In the real world, patience is a virtue. In Jerry World, patience is expensive. For the second straight contract cycle, team owner Jerry Jones and the Dallas Cowboys find themselves in an inexplicable game of contract chicken with quarterback Dak Prescott. The mistakes made leading up to his four-year, $160 million deal in 2021 have left the franchise in an intensely vulnerable position as the season approaches. With Prescott’s price only rising, the Cowboys run a serious risk of losing him for nothing in 2025.
Would that be a bad thing? What are Dallas’ options if it does move on from Prescott? Are the Cowboys doomed to fail if they re-sign him? I’ll answer those questions and a bunch more in a deep dive into the signal-caller’s future.
Let’s go all the way back to spring 2019. Coming off a 10-6 season and the team’s first playoff victory in four years, the Cowboys were riding high. After they started the 2018 season 3-5, their trade for Amari Cooper seemed to kick-start the offense. They won seven of their final eight games to claim the NFC East. Their official Twitter account bragged about trading their first-round pick for Cooper when it came up on draft day. To the extent the vibes are ever good in Dallas, things felt like they were heading in the right direction.
Prescott, who had struggled early in his third season, was eligible for an extension. One of the league’s biggest bargains during a rookie deal in which he made less than $700,000 per season, he had played the best football of his career after the Cooper trade. Across eight starts in the second half of 2018, he completed nearly 72% of his passes, averaged 7.7 yards per attempt and threw 12 touchdown passes against three picks.
With one year left to go on his rookie deal and no fifth-year option available, the Cowboys found themselves in the window in which virtually every team will sign their quarterback. When they’ve landed on a passer they like, most organizations will ink him to a long-term extension before he enters his fourth season, allowing them to spread a significant signing bonus over the longest window possible. For quarterbacks who don’t have a fifth-year option, such as Prescott with the Cowboys and Russell Wilson with the Seahawks, there’s really no choice but to do the extension between Years 3 and 4. Teams are almost always loathe to have their starting quarterback enter the final year of their deal in a lame-duck situation without an extension.
The Cowboys didn’t seem to feel the same way. With Prescott reportedly asking for more than $30 million per season, the two sides didn’t come to an agreement over the summer. They locked up offensive lineman La’el Collins and linebacker Jaylon Smith, but there was no deal for Prescott, arguably the team’s most important player.
The 2019 season didn’t go as well. The Cowboys fell to 8-8, but it wasn’t because of Prescott, who threw 30 touchdown passes and averaged a career-high 8.2 yards per attempt. With his rookie contract now complete, they had no choice but to franchise-tag him, guaranteeing him a minimum of $31.4 million for 2020. This allowed Dallas to retain Prescott’s rights while negotiating a long-term extension.
That deal didn’t get done. The Cowboys reportedly offered Prescott a contract averaging just under $35 million per season with more than $110 million in “guarantees,” some of which would have been for injury. (Injury guarantees aren’t guarantees. That’s an article for another day.) Along the way, team executive vice president Stephen Jones started talking about how teams are less likely to win a Super Bowl when their quarterback takes up a significant percentage of their salary cap.
The 2020 season was a disaster. Defensive coordinator Mike Nolan couldn’t get his unit to stop the run. The Cowboys ranked 28th in scoring defense. New coach Mike McCarthy promised he could get the most out of Prescott, but after five games, Prescott’s season was over, as he suffered a gruesome ankle injury in a game against the Giants. Prescott had averaged more than 370 passing yards per game before the injury, taking over as the focal point of the offense from a diminishing Ezekiel Elliott. The Cowboys went 4-7 and averaged just over 21 points per game after Prescott went down, cycling through Andy Dalton, Garrett Gilbert and Ben DiNucci at quarterback.
After failing to come to terms with Prescott on a deal before the 2019 and 2020 seasons and seeing him suffer a serious ankle injury, on one level it makes no sense that Dallas would come to terms with him on an even bigger contract than the deals they had offered in previous years. And yet, that’s exactly what happened. The team gave Prescott a second franchise tag for $37.7 million to retain his rights for 2021, then signed him to a four-year, $160 million deal.
