Established talent undeniably does not have to do so, yet we've seen multiple premium players do that in recent years. Bobrovsky would be the earliest in his career, but he's still going to be a 31 year old Goalie by the time his deal starts. That's not a completely different animal.
The problem with the guaranteed nature of NHL deals right now is the labor agreement. You're not going to be sure you see your money by definition. We don't have enough information to know if 2019, 2020, or 2021 is going to be the flashpoint, but I'm sure Theofanous is significantly more in touch than we can be. The built-in safeguards against a labor stoppage then become every bit as important as the dollar value.