When the Dallas Cowboys acquired Steeler’s standout wide receiver George Pickens in a post-draft trade this past May, many wondered whether he’d be a rental or long-term investment. Playing on the last year of his four-year rookie deal, Pickens is scheduled to hit free agency in 2026, placing his future with the Cowboys very much in doubt.

After CeeDee Lamb and Pickens, the cupboards are fairly bare at the WR position in Dallas.  Theoretically they’d be justified signing Pickens to an extension since he fills a need in the short-term as well as the long-term. Then again, Lamb accounts for a significant portion of the salary cap already, playing on a $136 million deal he signed last August. Locking in another expensive WR one year later would push an abnormal proportion of payroll into the WR position and leave the roster pretty unbalanced as a result.

Advertisement

The other side of the argument is good teams don’t let good players leave, especially not after spending a third-round pick to acquire them. The Cincinnati Bengals may have disproportioned money dedicated to the quarterback and WR positions, but they know better than to let good players walk out the door. It’s not ideal roster construction but when is anything in the real world ideal? Besides, the value of having a dominant WR2 is severely underrated. Recent data indicates they’re one of the most important components of a successful postseason run.

The wild card in the entire debate is what kind of man Pickens will be in the locker room and on the field.

According to scouting reports Pickens had multiple behavioral incidents in college, contributing to his slide to the second round in 2022. He recorded more questionable incidents with the Steelers, ultimately leading to his dispatch to Dallas. The Cowboys are all too familiar with problematic players and probably aren’t very eager to get back in bed with one long-term. They have to decide if Pickens’ various incidents are behind him or a sign of more to come.

Advertisement

Both sides of the argument make valid points, making a “prove it” season the only responsible course of action in 2025. Dak Prescott will be by far the best passer he’s ever worked with, and Lamb will be by far the best WR cohort he’ll line up alongside. He’s due for a massive statistical season with the Cowboys in 2025 and could balloon his value on the open market as a result.

There’s a temptation to get out ahead of said breakout and re-sign him now, but with so many unknowns surrounding his character and so many wild cards existing on the Cowboys roster (e.g. DaRon Bland, Jake Ferguson, Trevon Diggs) things could look much different nine months from now.

If Pickens and the Cowboys don’t make a good match in 2025 the two parties are set for a clean break. Assuming Pickens maintains value, the Cowboys could be recipients of third oe fourth-round compensatory pick as a result. Pickens has a current market value of $25 million per season. Maybe the two sides are a match made in heaven and the Cowboys re-sign Pickens to be Lamb’s running mate long-term. That route may be more costly in contract value but it’s hard to blame them for due diligence. Heck, maybe Bland has another All-Pro season and cornerback and takes priority instead.

There are a number of ways this situation could unfold on the Cowboys roster so it’s wise that Dallas wants to see how the chips fall in 2025 before they place their bets long-term.

Advertisement

You can follow Reid on X @ReidDHanson and be sure to follow Cowboys Wire on Facebook to join in on the conversation with fellow fans!

This article originally appeared on Cowboys Wire: Cowboys wise to keep Pickens on expiring deal instead of extending