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Two deadlines, two different situations: Examining who has leverage in the Dak Prescott contract saga

With two different deadlines on the calendar, where does the leverage lie in the Dak contract negotiations?

New York Giants v Dallas Cowboys Photo by Tom Pennington/Getty Images

Here we sit a week past Valentine’s Day and Jerry Jones has yet to ask his beloved franchise quarterback Dak Prescott to “Be Mine.” The relationship between the owner of the Dallas Cowboys and his young quarterback continues to be burdened by the strain of unsuccessful contract negotiations that started 20 months ago. In fact, the two quarterbacks that did get monstrous extensions back then have since been dealt away by the team that extended him.

Even more odd is that it is Dak Prescott’s game that has been taken to the next level as he’s has been the league’s top passer (in terms of yards per game) since then.

And yet despite Prescott’s performance in that span, here we sit waiting for the Cowboys quarterback to be given a second contract. Without getting into another one of those “Dak’s not worth it” or it “takes two to tango” debates, everything you read below comes with the assertions that:

A. Dak’s worth it

B. The Cowboys front office intends to keep him

Any attempt to dance around this and suggest otherwise isn’t what we’re doing here as we’re really wanting to focus in on what the Cowboys could be looking at in the coming months. In particular, how do things change as we approach two important deadlines?

Who has the leverage leading up to the March 9th franchise tag deadline?

It would be the biggest curve ball in the history of curve balls if the Cowboys front office allowed Prescott to hit the open market this year in free agency. Nobody is expecting that to happen. So the Cowboys have two choices here - sign him before free agency begins or franchise tag him.

If they choose to tag him, the front office will be forced to string together some restructures so they’ll have enough cap room to fit his 2021 tag price of $37.7 million. This is not a huge issue for the front office, but the less money they have to move out into the future, the better.

Not only does the team need to make room for Dak, but they should be trying to open up some extra room for possible free agent signings. Many teams are facing abnormal challenges to get under a reduced cap this offseason, and this will likely lead to a more quality group of players who will become cap casualties. The Cowboys front office needs to be lurking on this list of cuts to see if they could benefit from signing one of these cap casualties.

For the purpose of having the needed cap room to fit Dak’s tag price and have money for free agents, the Cowboys should try to do everything they can to get a deal done before the deadline. This gives Prescott a tremendous amount of leverage over the next two weeks.

As of right now, the Cowboys have done no restructuring. And while all that can happen incredibly fast, even the presence of one restructure would at least create the idea that they are preparing to tag Prescott a second time. Don’t be surprised if the front office starts this process real soon as they continue to project their negotiating stubbornness by putting a bug in Team Dak’s ear that they are willing to drag this thing out even further.

Who has the leverage leading up to the July deadline?

We could talk about how the dynamic of this whole ordeal would get a huge shake up if the Cowboys ended up drafting a quarterback with the 10th overall pick in April’s draft, but remember, we are operating on the assumption that the Cowboys believe Dak is their quarterback. And nobody in their right mind would waste such expensive draft capital to exercise some type of bluff to get Dak thinking they are going a different direction. Not even showman Jerry would pull off that type of stunt. If Dallas did draft a quarterback, it would be because they have a new salary cap strategy and it doesn’t include a big portion of that pie being eaten up by a quarterback. But that seems preposterous, so we’re not going to venture down that rabbit hole.

Instead, let’s fast forward to near the July deadline when it’s do or die time. If Prescott ends up playing on the tag a second time, that’s a wrap for his time in Dallas. A third tag would be astronomically expensive and things would be so sour between the two sides as Prescott would once again put his long-term financial security at risk playing under a one-year deal. And yes, he would have a part in that decision, but it doesn’t take a psychiatrist to get inside the mind of Prescott to determine which side of the negotiating table failed to allow that to happen. A divorce would be inevitable.

But again, the picture we are painting doesn’t feature the team parting ways with him, so what’s really going to happen leading up to Dak signing right before the July deadline? The Cowboys paying through the nose is the answer to that question.

When the front office is faced with losing Prescott forever, paying him a gazillion dollars for tag #3, or finally caving to his demands - it shouldn’t be hard to figure out which door they choose. In short, the tremendous amount of leverage Dak has right now exponentially increases by the July deadline. That leads us to this final conclusion: