The Dallas Cowboys have been NFL mainstays for decades, but their postseason success hasn’t matched their profile, thanks Stephen.
Since their last Super Bowl in 1995, the team has cycled through coaches, quarterbacks, and coordinators with no real breakthrough.
The hidden root of the problem? Stephen Jones’s rise to power in the front office.
From salary cap control to contract negotiations and free agency philosophy, Stephen’s cautious approach has reshaped the Cowboys, keeping them stable but rarely championship-caliber.
While Jerry Jones remains the owner and public face, Stephen has become the real architect behind the team’s strategy.
His style is defined by:
But in the modern NFL, teams do not win with this mindset and strategy.
Let’s look at specific decisions that shaped the current Cowboys, and why they reflect a pattern of missed opportunities.
Stephen refused to extend Dak early in 2018-2019, instead tagging him in 2020 and again in 2021, only to give him a four-year, $160 million deal after his value exploded.
Then in 2024, Stephen signed Dak to another extension. By then, the QB market had risen again.
The impact of waiting cost Dallas more money over time and reduced flexibility to improve the roster around Dak in his early prime.
The Cowboys traded wide receiver Amari Cooper to Cleveland for a fifth-round pick, a decision driven by “cap concerns”.
Cooper still had elite WR1 ability and a strong chemistry with Dak.
The impact of the trade left CeeDee Lamb without support and slowed the offense.
Zeke received a massive six-year, $90 million extension, then rapidly declined in efficiency.
He was released in 2023 with over $11 million in dead cap space.
The impact of this extension and subsequent release was misallocating resources and handicapping Dallas in other ways.
An elite cornerback when used properly and the ultimate team player, Byron Jones was allowed to leave without a competitive offer.
His absence weakened the secondary for years.
A deal was agreed to, then Stephen inserted language Gregory didn’t like.
Gregory left Dallas and signed a contract with the Denver Broncos.
The impact left the Dallas Cowboys without a great pass rush weapon with DeMarcus Lawrence and Micah Parsons.
One of the few recent wins.
Lamb officially signed a long-term deal in 2024, securing one of the league’s best wide receivers.
The issue is waiting to sign CeeDee Lamb increased the price of his contract, a common tactic of this front office since Stephen Jones took a more prominent role.
The...