Dak Prescott beat Jerry Jones at his own game – again – and that doesn't bode well for Cowboys

Dak Prescott’s critics often highlight his lack of signature wins in the NFL, but if there were awards for negotiating prowess, he’d be a perennial contender.

On Sunday morning, Prescott secured a landmark contract extension from Dallas Cowboys owner Jerry Jones, marking the second such negotiation in just over three years. This latest deal makes Prescott the NFL’s highest-paid player, with an eye-popping $60 million annual salary over four years and a record $231 million in guaranteed money. This impressive financial achievement underscores Prescott's exceptional business acumen, placing him alongside NFL legends known for their negotiating skills, like Kirk Cousins, Darrelle Revis, Drew Brees, Walter Jones, and Deion Sanders.

While Prescott’s agent, Todd France, played a crucial role, it was Prescott’s strategic maneuvering that maximized his leverage. Entering the final year of his previous four-year, $160 million contract, Prescott had just finished a stellar 2023 season as the league's MVP runner-up and led the NFL with 36 touchdown passes. Furthermore, his position as a four-time NFC East champion and the inability of the Cowboys to trade or tag him gave him substantial negotiating power, especially in a market where top quarterbacks were earning $55 million annually.

**September 8, 2024; Cleveland, Ohio, USA** — Dallas Cowboys quarterback Dak Prescott (4) takes the field before the game against the Cleveland Browns at Huntington Bank Field. Mandatory Credit: Ken Blaze-Imagn Images

Among those impressed by Prescott's recent achievements is perennial All-Pro linebacker Bobby Wagner of the Washington Commanders, who has represented himself as an agent for eight years. Wagner praised Prescott's approach, saying, “You have to be willing to do the work and learn. You need to take risks and understand your market. Those factors can put you in a strong position.”

Prescott demonstrated his understanding of the business side of football this summer, remaining calm even as Jerry Jones made various comments during prolonged contract negotiations. Prescott acknowledged the business nature of the game, noting that many NFL superstars end up switching teams late in their careers.

“I get it—this game is a business,” Prescott said on Sunday. “The only frustrating part was answering repeated questions about the negotiations. I just wanted to put that behind me and focus on playing.”

Jones, the legendary entrepreneur and Cowboys owner, opted to make another substantial investment as the Cowboys prepared to face the Browns. Following a recent deal making All-Pro wide receiver CeeDee Lamb the second-highest paid at his position, Jones secured Prescott with a contract making him the NFL’s highest-paid player at $60 million per year and $231 million in guarantees.

San Francisco 49ers tight end George Kittle commented, “It’s great to see players like Dak getting the money they deserve. When you win consistently, you earn that pay.”

Prescott's latest deal highlights his strategic approach to contract negotiations, similar to other high-profile players like Kirk Cousins and Deshaun Watson, who have also secured lucrative deals. However, Prescott's approach could have long-term implications for the Cowboys, who have struggled to enhance their roster while managing substantial salary cap commitments.

“Jerry’s offseason has been one of his worst,” said former NFL quarterback Alex Smith, now an ESPN analyst. “They’ve made no significant improvements, despite securing these big contracts.”

While the Cowboys performed impressively in their win over a depleted Browns team, there are concerns about how the team will manage future cap space and player salaries, including those of key players like Micah Parsons, Zack Martin, DeMarcus Lawrence, and Brandin Cooks.

Jones acknowledged the challenge, saying, “We need to build a strong supporting cast around Prescott. My hope is that we can make it work.”

Though optimism remains, history suggests that having a solid plan and managing financial resources effectively is crucial for sustained success in the NFL.