Jerry Jones Is Standing Firm in What He Believes Is the Biggest Disappointment in His Cowboys Tenure

There have been two primary eras, of sorts, during Jerry Jones’ tenure owning the Dallas Cowboys. Obviously, there were the days of Troy Aikman slinging touchdowns and Emmitt Smith barreling through defenses en route to America’s Team winning three Super Bowls in the 1990s.

Then, there’s been everything involving the last 25 years, a stretch where the Cowboys haven’t even reached the NFC Championship Game. Although Jones still experienced plenty of positive moments — including enshrinement in the Pro Football Hall of Fame — during that time, he also dealt with what he still considers his biggest disappointment.

Jerry Jones is still disappointed he didn’t win a Super Bowl with Tony Romo

Dallas Cowboys owner Jerry Jones in 2021.
Dallas Cowboys owner Jerry Jones says he is still tortured by the Tony Romo era | Jayne Kamin-Oncea/Getty Images

In the years following Aikman’s retirement in 2000, the Cowboys struggled to find a viable starting quarterback. Enter Tony Romo, an undrafted signal-caller from Eastern Illinois who took over in 2006 and held the reins until Dak Prescott replaced him in 2016.

Despite constantly suffering injuries and dealing with the overwhelming pressure of starting for the Cowboys, Romo kept the franchise in playoff contention each year. The Cowboys reached the postseason in four of his 10 seasons as the starting quarterback without ever making it past the NFC Divisional Round.

While he missed almost all of the 2016 season with a back injury, he watched Prescott lead the team to a 13-3 record that year. The Cowboys’ season ended with a home loss to Aaron Rodgers and the Green Bay Packers in the NFC Divisional Round.

That marked the end for Romo, who retired in the spring of 2017 without a Super Bowl ring. According to the Dallas Morning News, Jones recently called that failure “maybe my most disappointing thing” since he bought the franchise in 1989.

Jones isn’t exactly wrong about the Cowboys disappointing during the Romo era

On the one hand, the Cowboys went 101-75 from 2006-16 and reached the playoffs five times. Although Romo won 78 of his 127 starts in that span, it’s worth noting that his only appearance during the 2016 season came in relief of Prescott.

So from a certain point of view, the Cowboys played fine during that time. They weren’t miserable losers like the Buffalo Bills or Cleveland Browns, but they also weren’t the Indianapolis Colts or New England Patriots. Would you rather have five playoff berths or none?

With that said, the Cowboys definitely underperformed relative to the talent they had in those years. Even if the 2010 and 2015 campaigns get a pass because Romo missed large chunks of those years with injuries, the franchise should have been in the postseason more, especially with how mediocre the NFC as a conference was at points in that stretch. Remember, the 2008 Arizona Cardinals made the Super Bowl with a 9-7 record.

The 2011 Cowboys opened the year at 7-4 but lost four of their final five games and missed the playoffs. The 2007 and 2016 teams each went 13-3 before losing at home in the NFC Divisional Round.

There is no reason that the Cowboys, as talented as they were in the Romo era, should never have reached the NFC Championship Game — and yes, we know about the Dez Bryant-no catch in the 2014 NFC Divisional Round, but that’s not enough of a rebuttal.

Jones needs to ensure the Cowboys don’t have the same problem in the Prescott era

Things have certainly changed in Dallas over the years, even if Jones is still the owner and general manager. Romo is already entering his fifth year as a color commentator for CBS.

Jones has every reason to regret not reaching a Super Bowl with Romo, and he needs to ensure the Cowboys have the same failure in the Prescott era. The franchise won only a single playoff game, the 2018 Wild Card Round, since the start of the 2017 season.

Again, excuses only go so far. The Cowboys failed to take advantage of a terrible NFC East last year even after Prescott went down with an ankle injury in Week 5. This is the same franchise that barely managed a winning record in 2017 and needed a Week 17 blowout of Washington two years later to avoid a losing record in Jason Garrett’s final season.

Perhaps things will be better in 2021, especially with Prescott back in the fold again. However, Cowboys fans will be forgiven if they’re skeptical about the organization turning things around and finally making a deep playoff run anytime soon.

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