2 Star Players Predicted To Leave Cowboys in 2027 Offseason

The Dallas Cowboys were able to keep all 11 starters on offense from their 2025 season and made several improvements on the defensive side of the ball. Their roster makeover is far from over, and the same goes for some of the tough decisions they'll have to make with pending free agents.

This offseason, wide receiver George Pickens and running back Javonte Williams were their biggest free agents and they kept Williams by locking him up to a three-year deal. As for Pickens, he was retained with a one-year franchise tag.

Pickens, who had 93 receptions for 1,429 yards and nine touchdowns in 2025, wants a long-term deal but there's no guarantee Dallas will give him one, especially with CeeDee Lamb playing on a deal worth $34 million annually.

George Pickens might not be on the Cowboys' roster in 2027

Dallas Cowboys wide receiver George Pickens reacts during the game against the Philadelphia Eagles. | Kevin Jairaj-Imagn Images

That's why Inside The Star's Mark Heaney believes Pickens won't return to the Cowboys in 2027. Heaney says there's a chance Dallas could use the tag once again, but in the end, he sees Pickens being dealt for draft compensation, which would require initially placing the tag on Pickens for the second year.

"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," Heaney wrote.

Cowboys On SI writer Mike Moraitis shared the same sentiment, saying he can see the Cowboys using the tag again in 2027. What he doesn't envision is Pickens accepting the tag, ultimately leading to his exit.

DeMarvion Overshown's return is also up in the air

Dallas Cowboys linebacker DeMarvion Overshown reacts after making a tackle against the Cincinnati Bengals. | Tim Heitman-Imagn Images

Pickens isn't the only player Heaney expects to leave in the offseason. He also said there's a chance that linebacker DeMarvion Overshown isn't given a new deal when his expires following the 2026 campaign.

Heaney cites injury concerns as a primary reason that Dallas will be hesitant to sign him to a long-term deal. He also states that the franchise tag is unlikely due to the lack of positional value at linebacker.

In addition to Overshown being a free agent, Dee Winters is in the final year of his contract as well. While not as flashy of a player, Winters has been much more durable and is coming off a breakout season. That could lead to an extension for Winters, especially if he proves to be a fit under defensive coordinator Christian Parker.

— Sign up for the Cowboys Daily Digest newsletter for more free coverage from Dallas Cowboys on SI —

Add us as a preferred source on Google