The Cowboys were one of few teams to experience two big wins today: their win over the Browns in Cleveland and the signing of their star quarterback to the highest salary in NFL history. Both were a long time in the works, but Dak Prescott‘s new contract is perhaps the more gratifying of today’s victories because of the wait. 
Prescott’s extension, which includes $231MM in guaranteed money, an $80MM signing bonus, and a $60MM annual average, was the result of several months of negotiations. In that time, Cowboys fans frustratingly watched quarterbacks with arguably lesser accomplishments, like Trevor Lawrence and Jordan Love, become the highest-paid players in the NFL. The frustration wasn’t that players they deemed lesser were getting big contracts, it was that with every big quarterback contract that got signed, the price tag for Prescott kept going up.
There’s an argument to be made that if Cowboys owner Jerry Jones had worked faster to secure extensions for stars like Prescott and wide receiver CeeDee Lamb, the team could’ve have vastly saved on relatively cheaper deals. Instead of working to set the market, the Cowboys ended up being forced to react to it, leading to them being the only team in the NFL with two of the 20 highest-paid players in the NFL (by annual average) with Prescott at No. 1 and Lamb tied at No. 20.
The unofficial deadline that the team set for getting the deal done was the season opener, and Dallas snuck this one in before watching Prescott potentially test free agency at the end of the year. When asked if he was relieved to have got it done in time, Jones told reporters, “Relief? No, I’m happy that it’s done. This was the time when it was right there for us to do. We were all set to go. That’s so critical.”
Jones claimed that the issue with getting a deal done was never about Prescott being the answer for them at the quarterback position. The concentration was just finding a way to make everything work, and the stars didn’t align until just in time to get the deal done.
“I think we all felt a little energy to come on in and, so to speak, get to a point where we could say ‘yes,’” Jones continued, per Clarence Hill of All City DLLS. “I’ve really known all along what a great player Dak is…I’ve seen too many very important deals not work out just because of miscalculating 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.”
There was one other sticking point that kept holding Jones up throughout the process: the sheer magnitude of the money involved. “I’m talking about making him the highest paid player in the history of the NFL…$231 million guaranteed, I know, these numbers are beyond anything I could have ever imagined.”
In the end, the team got it done, and now, Prescott has the highest annual salary any player in the NFL has ever had. We don’t know all the specifics of the deal just yet, but ESPN’s Todd Archer tells us that his 2025 cap impact will include $26.13MM in bonus proration, in addition to the new proration of the signing bonus and new base salary. Jones claims he was working to put the Cowboys in the best position to win a Super Bowl in the future, and in his words, “(Prescott) was (their) best chance of getting one.”