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

Earlier this week, Dallas Cowboys owner Jerry Jones said his team should have won the Super Bowl last year. He said he feels sadness for fans who look forward to the fall every year only to have the Cowboys fall short. He also talked about his team’s poor performance in the playoffs, which he believes is the biggest disappointment in his tenure as owner.

When the Dallas Cowboys selected Texas A&M defensive end, DeMarcus Ware, at No. 1 in the 2006 NFL draft, it seemed like a no-brainer: Dallas was coming off a disappointing season and needed a spark to turn things around. The Cowboys lost that summer and, looking for a quick fix, Jerry Jones signed Matt Hasselbeck to a $62 million contract and drafted Ware, who was coming off a 10 sack, All-American season. Then, following a 3-13 season, Jones traded for the No. 1 pick again and took another defensive player, Jason Witten. And so began the trend of drafting defensive players with first-round picks.

With the Dallas Cowboys’ starting quarterback being a key figure in this years NBA draft, it’s no surprise that Cowboys owner Jerry Jones is keeping a close eye on the proceedings. While the consensus is that the Cowboys will be sending out a second-round pick to select Southern California’s Mark Sanchez, Jones is reportedly standing firm in his belief that the team will select Oklahoma’s Heisman Trophy finalist and top-rated quarterback, Brandon Weeden.

During Jerry Jones’ ownership of the Dallas Cowboys, there have been two distinct periods. Obviously, there was a time when Troy Aikman was throwing touchdown passes and Emmitt Smith was tearing apart defenses on way to America’s Team winning three Super Bowls in the 1990s.

Then there’s the past 25 years, a period during which the Cowboys haven’t even made it to the NFC Championship Game. During that period, Jones had many good experiences, like being inducted into the Pro Football Hall of Fame, but he also faced with what he now considers his worst disappointment.

Jerry Jones is still bitter that he and Tony Romo did not win a Super Bowl together.

Dallas Cowboys owner Jerry Jones in 2021.

Dallas Cowboys owner Jerry Jones in 2021. Jerry Jones, the owner of the Dallas Cowboys, claims the Tony Romo period is still torturing him | Getty Images/Jayne Kamin-Oncea

The Cowboys failed to identify a competent starting quarterback in the years after Aikman’s retirement in 2000. Tony Romo, an undrafted quarterback from Eastern Illinois, took over in 2006 and remained in charge until Dak Prescott took over in 2016.

Despite frequent injuries and the immense burden of starting for the Cowboys, Romo was able to keep the team in postseason contention each year. In four of his ten seasons as the starting quarterback, the Cowboys made the playoffs, but never advanced beyond the NFC Divisional Round.

While he was out for nearly the entire 2016 season due to a back ailment, he was able to witness Prescott lead the club to a 13-3 record. In the NFC Divisional Round, the Cowboys were defeated at home by Aaron Rodgers and the Green Bay Packers.

Romo’s career came to an end with that, as he retired in the spring of 2017 without a Super Bowl ring. Jones previously described the loss as “perhaps my most disappointed thing” since purchasing the team in 1989, according to the Dallas Morning News.

Jones isn’t entirely incorrect when he says the Cowboys have been disappointing throughout the Romo era.

Cabo, terrible sacks, INT in the end, but watching the 2008 Cowboys vs. Giants playoff game, it truly seems like things might have gone a lot differently if Patrick Crayton had just made this grab in the third quarter and kept running.

October 4, 2018 — Saad Yousuf (@SaadYousuf126)

On the one hand, from 2006 through 2016, the Cowboys went 101-75 and made the playoffs five times. Despite the fact that Romo won 78 of his 127 starts over that time period, it’s important remembering that his single appearance in 2016 came in relief of Prescott.

So, in some ways, the Cowboys performed well throughout that period. They weren’t as bad as the Buffalo Bills or Cleveland Browns, but neither were they as good as the Indianapolis Colts or the New England Patriots. Which would you prefer: five playoff berths or none at all?

With that considered, the Cowboys underperformed in comparison to the quality they had throughout those years. Even if the 2010 and 2015 seasons are excused since Romo missed significant parts of both seasons due to injury, the club should have been in the playoffs more often, particularly given how poor the NFC was at the time. With a 9-7 record in 2008, the Arizona Cardinals qualified for the Super Bowl.

The 2011 Cowboys started the season 7-4, but went on to lose four of their last five games, missing the playoffs. Both the 2007 and 2016 teams finished 13-3 before falling in the NFC Divisional Round at home.

There’s no reason the Cowboys, as good as they were throughout Romo’s tenure, shouldn’t have made it to the NFC Championship Game — and sure, we all remember Dez Bryant’s no-catch in the 2014 NFC Divisional Round, but that’s not enough of a response.

Jones must make certain that the Cowboys do not have the same issue in the Prescott era.

Even though Jones is still the owner and general manager, a lot has happened in Dallas over the years. Romo is already in his sixth season as a CBS color commentator.

Jones has every right to be resentful of the Cowboys’ inability to reach the Super Bowl with Romo, and he must guarantee that the same fate befalls the team in the Prescott era. Since the start of the 2017 season, the franchise has only won one postseason game, the 2018 Wild Card Round.

Excuses only go you so far. Even after Prescott went down with an ankle injury in Week 5, the Cowboys were unable to capitalize on a bad NFC East last season. This is the same team that barely made the playoffs in 2017 and needed a Week 17 thrashing of Washington two years later to escape finishing last in Jason Garrett’s last season.

Maybe things will be better in 2021, particularly now that Prescott has returned to the fold. Cowboys supporters, on the other hand, may be excused for doubting the team’s ability to turn things around and make a deep playoff run anytime soon.

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Jerry Jones’ irrationally bold goal involving Tony Romo will fail miserably. RELATED: Jerry Jones’ irrationally bold goal involving Tony Romo will fail miserably.

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