If it seems like nearly every decision made by the Dallas Cowboys’ front office this century has been wrong, that would be because that is precisely the case.
From draft picks to free agency moves and trades to coaching changes. When viewed in retrospect, they all have one thing in common.
Most of the time, the Cowboys made the wrong choice.
Draft Busts Abound
For every one pick Dallas got right, the next dozen or so were busts. The Cowboys made 23 picks in the three drafts combined between 2000-2002.
They only got two of them right in defensive back Roy Williams.
Center Aundre Gurode, picked in the second round of 2022 after Williams was taken first, gave Dallas several solid seasons.
The third round pick, Antonio Bryant, was gone by 2004 after 37 games. The rest of the 2022 class, and the entire classes of 2000 and 2001 were wasted picks.
For every DeMarcus Ware, Terence Newman, Jason Witten, Dez Bryant, Tyron Smith that followed over the years, we were treated to draft classes of 2006 and 2009 that were filled with busts from top to bottom.
Nor have the last three draft classes done much to buck this trend.
Only Luke Schoonamker and DeMarvion Overshown remain from the 2023 class. Schoonmaker may not make the 2026 roster.
Overshown can’t stay healthy and on the field.
Cooper Beebe is the cream of the 2024 crop.
Ryan Flournoy might become a stud in 2026. Tyler Guyton may need a change of position to avoid being the second-straight #1 pick to be a bust in Dallas.
Of the remaining six picks, one is dead, and the other five are benched or off the team.
The 2025 class is faring little better.
Tyler Booker will snap the streak of mistakes with the top pick. Donovan Ezieruaku looks solid.
Aside from the 5th pick, Shemar James, most of the rest may not make the team in 226 either.
Free Agency Fizzles
The Cowboys continue to adhere to their bargain bin shopping approach to free agency. They are never players when it comes to the high-value free agents.
For every Javonte Williams they luck into, they get several Jack Sanborns and Eric Kendricks.
Not that their approach to signing their own players, especially before they near free agency, is any more effective.
Dallas has played games in negotiations that have led them to pay far more than they should have. See Prescott, Dak; Lamb, CeeDee, and Parsons, Micah for more recent examples.
Meanwhile, players they’ve let go are playing this weekend in the playoffs.
Trades Not Paying Off
The Cowboys waited until one week before the season opener to kneecap their first-year defensive coordinator by trading away the best defensive player on the roster.
Not that they did Matt Eberflus any favors by bringing in a zone defense coach for a team filled with man-to-man defensive backs.
They traded for Logan Wilson at the deadline. Then they quickly discovered why Wilson had been benched in Cincinnati.
They got Quinnen Williams from the Jets and got a great first game out of him against the Raiders.
Williams had four tackles and 1.5 sacks in Las Vegas.
For the six games that followed, they got 17 tackles, zero sacks, and an interception off of a deflection. It cost them a first round pick for that production.
But to be fair, they were able to unload Mazi Smith, so we’ll call this a wash.
Still, the Cowboys overall draft record is dismal at best.
Coaching Changes
Following the shocking beat down the Packers put on Dallas in the 2023 Wildcard game, many expected Mike McCarthy to be fired before the Divisional round games kicked off.
The Cowboys’ defense was solid.
Then defensive coordinator Dan Quinn could have assumed the head coach position, kept the defense intact and brought in a young, innovative offensive coordinator to jump start the offense.
Like a Kliff Kingsbury, perhaps. Or Quinn might have already noticed Brian Schottenheimer was on staff and given him a chance to show his stuff.
Instead, the Cowboys choose poorly yet again.
Quinn was allowed to leave for Washington and lead the Commanders to the NFC title game.
The Cowboys defense imploded and McCarthy was finally fired at the end of 2024.
Mike Zimmer had served as the team’s defensive coordinator last year and did not return in 2025. The man who replaced him was an absolute disaster.
The Only Conclusion
Dallas’ front office has built up a shockingly bad resume of failure that would get everyone involved fired by any of the other 31 team owners.
Which reveals the cause of the Cowboys front office failures.
Until the current owner and his entire family are permanently severed from control of the team, these bad choices will continue. Jerry Jones’ dream of leaving the NFL with the most Super Bowls will always remain an unfulfilled fantasy.
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