Back in the early 2000’s, when Bill Parcells joined the Dallas Cowboys as the head coach, ESPN reporter Jim Armstrong was quite certain it would be one of the nastiest nuptials in sports history. He predicted Parcells would coach for a couple of years before bolting as Jimmy Johnson had. While Johnson stayed in Dallas for five seasons, Parcells stuck around for only four.

Of course, there were tense moments between Jones and Parcells, but as the latter maintained the narrative over the years, Jones was a great owner to work for. They shared a good connection and some hilarious moments, and that is confirmed by a little anecdote that former Cowboy DeMarcus Ware shared.

“They had a bet. Parcells wanted Shawne Merriman, and Jerry Jones wanted DeMarcus Ware. So, they made a dollar bet,” Ware revealed on the Fitz and Whit podcast. “The bet was if DeMarcus doesn’t average three sacks in his first three years, he’s a bust.

“Bill Parcells said, ‘If I win, I get to take my significant other anywhere in the world in your private jet.’ 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’.”

Here’s what happened: 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 Merriman, but Jones wanted Ware. What took place next?

Well, they ended up drafting Ware, and in his first year in Dallas, he put up 8 sacks, 11.5 in year two, and 14 in year three. But if you still don’t believe Ware’s story, how about Jones confirming the same?

“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 revealed in 2023, as reported by the Fort Worth Star-Telegram.

Hence, Jones placed the bet to draft Ware and won, as the defensive end had a Hall of Fame career over 12 seasons. He 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.

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. 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. But 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.

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, Jones believes his approach to managing the Cowboys is outdated.

“That ol’ mirror, that self-evaluation really is appropriate and has to be done,” Jones said in February. “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.

“I probably put too much emphasis on [coaches’] individual place in line, their place in the profession, and should have been more attentive to what’s coming out of the box today. All that counts is tomorrow, and all you can look at is yesterday and back. Knowing that, I spent a lot of time looking at the past with coaches’ positions. I did less of what I’ve been doing and more of what I haven’t been doing in this process.”

His approach has clearly shifted, and it comes off as a welcome change for someone who, over the last 30 years, has often been criticized for refusing to stray from his usual way of doing things.

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. It will be interesting to see how things move forward in 2026.