March 9, 2021
BY Lance Cartelli

Winners and Losers from Dak Prescott's $164M Contract Extension With Cowboys

The Cowboys have finally signed their franchise quarterback to a big-money contract. 

Dak Prescott agreed to a four-year contract worth up to $164 million Monday. And with a deal that massive, there are bound to be some big winners and losers. 

Prescott is a huge winner, of course, but what about Jerry Jones, Russell Wilson and Josh Allen? 

Winner: Dak Prescott

Let’s get the obvious one out of the way. Of course the guy who had all the leverage in the world and will pocket $75 million in the first 12 months of his deal is the winner. 

Prescott gets to remain on America’s Team that is full of offensive weapons in the passing game and on the ground. 

But let’s dig even deeper. This is almost like a lifetime deal for Prescott. While he’ll be able to hit the free-agent market when he’s 31 and potentially leave town, Dak remains the starting QB for the most popular franchise in the league. That helps his visibility and marketability while also setting him up to be a highly coveted color commentator waaay down the line. Past Cowboys quarterbacks Troy Aikman and Tony Romo have laid the groundwork for every successful Dallas signal-caller to have a lucrative job for life.  

Loser: NFC East Teams 

Following Prescott’s devastating leg injury last season, the Eagles, Giants and Football Team all got a taste of life without Dak and it had to taste pretty good. 

But now with Dak under contract for the next four seasons, those NFC East teams will have to deal with one of the best and most efficient passers in the league. It doesn’t help that all three teams in the NFC East have some level of uncertainty at quarterback. 

Now, will the Cowboys be able to capitalize on an extremely winnable division? They couldn’t last year. 

Winner: The Cowboys 

Here’s another obvious winner. The Cowboys ultimately played this whole negotiation terribly over the years, but they still won because they locked up Prescott for at least four years when losing him after this season was a likely scenario. 

Look, they could have locked up Prescott on a much more team-friendly deal, but even at $164 million over four years, that’s a bargain for the ‘Boys. By the time Prescott is renegotiating his deal in three seasons, his deal could look like a bargain. With the salary cap set to explode in the future due to new TV deals, Prescott might not even be a top-five paid passer in a year. 

The Cowboys paid more than they wanted to, but they ultimately got the deal done. Their negotiating, however, left a lot to be desired...

Loser: The Joneses negotiating tactics 

While the Cowboys should be praised for the result of finally signing Prescott to a long-term pact, their process was absolutely terrible. 

Jerry and Stephen Jones have been lauded for their business acumen, but they completely read this situation wrong. And what’s even worse is that they had to have seen this coming as Washington dealt with a similar situation with Kirk Cousins

The Joneses who apparently studied “The Art of the Deal” before embarking on this horribly thought out negotiation saw that the price of quarterbacks only goes up and once a QB is signed, they almost become a bargain. 

As with Cousins, Washington wasn’t completely sold so they kept franchise tagging the player until his salary became unruly. That allowed Cousins to have all the leverage and cash-in on the free-agent market which is exactly the power Prescott was wielding, except he’s a much better player than Cousins. 

To be fair, the Cowboys were probably a little scared off by the Jared Goff and Carson Wentz debacles. But Dallas knew Prescott was their guy and still waited way too long to sign him and it cost them dearly. 

Winner: Betting on yourself 

Betting on yourself might sound like a silly slogan on a motivational poster but it could be a big factor in the future of NFL contract negotiations. 

The Cowboys weren’t the only ones who saw what Cousins did with his power. So did Dak. 

Prescott and his agents utilized Cousins’ playbook which essentially boiled down to betting on yourself. Dak knew that if he played on the franchise tag and maintained his strong play that his price is only going up — as always — and that the Cowboys were losing leverage by the minute. 

Even after a season-ending leg injury, Prescott knew and his representatives knew his value and that the Cowboys were backed against the wall. 

It’ll be interesting to see if other QBs bet on themselves to force the franchise’s hand and pay them even more money. 

Speaking of other QBs who are ready to cash in… 

Winner: Josh Allen, Lamar Jackson and Baker Mayfield

The 2018 QB draft class has emerged with a fresh crop of superstar quarterbacks who are about to secure the bag. And they’re probably pretty happy with Prescott’s pricey pact. 

Josh Allen, Lamar Jackson and Baker Mayfield all have cases to be paid similar — or even more — than what Prescott just got. 

The only question is, will they bet on themselves and force their team to franchise tag them? Or will they accept a more team-friendly deal like Patrick Mahomes did with the Chiefs

While those young signal-callers are looking like winners, there’s one QB who might be a loser in all of this. 

Loser: Russell Wilson 

On his odd media tour this offseason, Russell Wilson has made it pretty clear that his days in Seattle are numbered. 

While the ‘Hawks don’t want to deal him, and Wilson says he doesn’t want to be traded, the rumors aren’t going away. Heck, Wilson even put out the four teams he’d consider a trade to. 

And one of those squads was the Cowboys, which will have to be crossed off Wilson’s list now. 

Of course, the spotlight-hungry Wilson wanted to join America’s Team, but he’ll have to go back to the drawing board. Maybe the Bears will risk it all and trade for him? 

The Wilson trade rumors do give life to an online industry that took a big hit with Prescott’s new pact, though. 

Loser: Amateur Jersey Swap Graphic Designers 

Pour some out for the Dak Prescott jersey swaps. 

All of that energy designing the perfect jersey swap will have to shift to Wilson or perhaps Sam Darnold, to a lesser degree. That’s a big hit to an increasingly popular trend on social media. 

Loser: Free-Agent Market 

Unfortunately, this free-agent class is, ahem, not great. And now with Prescott signing a long-term contract, the No. 1 available player is off the board. 

With franchise tags being handed out, the players available on the market will be even thinner. However, Trent Williams, Kenny Golladay and Hunter Henry will all hit free agency. 

Winner: Cowboys' Fantasy Football Value

The Cowboys have arguably the best trio of receivers in the league in CeeDee Lamb, Amari Cooper and Michael Gallup. It’s tough for an offense to support multiple fantasy players in a passing game, but with Prescott’s high level of play — and the Cowboys’ lousy defense — it was possible to have multiple WR1s on an offense until Prescott went down with an injury. 

With Prescott back, the fantasy football values of those in the Cowboys’ passing game — along with Ezekiel Elliott and Tony Pollard — all skyrocket, especially in dynasty formats with Prescott signed for four seasons. 

The biggest winner has to be Lamb, though. He’s the eventual No. 1 receiver on the Cowboys' offense. And with the Cowboys paying so many players, it might be the last year Cooper is a Cowboy. So while Lamb might have to wait another year to fully explode, he could overtake Cooper this season as Dak’s favorite target.  

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Photo: Getty Images/Lines Illustration