The Dallas Cowboys—and more specifically, their front office led by Jerry Jones—have become a case study in how not to run an NFL franchise. From botched negotiations to questionable contract decisions, they’ve taught the league plenty about front-office incompetence. One glaring example? Their handling of Dak Prescott’s contract. Despite just two playoff wins, Prescott now earns a staggering $60 million annually after signing a $240 million deal.
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Now, the San Francisco 49ers find themselves in a similar situation with Brock Purdy nearing a payday, and his upcoming contract could resemble Dak’s.
However, analyst John Middlekauff doesn’t believe Purdy should get that kind of money. For him, it’s all about negotiation. Dak played his hand well and secured the bag. But did he earn it? Middlekauff says no. While he respects Prescott’s story, work ethic, and professionalism, he firmly believes the Cowboys are overpaying.
” No one deserves anything, especially in business. You get what you negotiate. I don’t think Brock Purdy deserves anything. Based on his play and based on what I would feel comfortable paying him, given how good I think he is, I think Dak Prescott is grossly overpaid. I think they are in business with him at the number that limits their team because he isn’t good enough. That’s just bad business.”
Still, he doesn’t blame Dak for taking what was offered. The fault, he argues, lies with the Cowboys’ front office.
Purdy, with a far more impressive résumé and more significant wins under his belt than Dak Prescott at a similar stage, could command a comparable contract—if he negotiates it well. But while he may deserve the payday, that kind of deal wouldn’t be in the 49ers’ best interest long-term. The front office needs to recognize that and hold its ground.
Like Prescott, Purdy has exceeded expectations as a late-round pick, and John Middlekauff appreciates him for the same reasons: toughness, leadership, and production. Still, that doesn’t mean the 49ers should roll out the red carpet and let Purdy and his agent dictate terms.
San Francisco must learn from Dallas’ mistakes and strike a balance. Overpaying their quarterback, especially after making George Kittle the highest-paid tight end, could quickly shut their Super Bowl window.
Yes, the 49ers made George Kittle the highest-paid tight end this offseason, handing him a four-year, $76.04 million extension. Over the past two years, they’ve also paid Christian McCaffrey, Brandon Aiyuk, and Trent Williams, locking up key pieces of their core. But the biggest financial decision still looms: what to do with Brock Purdy. If and when they pay him, his contract will take up a significant portion of the salary cap.
The Niners already have substantial dead money on their books, so how deep they dig themselves into a financial hole is entirely up to them. Purdy wants to stay, and the organization sees him as the future. Negotiations are reportedly ongoing, and true to form, the Iowa alum is showing up, working out with the team, and handling things professionally.
That professionalism and consistency will certainly factor into the 49ers’ decision-making. Still, they must be smart. Handing him a Dak Prescott-style deal worth $60 million annually would be a mistake. At the same time, underpaying him isn’t realistic either, especially not with his résumé.
He’ll undoubtedly surpass the contract Tampa Bay gave Baker Mayfield (three years, $100 million), but there’s room for compromise. A deal in the range of $190–$200 million, with $90–$100 million guaranteed, could satisfy both sides, rewarding Brock Purdy while preserving the team’s ability to compete for years to come.
