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20 Questions: Who Cashes In First?


(Football season is finally approaching. After a long offseason, the Cowboys are set to depart for training camp on July 25. During this final month before they begin practice in Oxnard, Calif., the staff of is going to preview the 20 biggest questions facing the Cowboys heading into 2019.)

FRISCO, Texas – We might as well get this one out of the way early.

The Cowboys' 2018 season ended five months ago, and it feels like we've been talking about contracts ever since.

It started with the breathless speculation about DeMarcus Lawrence, as the front office franchise tagged him and needed a couple months to sign him to a massive extension. When Lawrence eventually got his $105 million deal in April, all eyes turned toward Dak Prescott and Amari Cooper.

That's still where things stand today. The Cowboys' starting quarterback and No. 1 receiver are both heading into contract years, and they're both due for big-time pay days. Both players are finishing out their rookie deals, although those figures couldn't be more different. Play time incentives boosted Prescott's salary to $2 million for the 2019 season, but that still pales in comparison to Cooper's fifth-year option, which is slated to pay him $13.9 million this year.

Suffice to say that both players need new deals, and as of right now it's anyone's guess who gets done first. Today, the staff of will make their best case for who is the team's biggest priority.

David Helman: I understand the Cowboys can save more money by getting Cooper done, but at this point in the offseason, what are those savings really doing for you? I'd much rather figure things out with Dak. This is the biggest deal you'll pay out for the foreseeable future, and it centers around the most important position on the team. I'm fascinated by how the Cowboys will structure their deal with Dak, and how much it will eventually affect their cap. On top of that, they run the risk of future quarterback deals altering the market once again. Cooper's deal needs to get done, but Prescott's will set the tone for where things move over the next few seasons. I think it would be huge if the Cowboys could get this deal done before the start of the regular season.

Rob Phillips: Since we're talking about big-time money, even by professional football standards – "life-changing money," as Dak Prescott said in May – it's tough to predict a timeline for completing Prescott's future new deal. These contract talks are always complex and extensive. But the Cowboys want him here long term. Prescott wants to be here long term, as his post-minicamp Stetson hat suggests. And, since several starting quarterbacks around the league have gotten new deals this offseason, there would seem to be a clearer financial range on which to negotiate. That's why I'll guess Prescott gets done first, if in fact both sides can find common ground in the coming weeks.

Mickey Spagnola: To me, from a salary cap standpoint, signing wide receiver Amari Cooper next makes the most dollars and sense. Cooper is in the final year of his contract since the Raiders picked up his fifth-year option at $13.9 million before trading him to the Cowboys last year at mid-season. And by signing Cooper to a long-term deal with a signing bonus and guaranteed money, the Cowboys will be able to prorate the bonus over the life of the contract. By doing so, likely will reduce his $13.9 million cap hit in 2019, probably saving the Cowboys upwards of $5 to $7 million for this year, just the way they saved nearly $9 million against the cap when re-signing the initially franchised DeMarcus Lawrence to his long-term deal. If the Cowboys should sign either Dak Prescott or Ezekiel Elliott to extensions now – still having two years of control on each – their somewhat modest cap charges for this year would increase significantly. Coooop first.

Bryan Broaddus: I want to believe it's going to be Dak Prescott, but it doesn't appear that anyone from the player's side is really interested in getting anything done at this time. I am not saying the organization or the agents aren't talking, but hammering out a deal at this time is really just a waiting game for all parties involved. Maybe as we get closer to camp those involved will pick up the conversations and we will have an announcement a day or two before we leave for Oxnard.

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