The Dak Prescott deal is done, but the Cowboys’ front office isn’t off the hook

The Cowboys broke the internet on Monday with the announcement that they had signed Dak Prescott to a four-year contract extension worth a total of $160 million, with a record amount of guaranteed money in the form of $126 million. It’s a moment that calls for plenty of celebration, both for the team locking down their franchise quarterback and for Prescott finally getting the big deal and long-term financial security.

So allow me to be the party pooper for a moment, because while it is objectively good news that the Cowboys got this deal done ahead of the franchise tag deadline, it should never have come this close to begin with. And while the next four years offer a lot of promise to the franchise because of Dak, the long-term outlook of this franchise is not bright if this trend continues.

And the word “trend” is appropriate to use here, because Prescott is not the first Cowboys player to be in such a position. First it was DeMarcus Lawrence, who put up a career year in 2017 with 14.5 sacks before his rookie deal expired. The Cowboys failed to come to a long-term deal and tagged him. Tank played the 2018 season on the tag, put up 10.5 sacks, and was once again tagged because the Cowboys were unwilling to pay top dollar to retain an edge rusher with consecutive double-digit sack seasons.

They waited a month to actually sign Lawrence a long-term contract, and only after the defensive end used his impending surgery as a bargaining chip. It was later revealed that Lawrence and his agent had more or less threatened to request a trade as part of the negotiation tactics because of how slow the Cowboys were moving their feet.

Next was Ezekiel Elliott, whose contract negotiations were much more memorable. That’s because Zeke was demanding an extension before his rookie deal even ended, and the running back even held out of training camp leading up to the 2019 season, going to Cabo to train in the meantime. The Cowboys, who had (in)famously refused to blink in their contract standoff with DeMarco Murray just a few years prior, didn’t want to overpay for their running back. But the pressure of the regular season became too much for Stephen Jones and his stingy approach to negotiations, and the Cowboys made Elliott the highest-paid running back in the NFL just four days before the start of the regular season.

The Dak saga was much more lengthy than the other two, and by now it’s well known that negotiations last year broke down because Prescott wanted a four-year deal - for the purpose of hitting the market sooner to cash in on a much larger salary cap - while the Cowboys insisted on doing no less than five years. Ultimately, neither side blinked and Dak played the 2020 season on the tag.

At the conclusion of the regular season, when Dallas was able to start negotiating with Prescott’s camp again, it took a while before phone calls were even dialed, and then no real news popped up until last week when NFL Network’s Jane Slater reported “good” talks between the two sides. However, Slater also added that it was “nothing meaningful.”

It seemed as if the Cowboys were barreling towards another tag for their quarterback due to Jones’ inability to strike a deal with the quarterback whose absence this past season largely contributed to a dismal 6-10 finish. Not only would that have added to the amount of money Dallas had to spend this season, but it would make it virtually impossible to prevent Dak from entering free agency next year.

And then came Monday, the day before the deadline to apply the tag, and Prescott ends up getting exactly what he wanted in a four-year deal. Just as they did with Lawrence and Elliott, Jones and the Cowboys played chicken for as long as they could before caving into the players’ demands.

And for what?

It’s ultimately a good thing that they locked up the guys they wanted to lock up, but the games they played to get there in each instance only made things much more complicated than they ever needed to be. All of this comes on the heels of Bryan Broaddus mentioning on GBAG Nation earlier on Monday that other NFL GM’s think very poorly of Jones and his handling of things in Dallas:

Here’s a quick piece of what Broaddus said:

“You know what, it’s funny, I’ve talked to people who used to, like, trust these guys for what they were doing... they don’t- nobody trusts these guys anymore. They actually think things will get worse.”

Broaddus goes on to essentially argue that the Cowboys, specifically Jones, wasted the years that Prescott was cheap (due to his rookie deal) by not being aggressive enough in building the team around him, as opposed to how other teams build around young quarterbacks.

And herein lies the problem: the decision maker at the top isn’t making the best decisions when they matter most. It’s why Dallas failed to reach the conference championship game while Dak was cheap, and it’s why they’ve dragged out contract negotiations with three star players before ultimately caving into their demands. That’s a problem that will loom large.

The Cowboys do have a lot of things working in their favor right now. Prescott will be there for at least the next four years, as well as several other really talented players. They’re led by a head coach who’s already won a Super Bowl in Green Bay, flanked by two coordinators who drew head coaching interest this past offseason and another who already won 43 games as a head coach and won a Super Bowl as a coordinator. And they have the tenth overall pick in the draft, a golden opportunity to add a really talented young player to this team.

But all of those positive things will wither away fast if the organization does get worse, as others around the league expect to happen. It’s a slippery slope, and one the Cowboys cannot afford to be on.