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While the NFL season is still several months away, Dak Prescott and the Dallas Cowboys have had no problem making headlines. Despite the quarterback’s strong statistical campaign, he and Jerry Jones haven’t been able to hammer out a new contract. Dak, however, has one Cowboys legend in his corner.

Darren Woodson was a member of the Dallas Cowboys dynasty in the 1990s, so he knows a thing or two about success. Not only does the former safety believe that Dak Prescott will get a new contract, but he thinks the quarterback has put in the work behind the scenes to earn it.

Dak Prescott and the Dallas Cowboys are stuck in a stalemate

During the 2020 NFL offseason, plenty of quarterbacks received new contracts. While the Dallas Cowboys signed Andy Dalton to a deal, they’re still locked in negotiations with Dak Prescott.

Despite Troy Aikman’s warnings, the Cowboys slapped their franchise tag on Prescott in March. While that one-year deal would provide the quarterback with a nice payday, he hasn’t signed it; understandably, he’s looking for a longterm deal with an elite salary.

As far as we can tell, though, the sticking point in negotiations seems to be the term, rather than salary. Shortly after the Cowboys decided to use their franchise tag, Chris Mortensen reported the club wanted to ink Dak Prescott to a five-year deal that would pay him more than Jared Goff and Carson Wentz. The quarterback, however, wanted a four-year contract, which would give him a better opportunity for another big payday.

While that doesn’t sound like a major disagreement, things have been stuck in limbo for roughly two months. Both parties have until July 15 to finalize an extension; as of now, it seems like they’ll use up most of that time.

Darren Woodson has plenty of praise for Dak Prescott

With Dak Prescott still unsigned, seemingly everyone in the football world has weighed in on the Cowboys quarterback situation. Former Dallas safety Darren Woodson recently entered the fray, predicting that a deal would get eventually get done.

“I think a deal gets done,” Woodson explained on The Pat McAfee Show. “I do. I really do. And if you talk to the Jones family… Stephen and Charlotte Jones, and even Jerry, they’ll tell you how in love they are with this young man.”

Woodson went on to explain that the love wasn’t entirely motivated by stats or Prescott’s numbers on Sunday. While those factors are important, Dak has done the extra work to earn a new contract.

“I’ve seen Dak, looking out my window, in June with the fifth guy, one of the special teams players, who’s running routes,” Woodson continued. “Out there by himself at two o’clock in the afternoon. He’d already done his early morning workout, comes back out, throws balls, and you just see this guy. His work ethic is tremendous. His leadership skills within the locker room… he came in his rookie year, and they called him a leader. You’ve seen this guy continue to grow and mature as a player, and the Jones family definitely respects it.”

Will the Dallas Cowboys work out a deal by July 15?

Given Jerry Jones’ track record, it’s easy to imagine the Dallas Cowboys and Dak Prescott failing to come to an understanding. As Darren Woodson suggested, though, cooler heads should eventually prevail.

For all of Jones’ flaws, he (theoretically) wants to win a Super Bowl to prove he’s the smartest guy in the room; while Andy Dalton might be a capable replacement, it’s hard to imagine him giving the Cowboys a better chance of success than Prescott would. Similarly, Dak probably won’t want to walk away from a massive contract extension due to a one-year difference. While he does have a few options, like holding out for an entire season or signing his franchise tag and hoping to hit free agency next spring, neither of those are without risks.

While we have plenty of examples of sports owners and executives making poor decisions, it’s not a forgone conclusion that Jerry Jones will completely botch Dak Prescott’s contract extension. Things haven’t gotten off to a great start, but there’s still time for everyone to come to their senses and hash out a deal.


Dak Prescott Has Earned Less Than $125,000 per Win With the Dallas Cowboys