The Cowboys have, well, a unique style of negotiating contracts for their stars.
Rather than extending players soon after they become eligible for a new contract, Dallas tends to wait as long as possible to work out new deals, which often leads to missed training camps and strained relationships.
As time goes on, price tags typically rise. The Cowboys waited until after Justin Jefferson's extension with the Vikings to sign CeeDee Lamb, and the same scenario played out when Myles Garrett and T.J. Watt raised the bar for defensive players before Micah Parsons could find a new deal.
The pattern is clear: owner Jerry Jones almost always finds a way to keep great players, but he doesn't make the process easy on anyone.
Here's a look back at some of the Cowboys' most famous contract disputes during Jones' tenure as owner.
MORE: Ranking the 18 greatest Cowboys players of all time
Jerry Jones timeline of Cowboys contract disputes
Michael Irvin, 1992
Fresh off a breakout season that saw him rack up 1,523 yards and eight touchdowns, WR Michael Irvin held out for a new contract throughout training camp in 1992. Irvin had been seeking a deal worth $1.4 million annually, but he instead settled for a contract that paid him $1.25 million per year over three years.
It wasn't until Sept. 4 — three days before the Cowboys' season opener — that Irvin agreed to a three-year extension with Dallas, but he was able to suit up on Sept. 7 and haul in five catches for 89 yards in a win over Washington. The Cowboys would win the Super Bowl despite the tense dispute, perhaps setting the stage for Jones to feel no urgency in getting deals done before training camp.
MORE: Who is on the Dallas Mount Rushmore of sports?
Emmitt Smith, 1993
A year after Irvin's holdout, RB Emmitt Smith was content to sit out into the regular season and missed the Cowboys' first two games. Seeking quarterback money rather than high-end running back money, Smith ultimately settled for becoming the NFL's highest-paid running back on a four-year, $13.6 million deal after the Cowboys lost each of their first two games and restarted negotiations.
Before Smith agreed to a deal, Jones told reporters he wasn't willing to listen if his running back wanted to be paid like a quarterback. "They're talking about quarterback numbers. If they're willing to talk about [Bills RB] Thurman Thomas' numbers, I'd certainly listen," Jones said.
As was the case a season earlier, the Cowboys put the saga behind them and won another Super Bowl with Smith still leading the NFL in rushing despite missing two games.
MORE: Where does Emmitt Smith rank among NFL Playoff rushing leaders?
© Jason Getz-Imagn Images
Dez Bryant, 2015
WR Dez Bryant never held out in search of a new contract, but the Cowboys still took his situation as far as it could go before signing him to a second NFL deal. Bryant played out his first five seasons without a second contract and was franchise tagged by Dallas in March of 2015, preventing him from hitting free agency. The deadline to get a long-term deal done was July 15. If Bryant didn't sign by then, he could only play the 2015 season on a one-year pact. Just ahead of the deadline — more than five calendar years after he was drafted — Bryant agreed to a five-year, $70 million extension with the Cowboys, preventing any training camp drama.
MORE: Are any Cowboys among the oldest players drafted in the NFL?
Ezekiel Elliott, 2019
RB Ezekiel Elliott could have played on his rookie contract all the way through the 2020 season, but with running backs' careers typically running shorter than most other position groups in the NFL, he held out for a long-term deal throughout training camp in 2019.
Jones wouldn't budge for much of the summer, but he insisted there was no concern about Elliott's future in Dallas. "When have I ever not done one?" Jones asked reporters, referring to other mega deals that ultimately reached the finish line. "So I don’t worry about that. You just keep plugging."
After missing all of training camp, Elliott finally agreed to a six-year, $90 million extension with Dallas just four days before the start of the regular season and played in a Cowboys Week 1 win over the Giants.
MORE: Revisiting Deion Sanders NFL career, relationship with Jerry Jones
Zack Martin, 2023
All-Pro guard Zack Martin held out of the first few weeks of training camp in 2023 in hopes of securing a revised deal from the Cowboys. With the season just over three weeks away, Martin got his wish, agreeing to a deal that increased his salary between 2023 and 2024 by a total of $8.5 million and fully guaranteed each season.
Martin credited Jones with meeting him in person and hammering out the deal. "We were able to have that one-on-one time, and I think that helped, just being able to talk face-to-face," he told reporters after agreeing to the revised contract.
Unlike previous Cowboys holdouts, Martin did not add any additional years onto his existing deal; he retired when the contract expired.
MORE: Why did Zack Martin retire from the NFL?
CeeDee Lamb, 2024
WR CeeDee Lamb sat out virtually all of Cowboys training camp in 2024 as he sought a new contract. Lamb became extension-eligible after the 2022 season, but the Cowboys instead watched a handful of high-end wide receivers selected either in the same draft or the following draft — including Justin Jefferson and Amon-Ra St. Brown — sign deals before they were able to hammer one out with their star receiver.
In mid-August, Jones expressed no panic about signing Lamb, telling reporters he did not feel any urgency to get a deal done. At the same time, Jones said Lamb was "missed" around the facility, with one major caveat. "But you're not missed out here competing, and it doesn't put any pressure any place on us," he said.
Lamb finally agreed to a four-year, $136 million extension on Aug. 26, and he was active to start the season just two weeks later.
MORE: Are any Cowboys among the 10 most shocking NFL Draft slides of all time?
Dak Prescott, 2024
QB Dak Prescott didn't hold out in search of a new contract leading up to the 2024 season, but the uncertainty surrounding his future lingered over the Cowboys throughout the summer just as Lamb's did. Prescott never issued any public demand that he receive a new contract before the start of the season, but Dallas gave him a record four-year, $240 million deal on the morning of the team's season opener to ensure no offseason contract drama crossed over into the regular season.
MORE: Most draft picks by a school in a single year
Micah Parsons, 2025
EDGE Micah Parsons became extension-eligible after the 2023 season, but 2024 went by quietly without much progress toward a new deal. Parsons turned up the pressure in 2025, with only the fifth-year option remaining on his rookie contract, but he went to training camp without a deal and has not practiced to this point.
On Aug. 1, Parsons turned the pressure all the way up by publicly requesting a trade out of Dallas as many of his teammates rallied around him on social media. "I no longer want to be here," Parsons said in a lengthy statement that referenced controversial comments made by Jerry Jones that implied the pass-rusher was an injury risk.
"Just because we sign him doesn’t mean we’re going to have him," Jones told reporters early in training camp. "He was hurt six games last year. Seriously. I remember signing a player for the highest-paid at the position in the league, and he got knocked out two-thirds of the year: Dak Prescott." Parsons missed four games with an ankle injury in 2024.
MORE: Complete list of Super Bowl MVP winners through the years