No matter what you do, Dak has 36m$ in dead cap money after this year. The reason for this is because Jerry Jones has been “credit carding” his previous salaries.
Remember when you’d hear Dak restructured his contract every year and Dallas suddenly would get a ton of cap space? What is actually happening is Dak gets exactly the same money, but Jerry Jones is changing it from a cap hit all that year to prorated cap hits. What prorated cap hits are is the same total cap hit but spread over 5 years, like a credit card for the cap. But all money paid out HAS to hit the cap eventually. Theres no getting out of it. So right now Dak has a 35m$ salary for this year. Why is his cap hit 59m$? Because you still have prorated money hitting the salary cap that you paid him many years ago. Make sense?
Prorated money is also commonly called dead money when the player is no longer on the team. Now let’s look at hypotheticals with that info in mind. Dak has 24m$ in prorated money just for this year, and 36m$ in prorated money spread out in future years (2025, 2026, 2027). He also has a 35m$ salary this year. In the event he leaves the roster, all future prorated money is accelerated to that year. So the 36m$ in the future spread evenly over many years all gets dropped right now with the 24m$, that’s how we get 60m$. So let’s go through them:
Cut or Trade Now: Save 35m$ salary, only have 24m$ prorated dead money for this year, but also have to take all accelerated prorated money from future years because he left the roster (36m$). So total is 60m$ cap hit this year but completely off the books in 2025.
Cut or Trade After June 1st: Save 35m$ salary, only have to pay 24m$ dead cap number. Difference here though is all prorated money is accelerated to next year, so it’s a 36m$ lump sum in 2025 because it all accelerated due to him being off the roster. Thats what June 1st allows, delaying the accelerated dead money that occurs after this year.
Keep him for 2024 with no new contract: You have to pay 35m$ salary, with a 24m$ dead cap number from previous money already paid and prorated. Then he’s off the roster next year and you take the remaining accelerated 36m$. So this is kind of similar to June 1sting him with the dead money next year, but you also have to pay him his salary. Thats how it’s still 36m$ next year still, but also 60m$ this year.
Extend him: You can rip up his 2024 salary, lowering his cap hit this year greatly, and give him bonuses to compensate that can be further prorated. His 2024 cap hit can never go below the 24m$ proration number as that’s still required from previous money given. With his continued proration, new signing bonus and 2024 new salary likely being around 40m$ total cap hit, you’re probably saving 20m$ overall for 2024 cap. But the most important part of extending him is he’ll be on the roster 2025, 2026, 2027, so the future prorations don’t get accelerated into a 36m$ lump sum, instead it stays spread out over those years.