Jason Garrett offers up his thoughts on Cowboys' 30-year Super Bowl drought

Garrett had nine chances to get America's Team to the Super Bowl and didn't get the job done.
Dallas Cowboys owner Jerry Jones and NBC commentator Jason Garrett speak before a 2025 game against the Green Bay Packers
Dallas Cowboys owner Jerry Jones and NBC commentator Jason Garrett speak before a 2025 game against the Green Bay Packers | Jerome Miron-Imagn Images

As every Dallas Cowboys fan and every Dallas Cowboys hater well knows, it's now officially been three decades since America's Team last hoisted the Lombardi Trophy, as January 28 marked the 30th anniversary of the Cowboys' 27-17 win over the Pittsburgh Steelers in Super Bowl 30.

Having won back-to-back titles to close out the 1992 and 1993 seasons, the win over Pittsburgh made Dallas the first franchise ever to win three Super Bowls in a four-season stretch, a feat since matched only by the New England Patriots (2002, 2004, 2005).

The difference is that New England went on to win more titles (three more, to be exact) while Dallas has obviously failed to do so. And not only have the Cowboys not won a Super Bowl in 30 years, but they haven't even gotten back to the Big Game since that win over the Steelers. And to make matters even worse, they haven't even been back to the NFC Championship Game since that '95 season, making them the only NFC team not to reach the NFL's version of the Final Four over the last three decades.

Jason Garrett was a member of those three title-winning teams in the '90s as a player, bouncing between the practice squad and the main roster as a backup quarterback. And in 2011, after serving in an interim capacity for the final eight games of the 2010 campaign after Wade Phillips was fired, he became the first former Cowboys player to be named the team's head coach, ultimately holding the position for nine full seasons.

Garrett, of course, now serves as an analyst for NBC's Football Night in America, and with the network covering Sunday's Super Bowl 60 matchup between the Seattle Seahawks and New England Patriots, the 59-year-old has spoken with several media outlets about his thoughts on the Big Game, one being the Dallas Morning News. Naturally, with a Dallas paper comes questions about the Cowboys, and when specifically asked about the team's Super Bowl drought, Garrett said he's surprised it's lasted this long.

"You certainly would think that by now that would happen,” Garrett said. “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."

Garrett certainly had his chances to get the Cowboys back into the title picture, as Dallas thrice won the NFC East during his tenure (2014, 2016, 2018), only to fall in the Divisional Round each time. It needs to be noted, however, that the first of those three defeats was the infamous "Dez Caught It" loss to the Green Bay Packers, which Garrett spoke about in a separate interview not that long ago.

If that call goes differently, perhaps the Cowboys go on to best the Seahawks in the NFC title game and maybe they go on to knock off the Pats in Super Bowl 49.

But what's done is done, and the drought remains.

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