The Dallas Cowboys are living on the edge when it comes to a contract extension for quarterback Dak Prescott, which could either pay off big or come back to bite them in a way that haunts the franchise for years.
Spotrac projects Prescott’s market value at $55.1 million annually over a four-year deal, which would equate to $220.4 million total. That would be the richest agreement in NFL history for any player at any position.
However, Bleacher Report’s NFL Scouting Department doesn’t believe he’s going to get that from the Cowboys — or anyone else. B/R projected on Sunday, September 1, that Prescott will ultimately ink a four-year contract ahead of the 2025 campaign for a total of $209 million.

That said, the scouting department immediately couched its projection by noting that a big year for Prescott in 2024 and unrestricted free agency to follow could easily combine to earn him more than not just $209 million, but also the $220 million-plus that would make him the most financially valued football player of all time.
“Prescott is a high-level quarterback in a league that doesn’t even have enough average ones, and multiple teams will be interested,” B/R wrote. “The next-man-up nature of contracts and the supply-and-demand nature of free agency could have [Prescott] earning much more than [$220.4 million] with another strong season.”

Cowboys owner Jerry Jones has been open with the media about a lack of urgency on the part of the franchise to get a deal done with Prescott, seemingly balking at the notion of making him the NFL’s richest player after so many playoff letdowns in recent years.
“We don’t need to get this done before the season,” Jones said in August. “Because it’s in all of our interest, Dak and everybody, to have a great season. And as a matter of fact, that’s probably not realistic to think before the season. But my thought sitting right here is we’ll have Dak [as the long-term QBJ. But all I’m gonna say is this — it’s not done yet.”