Mystery finally revealed: What Cowboys have to gain by waiting to extend their star players

The front office of the Dallas Cowboys has continuously been under fire this offseason for their complacency when it comes to signing players. Not only did they do very little in free agency after losing several key players, but they have not re-signed critical players who have soon-to-be expiring contracts. This behavior has perplexed the fanbase as it doesn’t make sense what the organization is trying to do. Are they preparing to hit the reset button after the 2024 season or is there something else brewing that is just hard to make sense of?

The truth is, the Cowboys have a plan. There is no looming reset as the team intends to field a competitive team in 2024. This plan includes careful roster-building decisions and saving as much cap space as possible when working on new deals. This approach is easy to see when we repeatedly watch them allow their players to walk in free agency and rely on the draft to replenish them. However, it’s a little harder to wrap our minds around when the front office continues to drag their feet in re-signing their big-name players.

Over the last month, we have spent extensive time trying to understand what the front office is trying to do. We conducted a troubleshooting exercise revealing that the Cowboys have dug themselves into a huge financial hole because of past restructures. In the spirit of being thorough, we’ve explored whether or not the front office wants to keep the big three - Dak Prescott, CeeDee Lamb, and Micah Parsons. We’ve also explained how doing so is possible as long as it’s understood that sacrifices must be made. We have even gone as far as identifying specific players the Cowboys aren’t likely to retain and their strategy to replenish those vacated spots on the roster. Finally, we explained how waiting to extend players is not hurting their spending power even though a player's asking price goes up.

If you missed out on any of those topics, don’t fret. They are still available if you are interested. To recap...

The Cowboys have dug themselves a financial hole

The Cowboys want to keep their star players

Keeping their star players is possible as long as sacrifices are made

Waiting to re-sign their players is not hurting them financially

Today, we put a bow on this topic as we try to understand why Jerry and Stephen Jones are dragging their feet. Here are some reasons a little patience could end up helping them in the long run.

A small dip in price
This may be weird to understand, but no quarterback or wide receiver has reset the market this offseason. It may look as if Justin Jefferson is the most expensive wide receiver in the league or Trevor Lawrence costs as much as Joe Burrow (since they both signed a five-year, $275 million deal). However, none of these recent extensions have elevated the cost of these positions. In fact, they’ve brought them down. Allow us to explain.

Every quarterback signed this year is taking up less of a cap percentage than any of the quarterbacks signed a year ago. Additionally, while Justin Jefferson was very close to Tyreek Hill’s cost, several other wide receiver signings cost considerably less. Here is a helpful chart to compare recent deals to contracts from previous years (Prescott and Lamb’s projected costs are included for fun).

As mentioned before, higher average annual salaries don’t represent a player’s true cost to the team. This is very important to understand. Their true cost is the ratio of the total cost of their contract to the total budget (league salary cap) throughout their contract. This is shown as cap % in the column on the far right.

The Cowboys’ front office waited for these new deals to use them as a guideline of where their players should fall. It gives them some extra negotiating power. The front office will try to fit Dak somewhere between Lawrence and Burrow and likely land close to what Justin Herbert and Lamar Jackson are making, even though Prescott will end up with the highest average annual salary of anyone in the league.

Similarly, Lamb should fall somewhere between A.J. Brown and Justin Jefferson, even though his average annual salary will exceed that of Tyreek Hill. On the surface, it will look as if waiting costs the Cowboys more money, but it will have cost them a little less.

Put the pressure on the player/agent
For Prescott and Lamb, there was never a time when the Cowboys' front office could have landed a good bargain price for their services. League rules prohibit negotiating a new deal before the first three years of their rookie contract is up and by that time, Prescott and Lamb were already proven commodities in the NFL. And nothing’s changed. They remain costly expenditures.

The timing of a contract extension is very important to a player as they want to sign a new deal when their stock is high. Players must carefully weigh the pros/cons of signing now versus waiting. Dragging it out could land them more money later, but it also comes with more risk. There are a lot of circumstances that can affect a player's value, most notably being a severe injury. When faced with an opportunity to secure a large amount of money, it’s hard to pass it up. Players want to get a deal done. This explains why many will resort to holding out to force the front office’s hand.

We’ve heard the phrase “deadlines make deals” so much that we’re sick of it, but it’s said so often because it holds a lot of water. People talk so much about a player’s leverage but oftentimes overlook the leverage a front office has. Teams will use deadlines to put more pressure on players to get a deal done. That moves us nicely into the next factor.

A little compromise
It’s always about the money. The Cowboys are doing what they’re doing because they want to gain a favorable outcome. They hope they can work something in the contract language that will benefit them. One big driver is the length of terms. A longer deal will bring down the cap % because of the larger budget those later years provide. That was one of the conflicting points last time during Prescott’s deal as the Cowboys couldn’t get a five-year deal done and had to settle for four.

Another factor is guaranteed money. This is the meat of the deal and what most agents fight for. Less guaranteed money means greater roster flexibility allowing teams to get out of the contract early if needed. It’s unclear what the front office is looking for here, but negotiating some favorable conditions within the contract has been a staple of the Joneses and could serve them down the road.

A little extra time
In some cases, “waiting to see” is beneficial. We know the Cowboys want to see what they have in Trey Lance in training camp, but barring some incredible turnaround, it’s not likely to change how they value Prescott. At the same time, there’s no harm in waiting.

There’s nothing more to see with Lamb, but if he wants to hold out a little, fine. That just means extra reps for the guys who need them.

When it comes to Micah Parsons, this extra time could prove valuable. There is a lot of talk about how he’s viewed within the organization and some have questioned his commitment to the team. We’re not going to get into any of that here, but if the Cowboys are going to make a huge investment into a player, it helps that he’s someone they can count on. With another year left on his rookie deal + the fifth-year option + a possible franchise tag, there is absolutely no reason to be in a rush with him.

Conclusion
All of these factors come into play. Some are more significant than others. It’s easy to be lulled into this narrative that the Cowboys’ front office is inept, but that’s just emotion talking. As the saying goes, this isn’t their first rodeo, and there is enough evidence in the past to show they are pretty good at building a roster. It may not be the decisions we want and things may not happen when we want them to, but ultimately this front office has a plan and is handling things in the best way possible to carry out the plan.