FRISCO, Texas -- Dak Prescott went to bed last Saturday thinking his ninth season as the Dallas Cowboys' quarterback would begin without a contract extension.
A little more than an hour before the team bus left for Huntington Bank Field on Sunday at 12:45 p.m., Prescott had become the highest-paid player in the history of the National Football League.
On Monday, some 20 hours after the Cowboys beat the Cleveland Browns, Prescott signed a four-year contract extension worth $240 million on a leather couch in Jerry Jones' office at the Star with the owner and general manager, and executive vice presidents Charlotte Jones and Stephen Jones sitting next to him.
By the time the 2024 regular season ends, Prescott will take home $81.25 million with $75.458 million of it coming in the form of a signing bonus. Of the $240 million, $231 million will be fully guaranteed by March 2027.
"If you would have asked me this [Saturday], I would have said I was going in the game without one," Prescott said in a small interview room after the Cowboys' 33-17 win against the Browns in which he threw one touchdown pass. "That didn't mean the contract talks was going to end, but I was just going to focus on what I could control."
Without the extension, however, Prescott would have been one game closer to free agency next March, potentially leaving the Cowboys without a franchise quarterback and with a $40 million salary cap charge in 2025.
"Dak had a good argument: If he went to free agency, there's no telling what that number would have ended up," Stephen Jones said on 105.3 The Fan in Dallas, adding, "He could've gotten more if he were to be a free agent."
Prescott played the negotiation game to make the threat at least believable. While always professing his desire to play for the Cowboys, Prescott opened the door for him to leave the first time he spoke to reporters at training camp on July 25 in Oxnard, California.
When asked about the freedom he could feel by knowing he would be paid millions upon millions by the Cowboys or another team next March, Prescott peeked 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'm going to say it: I want to be here, but when you look up, all the great quarterbacks I've watched played for other teams. So my point in saying that is that's not something to fear. That may be a reality for me one day. That may not be my decision."
Peyton Manning played for the Denver Broncos, but he was coming off a serious neck injury that led to his release after the 2011 season by the Indianapolis Colts, his team for 13 years. 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 play Jordan Love. Tom Brady left the New England Patriots after 20 years and six Super Bowls for the Tampa Bay Buccaneers in free agency in 2021.
Manning was 36 years old. Rodgers was 39. Brady was 42.
Prescott turned 31 in July.
Negotiations with Prescott's agent, Todd France, were intermittent during training camp. The Cowboys' first goal was to sign CeeDee Lamb to an extension, and that took longer than expected, with the All-Pro wide receiver not agreeing to a deal until Aug. 26.
With Lamb signed to a four-year, $136 million extension that made him the second-highest paid wide receiver, the focus turned to Prescott.
In 2019, Jerry Jones said a deal was "imminent" with Prescott after the Cowboys beat the New York Giants in the season opener. Negotiations took two more years.
This time, they had two weeks to get a deal worked out.
The highest-paid quarterbacks in the NFL, Joe Burrow, Love and Trevor Lawrence, were paid $55 million per season. The Cowboys were willing to make Prescott the highest-paid quarterback, and quarterback pay had made incremental increases, with the top eight paid quarterbacks making between $51 million and $55 million.
France started looking for more than $60 million per year, then slowly the price came down, according to multiple sources.
When Prescott signed his four-year, $160 million deal in 2021, France was able to get everything on the player's terms. A $66 million signing bonus. A $40 million average. A no-trade clause. A no-franchise tag clause.
And Prescott again has no-trade and no-franchise tag clauses in the deal.
The Cowboys were willing to do a three-year extension initially, but a longer-term deal was not a roadblock, sources said. The guaranteed money was the final obstacle.
Coincidentally, the Cowboys' opening opponent, the Browns, paid their quarterback Deshaun Watson a fully guaranteed $230 million over five years. The Cowboys topped that at $231 million -- on a four-year deal -- and while not fully guaranteed, it is 96% guaranteed.
For the first time, the Cowboys put guaranteed money into the fourth year for a veteran player. In 2028, $17 million of the $55 million base salary is guaranteed for injury at signing and becomes fully guaranteed by the fifth day of the league year in 2027.
Before flying to Cleveland on Sunday morning, Stephen Jones called France for one final chance to knock out a deal. Not three hours later, the deal was agreed upon.
With Prescott again getting everything he wanted, why did it have to take this long?
"Only the people involved know the dynamics," Stephen Jones said to 105.3 The Fan. "But, yes, that's what it took."
Prescott took part of the blame for the deal taking time to come together.
"It could have been me," he said. "I know my part in this whole deal and that's where negotiations come. I understand the business. Point blank. I understand the business. The game is a business. I've said it before that I didn't take anything personal. I wasn't upset where we were in talks; wouldn't have been upset if it didn't get done [Sunday]."
Jones was not worried about ill will based on public comments that could have been construed negatively.
"Well," Jerry Jones said on 105.3 The Fan on Tuesday, "I've never seen anybody get their feelings hurt enough that the money couldn't cure."
Making his regularly scheduled appearance on the team's flagship station two days before the opener, Jerry Jones was terse in his response regarding the Prescott negotiations. He said he wouldn't make any comments, sounding the same as he had before Lamb's deal was finalized.
Perhaps that was the sign a deal would be forthcoming. About two hours before kickoff against the Browns, Jones stood outside the Cowboys' locker room talking about the record-setting deal.
"I've seen too many very important deals not work out just because of miscalculating," Jerry Jones said. "The right time when everybody's ready to go -- it was apparent to me over the last few days that we were ready to go and could put this in place. That's from having done a lot of deals. Not just football deals. You strike when the crosshairs get in the target and we did. And he did."
When word broke of Prescott's deal, teammates, coaches and support staff were happy for the quarterback. He has earned their trust and respect with his play, work ethic and how he treats people.
Malik Davis, a practice squad running back, was the first to wonder what type of present Prescott might offer his teammates. Soon, a number of them were pointing to their wrists.
"They're expecting some Rolexes from me or some [Audemars Piguet watches] or something," Prescott said. "Everybody is trying to give me their wrist size."