Dallas Cowboys owner Jerry Jones just can’t help himself. The NFL’s most notorious contract stickler would rather play hardball to the bitter end than reset the market with one of his star players.
His latest act seems to be playing out with George Pickens, who remains unsigned after the team placed its non-exclusive franchise tag on the 25-year-old wide receiver. Pickens is in line for an extension, and following the Denver Broncos’ blockbuster trade with the Miami Dolphins for Jaylen Waddle, and Jaxon Smith-Njigba’s recent mega extension with the Seattle Seahawks, the situation between Jones, Pickens, and the Cowboys appears headed for chaos.
There might not be a better fit for Pickens than the Cleveland Browns, who just stirred up their own mini firestorm among fans after making a curious adjustment to Myles Garrett’s contract.
Per Field Yates of ESPN, Garrett and the Browns agreed to modified language around option bonuses due in 2026, 2027, and 2028. Those bonuses will now be paid in September, rather than late March. According to Over the Cap founder Jason Fitzgerald, the move creates no 2026 cap space, but does create cap flexibility in the future, especially if the two sides mutually agree to explore a trade; Garrett’s current deal includes a no-trade clause.
The chances of Garrett getting traded in 2026 remain slim-to-none. Since that move would almost certainly come after June 1 for cap purposes, it makes little sense for the Browns to explore trading Garrett this summer, as the team would be essentially punting on Year 1 of the Todd Monken era. Any draft pick compensation coming back would be for 2027 and beyond, and unless the team acquires a young, Pro-Bowl caliber player in the deal (preferably a quarterback or wide receiver), there’s no reason to even pick up the phone.
Enter Pickens, who has a history with Monken from their time together with the Georgia Bulldogs, and could soon find himself in a contract stalemate so fierce that a blockbuster trade package for Garrett could actually be worth exploring.
Why this Cowboys trade package for Myles Garrett might actually tempt the Browns
In this hypothetical trade for Garrett, the Cowboys go all in, sending Pickens to Cleveland along with a first-round pick in 2027 (via Green Bay), a first-round pick in 2028, and a third-round pick in 2028. The Browns land their new No. 1 wide receiver while securing more draft compensation than the Cowboys received from the Packers in last year's blockbuster Micah Parsons trade.
This move would reunite Pickens with Monken, who was his offensive coordinator at Georgia from 2020-21. The Browns are unsettled at the quarterback position, but after passing on the top wide receivers in free agency, no team could offer Pickens more targets in 2026 than Cleveland. Tight end Harold Fannin Jr. led all Browns receivers in targets, receptions, yards, and touchdowns last year as a third-round rookie.
Pickens’ availability remains a major question mark, though. The Browns are currently free to make Pickens a contract offer, but Dallas’ non-exclusive franchise tag comes with the right to either match any offer sheet, or receive two first-round picks from the acquiring team as compensation.
The Browns are obviously not going to immediately start shipping out first-round draft picks again in the wake of the Deshaun Watson disaster. Cleveland currently holds 17 selections over the next two draft cycles, and its plan should be to use those picks and continue building through the draft.
That’s where Garrett comes in. He’s the most dominant defensive player of his generation, and now entering his age-31 season, the clock is ticking on his chances to one day play in a Super Bowl. He’s spent the majority of his first nine years in the league chasing individual glory while his team cycles through head coaches and quarterbacks with too few wins to show for it. As Garrett made clear last offseason, a change would be welcomed, and his revised contract has at least paved the way for that to happen somewhere down the line, with his team netting a massive haul of draft picks.
There’s also this: Garrett grew up in the Dallas-Fort Worth area, attended Martin High School in Arlington, Texas, and later starred at Texas A&M. Cleveland’s now his home, but the Dallas Cowboys were once his hometown team.
The Browns could really use a young, ascending wide receiver like Pickens. The Cowboys could really use an elite edge rusher to replace Parsons as they look to maximize their current window with quarterback Dak Prescott and CeeDee Lamb.
For the record, Garrett is highly unlikely to get traded this summer. He’s much more likely to cross that bridge again with the Browns in 2027 or 2028, when a move would make more sense for him and the team from a cap perspective.
But in the hypothetical world where it does happen? Jerry Jones and the Cowboys would almost certainly be on the other end of one of the biggest trades in NFL history.