The Dallas Cowboys are heading toward the NFL trade deadline with a familiar kind of uncertainty hanging over them. The 2026 deadline is only a couple of weeks out, and once again Dallas is expected to be in the mix. The real question is whether that means pushing chips in or starting to think more carefully about the future.
Last year, the Cowboys made a splash by landing Quinnen Williams to help clean up a defense that had too many problems. His arrival helped, but not enough to change the bigger picture. Dallas still stumbled through most of the season and finished 7-9-1.
Now the same fork in the road is back, with the November 10 deadline closing in. Depending on how the next two weeks go, the Cowboys could be looking at very different kinds of moves. Three names stand out as realistic possibilities.
Josh Sweat is the first one, and the fit is easy to see. He has already thrived in Philadelphia, where he won a Super Bowl with the Eagles in 2024. Christian Parker was part of that staff that season, and he is running a similar scheme now, which makes Sweat a natural target.
The catch is the price. Reports say the Arizona Cardinals may be open to moving Sweat, but they want an early pick on Day 2. That would likely force Dallas to part with its 2027 second-round pick.
That’s not a small ask for a team that already sent its 2026 second-round pick to the New York Jets in the Quinnen Williams deal and its 2028 second-round pick to the Pittsburgh Steelers in the Joey Porter Jr. trade. Even so, if Dallas decides Sweat is the missing piece, it may have to pay up.
There is also the possibility that the Cowboys move in the opposite direction and start trimming down if the season slips away. If they lose again before the deadline, especially against the Cardinals or the Indianapolis Colts, the argument for buying gets a lot weaker. At that point, the focus would have to shift toward players who fit beyond 2026.
That’s where George Pickens comes in. He is obviously talented, but he also looks like the kind of asset Dallas might have to consider dealing if the season goes sideways.
CeeDee Lamb has made it clear this year that he is the superior WR1, and the Cowboys can’t realistically pay both receivers more than $30 million. That becomes even more complicated with Joey Porter Jr. now standing as their best cornerback and a player they also need to figure out how to pay.
Moving Pickens would sting, but the market could be there. The Kansas City Chiefs might be desperate enough to offer a second-round pick and perhaps another late-round selection. If Dallas reaches the point where it has to give up on the season, Pickens is the strongest trade chip it has to recoup some of the draft capital it has already spent.
Then there’s the biggest swing of all: Maxx Crosby. His name keeps popping back up around the Cowboys, and with the deadline nearing, the rumor is heating up again.
That would be a true all-in move, and Dallas should only go there if it wins its next game convincingly. Giving up a first-round pick for Crosby would make sense only if he is the final piece, the player who can elevate a struggling pass rush and give the defense a real centerpiece.
But there is a limit to what one star can fix. The Cowboys already tried the same basic idea with Williams last season and Porter this year. Both have done good work, but neither has been able to cover up larger problems, especially when communication breakdowns leave receivers wide open on third down.
So Crosby only works if the rest of the defense is finally trending in the right direction. If not, a premium pick becomes a costly bandage. If Parker starts finding his footing over the next couple of games, though, Crosby could become the move that puts Dallas over the top in the NFC East.
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