Let's breakdown the Prescott-Cowboys contract situation: Dak Prescott, per insiders, is not budging on a contract worth $40+ million dollars per year — and by all accounts, Jerry Jones and the Dallas Cowboys front-office feel out of their comfort zone with offering Prescott a contract worth $33-$35 million dollars per year.
As of yesterday, insiders say that Dak Prescott's latest counter-offer consists of a whopping $42 million dollars per year, for 4-5 years. Now: Le'ts take $42 million dollars with a grain of salt. While we have a number to report, we do not, however, have any information beyond that number. We do not know the proposed guaranteed dollar amount. We do not know if certain potential contract incentives favor the team. We simply have one number at this point: $42 million per year. In August of last year, Dak Prescott turned down a contract offer from the Cowboys that would've paid him $30 million per year, per CBS. We also learned in August of last year, that Prescott first demanded $40 million dollars per year, per USA Today. Yesterday's news of $42 million per year shouldn't be seen as anything other than symbolic: Dak isn't budging. And Jerry Jones seems unwilling to go up in price — as he is already at his limit with Prescott — offering the Quarterback $33-$35 million dollars per year. How will this play out? Well, the Cowboys responded by signing a well known, and well-established Quarterback — Andy Dalton. If Prescott does decide to hold-out due to himself not receiving $40 million+ dollars per year to play, Prescott would be saying he is willing to gamble his football future on Andy Dalton not being able to lead the Cowboys to a winning season.
However, if Andy Dalton were to lead the Cowboys to success, perhaps even to the playoffs... well, Prescott's price, of course, at that point, would be so deteriorated, the Cowboys would likely offer Prescott a much lower contract than previously proposed, and Prescott would then be likely to hit the free-agent market looking for a desperate team to over-pay him. Again, assuming he, A: Holds-out. B: Andy Dalton actually wins games and makes things spicy throughout the season (Jerry loves spicy.)
But will Dak hold-out? Per Mike Florio, the likelihood of Prescott holding out is "high."