What is Cowboys owner Jerry Jones’ biggest disappointment? Billionaire told all in 2019 interview

Cowboys owner Jerry Jones comes off as a much more present and future-oriented person. As a general manager, his next goal is to build on what he's done in the past to get his team to a Super Bowl.

However, in a 2019 interview, he spoke about his biggest disappointment in 30 years, and it is in regards to Tony Romo.

Speaking to CBS Dallas, the owner was asked if he regretted not getting the quarterback a team that could get to the Super Bowl. He said that he did regret it and it serves as the biggest regret of his tenure.

Here's how he put it

"It is my biggest disappointment as far as my time with the Cowboys is not having Tony Romo in a Super Bowl. He's very capable. He has that kind of talent. And most people will tell you in the NFL, if you've got that talent at quarterback, then that should get you there. We knocked at the door about three different times where we were a lot closer than it looked."

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Tony Romo and Jerry Jones at DirecTV Super Saturday Night Co-Hosted By Mark Cuban's AXS TV - Party

It is unclear which three times he was referring to, but looking at the team's history, three seasons appear to stand out more than the others. Romo started for the team from 2006 to 2014 and injuries derailed his career from there, ultimately leading to Dak Prescott's rise.

During those seasons, the team was well known for hovering around 8-8 or 9-7 in most years. That said, in 2007, 2009, and 2014, the Cowboys were able to put together regular seasons that were Super Bowl-quality.

In 2007, Romo and the Cowboys went 13-3, but lost in the divisional round of the playoffs. Romo threw for 36 touchdowns and 19 interceptions that season.

In 2009, the team went 11-5 and lost in the divisional round. The player threw for 26 touchdowns and nine interceptions. In 2014, the quarterback's team went 12-4 but once again lost in the divisional round. Romo threw for 34 touchdowns and nine interceptions.

In 2015, the quarterback was on a similar pace (3-1), but only played in four games that season. In his final season, he scored one touchdown in a brief appearance after recovering from an injury that ultimately resulted in Dak Prescott getting his job.

Will Jerry Jones be able to do for Dak Prescott what he was unable to do for Tony Romo?

If any of the above quotes are used, please credit CBS Dallas and H/T Sportskeeda.