Paying CeeDee was the easy part. Dak’s deal will be a problem

Stephen Jones knew his vantage point weeks ago in training camp.

The Cowboys executive vice president quoted his father, team owner Jerry Jones, in what he called “an old Jerryism.”

“Santa Claus doesn’t put the bicycle under the Christmas tree every year,” Jones told Yahoo Sports in an Aug. 13 interview. “You gotta come to grips that you gotta pay for it.”

Monday, the Cowboys “came to grips,” in Jones’ words, with paying their 2020 first-round draft pick a handsome contract.

The Cowboys and CeeDee Lamb agreed to a four-year extension worth $136 million with $100 million guaranteed, multiple sources with knowledge of the negotiation confirmed to Yahoo Sports.

The deal is easily the Cowboys’ biggest “offseason” move for those who consider the day before final roster cuts still the offseason. This deal inches Dallas a step closer to the urgency many fans have hoped the franchise would show to snap a decades’ long drought of deep postseason play.

And yet the Cowboys know that Lamb’s contract is only one of the proverbial Christmas presents on their wish list.

Quarterback Dak Prescott and edge rusher Micah Parsons are also going to get megadeals from Dallas or elsewhere before long, Prescott’s expiring contract the more urgent of the two.

Jones said Aug. 13 that Parsons was “not pushing to do anything right now,” though his salary will jump from $2.99 million to $21.32 million for his fifth-year option even if a more lucrative deal is not reached by the 2025 season.

So as the Cowboys score one contractual win Monday, they also advance down a road dotted with plenty more questions.

Lamb will celebrate earning the most expensive receiver contract for a team also paying upper-echelon money to a quarterback, while the franchise celebrates Lamb’s extension trailing rather than exceeding Justin Jefferson’s market-defining, four-year, $140 million deal with $110 million guaranteed.

“Obviously you plan for Dak and you plan for CeeDee,” Jones said Aug. 13. “The negotiations remain very cordial and everybody’s goal is to be a Cowboy in the future and come up with solutions to the challenges of their contracts — come up with those solutions that make it to where 1) we can have all three of them and 2) we can put a good team around them.”

Signing Lamb puts the Cowboys 33% of the way toward that goal. The deal should also give Prescott more confidence in the targets he’ll have if he reaches an extension.

But will he — and if so, when?

In the Cowboys’ contractual orbit, who and what come next?

What might hinder Prescott, Cowboys’ negotiation?Jones said it was “our goal” to extend Prescott “before the start of the season.”

Two key factors could hold up that outcome.

The first: Teams often say they want to extend star players without confirming they want to extend said player at the financial level the player requests and, at times, the market dictate. There’s little doubt the Cowboys would want their current $40 million quarterback at a similar price point beside which they could invest in a talented and well-compensated supporting cast. But do the Cowboys want to pay Prescott the $55-$60 million per year that the skyrocketing quarterback market may dictate?

Thirteen quarterbacks have reached extensions worth a higher average annual value than Prescott’s since his 2020 extension.

Even as the Cowboys will point to Prescott’s light playoff résumé in negotiations, Dallas won 12 games last season as Prescott led the league with 36 touchdowns, finishing second in the MVP race.

The second holdup is more atypical. In most quarterback negotiations, leverage tilts heavily toward the club. Teams often negotiate with years of control left on a player’s existing contract, not to mention further control tools like franchise and transition tags. Some teams could even threaten to trade a player.

The Cowboys have astoundingly little of that leverage in negotiating with Prescott.

Their ninth-year starter is entering the final year of his deal, which negates the ability to offset a pricey next contract with a reasonable current deal. Prescott already won his last negotiation’s fight for a four-year extension rather than the Cowboys’ preferred five-year deal. He likely will again push to get back to the market in a preferred time frame, which cuts into the Cowboys’ salary cap management flexibility.

And then there’s the biggest leverage point Prescott has: He has no-trade and no-tag clauses in his contract.

Put another way: If the Cowboys do not reach an extension with Prescott this year, they cannot “control” him — they cannot force him to play for them.

Would Prescott prefer that?

Expect Cowboys to show a lot of Dak to CeeDeePrescott isn’t angling to leave the Cowboys ASAP.

Just as Mark Twain once said “reports of my death are greatly exaggerated,” so too are any surefire reports of a divorce between Prescott and the Cowboys.

But it’s a possibility.

And perhaps there’s a world in which it’s best for everyone.

The Cowboys and Prescott must each ask themselves as they negotiate: Can we win a Super Bowl together after eight years of trying and coming up short? Year 9 was the lucky charm for Peyton Manning and the Indianapolis Colts, as well as Washington and Joe Theismann (his seventh starting). John Elway and the Broncos spent 14 seasons ringless before winning in 15 and 16.

And yet, Elway and the Broncos had advanced to three Super Bowls in their first eight years. Manning made it to the conference championship on his sixth try. Theismann was technically in his seventh season starting when he won it all.

The Cowboys and Prescott have not reached an NFC title game or Super Bowl together. It’s possible something changes. Do they want to keep trying?

Prescott thinks about this when considering his next contract.

“I’m deserving of it,” he told Yahoo Sports. But also “this game is judged off of winning the Super Bowl and I understand people’s angst, maybe their angst and me having not done that. Hey, if these people want to move on, it’s a business.

“It’s a two-way street. Things have to be right from my end as well.”

Put simply: Prescott can choose not to push for, or even accept, an extension in the coming weeks and months. He could again decide not to sign with Dallas in the spring, testing free agency.

Will he find stronger teams than the Cowboys? The New York Giants, Las Vegas Raiders, New Orleans Saints, New York Jets and Pittsburgh Steelers are among possible suitors.

Prescott is not rushing to make a decision.

“The best way to put it is I’m free,” Prescott said. “To say I’m free means I’m in no rush — whether it happens before camp, during the season or at the end of the season when other people have opportunities.”

For now, at least one more year of opportunity exists for a Prescott and Lamb-led Cowboys offense. Lamb posted videos this week practicing getting in and out of routes in the sand as well as working on body contortion catches in the gym. Dallas expects a smooth return thanks to his workout routine and pre-existing chemistry with Prescott.

The Cowboys expect, too, that Lamb will stay busy on the field. The Joneses didn’t want to compensate a receiver this handsomely without that assurance.

“I think he’s going to touch the ball a ton,” Stephen Jones said. “For what we’re going to have to pay him, he better. I told [head coach] Mike [McCarthy] things can’t change. He’s got to be targeted 12 to 15 times a game, you got to hand it to him a couple more times. So I don’t see that changing in the least bit.

“When you pay receivers that kind of money, they got to catch the ball eight to 12 times a game, 15 times, an occasional 15.

“He’s our No. 1 go-to guy.”