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Dak Prescott’s extension with the Cowboys could lead to the most lucrative career in NFL history

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Yahoo Sports’ Senior NFL Writer Charles Robinson explains how Prescott’s new deal could help him earn more money over his career than anyone in the history of football. While Prescott is the big winner, his contract extension will also save the Cowboys over $15 Million per season on the salary cap.

Video Transcript

[CHEERING]

CHARLES ROBINSON: So after two years of sometimes contentious negotiations, the Dallas Cowboys and their quarterback Dak Prescott have finally come to a four-year $160 million contract extension with $126 million guaranteed for Prescott.

And what was really interesting about this negotiation-- and I had a chance to talk to a source on Monday morning who is sort of on the inside of this thing. And what he told me is, look, you've got two sides that are searching for a win here.

Both the Cowboys and Dak Prescott's camp were trying to figure out a way to engineer a deal where they could walk away from the table and say, we have something in our hands that we feel like is a value we gave up something at the negotiating table. But we also walked away with a W in our column.

And really, how that breaks down, if you look at the Dallas Cowboys, yes, you give $160 million, $40 million a year to Prescott. That is a massive windfall-- puts him in the echelon with Patrick Mahomes, the Kansas City Chiefs and Deshaun Watson of the Houston Texans.

But for the Cowboys, they sit there and they say, OK, well, his franchise tag number in 2021 in a difficult cap year was going to be $37.7 million. The way the deal is structured lowers his number to $22.2 million via two voidable years at the end of the deal that will spread out the massive signing bonus.

So the Cowboys say, hey, that's a win for us. That helps give us some salary cap relief in 2021 which is going to be needed with a slight cap rollback due to the pandemic. And then the Cowboys also say, hey, we tried to get a five-year deal done with Dak Prescott prior to the 2020 season. That didn't happen. We had to franchise tag him.

But the fact that we got him done at a four-year clip now, if you include the 2020 season, that one-year contract from the franchise tag, the Cowboys say, well, we got a five-year deal out of this, ultimately. We will have him under contract from 2020 to 2024, which is what we wanted last off-season.

Now, we'll pay a bit more. It's going to come down to about $191 to $194 million, depending on incentives over that five years. But for Jerry Jones, he says, look, it's a market-setting deal, $38 million.

That's what you give quarterbacks. We did it with Tony Romo. Now, we've done it with Dak Prescott. It shows our commitment. That's another win for us. We did get five years of control, ultimately, that we wanted last off-season.

Now, from Dak's side, the win's considerable, and the W's are all over the place. Not only does he jump into the $40 million per season echelon, but he does it at 27 years old. And that's significant because with this four-year contract and the fact that the Cowboys kicked in a second franchise tag in this deal, he is franchised on Tuesday morning.

That eliminates any more franchise tags in Dak Prescott's future, which means he will absolutely have control over where he goes if free agency ever comes into play again. It gives the Cowboys added motivation to continue going to the negotiating table early during the course of his career.

And signing it at 27 means he could essentially hit free agency at 31, which will give the Cowboys motivation to go back to the negotiating table after year three of this deal and prior to year four. That means that Dak Prescott could be negotiating a new contract at 30. It means he could negotiate the contract after that at 34 if he continues to go in four-year windows.

And if he's one of these quarterbacks who wants to play until he's 40, he can negotiate another contract at 38. That's three deals. And really, including this one, four deals between the age of 27 and 38. And that really could make Dak Prescott one of the highest paid players in NFL history if not the highest earning player in NFL history.

That is a huge win for Dak Prescott. And ultimately, this was someone who bet on himself. He could have signed a deal back in 2018 after the 2018 season when he had been a starter for three years.

The Cowboys might have gotten that done at 25 million then. They might have gotten a deal done at 35 million prior to the 2020 season. But they waited. They bet against Dak Prescott's market. And ultimately, he wins in a big way and a very financially lucrative way.