I don't think he ever signs a max term deal until he's on the back end of his career. If you ask me he's leveraging his position to take shorter terms and just get raises sooner. The new wave of stars are taking a page from the NBA playbook and nobody wants to be stuck being underpaid on an 8-year deal anymore. Eight years is a loooooong time. There's always injury risk and things like that but these young guys seem fine betting on themselves and their health.
McDavid makes great money right now but in a few years he may wish he signed a 5-year deal too when guys start lapping him in AAV. You could say he's already underpaid even at $12M. Wouldn't mean he wants to leave Edmonton necessarily but he could have maximised his earning potential by taking shorter deals. It's going to be the new way for any young superstar player.
I think you make really good points here. Matthews (and his agent) changed the contract structure for young players going forward. The league was already paying young superstars big bucks on their 2nd contract... rather than waiting until their 3rd.
It's an age game: Superstar comes into the league at 18, and plays for minimal salary.
At 21, they sign a 3 or 4 year deal that pays them a lot more, but not a crazy deal.
Then at 24 or 25, while still a UFA, they sign a big contract. By the time that deal ends.... they're in their early 30s, and very few will get a second massive deal. Teams have figured out that you don't sign a 32 year old for 7 years.
Teams have gotten smart. The Oilers gave McDavid that 8 year deal. They will probably be the 8 most productive years of his career, and are a relative bargain at 12.5 million. He'll be 29 when the deal is up. He's probably the exception to the rule, and he'll be able to get another 7 or 8 deal at max(ish) money.... but most players at that age will not.
Matthews deal? It's so much better for the player. He gets max(ish) dollars for 5 years instead of 8.... but he'll be 26 when the deal is up, rather than 29. There's a great chance he hasn't even peaked, before his next contract starts. Nobody will hesitate to offer him a 7 or 8 year deal at that age.
Even if the plan is not to leave Toronto.... he'll be able to lock into an 8 year deal at that point, that's most likely worth more per season than his current contract. He's betting on himself: Gives up 3 years of security, but for a likely higher salary in those 3 years.... plus 5 more at whatever his career max likely turns out to be.
At 26, it's still likely that a player can get better. At 29, it's unlikely.
Any of the three guys that were mentioned here (McDavid, Matthews, Eichel): They do have the ability to put their teams into a tight spot. They can demand a trade if they want to. I'd suggest that Toronto has done a decent job of building around Matthews, and I'm cautiously optimistic the Oilers are starting to do things right too. Buffalo is still a mess though - and I do wonder how long before Eichel asks to be moved.
Anyway, back to the original question on Marner......
If you look at any "mid level" players out there (i.e. NOT a top tier guy, but arguably right below it) I think Marner has as good a shot as any player in the league to have his values skyrocket. If the Leafs ever go on a nice playoff run (and they very well could), and Marner is a big part of that (he's very likely to be) cards like his YG will double in value, I think.