Critics of Dak Prescott often highlight his failure to achieve prominent victories in the NFL. If only they awarded titles for besting the owner.

On Sunday morning, for the second time in a little over three years, the seasoned quarterback of the Dallas Cowboys negotiated a lucrative contract extension with team owner Jerry Jones. Prescott is now the first player in the NFL to earn $60 million per year (over four seasons), a considerable increase compared to his closest competitors. He also secured a record $231 million in guaranteed money, showcasing once again that he ranks among the greatest dealmakers in football history, similar to names like Kirk Cousins, Darrelle Revis, Drew Brees, Walter Jones, or Deion Sanders.

Although Prescott’s agent, Todd France, deserves significant recognition, the three-time Pro Bowler effectively placed most of the negotiating power in his agent’s hands. He entered the final year of his expiring four-year, $160 million contract following a season where he was the MVP runner-up and led the league with 36 touchdown passes in 2023. With four NFC East titles under his belt, Prescott also couldn’t be traded or tagged when the quarterback market had reached a peak of $55 million annually.

Bobby Wagner, an All-Pro linebacker with the Washington Commanders who has represented himself as an agent for eight years, is among those who find Prescott impressive.

“You need to have the desire to do the work and be open to learning. It’s essential to take calculated risks,” Wagner stated to YSL News Sports about the franchise tag Prescott was under in 2020, which was cut short due to a serious leg injury during five games.

“Knowing your market is vital. Combine these factors and you’ll find yourself in a strong position.”

Prescott displayed remarkable composure throughout the summer, not showing any frustration even as Jerry Jones took his time with several vague comments that could be interpreted in multiple ways. The quarterback nonchalantly recognized how many star players in his position ultimately ended their careers with different teams — a path he seemed to be on due to the slow negotiations.

“I get the business aspect of it, no question,” Prescott affirmed on Sunday. “This game is a business.”

Meanwhile, Jones engaged in a financial maneuver before the Cowboys’ match against the Browns in Cleveland on Sunday afternoon, opting to issue his second hefty contract in just two weeks after signing All-Pro CeeDee Lamb, making him the second-highest-paid wide receiver (four years, $136 million) in the league after Justin Jefferson.

“In the NFL, your career isn’t eternal,” remarked George Kittle, a tight end for the San Francisco 49ers, to YSL News Sports. “I applaud players who earn the pay they have worked for. When you consistently win games, it’s only right you get compensated well.”

“Dak has reliably taken the Cowboys to the playoffs, delivering top-notch performances.”

So yes, Prescott – knowing when to assert his influence behind the scenes and when to allow events to unfold naturally – has won another major financial skirmish three years after he first secured a deal that eclipsed all but Patrick Mahomes. Yet, this victory also highlights a crucial distinction — one that suggests Jones might keep facing challenges in the football arena nearly three decades after Dallas last made it to the Super Bowl or an NFC title game.

Prescott has consistently optimized his worth, much like Cousins and even Deshaun Watson from Cleveland, both advocates of fully guaranteed contracts.

“I don’t play for financial gain. When you focus on what you can control, good things happen,” Prescott commented after the Cowboys’ 33-17 victory over the Browns.

“I prefer not to discuss money. The recurring questions regarding the contract negotiations were the only frustrating part for me. I just wanted that settled. If it meant I wouldn’t be here, a thought I didn’t like, I reiterated that I only wanted to have clarity on the decision made.”

However, this decision will have consequences – and it already does. Prescott will certainly face more inquiries about financial matters moving forward. Players like Mahomes and Tom Brady, frequently featured in the NFL’s “Greatest of All Time” discussions, were generously compensated as well – but their contracts created enough financial flexibility for their respective teams, the Kansas City Chiefs and the New England Patriots, to enhance championship-caliber rosters.

Similar to Cousins, Prescott and Lamb have chosen shorter contracts that bring them back to negotiation sooner — although this often restricts their teams from making substantial free-agent signings. (As evidenced by the playoff outcomes for Cousins and the Cowboys, with only divisional round appearances marking their success this century.) This strategy could prove particularly challenging in Dallas, where Jones frequently finds himself playing catch-up when it comes to providing new contracts, and he may face a similar scenario next year when standout pass rusher Micah Parsons becomes eligible for a new deal.

Considering the raise he has already received.

Currently? The delay in finalizing contracts for Prescott and Lamb – which they undoubtedly contributed to – severely hindered the Cowboys’ ability to enhance or even sustain their roster this offseason. This is concerning for a team that has often struggled in the playoffs under coach Mike McCarthy, including a significant 48-32 defeat to the Green Bay Packers in the wild-card round last January, a game that was never really in doubt.

“This is the worst offseason I can ever remember for Jerry as the general manager. Do we really think they’ve made any improvements this offseason? I mean, what steps did they take?” questioned former NFL quarterback Alex Smith, who is currently an analyst at ESPN, on Sunday.

“Sure, they’ve secured these contracts, but they were outmatched in the first round of the playoffs and did absolutely nothing this offseason to enhance the team. … I just don’t see it. Even with 12 wins over the past three years, I doubt they can achieve that this year.”

This past Sunday, the Cowboys seemed unbeatable, though that was against a weakened Cleveland squad that was missing several crucial players and a quarterback in Watson, whose highly criticized deal exemplifies the risks associated with significant guaranteed contracts. Jones will heavily depend on an increasing salary cap because Prescott, Lamb, and Parsons will likely consume a substantial part of it in upcoming seasons while looking to rebound quickly. Additionally, Dallas will need to decide whether to pay or find replacements for players like G Zack Martin, DE DeMarcus Lawrence, and WR Brandin Cooks after this season.

“I’ve witnessed too many critical deals go wrong simply because of misjudging the right timing, when everyone is ready to move forward,” Jones remarked on Sunday.

“I hope we can provide support around (Prescott).”

Hopes can sometimes lead to success. However, in the realm of football, history indicates that a more reliable strategy would be better suited for Dallas.

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Follow YSL News Sports’ Nate Davis on X, formerly Twitter, @ByNateDavis.