Jerry Jones’ $7 Million Gamble? New Report Suggests Cowboys Owner Had a Master Plan for Dak Prescott

In today’s NFL, elite quarterbacks are securing record-breaking contracts seemingly every few months. The financial arms race at the position has changed the way front offices approach negotiations—and at the center of it all stands America’s Team: the Dallas Cowboys.

Star quarterback Dak Prescott recently signed a massive four-year, $240 million contract extension. But it’s not the numbers that are raising eyebrows—it’s the timing. A growing number of analysts believe Cowboys owner Jerry Jones may have intentionally delayed the deal as part of a bigger plan. That hesitation, however, may have cost the team an estimated $7 million.

During a recent appearance on 105.3 The Fan, ESPN insider Adam Schefter commented on the situation, suggesting that Jones might have had a strategic reason for stalling.

“Maybe Jerry liked that everybody was talking about Dak Prescott all summer. Maybe he got $7 million worth of PR. That definitely could be the case,” Schefter said.

This theory adds an intriguing twist to what has been a long and complicated relationship between the Cowboys and their franchise quarterback. According to Schefter, the team had a chance to get the deal done much earlier—perhaps even in February—but chose not to initiate early negotiations. That decision surprised many in the league.

Meanwhile, the quarterback market continued to soar. Jared Goff signed a new deal with the Detroit Lions worth $52 million per year. Other QBs soon followed with similarly massive contracts. By the time Dallas circled back to Prescott’s camp, his value had climbed to $60 million annually.

Had the Cowboys acted earlier—closer to when Goff signed—they likely could’ve locked Prescott in for around $52–$53 million per year. Waiting until September cost them an estimated $7 million more in average annual value.

And yet, Jones might have felt the delay served another purpose: keeping Prescott—and the Cowboys—front and center in offseason headlines. After all, the buzz around Prescott’s extension dominated NFL news cycles, possibly delivering significant media exposure and fan engagement.

When the deal finally came together on September 8, it made a splash. The Cowboys and Prescott agreed to a four-year, $240 million extension, making him the highest-paid player in NFL history at the time of signing. Even more notable was the $231 million in guaranteed money—surpassing Deshaun Watson’s fully guaranteed $230 million deal with the Browns.

The extension ensures that Prescott will remain in a Cowboys uniform through the 2028 season and provides some long-term stability for Dallas at the league’s most important position. However, critics argue that the team’s reluctance to negotiate earlier led to a higher price tag—one they could’ve avoided.

Whether or not Jerry Jones had a calculated plan, or simply waited too long, remains a matter of speculation. But one thing is clear: in today’s NFL, timing is everything. And in Prescott’s case, patience paid off—for the player.