Jerry Jones bought the Dallas Cowboys in 1989 and has served as the team’s general manager ever since. In the 1990s, Jones added three Super Bowls to the Cowboys’ illustrious history and has been a key figure in maintaining their relevance in the NFL.However, the Cowboys have failed to live up to expectations in recent years. America's team hasn't reached the NFC championship game in ages, and they've suffered numerous late-season collapses in the past two decades.While speaking at the Hollywood premiere for his Netflix series "America's Team: The Gambler and His Cowboys," Jones was asked about the lack of postseason success since the 1990s. He said:"I do always look and see if you are taking my risk, and there's a chance that when you really get accomplished in something, you may have shortened your risk tolerance. And so if I may run a wonderful thing over the last few years, so I'm taking my risk."And so that's the big one. When I look at this, I look so much at the risk that were taken during these early years."Jerry Jones is known for his risky decisions over the years, including the Herschel Walker trade and selecting Ezekiel Elliott early in the first round of the 2016 NFL draft.Those risks have led to a mixture of success and disappointment over time. However, it's hard to imagine Jones pivoting in the 2020s even though the Cowboys are yet to add to their Super Bowl rings from early in his tenure.What's next for Jerry Jones and the Cowboys?Jerry Jones is gearing up for another season as the owner and general manager of America's team. He has made some interesting moves this offseason.Jones remains in negotiations with star player Micah Parsons. The negotiations haven't gone according to plan, leading to a trade request from Parsons. However, there's still ample time for a deal to be done with the perennial Pro Bowler.Meanwhile, Jones selected Tyler Booker in the first round of the 2025 draft. He's the latest addition to a stacked offensive line. Furthermore, the Cowboys added wide receiver George Pickens via a trade with the Pittsburgh Steelers.Next up for Jones and the Cowboys are preseason games against the Ravens and Falcons. Then they'll start the regular season with a game against historical rivals, the Philadelphia Eagles.