Of course, it’s difficult to project any movement in an offseason that is still a little under a year away, but there are times when you can project out based on tangible roster and cap issues in advance; this is the situation for two Dallas Cowboys fan favorites.
America’s Team’s 2027 free agency class is headlined by one of those two guys, but it also features a few starters and some key depth pieces that may be boxed out of a contract extension after this season.
Here, I’ll talk about the two guys in particular, and the why behind their unlikely return to the Cowboys in the long-term.

1. George Pickens is Unlikely to Play in Dallas in 2027
Info: Unrestricted Free Agent Next Offseason, $30.6M Expected Market Value (via Spotrac), Unlikely to be Franchised Tagged due to % Increase.
Fans may not want to imagine it at this point, but it is hard to see a world where George Pickens remains with the Cowboys in 2027 and beyond.
The superstar wide receiver came to Dallas around this time last year in a trade with the Pittsburgh Steelers, and he flat-out exceeded all expectations. It was a genuinely spectacular year for a guy who was previously inconsistent, and even frustrating, at times.
However, we’ve seen the front office be unwilling to even negotiate a long-term deal, likely due to the issue of paying two wide receivers at the top of the market.
In theory, the Cowboys could franchise tag him again next offseason, but consecutive tags mean a 120% increase from the previous year’s salary; that’s unsustainable for the organization. Instead, I think we see him dealt for some compensation ahead of the 2027 NFL Draft.
2. DeMarvion Overshown’s Health and Potential Make Extension Unlikely
Info: Unrestricted Free Agent Next Offseason, Unlikely to be Franchised Tagged due to Positional Value & Uncertainty
The other guy, DeMarvion Overshown, is a genuine fan favorite, and it is easy to understand why.
Former Texas Longhorn, electric, high-energy player when healthy, true team leader. That all resonates with the Dallas faithful in a significant way, but it doesn’t change the facts around his situation, especially when it comes to health.
Overshown has had major struggles with staying on the field, and if he comes asking for a big bag in 2027 after more issues this year, Dallas will say no.
On the flip side, his elite potential could result in a huge year that, similarly to Pickens, prices Dallas out from extending him to a long-term deal. The addition of Jaishawn Barham in the draft adds another layer to it, as he should be able to replace Overshown next year.
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