Reality
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Before I start this, understand I am not on either the Cowboys or Pickens' side about this.
I have said many times that I think players should get as much as they can because their careers are short and may end at any time and I've also chastised the Cowboys for overpaying for players.
At this point, it's realistic to think that a new contract for Pickens would average around $33-35 million per year if not a little more.
Unfortunately for Pickens (and I'm sure other upcoming high salary players) he has a bad timing problem right now that has nothing to do with him.
The salary cap has increased considerably the last 2-3 years dollar-wise (not talking percentage points), but that increase is trailing the 5-year rolling salary average used in franchise tag salary calculations and it will continue to do so as long as the salary cap keeps increasing $20+ million every year.
Because the salary cap is increasing so much every year (again, dollar-wise) players are going to find themselves in Pickens situation more and more and teams are going to elect to pay them yearly (if they can via franchise/transition tags) instead of offering them contracts unless 1) they know they need that player very badly long-term, 2) they have another player they need even more so they need to keep that franchise tag for him, or 3) they need to free up a lot of salary cap space and have run out of options.
So from the Cowboys side, this is how they see it ...
If they sign him to a new contract, they have to pay him $33-35 million on average, but that will likely include a $40-$50 million signing bonus.
So on top of paying him up to $40-$50 million upfront, they will also pay him $6 to $8 million more for (assuming $33-$35m/year average) for 2026 than they would if they let him play on franchise tag.
If they don't sign him to a new contract, then they technically paid him for $3.6 million last year and would pay him $27.3 million this year. That means for a pseudo 2-year contract, they will have paid one of the top receivers in the league last year $31 million which yields an average of $15.5 million per season. That's a great deal for the Cowboys.
As such, the Cowboys are heavily incentivized to not sign him to an extension until next year unless they need salary cap space before July 15th for some reason.
In fact, the best strategy for the Cowboys FO would be to have Pickens play 2026 on the franchise tag, have a great season, then trade him next year for high draft pick(s).
Now, from Pickens side, this is how he likely sees it ...
He made $6.7 million the first four years of his career on his rookie contract.
He can make $1.6 milion per game this year on the franchise tag. That's a huge raise and a lot of money compared to what he was used to getting.
He also knows the Cowboys ultimately signed Prescott to a new contract the year after having him play on his franchise tag, so there is history there that the Cowboys might sign him to a long-term contract after the 2026 season. (not saying it will happen, saying there's precendent for it to happen).
My guess is that Pickens will reluctantly play on the franchise tag for 2026 barring the Cowboys offering him a contract, which they will likely only do if there is a big benefit to their salary cap books in 2026 or 2027.
He will make a lot of money this year, especially compared to his last 4 years.
Then in 2027 if the Cowboys franchise tag him again, I think he will sit out as he will have plenty of money and maybe their cap situation will be in a worse position either through existing high-contract escalating salaries impacting the salary cap or their desire to sign/trade for new players that creates the need for more salary cap space.
I am sure the NFLPA agreed to the franchise tag because it was put in to cause salary cap problems for teams with the one-year whole-salary-goes-against-the-salary-cap concept.
It was a simple trade ... teams got (months) longer to negotiate with the player and the player had leverage that would likely end with a new contract before July 15th.
Unfortunately for the NFLPA and players, teams have a huge advantage now because the rolling average is trailing the new contracts and I doubt that will change before the next CBA (in 2030 I think) unless the players give in to something the NFL wants badly like an 18th game or more international games.
I have said many times that I think players should get as much as they can because their careers are short and may end at any time and I've also chastised the Cowboys for overpaying for players.
At this point, it's realistic to think that a new contract for Pickens would average around $33-35 million per year if not a little more.
Unfortunately for Pickens (and I'm sure other upcoming high salary players) he has a bad timing problem right now that has nothing to do with him.
The salary cap has increased considerably the last 2-3 years dollar-wise (not talking percentage points), but that increase is trailing the 5-year rolling salary average used in franchise tag salary calculations and it will continue to do so as long as the salary cap keeps increasing $20+ million every year.
Because the salary cap is increasing so much every year (again, dollar-wise) players are going to find themselves in Pickens situation more and more and teams are going to elect to pay them yearly (if they can via franchise/transition tags) instead of offering them contracts unless 1) they know they need that player very badly long-term, 2) they have another player they need even more so they need to keep that franchise tag for him, or 3) they need to free up a lot of salary cap space and have run out of options.
So from the Cowboys side, this is how they see it ...
If they sign him to a new contract, they have to pay him $33-35 million on average, but that will likely include a $40-$50 million signing bonus.
So on top of paying him up to $40-$50 million upfront, they will also pay him $6 to $8 million more for (assuming $33-$35m/year average) for 2026 than they would if they let him play on franchise tag.
If they don't sign him to a new contract, then they technically paid him for $3.6 million last year and would pay him $27.3 million this year. That means for a pseudo 2-year contract, they will have paid one of the top receivers in the league last year $31 million which yields an average of $15.5 million per season. That's a great deal for the Cowboys.
As such, the Cowboys are heavily incentivized to not sign him to an extension until next year unless they need salary cap space before July 15th for some reason.
In fact, the best strategy for the Cowboys FO would be to have Pickens play 2026 on the franchise tag, have a great season, then trade him next year for high draft pick(s).
Now, from Pickens side, this is how he likely sees it ...
He made $6.7 million the first four years of his career on his rookie contract.
He can make $1.6 milion per game this year on the franchise tag. That's a huge raise and a lot of money compared to what he was used to getting.
He also knows the Cowboys ultimately signed Prescott to a new contract the year after having him play on his franchise tag, so there is history there that the Cowboys might sign him to a long-term contract after the 2026 season. (not saying it will happen, saying there's precendent for it to happen).
My guess is that Pickens will reluctantly play on the franchise tag for 2026 barring the Cowboys offering him a contract, which they will likely only do if there is a big benefit to their salary cap books in 2026 or 2027.
He will make a lot of money this year, especially compared to his last 4 years.
Then in 2027 if the Cowboys franchise tag him again, I think he will sit out as he will have plenty of money and maybe their cap situation will be in a worse position either through existing high-contract escalating salaries impacting the salary cap or their desire to sign/trade for new players that creates the need for more salary cap space.
I am sure the NFLPA agreed to the franchise tag because it was put in to cause salary cap problems for teams with the one-year whole-salary-goes-against-the-salary-cap concept.
It was a simple trade ... teams got (months) longer to negotiate with the player and the player had leverage that would likely end with a new contract before July 15th.
Unfortunately for the NFLPA and players, teams have a huge advantage now because the rolling average is trailing the new contracts and I doubt that will change before the next CBA (in 2030 I think) unless the players give in to something the NFL wants badly like an 18th game or more international games.
