When Dale Hansen stared across at Jerry Jones inside WFAA’s Victory Park studio, the silence felt like an eternity. Hansen had just delivered a pointed challenge, live on air: “Can you name a team in any sport that would hire you to be their general manager based on your record, unless of course you bring your checkbook with you? Name me a single team. Can you do it?”

Jones, never short on words, replied confidently: “Yes, I can.”

But 12 seconds of “blabbering around” later (which felt like 15 minutes to Hansen), there was no definite answer. In that moment, Hansen had cut to the heart of a reality Cowboys Nation has wrestled with for nearly three decades: Jerry’s insistence on being his own GM is both his trademark and his biggest flaw. And Hansen did it with a bold verdict. “Jerry, that’s my point. There’s not a single team in any sport that would hire you to be their general manager, not a one, and yet you insist upon being the general manager of one of the most iconic franchises in all the sports. That’s my problem with you as the general manager. That’s why the Cowboys can’t get back to the Super Bowl.” 

As Hansen recalls, Jones stormed out afterward, slapping away a handshake. Cowboys’ PR head Rich Dalrymple later told him why: “You sliced his Achilles tendon. You exposed him to the one thing that he knows he can’t answer. You exposed him, and it really set him off. … our drive back after that interview was maybe the maddest I’ve ever seen Jerry Jones.” 

It was raw, unfiltered Jerry: bold, indignant, unwilling to concede weakness. Jones is many things: oil wildcatter, salesman, risk taker, showman. He bought the Cowboys in 1989 for $140 million. Turned them into the world’s most valuable sports franchise at $12.8 billion. And in the process, he stamped his fingerprints on every headline along the way. But as a general manager? The evidence is damning.

Three Super Bowls in the 90’s still shape his reputation, but there’s a clear asterisk. Jimmy Johnson and, to a lesser extent, Barry Switzer built those winners. Since then, the Cowboys haven’t even reached an NFC Championship game. For years, the team has been caught between Jerry’s willingness to make bold moves and the glaring absence of a football buffer.

No one can accuse Jones of playing it safe. He has a flair for star power, whether by breaking the bank for Deion Sanders in 1995, trading two first-rounders for Joey Galloway, or overpaying Ezekiel Elliot long after the league had devalued running backs. The gambler within Jones always finds a way to deliver a new episode in the soap opera. Headlines come easy: Dak Prescott’s contract brinkmanship, Emmitt Smith’s historical 60+ days holdout, the annual pledge that this year, finally, is the year. The drama inflates ratings. But hardware? Not since 1995. Even his daughter, Charlotte Jones, noted in the latest docuseries, “We say ‘We’ll get ‘em next time,’ but we’re running out of ‘We’ll get ‘em next times.’”

Many echo Hansen’s point. Any other franchise would’ve fired its GM by now. But Jerry’s Cowboys are different, because Jerry is the Cowboys. Jones himself once admitted the contradiction. Asked why he refuses to hire a GM, he said: “You subject yourself to so much criticism, you need a buffer. I don’t like it like that. I like the pain.” Pain… both his and the Cowboys Nation’s, has become the hallmark.

A glimpse into “what if?”

Here’s where curiosity takes over. What if Jerry Jones had taken that mindset to another team? Before he stormed into Valley Ranch to rewrite the dynasty, there was a time he had considered buying elsewhere. The Chargers were once on his radar. Imagine if that deal had happened.

Disclaimer: What follows is speculation mixed with facts. But based on Jerry’s track record, it’s hard not to wonder.

As revealed in Netflix’s docuseries America’s Team: The Gambler and His Cowboys, in 1966, Jerry Jones considered taking a loan from  Jimmy Hoffa. Jerry’s dad talked him out of it. But if Jerry had seen through that deal, the Chargers’ story would have been a whole lot different. In San Diego, Jones would have sought the same recipe: splash moves to energize a franchise that often felt like a sleepy cousin in the AFC West. Picture Jones chasing marquee stars rather than the patient, draft-and-develop route the Chargers tended to follow. He might have doubled down on keeping Drew Brees in 2006 instead of letting him go. Or, he might have orchestrated a blockbuster trade for a defensive headline name to pair with LaDainian Tomlinson. The soap opera would’ve arrived in Southern California decades before the Spanos family ever moved the team to Los Angeles.

And what about the Bengals? Imagine Jerry walking into Cincinnati, where quarterback Joe Burrow‘s generational talent has met cautious, sometimes slow-moving ownership. While Burrow does have a sweet deal, it might have been Burrow, instead of Dak Prescott, who made the highest amount of yearly payout for a quarterback. Jones has always locked down his stars. Whether it was Dez Bryant getting top-dollar in the 2010s, or CeeDee Lamb and Dak Prescott in the modern era. If Jerry ran the Bengals, Burrow’s deal might have come sooner, richer, and flashier, with Jones front and center at the press conference, soaking in the spotlight.

Of course, the downside would remain. Would those aggressive signings have left the teams trapped under bloated contracts instead of sustainable rosters? History suggests yes. Ultimately, it always circles back to Dallas. This isn’t a ‘what if’ story for the Cowboys Nation. It’s the only story they’ve ever known. The team’s drought since 1996 isn’t for lack of talent. They’ve had HOFers like DeMarcus Ware, and current stars like Prescott and Micah Parsons. The constant has been Jerry’s hands controlling the wheel.

Dale Hansen’s question lingers because its answer hasn’t changed. That’s the paradox of Jerry Jones: the visionary who turned America’s Team into a global brand, and the stubborn GM who keeps that brand from reaching another Super Bowl. He admits he likes “the pain.” The rest of Cowboys Nation might just call it heartbreak.