This past offseason was notable for the Dallas Cowboys because of its inaction. The entire NFL world waited with bated breath for “America’s Team” to secure the future of their stars like quarterback Dak Prescott, wide receiver CeeDee Lamb and linebacker Micah Parsons. However, the team mostly sat on their hands despite Jerry Jones’ proclamation that they would be “all-in.” Ultimately, the Cowboys exercised Parsons’ fifth-year option in April. They would wait until late August to offer Lamb a contract extension, and Prescott was extended with a four-year, $240 million contract on the same day as the team’s Week 1 game against the Cleveland Browns.

When extending Prescott in September, Jones believed that negotiation would eventually lead Dallas to Super Bowl LIX. While talking to NFL insider Dianna Russini, he described it as a “shocker” that he would not be in New Orleans for “The Big Game.” “I wouldn’t have signed Dak Prescott – the highest-paid player in the NFL – if now wasn’t when we wanted to win.”

More from Jerry Jones on the red carpet pic.twitter.com/6Zn2QJQbxd — Dianna Russini (@DMRussini) February 7, 2025 “I wouldn’t have signed Dak Prescott, highest-paid player in the NFL, if now wasn’t when we wanted to win. This is a shocker to be here at this Super Bowl and not have the Cowboys here. “I didn’t plan on that when I made that agreement with him. So we’re going to do everything we can to get (to a Super Bowl). … I know what it takes to get there.” Like the famous line says, “The best-laid plans of mice and men often go awry.” Meaning in this context, Jones had plans but he may have been unwise to believe in them with such certainty.

Jones, the Cowboys’ owner and general manager, has not led his team to the NFC Championship game since 1995, the year the franchise last won the Super Bowl. To his credit, Jones led Dallas to three Super Bowl titles in four years in the ’90s. However, the team has been in a serious drought since then, and ultimately, the Cowboys’ lack of postseason success lies at the feet of Jones’ decision-making.