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.
The Shift From Splash to Caution
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:
- Avoiding expensive free agents
- Delaying contract extensions
- Draft-focused roster building
- Minimal external voices in decision-making
But in the modern NFL, teams do not win with this mindset and strategy.
Stephen Jones’ Costly Decisions
Let’s look at specific decisions that shaped the current Cowboys, and why they reflect a pattern of missed opportunities.
1. Dak Prescott’s Contract Delays (2018-2024)
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.
2. Amari Cooper Traded for Pennies (2022)
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.
3. Overpaying Ezekiel Elliott (2019), Then Cutting Him (2023)
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.
4. Letting Byron Jones Walk (2020)
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.
5. Losing Randy Gregory Over Contract Language (2022)
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.
7. Signing CeeDee Lamb (2024)
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 impact was salary cap space as Lamb was signed after other receivers reset the market.
Culture is the Problem: No urgency, No Innovation
The Cowboys’ culture once Stephen Jones gained more control is one of calculated risk avoidance. That philosophy has fostered:
- Stagnant postseason performance
- Minimal coaching staff shakeups
- No external GM or football czar voices
- Over reliance on internal development
While other teams aggressively improve, Dallas stays in place—and gets passed up when it matters most.
Why the Cowboys Can’t Take the Next Step
In today’s NFL, the contenders:
- Extend stars early
- Use free agency to plug holes
- Trade picks for proven players (George Pickens-type trades aren’t the norm)
- Pay market value without hesitation
Dallas often does the opposite, and pays the price.
The Cowboys’ front office may look clean and efficient on spreadsheets, but the product on the field tells a different story: regular-season kings, postseason pretenders.
Stephen Jones Must Adapt or Relinquish Control
Stephen Jones has kept the Cowboys from bottoming out, but also from breaking through.
Until he brings in bold football minds, aggressively targets external talent, and shows urgency with his own stars, Dallas will remain stuck in neutral.
The Cowboys’ issues didn’t start with the coach or quarterback. They started when calculated caution became the franchise’s default identity.
