We’ve had this debate before, and I think fundamentally, you must just be more of a risk-taker than me.
But the other thing is that I feel we see a lot of hockey players hit a peak in their early-to-mid-20’s, and then never reach that height again.
What if Raymond signed for two years, then follows up his 30-goal/70+ point season with a couple of solid but not spectacular 20-25 goal, 50-point seasons? The team isn’t going to be looking to juice the number of years and AAV they’re willing to offer him based on his potential anymore.
Everything is a risk, depending on your point of view. If Raymond regresses to a 50 point player, then he'll be overpaid for a few years until the cap increases, but at least he'll have guaranteed money. But if he continued to progress? And becomes a 40g/90+point player? He'll be kicking himself because he'll have left money on the table.
I look at it more as a case by case scenario than anything else.
The super elite players - McDavid, Makar, etc. - should never be taking 8 year contracts in their early 20s if they're looking to maximize their gains.
Auston Matthews, to his credit, is the only player to have properly leveraged his contractual situation to maximize his potential gains. He'll be a UFA at 30 years old and will probably then sign his 8 year near-retirement contract. And even then, I wouldn't be shocked if he decided to sign another 3-4 year contract.
For players who aren't on the same level as them, it's simply a question of how much risk they're willing to take and how much leverage they have. Injuries have almost never derailed an established player in his 20s from getting paid real money in the NHL.
I understand it's not my life, and it's not my potential career earnings I'm gambling with, but I'd be much more willing to go shorter team immediately and try for longer term later if I'm a top-6 forward or top-4 d-man. If I'm a depth player, though? I jump on term the second I can.