I agree, but if Sid comes out and says he wants to play until he is 45 and he feels he is in great shape and he wants to take less so they can build a winner around him then I believe intent would be hard to prove.
Yes, the NHL does not require a court level burden of proof but this is Sid. They don't want to battle with him and the Pens over this. Maybe the front end loading would set off too many bells.
It's an interesting case though and the league would enforce the cap hit for years, that's a stiff penalty for most years...five x $4M on the cap.
Once you front load the contract, it does become a 35+ contract by the new rules. So, the balance of the contract has to hit a team's cap, be it the Pens or they end up trading the contract like so many other LTIR deals have been done. Without front loading, Sid can retire at any point in time and the remaining term does not need to hit any team's cap.
Again, the only reason to give him a deal that isn't a 35+ deal is to basically allow him to collect money on LTIR.
Then you are hoping that insurance does cover it. But, insurance probably flags the deal and could very well say, no, we don't want to insure someone from 38 all the way to 45 at $9 mill per season.