At this point, it’s become fully clear that both the Cowboys and the quarterback Dak Prescott are intent on further extending their time together. With that expectation fully established, we can turn our attention to what that could look like and when that could occur. 
The Cowboys have no intention of letting Prescott leave Dallas. The Cowboys are likely also not too excited about the $59.4MM hit to the team’s salary cap that Prescott is posed to deliver in 2024, the second-highest figure in the league. Those two motivators are sure to steer Dallas in the direction of an extension and soon. This week is known as an opportunity for agents to get together with team officials at the NFL scouting combine in Indianapolis to broach such topics.
Obviously, no one is expecting a deal to get done in the next few days, though. Prescott is due a $5MM roster bonus on his current contract come March 18, but the Cowboys are likely more than willing to sacrifice that for a bit more time to craft a new extension. Still, Calvin Watkins of The Dallas Morning News claims that the team has every intention “of extending Prescott at some point this spring.” So whatever discussions are being had in the infamous Cowboys team bus in Indianapolis this week should lay the groundwork to get a new deal done relatively soon.
Prescott’s previous four-year, $160MM extension back in 2021 was massive at the time, but nowadays, the deal pales in comparison to the most recent contracts we’ve seen going to passers that are starting to inch towards $60MM per year. Currently, Bengals quarterback Joe Burrow holds the league’s highest annual average value at $55MM. Yes, Burrow has led his team to a berth in the Super Bowl to earn that figure, but Chargers passer Justin Herbert is making $52.5MM per year with a regular season record of 30-32 and a loss in his single playoff appearance.
In comparison, Prescott has led the Cowboys to a 74-41 regular season record and five playoff appearances. People will draw attention to the 30-year-old’s 2-5 playoff record and the team’s inability to advance past the Divisional Round, but other quarterbacks have cashed in more with less. Also, despite the lack of playoff success, in 2023, Prescott led his team to their best record since his rookie year and led the league in completions and passing touchdowns. The expectation is that Prescott will once again set the mark for quarterbacks.
With how things are trending, a $60MM per year deal doesn’t seem out of reach. It’s simply the direction things continue to go towards. Yes, the Cowboys have other stars like Micah Parsons and CeeDee Lamb who will need new deals in the next two years, as well, but unless a team is willing to go back to a rookie contract and start from scratch, they will need to pay their quarterback. The higher-than-expected increase to the league’s salary cap this year makes $60MM a bit more palatable, and future rises to future salary caps make deals with Parsons and Lamb seem doable, as well. Not to mention that a new deal would result in a lower cap hit in 2024 for Prescott, freeing the Cowboys up to make some other moves to improve the team this offseason.
So, we expect conversations to be taking place this week to set the stage for a Prescott extension sometime this spring. And we expect that extension to once again move the bar for paying quarterbacks in the NFL. At this point, it all seems like a matter of time and details.