“He’s got three Super Bowls. He’s got the richest franchise in sports.” That line alone could be a badge of honor for most NFL owners. But when Clarence Hill said it this week, it didn’t feel like admiration—it felt like a challenge. A reality check. Because for a guy like Jerry Jones, who used to eat, sleep, and breathe winning, the question being whispered louder and louder around Cowboys Nation is this: Does he still have that same fire?

Because if the last few offseasons have taught fans anything, it’s that something feels…off. The big splashes are smaller. The urgency is quieter. And in a league where everyone’s chasing, Dallas seems strangely content. But why? What’s changed? Clarence Hill didn’t sugarcoat it when he claimed that maybe, just maybe, Jerry’s not chasing that Super Bowl dream with the same all-out obsession he once did. “They don’t spend the same money they used to. They don’t go all in. 82-year-old Jerry is enjoying working with his sons.”

And that hits different when you see the numbers for yourself. The Cowboys started the 2025 offseason with a healthy $50–56 million in cap space. Plenty of space to go look for top talent, right? But instead of making a splash, they stayed quiet, settling for smaller one-year deals with guys like Javonte Williams, Robert Jones, and Solomon Thomas. That’s a far cry from the all-in, headline-grabbing moves we used to see from Jerry Jones.

Throw in the Micah Parsons contract drama, and the pattern gets even harder to ignore. We’re talking about a guy with 52.5 sacks in 63 games, back-to-back All-Pro nods, and a DPOY trophy. And yet, no extension on the table. Jones has brushed it off as “nonessential” heading into camp, which raised more than a few eyebrows. Even more telling? He publicly questioned Parsons’ durability, hinting at injury concerns just as names like J.J. Watt started speaking up in Parsons’ defense.

Has he become…complacent? Because the shift in priorities is clear. For decades, Jones was known for matching or exceeding market rates to maintain elite talent (just ask Prescott and Lamb). Now? He’s taking his time, prioritizing control and family over contract urgency. And insiders are noticing. And they can’t help but wonder: How is the most valuable sports franchise in the world struggling on a sporting level?

More of a media house than a football franchise?

While the Cowboys are tightening the wallet on the field, off the field? Business is booming. The Star isn’t just a practice facility anymore; it’s a full-blown media house. Fans roll through by the thousands, snapping pics, shopping merch, watching shows get filmed right there in the building. It pulls in nearly half a million visitors a year and over $10 million in revenue. At this point, it kinda feels like Jerry’s building more of a media empire than a Super Bowl contender.

And Hill? He noticed. “He has three Super Bowls and the Netflix special he can sleep with, you know. Life is good,” he said. Yeah, that media-first philosophy? It extends to streaming now.

Netflix is dropping a new doc on August 19, 2025: America’s Team: The Gambler and His Cowboys. And the timing couldn’t be more on-the-nose. It dives into Jerry Jones’ rise, the wild ’90s dynasty, and everything that made the Cowboys iconic. But while fans relive the glory days, the current reality stings: it’s been nearly 30 years since Dallas even sniffed an NFC title game. Does Jerry Jones only live on nostalgia now?

To a lot of Cowboys fans, it’s hard to ignore the disconnect. The brand? Stronger than ever. Revenue? Through the roof. But on the field? It’s been a steady slide into frustration. Fans are pouring in their time, money, and passion year after year—but the payoff just isn’t there. And like Clarence Hill hinted, maybe it’s not just about dollars and cap space anymore. Maybe the Cowboys are running like a five-star business… while the football side feels stuck in neutral.