The ESPN Cover That Shocked the World: Ricky Williams & Mike Ditka’s Unforgettable 1999 Moment

In August 1999, ESPN The Magazine released one of the most controversial and talked-about covers in sports media history. The image featured New Orleans Saints rookie running back Ricky Williams wearing a full wedding dress, posing next to head coach Mike Ditka—a symbolic “marriage” meant to capture the team’s all-in commitment to their new star.

The cover, titled “For Better or Worse,” referenced the unprecedented move the Saints made in the 1999 NFL Draft. To secure Williams with the fifth overall pick, New Orleans traded eight draft picks to Washington—one of the largest trade packages ever given up for a single player. It was a gamble that defined the franchise’s bold, win-now mindset under Ditka.

A Cover That Sparked Outrage

What ESPN intended as a clever and bold metaphor caused immediate backlash throughout the sports world. Fans, analysts, and players criticized the cover as bizarre, embarrassing, and over-the-top. Surprisingly, Ricky Williams himself was one of the few who embraced the concept.

He later explained he thought the idea was funny, creative, and harmless, saying he didn’t expect such a strong negative reaction.

The sight of a hard-nosed NFL coach dressed in a tuxedo “marrying” his rookie running back was simply too unconventional for many in 1999—making the cover instantly iconic.

The Fallout: A Marriage That Didn’t Last Long

While the cover lives on in sports culture, the partnership it symbolized didn’t last.

• Mike Ditka was fired after the 1999 season following a disappointing 3–13 record, ending his tenure in New Orleans on a sour note.

• Ricky Williams played only three seasons with the Saints before being traded to the Miami Dolphins, where he found new success and continued his complex, captivating NFL journey.

What was meant to represent long-term commitment ended up becoming a symbol of a gamble that never paid off.

A Moment Cemented in Sports History

Decades later, the Ricky Williams–Mike Ditka wedding dress cover remains one of the most memorable and debated sports magazine covers ever produced. It captured the boldness, absurdity, and unpredictability of the NFL—and left a lasting mark on pop culture.

It was shocking. It was outrageous. And it was unforgettable.