You know it’s been a rough stretch for the Dallas Cowboys when even Hollywood royalty is taking shots at your owner on national television. But that is exactly what happened when Denzel Washington decided to roast Jerry Jones during his appearance on ESPN’s “First Take.”
The 70-year-old Academy Award winner wasn’t supposed to be talking Cowboys drama when he showed up alongside director Spike Lee to promote their new film “Highest 2 Lowest.” But when you’re a lifelong Cowboys fan watching your team stumble through yet another disappointing era, sometimes you just can’t help yourself.
Washington didn’t hold back, delivering what might be the most elegant takedown of Jerry Jones we’ve heard in years. “There’s box office and there’s Oscars,” Washington said, clearly drawing a parallel between his own success and the Cowboys’ lack thereof. “Jerry, been a while, huh? You ain’t been to the show, you wouldn’t know. Haven’t been to the show, so you wouldn’t know what it is to win.”
Ouch. That is the kind of burn that leaves a mark. But Washington wasn’t done. He followed up with perhaps the most quotable line of the entire segment: “All money ain’t good money, Jerry. All money ain’t good money.”
Here’s the thing. Washington isn’t wrong, and that is what makes this whole situation so painful for Cowboys fans. Jones has turned the Dallas Cowboys into one of the most valuable franchises in all of sports, worth an estimated $10 billion according to recent valuations. The man knows how to make money. There is no denying that.
But when was the last time all that financial success translated into actual football success? The Cowboys haven’t been to a Super Bowl since 1996.
Jones does have three Super Bowl rings to his credit, but they all came in the 1990s with the Troy Aikman, Emmitt Smith, and Michael Irvin dynasty. Since then? It has been a bunch of regular season hype followed by playoff disappointment.
What makes Washington’s comments so powerful isn’t just that they came from a beloved actor. It is that they perfectly capture the frustration that Cowboys fans have been feeling for decades. This is a man who genuinely loves the team, which makes his criticism all the more stinging.
The Cowboys have made the playoffs in three of the last four years, which sounds impressive until you realize they haven’t even reached an NFC Championship Game since the 1990s. That’s not just disappointing; it is historically bad for a franchise that calls itself “America’s Team.”
And now, with star pass rusher Micah Parsons holding out and creating even more drama, things seem to be getting worse rather than better. The dysfunction has become so apparent that even celebrities are calling it out on national television.
Before Washington and Lee even arrived on the show, Stephen A. Smith was already in full Cowboys-bashing mode, focusing on quarterback Dak Prescott’s contract situation. Smith highlighted how Prescott’s multiple contract restructurings have created $82 million in salary cap space, but questioned what good all that financial maneuvering does when the team can’t win when it matters most.
It has become a pattern with this organization: make splashy moves that generate headlines, restructure contracts to create cap space, talk about championship aspirations, and then fail to deliver when the lights are brightest.
There’s something almost poetic about the timing of Washington’s comments. He was there to promote “Highest 2 Lowest,” and honestly, is there a better description of the Cowboys’ trajectory over the past three decades? They went from the highest of highs, three Super Bowl wins in four years, to the lowest of lows: becoming the NFL’s most expensive soap opera. A team that generates more headlines for off-field drama than on-field excellence.
The most frustrating part of all this, from a fan perspective, is that Jones has created this situation himself. He is the owner, general manager, and de facto face of the franchise. Every decision, every contract, every coaching hire goes through him.
And yet, for all his business acumen and marketing genius, he can’t seem to build a team that can get over the playoff hump. The Cowboys are the NFL’s equivalent of a luxury car that looks amazing in the driveway but breaks down every time you try to drive it somewhere important. All flash, no substance.
Washington’s comments should serve as a wake-up call for Jones, but let’s be honest, it probably won’t. This is a man who’s been hearing criticism for years and has shown little inclination to change his approach.
The real tragedy is that Cowboys fans deserve better. They are some of the most passionate supporters in all of sports, and they have been remarkably patient considering the circumstances. But even patience has its limits, and you can sense that many fans are reaching theirs.
When Denzel Washington, a man who could easily stay quiet and avoid controversy, feels compelled to call out your organization on national television, maybe it is time to take a long, hard look in the mirror.
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