Dak Prescott became the NFL’s highest-paid player last year, but he still holds that crown with a staggering $60 million annual salary.
But what’s even more surprising is how his team chose to go short-term on the deal, despite the Cowboys owner Jerry Jones favoring longer contracts for his star players.
In a recent sit-down, Prescott’s contract negotiator, AJ Stevens, revealed why they turned down long-term security for flexibility, betting on Dak’s continued rise, and keeping the leverage exactly where they wanted it: in their hands.
Why Dak Prescott’s Team Chose Control Over Comfort in Contract Talks
Dak Prescott’s blockbuster contract wasn’t just about dollars; it was about strategy. His agent, Todd France, and AJ Stevens, VP of Client Strategy at Athletes First, carefully crafted the deal alongside Dak himself. In an interview with NFL analyst Ari Meirov, Stevens broke down how involved Prescott was in every step.
“We sat down, specifically with Dak, multiple times on multiple occasions,” Stevens said. “We showed him what’s on the table, the risks, the worst-case scenarios, and the upside of saying no.”
They used a clear sliding scale approach, mapping out every outcome, from walking away with guaranteed money to maximizing earnings through short-term leverage. Instead of locking into Jerry Jones’ preferred long-term structure, they chose control.
By understanding every angle, Prescott didn’t just sign a contract. He made a calculated bet on himself. And so far, it’s paid off perfectly.
Why Dak Prescott’s Team Fought for a Shorter Deal With the Cowboys
While the Dallas Cowboys typically aim for long-term contracts with their star players, Dak Prescott’s agents had a different plan. According to AJ Stevens, they intentionally pursued a four-year deal during negotiations, shorter than what team owner Jerry Jones would prefer.
“Our focal point of that negotiation was we should have a four-year contract because that’s going to maximize the guarantees,” Stevens said. “Three years are going to be guaranteed, and then we’re going to be back at the table.”
Their strategy was simple: a shorter deal gives the player control. “After the guarantees run out, it becomes a team option,” Stevens noted. “The team gets to decide, do we pay this, or go another route?”
By negotiating a shorter deal, they created a path for Dak to reenter the market while still in his prime earning years. “The QB market is evolving rapidly,” Stevens added. “We want to be back at the table after four years.”
In short, control beats comfort when maximizing a quarterback’s career earnings.