ARLINGTON, TX - AUGUST 26: Dak Prescott #4 of the Dallas Cowboys warms up before a preseason game against the Las Vegas Raiders at AT&T Stadium on August 26, 2023 in Arlington, Texas.
Photo by Ron Jenkins/Getty Images

What A Dak Prescott Extension Might Look Like, According to NFL Agents and Executives

Dallas Cowboys quarterback Dak Prescott is facing a big 2023 season, but another massive contract extension could be on the horizon.

If there was any notion that the Dallas Cowboys trade for quarterback Trey Lance was somehow an indictment on how the organization views Dak Prescott or his future, Jerry Jones was quick to put those thoughts to rest, while suggesting a Prescott extension could be in the offing.

"Those numbers on those contracts, those types of numbers, especially the big ones, you live with constantly, that's always on your mind. There's never a time when it goes away because you've got to make the entire thing fit," Jones said on 105.3 The Fan in Dallas. "So it's on the mind on a player decision in the middle of the year. So it's just a fundamental. We expect Dak to be with us a long time."

Prescott enters the 2023 season with two years remaining on his current contract, set to count $26.83 million against the cap this season before his cap number balloons to $59.45 million in 2024, which is certainly motivation for the Cowboys to get some sort of extension done.

Entering his eighth NFL season, Prescott led the Cowboys to just his second postseason win, as Dallas knocked off the Tampa Bay Buccaneers 31-14 before coming up short against the San Francisco 49ers in the NFC Divisional round back in January.

A career-66.6 percent passer with 166 passing touchdowns to 65 interceptions, any extension would be Prescott's third contract, after signing a four-year deal worth $160 million back in 2021. Sources both inside buildings around the NFL, and agents familiar with the quarterback market, disagree on what Prescott's next deal might look like.

"I'd have to think he'd at least have to be among the top-four highest-paid quarterbacks," a rival pro personnel director told FanBuzz. "Or else his agent probably wouldn't entertain even having the conversation at this point."

With Joe Burrow potentially in line to become the highest-paid quarterback in league history, the current average of the top-five quarterback contracts in the NFL is $297 million in total value and $48.7 million annually.

Under his current contract, Prescott is averaging $40 million annually, as the ninth-highest paid quarterback in the league. Would Jones and the Cowboys, knowing what they have seen to date in his career, make Prescott one of the highest-paid quarterbacks in league history?

Prescott turned 30 years old on July 29, so any extension the Cowboys would sign him to at this stage would need to be viewed at least partially through the lens of paying for his past production rather than projecting future upside. Especially when compared to the behemoth contracts signed this offseason by Justin Herbert, Jalen Hurts, and Lamar Jackson.

"I wouldn't be too concerned about his age," a former general manager currently in an NFC front office told FanBuzz. "But if it were me, we'd be offering a team-friendly deal with lots of incentives. His age might not be a worry, but the interceptions and turnovers are both really big deals."

Last season, Prescott tossed a league-high 15 interceptions, while appearing in only 12 games, and has thrown 40 interceptions over his past 49 starts dating back to 2019.

But, it sure sounds as though Jones does not share the executive's concerns about Prescott's turnovers, nor does it like the Cowboys would put off any contract talks until after the season, even if as a matter of precedent.

"Absolutely, absolutely, at any time," Jones said, explaining the Cowboys would continue negotiations during the season. "And it may be a better time for them to get to a point where they can make a decision. We all have — I know I do — have times that I get up and I feel like locking something down that may be a loose end, and if I get a chance to, well, I'll do it."

While Jones might be motivated to get a deal done as quickly as possible, one prominent agent tells FanBuzz that his approach would be to pump the brakes on any talks.

"I wouldn't even pick up the phone," the agent said, on the condition of anonymity to speak freely about a player he doesn't represent. "Those talks can happen after Burrow's deal and Patrick Mahomes' extension get done."

As the agent points out, Prescott would be the most coveted starting quarterback on the market next spring, if he makes it to free agency, and as a result the Cowboys have minimal leverage over any current negotiations.

But, the Cowboys have built a roster that is capable in the NFC of challenging the likes of the Philadelphia Eagles, San Francisco 49ers, and Detroit Lions for a berth in the Super Bowl, in large part because of Prescott's consistent regular season play since his arrival in 2016.

That consistency — and Prescott's age, is a big reason why a second agent, familiar with the quarterback market, would make a push for as much early money as the Cowboys would offer.

"I'd be more worried about front end cash flow than AAV," the agent explained. "If he plays to the value of the deal, you're ripping up the last year anyways. I'd try to frame it as a paper deal instead of new money and try to get as far above $200 million on a four-year deal as I can, that would be a 3 year extension. Dallas won't do that though. So to do a four-year extension, they would have to blow me away with cash in 2024 and 2025."

Jones and the Cowboys have already extended Trevon Diggs, Malik Hooker, and Terence Steele. But, the biggest extension of all, and the one most likely to determine Dallas' trajectory as a franchise, could be Prescott's, and could be coming soon.

MORE: "I Have the Obligation to Carry On Another Legacy.": Dak Prescott's Brother's Death Changed Everything