Could Cowboys' Super Bowl window be closing? 

Almost thirty years after lifting their last Lombardi Trophy, the Dallas Cowboys may be approaching one of the most critical seasons in the team’s illustrious history.

Head coach Mike McCarthy and quarterback Dak Prescott‘s futures beyond 2024 seem to be in question, but they’re not the only ones.

The Cowboys have had a commendable regular-season record of 36-15 since 2021, only surpassed by the Kansas City Chiefs in the NFL. However, in contrast to the Chiefs’ dynastic rise, the Cowboys have only managed a single playoff win during this period. As we approach 2024, a pressing question arises: Is the Cowboys’ opportunity to win the Super Bowl dwindling?

NFL Research’s detailed analysis highlights the significance of this period for the franchise, as they once again aspire for Super Bowl glory, a dream unfulfilled since the 1995 season.

During the franchise’s golden era, marked by the Hall of Fame trio – quarterback Troy Aikman, running back Emmitt Smith, and wide receiver Michael Irvin – the Cowboys won three Super Bowls between 1992 and 1995. This remarkable team was mostly built by HOF head coach Jimmy Johnson. However, those glory days are now a distant memory, with the Cowboys’ repeated failures in the postseason pushing them further away from their past triumphs.

According to NFL Research, Dallas has the worst record in the Divisional Round since 1996, with 0-7.

During the previously mentioned Lombardi-dominated period from 1992-95, the Cowboys had an overall playoff record of 10-1.

Since 1996, the Cowboys have a playoff record of 5-13. According to NFL Research, no other team has had ten or more playoff losses with only five or fewer wins during this period.

Since their last Super Bowl win, they’ve failed to progress past the Divisional Round, marking 28 seasons without an NFC Championship Game appearance. This is the second-longest active streak, only overshadowed by their rivals, the Washington Commanders, who haven’t reached this stage in 32 seasons.

Dallas’ latest playoff setback came with a stunning upset loss in last season’s wild-card round to an upstart Green Bay Packers team. It was the Cowboys’ third 12-5 season in a row and it was yet another year of a much-ballyhooed, high-profile roster ultimately falling short. McCarthy, whose first season was a 6-10 showing in 2020 marred by a horrendous Prescott injury, is just 1-3 in the postseason as the Cowboys head coach, with the lone victory coming against an eight-win Tampa Bay Buccaneers team.

The Cowboys are consistently focused on winning immediately, with hardly any visible phases of rebuilding.

Though, this year feels a bit different.

Dallas lost Pro Bowlers Tyron Smith, Tyler Biadasz and Tony Pollard to free agency, Leighton Vander Esch retired and Stephon Gilmore remains on the market. In turn, the Cowboys welcomed only two free agents who are projected to be 2024 starters — Ezekiel Elliott and Eric Kendricks.

More concerning is that Prescott, CeeDee Lamb and Micah Parsons are each in the market for extensions, but the faces of the franchise remain on their old deals as the summer burns on. They aren’t the only ones. A staggering nine former Pro Bowlers on the Cowboys have only one or two seasons left on their current contracts.

Cowboys owner Jerry Jones has drawn the ire of fans and the criticism of pundits for stating that Dallas was going “all-in” for the 2024 season and following it up with an offseason that was next door to silent and a draft that was hardly splashy. However, if Phil Ivey, Daniel Negreanu, John Monnette or any other pro poker player pushes his chips all-in, it’s very much a win-or-go-home situation. Perhaps that’s what lies ahead for the 2024 Cowboys.

If Dallas manages to win the Super Bowl, or even just make it to the NFC Championship Game, it would be crucial to maintain the current team. However, if this group of Cowboys fails in the postseason once more, a significant restructuring would not be surprising.

Expectations are high that the reigning NFC East champions will be strong contenders for the Super Bowl. However, it’s still early, being only June. By February 2025, we may know the answer to whether the Cowboys’ opportunity for Super Bowl victory is still viable.