Trending Now - Skip Bayless Predicts Cowboys' Super Bowl Win With New GM

WHO:

Skip Bayless, sports commentator

Jerry Jones, owner of the Dallas Cowboys

Howie Roseman, General Manager of the Philadelphia Eagles

WHAT:

Skip Bayless claims that the Dallas Cowboys would win a Super Bowl in two years if Howie Roseman replaced Jerry Jones as the team's General Manager.

The Dallas Cowboys have not won a Super Bowl in 30 years.

The last Super Bowl victory for the Cowboys was a 27-17 win against the Pittsburgh Steelers in Super Bowl XXX.

WHERE:

Dallas, Texas (home of the Dallas Cowboys)

Philadelphia, Pennsylvania (home of the Philadelphia Eagles)

WHEN:

The Dallas Cowboys last won the Super Bowl in 1995.

WHY:

The claim suggests that a change in management could lead to improved performance and success for the Cowboys.

HOW:

Bayless's prediction is based on the hypothetical scenario of Howie Roseman taking over the management of the Cowboys.

(UPDATED March 23, 2026 01:33 UTC)

In a bold statement, sports commentator Skip Bayless suggested that the Dallas Cowboys could win a Super Bowl in two years if Howie Roseman replaced Jerry Jones as the team's General Manager. The Cowboys, who haven't claimed a Super Bowl title in 30 years since their last victory against the Pittsburgh Steelers in 1995, are currently seeking a path to success. Bayless's prediction hinges on the idea that a change in management could significantly enhance the team's performance.