Chris Simms names the ‘biggest regret’ in football history which was also the Cowboys’ saving grace

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America’s Team is one of the most successful teams in NFL history as they reside on five Super Bowl wins but Chris Simms believes the biggest regret in football history was the catalyst for their huge success.

In recent memory, the Dallas Cowboys have been one of the most underwhelming teams of the last two decades.

In the last 20 years, they have won seven NFC East division titles and finished with 10+ regular season wins on eight occasions.

The Dallas Cowboys have high expectations due to their successful history

However, the most popular and expensive team in the NFL has high expectations. Being just ‘good’ is no longer acceptable and the standards have been raised.

America’s Team has disappointed in the postseason for the last 29 years as they have failed to reach an NFC Championship.

Yet, the growing and consistent pressure on the current team was set by one of the greatest NFL dynasties to grace the field.

The Cowboys became one of the biggest powerhouses in the league with Troy Aikman, Emmit Smith, and Michael Irvin leading the charge.

Although Dallas may not been blessed with superstars like them if it was not for the ‘biggest regret’ in NFL history.

Chris Simms says the Herschel Walker trade is the ‘biggest regret’ in NFL history

On NBC’s Pro Football Talk, Mike Florio and Chris Simms discussed the ‘biggest regrets’ in NFL history.

Occupying the number one spot for Simms was without a shadow of a doubt the Herschel Walker trade to the Minnesota Vikings.

The Dallas Cowboys were in full-on rebuild mode under their new, soon-to-be-legendary, head coach Jimmy Johnson.

A diabolical 0-5 start to the season saw the Cowboys make a paramount decision and trade away their only lucrative asset Herschel Walker.

At the time, the Vikings were confident they were only one piece of the puzzle away from winning a Super Bowl.

The Cowboys secure invaluable draft picks to build their super team

Therefore, the Cowboys finalized a behemoth trade with the desperate Vikings and acquired a bucketload of draft capital.

Overall, the Cowboys acquired three first-round picks, three second-round picks, a third-rounder, and a sixth-rounder – good luck getting anything close to that in today’s age.

These picks laid the foundations to acquire vital players, allowing the Cowboys to win three Super Bowls in the next seven seasons.

Herschel Walker did not prove to be the final player the Vikings needed for a ring and he eventually wound up on the Philadelphia Eagles roster by the time America’s Team was winning championships.

One of the ‘biggest regrets’ in NFL history proved to be the saving grace for the greatest Cowboys team.