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Evaluating Dak, Part III: How the Cowboys should handle Dak Prescott and his high-priced contract

Today, we conclude our three-part series by suggesting how the organization should handle their star quarterback.

NFL: Chicago Bears at Dallas Cowboys Tim Heitman-USA TODAY Sports

Ride or Die.

That’s the mindset fans of the Dallas Cowboys need to have when thinking about their franchise quarterback, Dak Prescott. We understand not everyone shares that same sentiment, and that is why we’ve tried to bring some of those fans closer together. Earlier this week, we attempted to get a better feel for how good Dak is and then we followed it up by examining potential issues that could be making things a little harder for him. Today, we’re going to put a bow on this by suggesting how the front office should handle the Prescott situation.

The Cowboys have a couple of different options here, however, one of them is not moving away from him. We’ve already discussed how he is one of the better quarterbacks in the league, so going in another direction wouldn’t make sense. But even if you are not convinced, there is one element that drives a nail in the narrative that Prescott isn’t going anywhere, and that’s his contract.

Prescott signed a four-year, $160 million deal two offseasons ago. $126 million of that is guaranteed. The Cowboys have only accounted for $37 million of that guaranteed money thus far, meaning Prescott is going to take up some considerable cap space over the next few years. Cutting Dak would cost them nearly $90 million in dead money and trading him would cost $58 million in dead money. Clearly, neither of those things will happen.

Dak is now halfway through his deal, but with back-loading and a couple of restructures already, the Cowboys are looking at a Dak cap hit of $49 million in 2023 and $52 million in 2024. Here are the details of his contract courtesy of

Realistically, the Cowboys can do one of two things. They can either let his contract play out and re-evaluate things in 2025. Or, they could be proactive and sign him to an extension. It might seem odd to think about throwing even more money at Dak after coming off a season where he led the league in interceptions, but we’re operating under the assumption that he’s our ride-or-die. Even when things weren’t great, he still finished as a fringe top-10 quarterback based on the metrics we showed in Part I of this series. If he’s that good, then the Cowboys can justify paying a high price for his services.

Additionally, a contract extension would lower his cap hit for the 2023 season. The Cowboys have operated with previous cap hits of $17.2 million (8.2% of the cap) in 2021 and $19.2 million (9%) in 2022. He is currently set to take a cap hit of $49.1 million (21.4%) of the team’s cap space. The front office would prefer to have more cap space available to help shore up other positions on the roster, and one way to accomplish this would be to add more years to Prescott’s deal. In doing so, Dak would receive more guaranteed money, including a bag of cash in the form of a signing bonus, but they could also redistribute some of his 2023 base salary.

Of course, for that to happen, Prescott and his representation would have to agree. When they came to terms originally in 2021, they fought over the length of terms. Team Prescott bet on themselves looking to cash in on an even bigger deal when his four-year deal expired in 2025. Do they still feel this confident after a slightly down year?

For the Cowboys, this could be a great time to react as Prescott’s stock has dipped. It could accomplish three things, free up cap space now, lock down the quarterback they want even longer and possibly get a better price than they would get if they waited. The Cowboys are going to let it ride with Dak, so why not tweak the financials and use some extra resources to make things even easier on Prescott?

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