For nearly three decades, the Dallas Cowboys have searched for answers to a championship drought that continues to define the franchise. Now, one of the most respected voices in team history is offering a brutally honest diagnosis.

Three-time Super Bowl winner Darren Woodson has placed responsibility squarely on ownership, arguing that the organization’s persistent failures sit firmly with Jerry Jones.

Woodson did not mince words when discussing the structural problems that have plagued the Cowboys since their last title run in the 1990s.

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In his view, the shortcomings are not rooted in effort or even talent, but in leadership philosophy: “It always starts from the top up, top down,” Woodson asserted, taking a direct shot at Jones and the way the franchise has been managed over the years.

Importantly, Woodson pushed back against the narrative that the Cowboys simply have not fielded good enough teams.

He believes multiple rosters over the last two decades were capable of winning a Super Bowl, but failed due to deeper organizational issues.

“There’s been some good teams. Tony Romo had some good teams. That could have went and won the Super Bowl. So he did put some good products out there,” Woodson added. “They just couldn’t get over the hump.”

The Cowboys’ 30 years of pain under Jones

That “hump” has now lasted 30 years. January marked three full decades since the Cowboys last appeared in a Super Bowl, and even longer since they were a consistent postseason threat.

Their last NFC Championship appearance came on January 28, 1996, following a win over the Pittsburgh Steelers. Since then, the gap between expectations and reality has only widened.

Even Jones appears to be feeling the weight of that history. Following the disastrous 2025 campaign, Jones publicly acknowledged that management failures played a major role in the team’s collapse.

“I’ll admit that the Cowboys management has played a big role,” he said earlier this month.

“But seriously, I’m very disappointed that the way we’re structured and my role puts us here tonight. I’m tremendously disappointed.”

The 2025 season unraveled quickly, beginning with the shocking preseason trade of Micah Parsons to Green Bay. Without their defensive cornerstone, the unit never recovered.

Former Defensive coordinator Matt Eberflus installed a rigid scheme that players struggled to execute, and his refusal to adapt only compounded the damage.

A defensive collapse exposes deeper flaws

By season’s end, the Cowboys were surrendering a league-worst 30.1 points per game. Opposing quarterbacks routinely posted career performances, as the secondary allowed explosive plays while failing to generate turnovers.

The situation grew so dire that first-year head coach Brian Schottenheimer had to relinquish his offensive responsibilities just to stabilize defensive meetings.

A midseason trade for All-Pro tackle Quinnen Williams briefly sparked optimism, but it proved fleeting. Eventually, Eberflus was moved from the sideline to the coaching box, and just two days after the season ended, he was fired.

Dallas has since turned to former Philadelphia Eagles assistant Christian Parker as the new defensive coordinator, but Woodson is already sounding the alarm.

“They have to get better on the personnel side and allow Parker to do his job,” Woodson warned.

The team plans to surround Parker with experienced voices, including interviews with former Baltimore Ravens defensive coordinator Zach Orr and Arizona Cardinals cornerbacks coach Ryan Smith.

Still, for Woodson, none of it matters unless the organizational mindset changes. Until it does, the weight of 30 years without a Super Bowl will only grow heavier in Dallas.



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