FRISCO, Texas – Dak Prescott went to bed last Saturday with the thought that his ninth season as quarterback of the Dallas Cowboys would begin without a contract extension.

Just over an hour before the team bus left for Huntington Bank Field at 12:45 p.m. Sunday, Prescott had become the highest-paid player in National Football League history.

On Monday, about 20 hours after the Cowboys’ victory over the Cleveland Browns, Prescott signed a four-year, $240 million contract extension on a leather couch in Jerry Jones’ office at the Star. Sitting next to him were the owner and general manager and executive vice presidents Charlotte Jones and Stephen Jones.

Through the end of the 2024 regular season, Prescott will take home $81.25 million, including $75.458 million in a signing bonus. Of the $240 million, $231 million will be fully guaranteed through March 2027.

“If you had asked me that (on Saturday), I would have said I was going into the game without one,” Prescott said in a small interview room after the Cowboys’ 33-17 win over the Browns, in which he threw a touchdown pass. “That didn’t mean the contract negotiations were going to end, but I just wanted to focus on what I could control.”

Without the contract extension, however, Prescott would have been one game closer to free agency next March, potentially leaving the Cowboys without a franchise quarterback and facing a $40 million salary cap in 2025.

“Dak had a good argument: If he had become a free agent, there’s no telling what the final number would have been,” Stephen Jones said on 105.3 The Fan in Dallas, adding, “As a free agent, he could have gotten more.”

Prescott played the negotiation game to make the threat at least believable. Although he always stated his desire to play for the Cowboys, Prescott opened the door to leave when he first spoke to reporters on July 25 at training camp in Oxnard, California.

When asked how free he felt knowing the millions of dollars he would be paid next March by the Cowboys or another team, Prescott glanced quickly at Tad Carper, the Cowboys’ senior vice president of communications, and smiled.

“At the end of the day, it’s a business,” Prescott said, turning to Carper. “I’ll say it: I want to be here, but when you look up, you see that all the great quarterbacks I’ve seen have played for other teams. My point is, that’s nothing to be afraid of. That could be a reality for me one day. That might not be my decision.”

Peyton Manning played for the Denver Broncos but was coming off a serious neck injury that got him released by the Indianapolis Colts, his team for 13 years, after the 2011 season. Aaron Rodgers was traded to the New York Jets in 2023 after 18 years with the Green Bay Packers when the team felt it was time to let Jordan Love play. Tom Brady left the New England Patriots as a free agent in 2021 after 20 years and six Super Bowls, joining the Tampa Bay Buccaneers.

Manning was 36. Rodgers was 39. Brady was 42.

Prescott was born in July 31.

Negotiations with Prescott’s agent, Todd France, were slow during training camp. The Cowboys’ first goal was to extend CeeDee Lamb’s contract, and that took longer than expected. The All-Pro wide receiver didn’t agree to a contract until August 26.

After Lamb signed a four-year, $136 million contract extension that made him the second-highest-paid wide receiver, the focus turned to Prescott.

In 2019, Jerry Jones said a deal with Prescott was “imminent” after the Cowboys beat the New York Giants in the season opener, but negotiations continued for two more years.

This time they had two weeks to negotiate an agreement.

The NFL’s highest-paid quarterbacks, Joe Burrow, Love and Trevor Lawrence, earned $55 million per season. The Cowboys were poised to make Prescott the highest-paid quarterback, and quarterback salaries gradually increased, with the eight highest-paid quarterbacks earning between $51 million and $55 million.

France initially demanded more than 60 million dollars per year, but later the price slowly dropped, several sources report.

When Prescott signed his four-year, $160 million contract in 2021, France was able to get everything on the player’s terms. A signing bonus of $66 million. An average bonus of $40 million. A clause prohibiting transfers. A clause prohibiting franchise tags.

And Prescott’s contract again contains clauses that prohibit transfers and franchise tags.

The Cowboys were initially willing to sign a three-year extension, but a longer-term deal was not an obstacle, sources said. The guaranteed money was the final obstacle.

Coincidentally, the Browns, the Cowboys’ opening opponent, paid their quarterback Deshaun Watson $230 million guaranteed over five years. The Cowboys topped that amount with $231 million – on a four-year deal – and while that amount is not fully guaranteed, it is 96% guaranteed.

For the first time, the Cowboys have provided guaranteed money for a veteran player in the fourth year. In 2028, $17 million of the $55 million base salary is guaranteed for injuries at signing and is fully guaranteed through the fifth day of the 2027 league year.

Before Stephen Jones flew to Cleveland on Sunday morning, he called France for one last chance to negotiate a deal. Less than three hours later, the deal was agreed.

Prescott once again got everything he wanted. Why did it take so long?

“Only the people involved know the dynamics,” Stephen Jones told 105.3 The Fan. “But yes, it was necessary.”

Prescott took some of the blame for the deal taking so long to close.

“It could have been me,” he said. “I know my part in this whole deal and that’s where the negotiations come in. I understand the business. Absolutely. I understand the business. The game is a business. I’ve said before that I didn’t take anything personally. I wasn’t upset about the state of our talks; I wouldn’t have been upset if it hadn’t worked out (on Sunday).”

Jones was not concerned that public statements that could have been interpreted negatively would attract bad blood toward him.

“Well,” Jerry Jones said Tuesday on 105.3 The Fan, “I’ve never known anyone whose feelings were so hurt that money couldn’t heal them.”

In his regular appearance on the team’s flagship station two days before the opening game, Jerry Jones responded succinctly to negotiations with Prescott, saying he would not comment and sounding the same as he did before signing Lamb’s contract.

Maybe that was the sign that a deal was about to happen. About two hours before kickoff against the Browns, Jones stood outside the Cowboys’ locker room and talked about the record deal.

“I’ve seen too many very important deals that just didn’t work out because of miscalculations,” Jerry Jones said. “The right time, when everybody’s ready – I’ve been clear the last few days that we’re ready and we can do this. That’s because I’ve done a lot of deals. Not just football deals. You strike when the crosshairs hit the target, and that’s what we did. And he did it.”

When it was announced that Prescott had signed, teammates, coaches and staff were happy for the quarterback. He has earned their trust and respect through his play, his work ethic and the way he treats people.

Malik Davis, a practice squad running back, was the first to wonder what kind of gift Prescott would give his teammates. Soon, several of them were pointing to their wrists.

“They expect me to give them a couple of Rolex watches or a couple of (Audemars Piguet watches) or something like that,” Prescott said. “Everyone tries to tell me their wrist size.”