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“Since 1995-96”: Billion Dollar Man Jerry Jones Reveals a Cowboys Misery That Made Him Wait for 27 Years

Published 01/14/2023, 5:00 AM EST

3 min read

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The Dallas Cowboys rose to become the world’s most lavish sports franchise. Jerry Jones took the gamble and pulled off a turnaround to make it a vastly valuable team. The Blue Star has had prosperity in terms of assorted aspects and is closing in on the Wild Card game. However, the franchise tycoon admits to having only one despair for the past 27 years.

This year was a big draw for America’s team. The franchise had an unexpected rise this year and made its way to the postseason. The Cowboys could finally make their way to clinching their long-lasting wish; clinching the Vince Lombardi Trophy. It is something Jerry Jones has been waiting for a long spell.

Jerry Jones’ 27-year-old grief


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During his interaction with USA TODAY Sports’ Jarrett Bell, Jerry Jones reminisced about the 1995 season. The Cowboys won their third Super Bowl in four years. The Billion-Dollar Kingpin said, “Since 1995–1996. You add ‘em up, and that’s four, and 23 is 27.” Jones seems salty about it despite having world-class athletes and coaching staff.

Jerry Jones added, “I’m sick about it. I really beat myself up over not getting a Super Bowl with [Tony] Romo here. And we had Bill [Parcells] here. Excellent coach and an exceptional quarterback. To not have gotten it done during those years really tears me up.”


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The Dallas Cowboys have an illustrious past of missing out on the Super Bowl. Many fans may see it as a jinx. However, the Dak Prescott-led Boys have a chance to break through and advance this season.

The Cowboys have a big target in the Wild Card round this year. But it could be a must-see game in one aspect.

The Cowboys’ first postseason game has a big Tom Brady draw

Dallas’ season began against Tampa Bay, and they would open it against them in the postseason. The NFL’s first postseason game would have the Cowboys and the Bucs go to war against each other. But there is a Tom Brady factor that would make the Wild Card game a must-see. 


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Unlike Tampa Bay, Dallas has had a better record. However, Tom Brady may appear to be the supreme one because he is undefeated (7-0) against America’s Team in his career. It could be the moment for them, but TB12 and company would not back out of giving them a vigorous game.

It is yet to see if the Cowboys can defeat the demon, who has had an undisputed reign over the years.


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Watch This Story: 80-year-old Jerry Jones shows vulnerable state in the middle of a radio interview




Pavitra Shome

1720 articles

Pavitra Shome is an NFL author at EssentiallySports. He began writing while working for an online news portal and holds a Master's Degree in Journalism and Mass Communication. Although Pavitra enjoys watching WWE, Gronk and Brady turned him into an NFL aficionado.