Per ESPN's Ed Werder, reported Prescott is seeking a four-year deal and anything else is a "non-starter" in negotiations with the Cowboys.
The Cowboys have traditionally given their own players substantial long-term deals. Demarcus Lawrence, Ezekiel Elliott, Amari Cooper, Tyron Smith, Zack Martin, Jaylon Smith and La'El Collins have all signed extensions of at least five years since 2014.
Starting quarterbacks have taken to signing shorter deals recently. Last year, for instance, Russell Wilson, Carson Wentz and Jared Goff all signed four-year extensions with their respective teams.
In March, ESPN's Jeremy Fowler and Dan Graziano reported Prescott might prefer a shorter deal so he can become a free agent while still in his prime. The two-time Pro Bowler would hit the market at the age of 30 in 2024 if he gets a four-year extension from Dallas.
One potential financial component to agreeing a short-term deal is the NFL's television contracts. John Ourand of the Sports Business Journal has reported the league hopes to sign new rights deals this year, with its current contracts with CBS, FOX and NBC set to expire after 2022; ESPN's deal for Monday Night Football expires after 2021.
If the NFL's new TV rights deals increase from their current value—$5 billion annually—the salary cap will likely increase exponentially as soon as 2022.
Prescott seems to be in a position of leverage with the Cowboys because he already has $31.4 million guaranteed in 2020 if he plays on the franchise tag. He is coming off the best season of his career with 4,902 yards, 30 touchdowns, 11 interceptions and a 65.1 completion percentage.