On the eve of their season opener, it remains to be seen if the Cowboys will reach agreement on a Dak Prescott extension. Team and player are negotiating a deal to continue their relationship beyond the 2024 campaign. 
Recent updates on the situation have noted progress at the bargaining table, with an agreement reportedly being reached with respect to the length of a new contract. Value and guarantee structure will be key points of contention as in any high-profile negotiation, and Sunday represents an artificial deadline for an extension to be in place. In the latest development on this story, Mike Florio of Pro Football Talk reports there is a “small chance” the Cowboys and Prescott will get a deal over the finish line in time.
While a final agreement is not in place, DLLS’s Clarence Hill Jr. confirms the sides are still negotiating at this point with a very small window of time remaining. Owner Jerry Jones said last week a deal does not need to be signed by the start of the regular season, although teams generally prefer to get contract work done in time for Week 1. Prescott is currently slated to carry a cap hit of over $55MM in 2024, a figure which could be lowered on a long-term pact. The 31-year-old will leave Dallas with a dead money charge of more than $40MM if he departs as a free agent next spring.
Both Prescott and Jones have made clear their desire to avoid that, although the three-time Pro Bowler has also noted the multitude of longtime starting quarterbacks who have played for multiple teams during their careers. Prescott appeared to be open to negotiations continuing into the season, but he has since clarified he is not the one primarily responsible for whether or not that happens. Given the efforts made to reach an eleventh-hour agreement, it is clear all parties involved are interested in achieving clarity in advance of the season starting.
CeeDee Lamb inked a four-year extension averaging $34MM per season this summer, and edge rusher Micah Parsons will be in line for a deal putting him at or near the top of his position’s market during the 2025 offseason. Prescott could very well move to the top of the quarterback pecking order on his next deal, either on another Dallas extension or a contract sending him to a new team in March. The latter scenario being eliminated is still possible with mere hours remaining until the Cowboys’ season starts.
With him being 31 already I could see Dak trying to get more than 4 years like the Tua/Love high AAV deals were as this could be he last big payday before having to go year to year during the decline years for QBs.
And Dallas really screwed themselves over by not paying him when other similar QBs were getting paid now he’ll cost more
How about Jerry Jones resigning as GM and selling the team before Week 1 …what are the chances of that?
If you’ve ever seen Futurama, you’d know Jerry jones will be one of those talking heads in a jar still alive hundreds and thousands of years into the future-still owning and operating the Cowboys.
This would make a good poll question on this site: Do you think Dak Prescott should be extended by the Cowboys?
Yes, 4/$240 is probably what he’ll end up getting if I was a betting man