If Hextall has the cap room, I'd rather give the money to Simmonds than sign another FA for $7-8M for 5-7 years and be forced to lose some kids.
Simmonds has the intangibles you'd like on a team where you're going to have a bunch of kids the next 3-4 years.
Yes, he won't perform up to his contract, but it's not my money - so if Hextall has the room, keep him.
But you can't go over 4 years, I think that's the point where the new contracts will start to squeeze.
When the veteran contracts expire, you'll either have to let them walk or resign them to short-term deals at a huge discount.
So keeping Simmons from 31-34 is not infeasible, 2023-2024 the contract expires, when he's 34.
Giroux in 2022-23, when he's 35. $8.25M toward Cout's new contract which will start that year when he's 30.
JVR in 2023-24 when he's 34. And Simmonds, $13M freed up.
Voracek in 2024-25 when he's 35.
Now Simmonds is also in a bind, if he doesn't sign an extension, he should request a trade to a team where he can be on the 2nd line and PP1 to pad his stats going into free agency.