A new Netflix docuseries on Jerry Jones’ glory years with the Dallas Cowboys helps explain why his teams haven’t won big in 30 years.
Why are the Dallas Cowboys so bad at treating their star players well?
Instead of locking up superstars like Dak Prescott, CeeDee Lamb, and Micah Parsons early, owner, team president, and lead decision-maker Jerry Jones waited until right before the final season of Prescott and Lamb’s respective deals to sign them to contract extensions at top-of-the-market rates. This strategy not only compromises future salary cap space but also creates friction with your best, most marketable players and sends a signal to other top players around the NFL that they won’t be treated with the proper respect and reverence should they choose to play in Dallas at some point during their careers.
The 26-year-old Parsons, who’s a two-time All-Pro at linebacker and has been selected to the Pro Bowl in each of his four NFL seasons, asked for a trade on Aug. 1 as he enters the final year of his contract before he hits unrestricted free agency. Jones claims that he and Parsons had a handshake agreement on a new deal, and that type of negotiation style “is how I bought the Cowboys.” But things have changed since he purchased the franchise in 1989. And Jones may have never actually been good at all in dealing with superstar players or managing the salary cap.
Cooper Neill / Getty Images
Jones’ battle with Parsons, who may hold out of Dallas’ Sept. 4 opener against Philadelphia, comes just as Netflix is set to release its comprehensive docuseries on the billionaire businessman, America’s Team: The Gambler and His Cowboys, on Aug. 19. The series goes way back to Jones’ days growing up in Arkansas, takes us through Dallas’ three Super Bowl wins in four years, and brings us to the modern era.
The series chronicles how Jones began forming the way he operates 60 years ago, dreaming every day during college at Arkansas about making the Razorback football team. He not only achieved that goal but also won the 1964 national championship, with Jimmy Johnson as his teammate and roommate, and Barry Switzer as an assistant coach. After hitting big on a massive oil rig, Jones achieved his other dream of owning a football team, buying the Cowboys — America’s Team — for $140 million. According to CNBC’s valuations from last year, the Cowboys are now worth $11 billion.
Nobody’s ever questioned Jones’ business acumen, but his skills as a general manager are a big reason why the Cowboys haven’t won a championship going on 30 years.
“Why don’t I hire a general manager?” Jones asks himself in the final episode, “I’ve had people that say, ‘Jerry, you subject yourself to so much criticism. You need a buffer.’ I don’t like it like that. I like the pain.”
Jones faced immense criticism immediately upon taking over the team in 1989. His first infamous move was to fire the legendary Tom Landry and hire Johnson, a college coach with no pro experience, to replace him. Jones, of course, installed himself as team president, a title he still carries today at age 82. As Dallas went 1-15 in its first season under his ownership, he traded franchise running back Herschel Walker in a shocking move that ended up providing many of the foundational draft picks that ultimately built the team’s dynasty.
As the Cowboys drafted Troy Aikman, Michael Irvin, and Emmitt Smith, there were no cap constraints to hold Jones back from building around his trio of homegrown superstars. Three years later, in the 1992 season, Dallas won its first Super Bowl in the Jones era in a romp over the Buffalo Bills, quickly becoming the most valuable franchise in sports and never looking back.
Jones’ business instincts off the field have always been amazing for the team and the league as a whole. He’s acted as a leading voice for the owners, helping them reach unimaginable heights in terms of revenue, reach, and valuations, guiding the membership on TV contracts, corporate sponsorships, stadium deals, relocation, and so many other aspects of the way the league operates. His track record on the field has been a different story.
“He disrupted the way the NFL did business,” NFL Commissioner Roger Goodell said in the doc.
Problems with Johnson and others began to surface after winning that first title.
Everyone started wanting more. When the Jacksonville Jaguars were awarded an expansion franchise in 1993, they expressed interest in Jimmy right away. Johnson and Jones began to argue about who got credit for what. Jones couldn’t handle Johnson’s perceived disloyalty, and to this day, they disagree on who possessed the contractual authority to draft and trade players.
“It became clearer and clearer to me,” longtime Dallas sports columnist and eventual TV megastar Skip Bayless said, part of a who’s who list of on-camera contributors that included George W. Bush, Phil Knight, Al Michaels, and Rupert Murdoch, “that Jimmy had next to no respect for Jerry’s football acumen. And yet Jerry would not back off from Day 1.”
Jones was always going to be the president and GM, and it drove Johnson crazy.
“He wants to be the guy on everything,” Johnson said while shooting the doc.
