Dallas Cowboys didn’t make ChatGPT’s Super Bowl list for the next 50 years

A playful social-media post went viral this week. Someone asked an AI model to predict the next fifty years of Super Bowl winners. The list was full of expected teams like the Patriots, Chiefs, 49ers, and Ravens, but conspicuously absent from the entire predicted span was one franchise: The Dallas Cowboys.

According to this particular simulation, the Cowboys don’t win a single Super Bowl between 2026 and 2075. It’s been 30, and AI predicts it’ll be at least 50 more. And honestly, I can’t say I disagree.

Why an 80-year Super Bowl drought isn’t out of the question for Dallas

Since their last title in Super Bowl XXX (1995) - a time when Bill Clinton was president, Windows 95 was new, and most NFL fans had flip phones - Dallas has been a perennial contender, a perennial storyline, and a perennial “almost, but not quite.”

That’s a long drought for a franchise that once delivered championships like clockwork. Sure, they’ve made playoff runs. Sure, they’ve had Hall of Famers and Pro Bowlers. But when it comes to finishing the job, it’s been a long dry spell.

And if you’ve been paying attention to personnel choices, coaching decisions, and front-office moves… you might see why even an AI model would hesitate to put the Cowboys on a long list of future champions.

Jerry Jones: visionary or villain of Cowboys’ title hopes?

The reason this AI prediction isn’t completely off course is because of none other than Cowboys owner and general manager Jerry Jones. What Jones says - if he could buy a Super Bowl, he would - and what he does - refuses to give up control and scrimps on coaching spending - directly contradict each other. He is the only NFL owner who is also a general manager of the team, and the only thing he’s succeeded at in the last three decades is being a salesman, with his main product being hope.

LOL

We could write volumes about the Jerry Years. But here are some recurring themes:

• Delayed coaching decisions: From Jason Garrett to Mike McCarthy to Matt Eberflus, Dallas has waited too long to pull the trigger or pivot when clearly needed.
• Roster missteps: Draft picks and big-money signees have had some hits, but the misses have been costly enough to slow momentum.
• Identity issues: Great offense at times; inconsistent defense too often. Hall of Fame talent with too many holes.
• Ego over success: Jones lets his ego rule, whether it’s in not giving up the GM role or refusing to speak with star players’ agents to sign a deal. Ego rules all.

And all of this adds up to a franchise rich in history but lacking the disciplined blueprint for sustained championships. And while the AI prophecy is certainly not etched into a tablet stone, it is a platform which works from patterns. I.e. real historical data, real coaching outcomes, real roster velocity and organizational stability. And based on those inputs, an AI might reasonably conclude that Dallas hasn’t consistently done the things winners do.

The Cowboys could buck this trend if they wanted. If only they would embrace modern front-office structures instead of old ownership habits. Or get a quarterback who becomes truly elite for more than one season. Or hire the right head coach and let them build system stability. Or establish a consistent defensive identity.

Dallas isn’t devoid of talent or resources. They still have brand equity, draft capital, and access to top coaching minds if they choose wisely. But as long as the Jones family is in charge, it’s difficult to see any of that happening...even for AI.

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