The Cowboys have a rough start to 2020 legal tampering/free agency

As soon as the 2019 regular season ended and it was official that the Cowboys weren’t going to the playoffs, a countdown began for a long list of talented players whose contracts were set to expire. Of course, that process was delayed a bit by the team’s search for a head coach and the subsequent time that Mike McCarthy took to build a new coaching staff.

Everyone knew that the Cowboys had three big names on their list: Dak Prescott, Amari Cooper, and Byron Jones. With lots of cap space, they had the ability to extend all three of them. However, Jerry and Stephen Jones seemingly had a stronger desire to retain a few other key pieces - such as Blake Jarwin, Jamize Olawale, and potentially Robert Quinn and Maliek Collins - and that desire convinced them that Dallas could only keep two of their top three impending free agents. While they haven’t outright said this, the general lack of enthusiasm they’ve expressed over Jones - usually coupled with platitudes about having to be careful with how the teams doles out money - suggests it may have been their thought process.

There was never any question that Prescott, coming off an insanely good year, was the top priority. And the steep price the team paid to get Cooper, as well as the production he’s put up in his year and a half in town, ensured he was the second priority. That, along with the new coaching staff’s very open desire for ball hawks in the secondary, pretty much sealed Jones’ fate.

There are some very legitimate arguments to be made that the Cowboys should still have prioritized re-signing Jones as well, but at the very least the team had a fairly clear and well thought out process for deciding against such a move. But at that point, it became imperative that the team get both Prescott and Cooper locked up ASAP.

It was the perfect time to throw a big bag of money at both players, too. Patrick Mahomes is entering the fourth year of his rookie contract, and although the Chiefs have a fifth-year option for him, they’re expected to ink a deal before that anyway; and after winning an MVP in 2018 and a Super Bowl in 2019, there’s no doubt that Mahomes’ deal will drastically reset the market, rendering any deal done beforehand (including a Prescott deal) as a bargain in hindsight.

At the receiver position, the league is going to see new contracts paid out to top stars like Keenan Allen, TY Hilton, and Allen Robinson very soon, all of whom have contracts expiring after the 2020 season. Additionally, the Bengals’ decision to franchise tag AJ Green kicked his can down the road to the 2021 offseason as well. In short, any deal that Cooper signs now will be smaller in comparison to the deals those four sign just one year from now.

Yet the biggest factor that made all of this so perfect for the Cowboys was the expiration of the old collective bargaining agreement (CBA) and relatively quick approval of the new CBA. There’s a whole lot of complex, moving parts in the CBA but in short it’s leading to an overall bump in money for all players, and with a rising salary cap it gives teams more flexibility to move money around. So getting a deal done now under the restrictions of the current cap is significantly more advantageous for a team.

However, much like they did at so many points throughout the 2019 regular season, the Cowboys failed to take advantage of the opportunity staring them in the face.

So now the Cowboys have been forced to tag Prescott and Cooper is hitting legal tampering/free agency without a deal, where other teams will be able to court him and drive his asking price up even more. It’s still expected that Cooper will stick around, but the receiver has gained even more leverage than he already had.

Oh, and the Cowboys still haven’t made any progress on their other free agents, save for Olawale and Jarwin. Collins, Anthony Brown, Randall Cobb, Jason Witten, Michael Bennett, Jeff Heath, and of course Jones are all officially on the open market. Quinn is also getting interest. But at least the team is working on an extension for Sean Lee, right?

There’s obviously still a lot of time for the Cowboys to retain old talent and add new talent, but their bungling of things to start out has put them in a hole they dug themselves. And that’s rarely a good way to start off the offseason, especially in such a pivotal year as the team is in with a head coaching change.