A franchise that once achieved the extraordinary feat of winning three Super Bowls in four years now endures the sting of a 30-year championship drought under Jerry Jones. Adding salt to that gaping wound are the glaring leadership issues with Dak Prescott and company, something a Cowboys legend can no longer ignore, as it holds the team back from its best.

“I don’t know what’s wrong with them boys. You know how the locker room is. I look at the Steelers as a championship organization just like the 49ers. You know how to win. You know what the culture look like and players come in [with] what’s to expect. I don’t have to tell you. Because your leadership is going from top down. I don’t know if we [Cowboys] have that kind of leadership from top down,” Hall of Fame running back Emmitt Smith said on the Deebo & Joe podcast on February 8th. 

According to Hall of Famer Emmitt Smith, the reason the Cowboys keep failing to reach the playoffs and win the Super Bowl is that the culture in the organization is just off.

The leadership doesn’t flow in a top-down style, where every leader instills a winning culture in the players and sets high standards. This is exactly what former Steelers head coach Mike Tomlin and San Francisco 49ers head coach Kyle Shanahan do so well in their teams.

Those two leaders are known for the way they balance the players and the front office, something that’s clearly missing in Dallas. Smith says the vibe around the Cowboys organization seems confused, where everybody is not on the “same page,” and they don’t come into the organization with the “right intentions.” 

The NFL Players Association Report Card for 2025 showcased exactly what Smith is talking about. In ownership, the Cowboys received a B ranking, placing them 18th in the league. What’s disappointing is that Jones ranks 23rd in contributing to team culture and 25th in building a competitive team. 

That’s the point Smith has been trying to get across for a long time: the Cowboys have latched onto a showoff culture. Everyone, starting from the owner, seems more interested in being relevant and running a PR show than focusing on championships. 

Former Steelers linebacker James Harrison asked Smith something similar on the podcast: “When you come into the organization, your goal [is] to win championships, or is your goal to get fame and fortune?” To which Smith pointedly said, “That’s what I’m talking about.” 

However, while Smith has an issue with the headline-grabbing culture in Dallas, there’s another Cowboys legend who has an opposite take on it. This contrast shows how divided even the icons are about what’s plaguing the team.

Jason Garrett: Cowboys should’ve won a Super Bowl by now

Jason Garrett played with the Cowboys for eight seasons during their two Super Bowl wins in 1993 and 1995. He then became the first former Cowboys player to serve as head coach, taking over in 2010. So, even he feels Dallas should have won a Super Bowl by now after all this time.

“You certainly would think that by now, that would happen,” Garrett said in the Dallas Morning News. “We have our stories when we were there as a coaching staff, and some close games we played in the divisional round and chances to go to the championship game. But we didn’t get it done, and there’s a bottom line to this. The Cowboys, until they break through, people are still going to be talking about it.” 

The close games Garrett’s talking about come from his over nine-year tenure with Dallas as head coach. During that time, they reached the divisional round three times but lost to the Packers twice and then to the Rams in 2019. 

But his words about people talking about the Cowboys despite their 30 years of no ring do ring a bell. It’s like an identity that’s attached to who America’s Team is. So, no matter the debates over whether it’s good or bad, it is what it is, and it keeps the conversation alive year after year.

However, it obviously doesn’t hurt any less for the fans eagerly waiting for the Super Bowl curse to lift. Their 30th anniversary on January 28th came and went without that rebirth to end the drought. Only time will tell if Dallas can finally turn the page.