The dust has firmly settled on the Dallas Cowboys trading for wide receiver George Pickens and it feels fair to say that we have all moved on to the point of excitement for what he can offer this football team.

Pickens will hopefully serve as a rising tide to lift the boats of CeeDee Lamb, Jake Ferguson, whoever the starting or most-used running back winds up being, and obviously of Dak Prescott. That he is only 24 years old, as of just two months ago, suggests that this can be the case for the foreseeable future as well.

This is likely part of the logic that led the Cowboys to calling the Pittsburgh Steelers and agreeing to give up their third-round pick (in terms of the major asset spent). It stands to reason that the Cowboys made the move with the assumption that they and Pickens would be working together for a long time.

So they should pay him now.

The Cowboys should give George Pickens an extension now

One of the cons, if you will, to spending a third-round pick on Pickens is that 2025 is the final year of his rookie contract. You are giving away a top 100 selection for a player who, if he is in fact going to be around past this season, you now have to pay top dollar for.

This is a conundrum that would exist for any NFL team to be clear, but it isn’t picking on the Cowboys to say that they have handled this exact type of situation poorly in recent history. Look at CeeDee Lamb, Dak Prescott (multiple times), Micah Parsons currently or anybody else who you want to name as examples. Proactivity is not something that Dallas prioritizes relative to contract extensions for their players.

When we have conversations around those types of things the word leverage often comes up. Players obtain more leverage against the Cowboys because the team allows them to get so close to free agency and the players can then weaponize that in the name of getting the best deal possible for them. Tale as old as time.

Examining the spirit of leverage when it comes to George Pickens, the Cowboys have already given him and his representation a lot. They spent a third-round pick to get him as he enters a contract year, which as we spent some time discussing up top, suggests that they have no plans of him leaving elsewhere. So why not nip that in the bud right now?

From a logistical standpoint the Pickens trade has reminded me, and many others, of the Philadelphia Eagles acquiring A.J. Brown when the 2021 NFL Draft began. Philly spent a first-rounder to land Brown and clearly the move has worked out for them. But what is notable about that whole sequence is that the first thing the Eagles did was give Brown an extension to tie him to their organization for the future. They did this before he ever played a down for them. Why? Because you don’t trade a premium pick for someone who you don’t plan on being around and the earlier you pay, the better the rate you get.

Is there a situation that you can conceive where all of these things come to pass?

• Pickens has an exceptional season for the Cowboys
• The team has incredible success, largely because of this
• He signs a deal with the team in the offseason (weeks before entering the open market) that is beneficial to the team from a financial standpoint

The answer to the question is no. These things cannot coexist with one another. If the first two things happen, which is our collective hope by the way, then the team will be kicking themselves for not getting ahead of the curve on an extension (another tale as old as time).

For context, I would not have made the Pickens trade but am obviously rooting for it to succeed. Given that the trade is complete, the immediate thought was that an extension makes sense. Not getting it done feels like wandering down the same path that we have been yelling at the front office to avoid. When sharing those thoughts, one popular response is that Dallas could get a third-round compensatory pick for Pickens if he walks so an extension isn’t anything to worry about.

While this is certainly possible in a literal sense, it is important to also contextualize that possibility. In order for Dallas to get a third-round comp pick for Pickens the following things would all have to (generally speaking) happen as well.

• Pickens would have to play moderately to very well
• Dallas would have to let him walk in free agency
• Team X would have to pay him something substantial (which would suggest he did in fact play very well)
• The Cowboys would have to sit idly by in free agency (which we don’t want)

Even if all of these things happened, the comp pick in question would not come until 2027. By that point in time the Cowboys could have benefited from another season of Pickens’ play if it is to the level that we are all hoping and predicting. This feels like a mirage of a carrot.

Ultimately this all comes down to whether or not the Cowboys believe Pickens to be a player worth having around at a serious price. They have already signaled that to a serious degree by trading for him with the price they paid on top of the contract situation he is currently in.