Could Cowboys’ Super Bowl window be closing? 

In the glory days of the franchise’s Hall of Fame triplets — quarterback Troy Aikman, running back Emmitt Smith and wide receiver Michael Irvin — the Cowboys claimed three Super Bowls from 1992-1995 with an astounding roster largely constructed by HOF head coach Jimmy Johnson. Those days are long gone by now, the years of the Cowboys coming up short in the postseason putting them further and further from it.

Since 1996, Dallas is 0-7 in the Divisional Round, worst in the NFL in that span, according to NFL Research.

During the aforementioned Lombardi-filled run of 1992-1995, the Cowboys were 10-1 in the playoffs overall.

Dating back again to 1996, the Cowboys are 5-13 in the playoffs overall. No other club has double-digit playoff losses with five or fewer wins in that span, per NFL Research.

As they’ve come up short in every Divisional Round appearance since winning their last Super Bowl, they’ve now gone 28 seasons without an NFC Championship Game berth. It’s the second-longest active drought behind only the rival Washington Commanders (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 perennially in win-now mode, with nary a rebuilding phase to be seen.

This year has a bit of a different feel, though.

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.

Should Dallas win the Super Bowl — or perhaps even reach it or the NFC Championship Game — keeping its current cast together would seem to be paramount. If this posse of Cowboys goes bust in the postseason yet again, though, it wouldn’t be hard to fathom a massive overhaul.

The reigning NFC East champions are very much expected to be in the mix when it comes to Super Bowl contention. But it’s still just June. Come February of 2025, perhaps the question of whether the Cowboys’ Super Bowl window is open or closed will be answered.