The Toronto Maple Leafs are in a tough position when it comes to the contract situation of their three big forwards. Obviously Auston Matthews will get extended to whatever keeps him in Toronto, but the deals for William Nylander and Mitch Marner aren't as clear-cut. They aren't 22 anymore with only their good years ahead of them, there's decline risk now.

Who might be traded?

Nylander has always made significantly less than his teammates and he's done everything asked of him in Toronto. He's a great player on a sweetheart contract and will probably get another one again, possibly in the $9 million range fairly soon into this summer.

But Mitch Marner is different, because as Cathy eloquently described in her articles yesterday, he wants Auston Matthews money. Is $15 million reasonable for Marner? What about 14? 13? 12? 11? When does it start to make sense for the Leafs to keep him, and is the floor of Marner's ask already pushing the Leafs towards trading him?

The Case For a Core 4 Trade
There is no case to trade one of the Leafs top players because somehow that magically makes the team better. It is extremely hard to make a team better trading elite or near-elite talent in the immediate term, even if you’re happy with short term gains.
Cathy SquiresPPP Leafs

This won't be a trade to make someone walk the plank, or die by the sword, or punish the others for lack of playoff success, but the harsh reality of money. Marner's no-movement clause kicks in on July 1st and has no trade protection until then, meaning if Brad Treliving can't be assured there's a path toward extending the right winger then he'll have to trade him. Having Marner walk for nothing (Johnny Gaudreau), or have him dictate where he wants to be traded (Matthew Tkachuk) are both paths Treliving has walked in the past and knows can't be trod again.

So the question becomes how do you trade Mitch Marner? Or any star for that matter. What trades have been made in the past?

Just to reiterate, this path only gets taken if Marner wants Matthews money, and why shouldn't he want the most he can get. All power to him, the Leafs will just have to do what they gotta do.

Back to the Future or not?

There are two ways star forwards have tended to be traded. One is for a collection of mostly playable, but overpaid, skaters, a first round pick or two, and some semi-equivalent prospect bets. Often it's the scouted prospect that's fought over till the end, and in a lot of cases has been the gem amongst the bag of pucks.

Many players have been traded this way. My list ranges from Phil Kessel and Jack Eichel to Ryan O'Reilly and Brayden Schenn. In some cases, someone in the return becomes a star (Tage Thompson from the ROR deal), but in others it's all a flop (Kapanen and the picks for Kessel).

There's a surprising number of times the young talent acquired has led to great things, though it's come with years of waiting. Ottawa got Tim Stützle and Josh Norris for Erik Karlsson. They also traded away Bowen Byram for Matt Duchene. Some other examples are Jeff Carter (Philly got Voracek and Couturier), and Sam Reinhart (Buffalo got Devon Levi and Jiri Kulich).

But if we're being honest, trading for a handful of lottery tickets is what bad teams do because their entire outlook is towards the future. What really matters to the Leafs is staying competitive and winning now. So more likely they will look for other stars in the league and try to do a swap. There are some examples of this: the famous Hall for Larsson and Subban for Weber trades, and more recently Tkachuk for Huberdeau and Weegar.

These trades often end up being for a player at a different position or the younger player gets traded for the older version of themselves, or both in Tkachuk's case. This is usually because third contracts are expensive for stars and the only way for the buying team to give back the same contract situation is with a player who just went through it a few years before. It's very unlikely a trade is made for a player with more cost-controlled years, because that is more valuable.

Essentially, if Marner were to be traded, it's more likely to be for Tyler Seguin than Jason Robertson, to pick Dallas out of a 10 gallon hat.

Trading Elite Players

The next big consideration is not only how you trade a star, but how do you trade a high-end, elite star. Or at least one who's paid like it. When I filtered the list of traded players down to the ones who made/ended up making more than $9 million and got traded in their prime, the short list screamed "Do Not Do".

  • Jack Eichel - 10 mil, traded at 25 for a big package of picks, prospects, and contracts back (Tuch, Krebs, a first (Ostlund), and a second)
  • Mark Stone - 9.5, traded at 26 for not nearly enough by Ottawa (Brannstrom, Lindberg, and a 2nd. Woof.
  • Jeff Skinner - 9, traded before his big extension at 25, for a prospect, a 2nd, 3rd, and 6th. Not very much, though he's probably several million overpaid.
  • Artemi Panarin - 11.6, traded before his big contract at 25, for Brandon Saad
  • Matthew Tkachuk - 9.5, for Jonathan Huberdeau and MacKenzie Weegar

A couple of the trades had good "win now" players coming back the other way, like Saad, Huberdeau, and Weegar, but unless you have time to wait for prospects it's never the same amount of value coming back. Treliving probably did as well as he possibly could considering he absolutely had to trade Tkachuk and everyone knew it. The thing I worry about is player management getting to that deteriorated state. Marner needing to be traded with a NMC in his back pocket would be one such state.

Taking Risks

I think it’s interesting that the Golden Knights did two of these deals for probably two of the four best players on the list above and it worked out excellently for them. Maybe the solution isn't one trade to move the talent out and bring some back in, but two deals?

Regardless of what the Leafs do with Marner, the concept of playing aggressive and going after stars when they are available is a smart way forward, especially when they might have a big scary contract associated with them. Usually the star will be worth it -- but not always, yes I'm talking to you, Jeff.

There are some very good young players in tricky situations contract-wise around the league. Pierre-Luc Dubois wants his ass out of Winnipeg, there are reports the Senators are shopping Alex Debrincat, and Elias Pettersson has been taking bridge deals in Vancouver waiting for cap space to show up that likely never will. He's in the last year of his deal, as is Kaapo Kakko.

One might say Pettersson or some other young star is unattainable, but to them I ask where is Jack Eichel right now? Impossible is nothing (this post is not sponsored).