Dallas Cowboys quarterback Dak Prescott is coming off of what was undoubtedly the finest season of his eight-year NFL career.

The runner-up for league MVP, Prescott led the NFL in touchdown passes and QBR, was third in passing yards, and boasted the highest passer rating of his career.

Not to mention, it was Dak’s steady play that was the primary reason the Dallas Cowboys won 12 games for the third consecutive season.

And yet, we’ve most definitely arrived at a crucial pivot point within the relationship between Dak Prescott and the Dallas Cowboys.

With just one year left on his current deal, Dak Prescott is up for a contract extension that would likely make him one of the highest paid quarterbacks in NFL history.

Now common sense would seem to indicate that the Cowboys and their three-time Pro Bowl quarterback would be able to work toward an extension before the 2024 season began, preventing there from being any lingering tension due to the standstill or questions about commitments from either side.

But that’s not always how things work, especially when we’re dealing with a team that has yearly Super Bowl aspirations, and a quarterback who has proven he is unwilling to budge at the negotiating table.

Why Dak Prescott, Cowboys contract extension talks will be tricky

“We shouldn’t assume the Dallas Cowboys and quarterback Dak Prescott will agree on a contract extension before the start of the 2024 season,” according to ESPN NFL insiders Jeremy Fowler and Dan Graziano.

“There are multiple reasons, but the main one is Prescott has unprecedented contract leverage and a history of not conceding easily in contract talks.”

In 2021, the Cowboys briefly placed a franchise tag on Dak Prescott for the second consecutive season before giving Dak an expensive four-year, $160 million extension just one day later.

Within that deal, there’s a clause that prohibits Dallas from tagging Prescott again, and that could spell trouble for the Cowboys.

“Considering there’s a clause in his current deal that prohibits the team from using a franchise or transition tag on Prescott, it also means the quarterback doesn’t have to do a deal if he’s not completely happy with it,” per Fowler and Graziano.

“His worst case scenario is that he becomes a free agent next spring at age 31, which would be quite lucrative.”

Even though Dak Prescott’s postseason success has been limited to say the least, it’s hard to imagine him and the Cowboys going through a divorce.

Believe it or not, Dak Prescott has now started exactly as many games in a Cowboys uniform as Hall of Famer and two-time Super Bowl champion Roger Staubach did, and for what it’s worth, Staubach is the only Cowboys quarterback with over 100 starts that has a higher winning percentage than Dak Prescott.

Whether a historical nugget like that would play into the Cowboys decision is unclear, but what is clear is that very soon, Dak Prescott is going to be an even richer man than he already is, because if it’s not the Cowboys, some team will be more than willing to back up the Brinks truck for him in 2025.