The Cowboys managed to keep most of their offseason business from turning into a full-blown mess, but the next wave of contract decisions is already lining up. After the Dak Prescott and CeeDee Lamb negotiations in 2024 and the failed Micah Parsons talks in 2025 that ended with a trade to the Green Bay Packers, Dallas now has a new group of players headed toward major paydays.
George Pickens is the headliner. The wide receiver is coming off a huge season, and the Cowboys kept him in place by using the franchise tag, which will pay him $27.3 million in 2026. That still leaves him set up for another contract push in the 2027 offseason, and if he delivers again, the leverage swings in his favor fast.
Pickens is not alone in that conversation. Four Cowboys are positioned to hit free agency in 2027, and each one has a very different path to a new deal.
Cobie Durant looks like one of the sneakiest value additions Dallas made this year. He signed a one-year deal that could reach $5.5 million, and if he backs up his 2025 level of play in 2026, that number will jump dramatically next offseason.
Durant picked off three passes in the regular season and added three more in the playoffs. He’ll compete with Shavon Revel Jr. and DaRon Bland for snaps, but even if he doesn’t lock down a starting job, he still figures to be a key piece.
That kind of role should set him up for a strong raise.
Projected contract: Three years, $46 million, $15.33 million average per year
Ryan Flournoy turned heads in 2025 with a breakout year that included 40 catches, 475 yards and four touchdowns. Now in his third season and firmly in place as Dallas’ WR3, he’s also in the final year of his rookie contract.
Because he’s a restricted free agent, the Cowboys can keep him around by using either a first- or second-round tender. A first-round tender would likely require him to get close to 1,000 yards, so the more realistic outcome is the second-round tender, which would keep him in Dallas for another year while he continues to build his case for a long-term deal.
Projected contract: Second-round free agent tender, $6.2 million
DeMarvion Overshown brings the kind of impact that can change a defense, but health has been the issue. In 2024, he put together a big season with 90 tackles, five sacks and a pick-six in 13 games before a knee injury cut it short.
He played only six games in 2025, which keeps his value tied closely to durability heading into the final year of his rookie deal. If he stays on the field, Overshown could push toward $20 million per year, though even a full season might not get him all the way there.
Projected contract: Three years, $48 million, $16 million average per year
Then there’s Pickens, who will draw the most attention of anyone on the roster in 2026. He was described as a model teammate in his first season with Dallas, and now he has the franchise tag as proof of how important he is to the offense.
The Cowboys could tag him again in 2027, but another big year would give him far more leverage than he had this time around. If he reaches the open market after another strong season, the number could get massive.
Projected contract: Four years, $160 million, $40 million average per year
In Other News...
Tony Romo Just Got A Surprising CBS Verdict After Latest Trouble
Tony Romos latest off-field trouble has put him back in the spotlight for reasons far removed from the broadcast booth. The former Cowboys quarterback was arrested in Milwaukee on suspicion of operating a vehicle while intoxicated, and the fallout has already reached beyond the legal side of the story, with Romo withdrawing from a golf tournament he had been set to play in.
There is at least one immediate piece of stability for Romo, though the situation is still far from settled. He is scheduled to appear in court on September 21, and CBS has opted not to move on from him in the wake of the arrest, leaving his future in place for now even as the case continues to unfold. [Read more 🡒]
Cowboys Just Unveiled Another Offensive Line Experiment Fans Will Be Watching
Training camp in Oxnard opened with the Cowboys already sorting through a familiar kind of puzzle up front. Brian Schottenheimer said the staff is still looking at different ways to piece together the best offensive line, with Tyler Smith getting work at tackle and Terence Steele among the veterans who could be shifted around as the group tries to find the right fit.
For Dallas, the intrigue is less about whether the line will be altered and more about how far the team is willing to go to make it work. The Cowboys have not settled on an alignment yet, and the early weeks of camp should give a clearer picture of which combinations are being tested most often and which players are being asked to handle new responsibilities. [Read more 🡒]
Tyler Smith Just Put Cowboys Fans On Edge At Camp
The Cowboys settled into Oxnard, California, to open 2026 training camp with one of their most important offensive linemen already drawing attention. Tyler Smith met with reporters as camp began and addressed the kind of early-summer uncertainty that can shape an entire line, with his standing still tied to where the staff ultimately wants him working as the competition unfolds.
Smith also made clear he sees a real championship path for Dallas if the group keeps grinding, a familiar message in late July but one that lands differently when the roster is trying to sort out its best five up front. The final call on where Smith lines up is expected to come during camp, and for Cowboys fans, that means a key piece of the puzzle is still waiting to be placed. [Read more 🡒]