It's a great question. I don't think the NHL can reject a compliant contract, but they can endorse the 35+ rule.
Let's say Sid wants to play there more years and he wants $9.5M per year. That's $28.5M in total value.
Let's say the Penguins sign him to an eight year deal at $4M per year. That's $32M and maybe it is front end signing bonus loaded so he gets most of that money in the the first three of four years.
Sid's happy and the team is happy because they get an AAV of $4M for the next three years and $5.5M in savings to spend on pieces around Sid...also making Sid happy.
So, what happens?
- Sid doesn't retire after three years and is signed at a deal for the team and not a terrible number for 40 year old Crosby.
- Sid suffers a career ending injury and goes on LTIR. It doesn't hurt the Penguins cap moving forward.
- Sid retires after three years and the Pens have $4M on the cap for five years. When the cap is over $100M, the Pens are rebuilding, and Sid is some sort of ambassador.
Aren't all three of these better than a $9.5M cap hit the next three years? Why would the league care, no circumvention going on.