Troy Aikman on Cowboys’ Playoff Failures: ‘It Starts at the Top’

Much like the rest of the Dallas faithful, Troy Aikman never imagined his third Super Bowl victory with the Cowboys would mark his final one. Yet, that triumph did not just signal the end of the Aikman era’s championship run; it also stands as the most recent title secured by one of sports’ most iconic franchises.

The approaching campaign marks 31 years since Dallas last hoisted the Lombardi Trophy, let alone reached the big game. This three-decade-plus absence from the conference championship is the longest ongoing slump in the NFC. To Aikman, a Hall of Fame passer and Super Bowl XXVII MVP, the team’s lack of deep postseason runs over the last three decades is simply mind-boggling.

“It is difficult to process,” Aikman remarked during an appearance on the “Dallas Dialogue with Dale” podcast earlier this month. “It truly is. Every single season, we discuss league parity and witness clubs rising from the cellar to the top, or historically struggling franchises putting together deep runs. They manage to reach a conference title game or even the Super Bowl. But for Dallas, that breakthrough has remained elusive.”

Making the dry spell even more baffling, according to Aikman, is that his old squad has actually performed remarkably well during the regular season over the past thirty years, though that consistency has repeatedly failed to carry over into the playoffs.

While Aikman cannot pinpoint the exact reason for the team’s postseason shortcomings, he is certain of one thing: the dedicated Dallas fanbase is long overdue for some gratification.

“The Dallas faithful deserve a better outcome,” Aikman stated. “That much is clear to me. This is the Cowboys we are talking about, the premier brand in the league, and the reality that they haven’t even played for a conference title in thirty years, let alone a Lombardi Trophy, is just hard to wrap your head around.”

Supporters of the team can easily point to the moment the franchise began its downward trend. It occurred not long after Dallas secured consecutive titles, when head coach Jimmy Johnson and owner Jerry Jones reached a mutual decision to split. The separation was partly triggered by Jones boasting to members of the press that “500 coaches” were capable of winning a championship with that specific roster.

A year following Johnson’s exit, Dallas managed to capture a historic third title in a four-year span, yet the vulnerabilities in their dominant foundation were starting to show. While they secured the championship in 1995, that squad lacked the strength of the 1994 group, which in turn was not as dominant as the 1993 roster—the final year Johnson coached the team.

Beyond the loss of Johnson, critics often attribute the prolonged dry spell to Jones’ persistent refusal to relinquish his roles as president and general manager while remaining the owner. Although Jones is worthy of praise for the triumphs achieved during his tenure, it is equally evident that he bears significant responsibility for the franchise’s ongoing inability to win another title.

“In my view, whether you are looking at athletic teams or corporate entities, leadership at the very top sets the tone, for better or worse,” Aikman explained. “It really begins at the peak. I doubt Jerry would dispute that. He is certainly quick to accept credit when they succeed, so it only follows that you must also accept blame when things fall short. And they definitely have fallen short.”

When defending his choice to retain the general manager and president duties, Jones has argued that hiring someone else offers no certainty of improved results. Though that logic is technically true, Aikman does not view it as a valid excuse for maintaining the status quo.

“If you operate under that mindset, you would also never replace a head coach,” Aikman noted. “You would avoid making any adjustments because nothing is ever guaranteed. However, they have been following this exact path for decades without any postseason results to show for it, which means something fundamental is holding them back.

“Obviously, I am not inside the facility. People have various theories on what the issue is, but the math simply doesn’t make sense. From my perspective, you have to alter your approach. If you go thirty years without winning consecutive postseason matchups to reach the conference finals—even failing to advance past the divisional round when holding the top seed and a first-round bye—something is wrong. Recording only four playoff victories over three decades is completely unacceptable.”