to trade a player like JVR or Bozak to free up cap space and maybe get some draft picks in return.

With those deals in place, what kind of contracts will the Maple Leafs have to sign the big three to in order to not have to trade either of those players already signed to free up cap space?

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Matching 97

Let’s start off with the worst case scenario, just to get it out of the way. The rumours circulating is that McDavid could ask for as high as $14 million. While the Oilers would have no choice but to sign McDavid to that deal, I have a hard time believing it’s what McDavid wants. McDavid wants to be known as the best in the world and while individual trophies are great, Stanley Cups are better. If McDavid wants to win, he can’t ask for that. Especially with Draistl wanting a number in between McDavid’s and the $6 million that teammate Milan Lucic is signed over the next six years for. Anything over $10 million would put the Oilers right beside the Blackhawks in salary cap jail.

If McDavid asks for a more realistic $10 million, comparable to Toews and Kane’s deal, Matthews will ask for the same. If Marner and Nylander ask for the same, that would be a $30 million cap hit between the three. Something no NHL team can work into their budget and still think they can build pieces around them to win the Cup. That would tie up 40% of today’s salary cap between the three.

When you factor in the four Maple Leafs already signed, that is $49 million and close to two-thirds of today’s cap between seven players. While those seven players will make any team competitive, it would be hard to win a Cup when you have a third of the salary cap to build the other half of the team.

Realistically, I couldn’t see Lou signing all three to the same cap hit. He’s smarter than that and wants to see his team win. If this scenario did play out, I’d expect him to sign two of the three and trade the one left out. Whether that be Marner or Nylander, you can get a lot for $10 million in today’s NHL.

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Who is the Maple Leafs Draistl?

With Marner and Nylander both having an amazing rookie season, there is a case that they are 2a and 2b behind Matthews and in turn could both look for a similar offer as Draistl. He could be looking for as high as $8 million, which would only be a $4 million difference than paying all three McDavid money.

Both Marner and Nylander have a case to say they are number two on the Maple Leafs behind Matthews and strive to say they are the best overall but paying all three in the $8-10 million range would put them shackled in cap jail.

Signing Matthews to $10 million and Marner and Nylander to $8, with the four Maple Leafs already signed it puts the Maple Leafs at $45 million for seven players, a combined 62.5% of today’s salary cap.

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Hometown Discount

If Matthews decides he wants what McDavid gets, which he should and more than likely will, then either Marner or Nylander have to take a hometown discount. Between the two, Marner is the most likely to take it. He is a hometown boy and will take even more pride wanting to bring a Cup to Toronto. Although Nylander is just as likely to take the hometown discount, seeing how he has been seen wearing either Maple Leafs gear while representing Sweden during the World Championship or seen sporting Babsocks while taking pictures with his friends. It’s safe to say Nylander enjoys being a Maple Leafs.

If either player were willing to take a hometown discount in the range of $6-6.5 million, it would create cap space to build around your core. With either Marner or Nylander taking $6.5 million, the other taking $8 million and Matthews taking $10 million, that would be a combined cap hit of $24.5 million or close to 30% of today’s salary cap. With the four other Maple Leafs already signed, puts the Maple Leafs at $43.5 million or a little more than half of today’s salary cap. It would leave you with $38.5 million in salary cap space to build a team around your core that would be more than enough to build a Cup winning team.

In Lou’s Shoes

If I were in Lou’s shoes, there is no way I lose either of these three players but it has to make sense in order to set the Maple Leafs up for failure. There is no guarantee that the salary cap rises, so you have to pretend it is going to stay the same year to year or you’ll find yourself locked into a bad contract.

Matching Matthews with whatever McDavid gets make sense, as long as it isn’t more than $10 million. In a perfect world, Matthews goes the Sidney Crosby route and takes anywhere between $9-9.5 million but $10 million for one of the greatest players in the world is something Lou shouldn’t have a problem doing.

Offering $7-7.5 to both Marner and Nylander and establishing them both on the same pay scale as your 2a and 2b would make the most sense. If your going to offer them similar numbers, going above $7.5 million is going to start to diminish your chances of building depth.

Next: Top Five Free Agent Defenders

In a perfect world, the Maple Leafs sign JVR, Bozak, Komarov along Marner, Nylander, and Matthews, but in a world of the NHL salary cap, that can’t happen. Instead, they’ll have to focus on their trio of rookies, but as long as they make sure to lock down Matthews long term, it’s hard to imagine much going wrong in Leafs Nation.

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