Despite on-field activities beginning, it is an off-field issue that is hanging over the Dallas Cowboys’ heads right now. They have yet to strike a deal on a Dak Prescott contract extension, and at this point, why would he try?
The superstar quarterback will hit free agency this offseason if they can’t come to terms on a new contract. Early in the offseason, it was a foregone conclusion that they’d extend him early.
Could Dak Prescott get a contract extension this offseason? It's definitely on the table.
Prescott: "100% I'm excited, to be a Dallas Cowboy. Always dreamed to be here. And now that I'm here, I don't expect to play for any other team." pic.twitter.com/m0LE2oFzlh
— Mike Leslie (@MikeLeslieWFAA) March 8, 2023
That never happened, nor did it get close, and now he has a unique opportunity in his hands if he wants it.
Prescott can hit the open market as one of the top quarterbacks in the NFL.
Very, very few players at his position and with his talent have had that chance in recent years.
The prospect of fielding offers from teams, creating a bidding war, and seeing all of his options could be a fascinating adventure for Prescott.
So, should he even consider signing an extension now with Dallas? Let’s talk about it.
The Case For Dak Prescott Entering Free Agency
Let’s not mince words here: a Dak Prescott contract in free agency, rather than now, would shatter every financial record the NFL has. Just look at the recent history of All-Pro level quarterbacks hitting the open market.
Kirk Cousins, at 35 years old, while recovering from an achilles tear, got a 4-year, $180M deal from the Atlanta Falcons.
If Prescott has a season similar to his last, he would enter free agency four years younger and much more productive.
Quarterback-needy teams like the Giants, Raiders, and Steelers would blow that Cousins deal out of the water for a chance at an MVP-caliber player like Dak Prescott.
.@RapSheet on if #Cowboys Dak Prescott hits free agency:
“People ask me how much money Dak would make in free agency—how high can you count?”
Eisen asks, “$60 million per?”
Rapoport: “In free agency next year? Higher. More. Always over. Over, over, over.”
(🎥: @RichEisenShow) pic.twitter.com/IzGMm7qHfb
— Brandon Loree (@Brandoniswrite) August 2, 2024
From a money perspective, it makes the most sense for Prescott to ignore a late push by the Cowboys right before the season. There is no doubt about that.
There could also be a bonus here for him in terms of just switching teams, however.
Let’s face it, dysfunction is the Cowboys middle name at this point, and shockingly, that does not result in significant on-field success.
Moving to a team with a football-focused front office and a clear motivation to win in the postseason could be an even bigger deal for Prescott than the additional financial compensation.
The Case For Extending Dak Prescott
All of those reasons for Dak Prescott to hit free agency are valid, but we also have to remember he is still negotiating with the organization, which means there are significant reasons for him to stay as well.
First off, we have contract security.
Why do players push for new deals as early and as frequently as they can? In large part, it’s because they don’t want to risk an injury that damages that future contract.
We saw that exact scenario play out in 2020 when Dak suffered that gruesome ankle injury after waiting to sign an extension with Dallas.
The business side of the NFL: The injury risk that Dak Prescott accepted when rejecting multi-year offers to play on the one-year franchise tag becomes an untimely reality. He was having a record-setting season.
— Ed Werder (@WerderEdESPN) October 11, 2020
Basically, with no contract extension for Dak Prescott before the season, he would once again be playing out the entirety of this season with a huge risk hanging over his head.
That is not a risk many players are willing to take.
With how it turned out last time, I have a hard time believing he wants to take that risk four years older and with more to lose.
Additionally, the guy just loves Dallas. You can question the playoff record, the lack of a championship, or whatever else you can conjure up, but you can’t knock his loyalty.
“I’m excited to be here and to never leave.”
– Dak Prescott says he wants to be a Cowboy for life.
— Andrew Siciliano (@AndrewSiciliano) March 10, 2021
Dak Prescott bleeds silver and blue, and has said on multiple occasions that he wants to be a Cowboy for life. I take him at his word there.
After all, this season and this contract dispute could be his last chance to cement himself as the greatest quarterback in franchise history. One ring and a new deal could give him that title.
He wants to play in Dallas, get paid a significant amount to do it, and win a championship. You have to respect that. The question now is, will those motivations outweigh the potential of a free agency frenzy?
