The problem with extending players before their contracts are up is they may not want to. And I don't blame them. A player like Diggs, for example, might want to hit the open market and see what the highest bid is.
I think the Cowboys will extend Dak. I don't think they have a choice. They cannot have him play the 2023 season with a near $50 million CAP hit. They are already over the CAP and they need CAP relief so Dak is the most logical place to go unless Jerry is willing to take a year off to absorb the pain. But don't be surprised if Dak gets another 4 years added to his contract for $45 to $50 million a year.
Judging from the way the Cowboys cut some coaches this year I think we could see some big moves with the roster too. Zeke and Tyron may both be gone, although I think Zeke will do something with his deal to try to stay. Tyron has one year left on his contract so he maybe be willing to do a restructure, add a year or two onto his deal and lower his CAP as well. But I would not be shocked if Tyron is a June 1 cut. I don't know if they will sign LVE either. He may have played himself into a contract too big for Jerry and Stephen. They may bet on Damone Clark in 2023. We may see Jabril Cox, Damone Clark and Micah Parsons at LB next year. I wish we had seen more of Cox in 2022 but I think he has good potential. Good LBs can be found in the middle rounds. Fred Warner was a 3rd round pick. Coincidentally, he is the same size as Cox, 6'3" 230 lbs (Cox is listed at 233). Who did Cox remind you of when he raced across the field to stop Danielle Jones from scoring, knocking him out in the process? I know it is one play but that's why I wanted to see more.
I don't think the Cowboys will sign TY Hilton. I could be wrong. I do think they will try to re-sign Donovan Wilson. I do think they will try to re-sign Carlos Watkins, and I don't think they will re-sign Dante Fowler.
The Cowboys will expect bigger years from Damone Clark, Jabril Cox, Bohanna, Tolbert, Sam Williams, and Israel Mukuamu.