Although the NFL has countless interesting characters, none can top Dallas Cowboys owner Jerry Jones, who for years played by his own rules to build one of the biggest sporting empires in the world. Highlighting this Maverick style, a Cowboys legend has revealed an interesting story when Jones won a bet and, as his prize, could take former head coach Bill Parcells’ wife out in his private plane.
“So the dollar bet was if DeMarcus doesn’t average three sacks in his first three years, he’s a bust,” Cowboys legend DeMarcus Ware said during an appearance on the Fitz and Whit podcast. “Bill Parcells said, “If I win, I get to take my significant other anywhere in the world in your private jet.” So you know how Jerry Jones is. He says, “But if I win, I get to take your significant other without you in my jet to where I want to go.”
As narrated by DeMarcus Ware, Jones and Parcells were debating on who to pick with the Cowboys’ two first-round picks, 11th and 20th, in the 2005 NFL draft. With the franchise moving from the 4-3 defense to the 3-4 defense, Parcells wanted to take LSU defensive end Marcus Spears. Jones wanted Ware, who played defensive end in college at tiny Troy University.
Jerry Jones also confirmed his bet with Bill Parcells, as revealed by the Fort Worth Star-Telegram.
“I wrote back, ‘So agreed, provided Bill accepts this addendum: You can have the five trips a year if he doesn’t, but if he does make double-digit sacks during that time, then the plane will go and Bill’s significant other will be on it, but Bill won’t. It will just be Jones and the significant other,” Jones said.
Hence, Jones placed the bet to draft Ware and won, as the defensive end had a Hall of Fame career over 12 seasons. Ware played nine seasons in Dallas, becoming the Cowboys’ all-time leader in sacks with 117 while earning seven Pro Bowl invites and four first-team All-Pro nods. He then finished his career with three years in Denver, where he recorded two sacks to key a 24-10 victory against the Carolina Panthers in Super Bowl 50, before finishing his career 13th on the all-time sacks list with 138.5.
Although Jerry Jones won this bet and has often opted for the high-risk, high-reward approach, as he did when he gambled his fortune to buy the financially struggling Cowboys in 1989, the 83-year-old has faced criticism for his methods. Similarly, these methods haven’t always worked out for Jones, with America’s Team failing to win the Super Bowl in 30 years. Hence, ahead of the 2026 offseason, Jones revealed that he reflected on his methods and believes a change is important.
Jerry Jones gives up on his methods after the Cowboys’ failures
For 30 years, the Dallas Cowboys’ lack of success has been attributed to their coaches, quarterbacks, and bad luck. Now, Jerry Jones is finally questioning the man in the mirror. Since the franchise’s last Lombardi Trophy win in 1996, America’s Team has a 258–226–1 regular-season record. However, the franchise has struggled in the postseason, holding a 3–11 record in the playoffs and has not advanced past the Divisional Round.
After this disappointing period, Jerry Jones believes his approach to managing the Cowboys is outdated.
“That ol’ mirror [pronounced more like ‘mirrah’ in Jones’ Arkansas twang], that self-evaluation really is appropriate and has to be done,” Jones said, as per the Fort Worth Star-Telegram. “My way of things doesn’t work. If I don’t change, I’m not successful. There’s no other way if you want to be hot and go to the dance.”
Jerry Jones built one of the NFL’s biggest empires through unconventional decisions, and the DeMarcus Ware bet is a perfect example of his brash confidence. However, 30 years without a Super Bowl title have forced even the famously stubborn Jones to look in the mirror and admit his methods are outdated.
