Ranking Cowboys' Biggest Contract Dilemmas For 2027 Offseason After Joey Porter Jr Trade

The Dallas Cowboys swung a massive trade on Wednesday night and are now staring down the barrel of having yet another contract dilemma in 2027.

That trade is the acquisition of cornerback Joey Porter Jr., who was acquired from the Pittsburgh Steelers in exchange for a few draft picks.

While the expectation was that a contract extension would be part of any trade for Porter, who has been in a standoff with the Steelers, that turned out not to be the case.

Now, Porter is one of the biggest contract dilemmas the Cowboys are facing ahead of next offseason when it comes to players who are slated to be free agents.

But, is Porter the biggest? Find out now as we rank the top four.

4. Broderick Jones

Pittsburgh Steelers offensive tackle Broderick Jones. — Pittsburgh Steelers offensive tackle Broderick Jones (77) against the New York Jets during the fourth quarter at Acrisure Stadium. Mandatory Credit: Barry Reeger-Imagn Images | IMAGN IMAGES via Reuters Connect

The Cowboys didn't give up a ton for Jones, with Dallas sending third- and sixth-round picks and getting a fourth-rounder back. Still, the downgrade from a third to a fourth is not nothing.

If Terence Steele and Tyler Guyton avoid meltdowns and stay healthy, we might not see Jones play any significant snaps in 2026, which will make it more difficult to evaluate him before becoming a pending free agent in 2027.

That said, given the fact that Jones' stock is incredibly low, the Cowboys can keep him around for cheap as a backup tackle for another season, which makes Jones a low-risk investment as a backup tackle. That said, if that's all Jones ends up being, the Cowboys' trade for him will not be viewed fondly.

3. DeMarvion Overshown

Dallas Cowboys linebacker DeMarvion Overshown. — Dallas Cowboys linebacker DeMarvion Overshown (0) during the game against the Seattle Seahawks at Lumen Field. Mandatory Credit: Steven Bisig-Imagn Images | IMAGN IMAGES via Reuters Connect

Overshown showed a ton of promise early in his career, but serious injuries have derailed him significantly.

In a contract year, Overshown desperately needed to show he is no longer injury-prone and can play at a high level, but through three weeks, he hasn't shown either of those things.

Overshown didn't have a good game in Week 1, and he has missed each of the last two games due to a hamstring injury and doesn't seem likely to play in Week 4, either.

The clock is ticking and Overshown is running out of time to show he's worthy of a lucrative, long-term deal. He's still got time, but his latest injury might have already sealed his fate with Dallas, especially with Jaishawn Barham emerging.

2. George Pickens

Dallas Cowboys wide receiver George Pickens. — Dallas Cowboys wide receiver George Pickens (3) reacts against the Washington Commanders during the second half at AT&T Stadium. Mandatory Credit: Kevin Jairaj-Imagn Images | IMAGN IMAGES via Reuters Connect

Pickens was once far and away the biggest contract dilemma the Cowboys were set to face in 2027, but we believe Porter now takes that title (more on that shortly).

With Pickens, the Cowboys will get at least two full seasons out of him before he potentially departs in 2027, whether that be straight up via free agency or a tag-and-trade scenario. And, at least one of those seasons saw Pickens post elite production.

Adding to that, the Cowboys already have a locked-in No. 1 wide receiver in CeeDee Lamb, so Dallas can replace Pickens with a lesser talent and still be fine at the position, especially if Ryan Flournoy can ascend in 2026 like most expects him to.

1. Joey Porter Jr.

Pittsburgh Steelers cornerback Joey Porter Jr. watches warm-ups for a game against the Cincinnati Bengals at Acrisure Stadium. Mandatory Credit: Barry Reeger-Imagn Images | IMAGN IMAGES via Reuters Connect

The Cowboys didn't give up an obscene amount for Porter, with Dallas surrendering a second-round pick and a conditional sixth. However, the 2028 second-round pick is still a valuable one, so Dallas didn't exactly give up peanuts, either.

The problem here is that Dallas did not sign Porter to a contract extension, and it doesn't look like that's going to happen, which leaves the Cowboys in a position to have a holdout situation in 2027 if they tag the cornerback.

Porter has already shown a willingness to sit out if he doesn't get what he wants, and it's a safe bet he will do the same next year if Dallas tries to take the same route it did with Pickens.

Porter is going to be looking for top-of-the-market money if he plays well and we're not so sure he's worth it. Porter is good, but he isn't among the elite of the elite, so a top-of-the-market contract amounts to a risky bet.

It's very possible the Cowboys may only get 13 or 14 games out of Porter after giving up a valuable draft pick for him. Perhaps Dallas can get that pick back in a tag-and-trade, but the Cowboys will be running into the same situation Pittsburgh did in that teams won't want to give full value for the cornerback knowing he needs a contract extension.

Maybe everything works out, but right now there's a good chance the Cowboys could have some drama with Porter in 2027.]

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