Whenever things have gotten good for the Cowboys under Jones, a power struggle seems to emerge, undermining the team’s strength and stability and ultimately making the on-field product worse. Under Jerry, most things never change. Prior to the 1993 season, Smith held out of training camp, wanting a raise from his rookie contract after winning two straight rushing titles.
“Contract negotiations are full of ambiguity,” Jones said in Episode 4, describing the holdout more than 30 years later, “but I have a very high tolerance for ambiguity and I can go longer than most and not have the answer.”
Smith missed the first two games of the regular season, both Dallas losses, before Jones gave him a four-year extension that made him the highest-paid running back in the league. Jones’ tolerance for ambiguity in 2025 could cost him one of the very best defensive players in the NFL.
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Two months after the Cowboys won their second straight Super Bowl in 1994 over the Bills, the last in the league before it introduced a salary cap, Jones and Johnson agreed to part ways. Jerry had already lined up his replacement, a familiar face in Switzer, upsetting his star players in the process.
The newly hired Brian Schottenheimer, who makes his regular-season debut in a few weeks as a first-time head coach at any level, had served as the team’s offensive coordinator in 2024. Jason Garrett, who was head coach from 2010-2019, was Aikman’s longtime backup. Many of Jones’ coaching choices over the years seemed to prioritize familiarity over ability, including Switzer, who was hired after Jones publicly said that 500 coaches could’ve led Jimmy Johnson’s teams to championships.
A season after losing in the NFC title game to San Francisco largely due to the impact of Deion Sanders, the Cowboys signed the two-way, two-sport superstar to a then-unheard-of five-year, $35 million deal that included a $13 million signing bonus that didn’t count against the newly installed cap. The Cowboys won the Super Bowl in the 1995 season, led by Switzer, justifying Jerry’s gamble again, with Switzer proclaiming that we won it our way after the victory over Pittsburgh.
Jerry Jones never got that close since.
The Cowboys were ultimately penalized for signing Sanders to that bonus-heavy contract that circumvented cap rules, costing them valuable space as free agents left in droves for bigger paydays following those championships, and Jones failed to deliver Pro Bowl talent in subsequent drafts.
On March 5, 1996, Irvin was arrested on drug charges after he was found with cocaine in his hotel room, and the Dallas dynasty quickly unraveled. A loss in the divisional round in January 1997 was only the beginning, signaling a rapid decline in talent under Jones’ stewardship without Johnson.
Irvin suffered a career-ending injury in 1999, and a string of four concussions in 14 months caused Aikman to call it quits after the 2000 season.
“There’s no disguising who was in charge,” Aikman said. “And Jerry, I was transparent with him, and he was transparent with me. I had felt in the end that there just wasn’t a light at the end of the tunnel. I didn’t see anything that was being done that offered any hope.”
Prescott, the team’s second franchise quarterback since Aikman after Tony Romo, will have the league’s highest cap hit this season because Jones mishandled contract negotiations. He and Lamb are projected to cost more than $102 million against the cap during the 2026 season, and that’s before factoring in the monster deal Parsons is due.
Is Jerry Jones confident Micah Parsons will play in the opener? “No absolutely not,” he said. “A big part of it is his decision. How would I know that? … No but I’m urgent.”
— Todd Archer (@toddarcher) August 5, 2025
Jones still believes he can negotiate handshake deals with superstar players like Parsons, who now have agents, a modern aspect of being a general manager that he struggled with, even when Dallas won. Yet Jerry has consistently refused to have executives in place, unless you include his son Stephen and daughter Charlotte, who know how to excel in the modern era, instead of trying to run sports’ most valuable club like a family business.
Jones continues to hold on to the principles laid out in the docuseries that are decades old, long antiquated, and haven’t yielded championship results in 30 years.
“After we won that third Super Bowl,” Jones said to conclude the docuseries’ seventh episode, “it never would have occurred to me that I wouldn’t get one in the number of years that have passed by.”
In the series finale, Jones said he’d be embarrassed if he wrote down the amount he’d be willing to pay for another Super Bowl, saying the kids’ inheritance would be out the window. He’s just not willing to let someone other than himself call the shots.
Jones has always wanted the credit and has always wanted to do things his way, buffers be damned. As he’s continued to mishandle his superstar players’ contracts the last several years, the biggest reason Jerry Jones has yet to return to the promised land is, as always, staring at himself right in the mirror.
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Shlomo Sprung
Shlomo Sprung is a Senior Staff Writer at Boardroom. He has more than a decade of experience in journalism, with past work appearing in Forbes, MLB.com, Awful Announcing, and The Sporting News. He graduated from the Columbia University Graduate School of Journalism in 2011, and his Twitter and Spotify addictions are well under control. Just ask him.