After Jerry Jones purchased the Dallas Cowboys in 1989, the team captured three Super Bowl titles within seven years. Since then, however, the franchise has endured a prolonged championship drought, failing to reach even the NFC Championship Game.

Over the past two decades, the Cowboys have experienced a mix of losing seasons and late-season collapses. While Jones successfully built the franchise into a sports empire valued at over $10 billion, the Vince Lombardi Trophy has remained out of reach for nearly thirty years.

At the Netflix premiere event for America’s Team: The Gambler and His Cowboys, former Eagles linebacker Emmanuel Acho took a jab at Jones. The 10-episode docuseries, premiering August 19, explores the Cowboys owner’s journey and the building of the multi-billion-dollar brand.

When asked if he was surprised by the Cowboys’ struggles, Acho responded:

“I’m not surprised. I’ve always said this with the Cowboys—good is the enemy of great, and they’re always good. Always good. I think that’s why they haven’t been great, because they’ve been content being good.”

Acho also suggested that the organization’s focus on glitz may come at the expense of championships:

“It costs to have this, and I think the cost of this—red carpet premieres, all the stars out—is championships. I think that’s the cost of it.”

“Good is the enemy of great…and they are always good.”

Dallas native @EmmanuelAcho isn’t too surprised that the Cowboys haven’t hit the heights recently that they did in the 1990’s@clarencehilljr | #Netflix | #DallasCowboys pic.twitter.com/3WJuopX0lI

— DLLS Cowboys (@DLLS_Cowboys) August 12, 2025

The event drew several Cowboys legends, including Michael Irvin and Emmitt Smith.

Jerry Jones on the Cowboys’ postseason struggles
The Cowboys remain the NFL’s third most successful franchise with five Super Bowl titles. Yet, their lack of recent postseason success continues to raise concerns. Addressing the matter at the premiere, Jones reflected on his risk-taking approach:

“I do always look and see if you are taking my risk, and there’s a chance that when you really get accomplished in something, you may have shortened your risk tolerance. And so if I may run a wonderful thing over the last few years, so I’m taking my risk. That’s the big one. When I look at this, I look so much at the risk that were taken during these early years.”

Jerry Jones at the Hollywood premiere for his Netflix series “America’s Team” when asked about the lack of postseason success since the 1990s pic.twitter.com/rvMP3fxisC

— Jon Machota (@jonmachota) August 12, 2025

Jones’ bold moves—such as drafting Ezekiel Elliott in 2016 and trading away Herschel Walker—remain defining moments in Cowboys history. While some gambles paid off, others contributed to the team’s ongoing frustration in their pursuit of another championship.