‘Remaining Issues’ Exposed in Dak Prescott, Cowboys Contract Situation

Dak Prescott

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Round and round we go, where the Dak Prescott saga stops nobody knows. But ESPN’s Jeremy Fowler has an idea why the Dallas Cowboys can’t get off the hypothetical ride.

Appearing on Monday’s edition of SportsCenter, Fowler reiterated that length and structure — not necessarily total value — are the biggest hurdles to clear before Prescott and the Cowboys reach an agreement.

“Here are the remaining issues, as I understand them. It’s not simply about Dak Prescott being one of the highest-paid players on a per-year average, it’s about the guaranteed money. It’s about how much money he’s going to get in his first two years and it’s largely about how long the contract is going to be,” Fowler said, via Bleacher Report.

“The Cowboys love to typically do long-term deals, five, six, seven years,” he added. “Prescott, from my understanding, does not want to be beholden to a long-term deal when he wants to get back to the negotiating table at some point.”

While this update is technically the latest in ongoing talks, which began all the way back in September, it’s nothing that hasn’t already been leaked. Fowler and his ESPN colleague, NFL insider Dan Graziano, reported on March 2 that Prescott prefers a short-term deal, culminating in a massive windfall now and an opportunity to re-test the market later, before the 26-year-old turns 30.

“One source suggested that Prescott might prefer to do a shorter-term deal than the traditional long Cowboys deal that allows them to keep restructuring for cap relief. If Prescott signed a Kirk Cousins-style three-year deal, for example, he’d hit free agency again at age 29. Prescott might also be waiting to see whether the Texans extend Deshaun Watson this offseason, and then he could work off of that deal if it establishes new quarterback standards.”

Even that wasn’t the first time a band-aid contract was proposed. NFL Network’s Ian Rapoport reported on Sept. 15 that Prescott was “holding out” for a shorter, lucrative pact rather than the extended-years megadeal some of his teammates had received.

“My understanding is these Dak Prescott extension talks which Jerry Jones termed imminent just a week ago have reached a little bit of an impasse,” he said, per NFL.com. “It doesn’t seem like things will happen for the foreseeable future. Obviously that could change but that is the read right now. …

“The Cowboys have signed a lot of their key players to really long-term deals. Zeke Elliott the latest all their offensive lineman are on long long-term deals. But then look at the recent deals quarterbacks have done. Four-year extension for [Rams QB] Jared Goff. Four-year extension for [Eagles QB] Carson Wentz. It would make a lot of sense if Dak is holding out for some of those shorter term deals to cash in at a sooner time.”

No matter how they slice it, Prescott’s new deal assuredly will make him one of, if not the highest-paid player in league history, Rapoport reported last week, claiming the two-time Pro Bowler — who rejected an offer last season which would have paid out $33 million annually and included $105 million in guarantees — is “actively” negotiating with the team regarding a “big-money, long-term extension.”

The Cowboys reportedly have floated two offers to Prescott’s superagent, CAA’s Todd France, once during the 2019 campaign and once following last month’s NFL Scouting Combine. The second offer supposedly was in the $33.5 million-per-year range, likely eclipsing Los Angeles Rams QB Jared Goff, who received an NFL-record $110 million guaranteed.

Dallas applied the exclusive franchise tag to Prescott on March 16. The tag, which prohibits him from speaking with outside teams, is valued at approximately $28.7 million for 2020. If it’s signed, he’d earn the most money in a single season by any player in franchise history.

As it stands, the team has until July 15 to ink Prescott to a multi-year deal.

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Cowboys Expert Says Team Will ‘Cave’ To Dak’s Demands

If the standoff between the Cowboys and Prescott could be reduced to a staring contest, the franchise is likely to blink first. This is the opinion of venerable SI.com reporter Mike Fisher, who predicted the Cowboys will “cave” to the signal-caller and his lofty contractual desire.

“I think we’re looking at $110 million guaranteed. I think we’re looking at $35 million average per year,” Fisher said Saturday. “The debate that’s left is, the Cowboys would like to have a longer-term commitment of five years. Dak Prescott and his side, [agent] Todd France of CAA, would like a shorter commitment.”

A report earlier this offseason revealed the 2016 fourth-round pick is pushing to surpass Seattle’s Russell Wilson, who’s on the books for a league-high $35 million in average annual value. Wilson signed a four-year, $140 million ($107 million guaranteed) megadeal in April 2019.

Atlanta’s Matt Ryan is the sport’s richest signal-caller (and player) in terms of total value. Ryan landed $150 million and $94.5 million in fully guaranteed cash on a five-year contract — or $30 million per year.

“You can debate how good Dak Prescott is, but we know what the Cowboys think,” Fisher said. “We know they’ve gotten to $106 million guaranteed. [Owner] Jerry’s [Jones] point, and I’ll paraphrase is, ‘I wouldn’t commit $106 million to somebody if I wasn’t sure.’ So, the Cowboys’ commitment to him is very real.”

“I think, in the end, the Cowboys cave, for lack of a better word, and this ends up being a four-year deal, and Dak Prescott is a long-term, face-of-the-franchise quarterback in Dallas,” he added.

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Follow Zack Kelberman on Twitter: @KelbermanNFL