The Dallas Cowboys have developed this reputation of waiting to sign their top players to new contracts. For whatever reason, they are content to let negotiations keep going and going, but that ultimately pushes up the price. As NFL contracts work, the next top guy always wants to get paid more than the previous guy, so there is perpetual growth in the market. If you wait, you’re going to pay more, and that is exactly what has happened with the Dallas Cowboys.

When the 2024 offseason began, the top of the market for quarterbacks was the $55 million per season deal Joe Burrow signed with the Cincinnati Bengals last year. Then Jordan Love and Trevor Lawrence matched that number with Tua Tagovialoa and Jared Goff just behind them.

A normal incremental increase would put Prescott at $56 or $57 million per season, just ticking up a little. But this is where Dallas’ earlier contract games with Prescott have come back to bite them.

In 2020, the Cowboys franchise-tagged Prescott instead of signing him to a long-term deal. Then they were set to repeat the franchise tag in 2021 before ultimately agreeing to a record-breaking contract extension. They waited until the last possible minute and after Prescott’s reps saw the Cowboys were prone to (repeatedly) using the franchise tag, they negotiated a no-tag clause in his 2021 deal. When the deal expired following the 2024 season, the Cowboys would need to extend him with a full contract if they wanted to keep him.

With that player-friendly leverage, it’s pretty likely that Prescott’s reps walked in and said $60 million right off the bat and held until he got it instead of the smaller incremental increase. So the negotiations in 2020 and 2021 potentially cost them $16 million from 2025 to 2028.

In 2023, the highest-paid wide receiver made $28 million per season (Davante Adams), but an explosion at the top of the market this offseason saw seven players eclipse that mark including CeeDee Lamb. Lamb signed his deal on August 26th, and by that time the market had climbed all the way to $35 million per season.

When the offseason opened in March, they theoretically could have agreed to a deal above the top of the market for around $30 million per season, but by the end of April, that was thrown out the window. Amon-Ra St. Brown and A.J. Brown moved the needle to $30 million and then $32 million within a couple days of each other prior to the NFL Draft. Then the big domino fell in early June when Justin Jefferson pushed the market to $35 million per season.

After Jefferson capped the market, Lamb and the Cowboys ultimately agreed to a deal worth $34 million per year as the second-highest contract in the wide receiver column. Over the course of the four years of the deal, it’s $16 million the Cowboys cost themselves by not doing the deal earlier at $30 million annually.

Looming now for the Cowboys is a deal for All-Pro edge rusher Micah Parsons. Parsons was eligible to sign a new deal this offseason, but instead the two sides will see him play on the final original year of his rookie contract. In 2025, he is under contract on the fifth-year option for $21 million. Surely he wants to make money money than that and make it sooner than those game checks more than a year from now.

Nick Bosa completely reset the market at EDGE in 2023 when he signed a deal worth $34 million per season, easily demolishing the previous high of T.J. Watt at $28 million per season. But with two more pass rushers topping $28 million this offseason, the market is going to rise rapidly to pass Bosa.

Waiting on Parsons could let Myles Garrett, T.J. Watt, Maxx Crosby, Joey Bosa, Haason Reddick, and Aidan Hutchinson continue to push the market higher, and as we’ve seen, the Cowboys aren’t afraid to use the franchise tag to push a new long-term deal all the way to 2027.

Interestingly, there is one bigger-money deal recently that they didn’t wait on. After rookie Trevon Diggs finished his third NFL season, Dallas paid him heading into 2023. He was the fifth-highest-paid cornerback in the NFL at the time and signed the biggest CB deal of the 2023 offseason. So how did his deal get done when the others didn’t?

Diggs was way more motivated to get a contract signed than Prescott, Lamb, and Parsons. As a second-round pick, he did not have the cash these other players have. At the time of his signing, he had only made $5 million over three NFL season. His $21.2 million signing bonus looked pretty great and they got him into the upper echelon, not reseting the market.

Lamb and Parsons were first-rounders and Prescott is coming off a big-money second contract, so they could afford to wait to increase leverage. Diggs chose not to do that.

Ultimately it takes two to tango, and the Cowboys haven’t wanted to dance with their star players until late at the ball, instead opting to wait it out on contract extensions. Despite the hand-wringing, they were able to get deals with these players and keep most of their core intact.

It’s hard not to think, though, about deals for other important players they franchise-tagged and let leave like RB Tony Pollard and TE Dalton Schultz, or a player they traded away instead of signing long-term like WR Amari Cooper.