Mike Ditka’s Ricky Williams Trade Was Wildest Deal In NFL Draft History

For better or worse, Mike Ditka was unapologetically himself.

The NFL community sadly learned Friday that Ditka passed away at the age of 86. The Hall of Famer was a Pro Bowl tight end for the Chicago Bears, racking up 427 receptions for 5,812 receiving yards and 43 touchdowns. He was also an extraordinary coach for the Bears, leading the franchise to a Super Bowl title in 1985.

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“It is with profound sadness that we announce the passing of our beloved husband, father, grandfather, and friend, Mike Ditka,” Ditka’s family said in a statement. “While the world knew Mike as a Hall of Fame football player, legendary coach, and leader of the Chicago Bears’ Super Bowl XX championship team, we knew him as the heart of our family. Mike will be missed beyond measure and remembered forever.”

Once it was confirmed that Ditka passed away, NFL fans honored him by bringing up his fondest moments. Some even revisited his infamous trade from the 1999 NFL Draft.

When Ditka was the head coach of the New Orleans Saints in 1999, he was so convinced that Ricky Williams was going to change the franchise that he got the organization to pull off a deal we may never see again.

In order to acquire the rights to draft Williams, the Saints sent all of their picks for the 1999 draft as well as their first-rounder and third-rounder in the 2000 draft to the Redskins.

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The Saints ultimately traded the following picks:

  • 1999 1st Round Pick
  • 1999 3rd Round Pick
  • 1999 4th Round Pick
  • 1999 5th Round Pick
  • 1999 6th Round Pick
  • 1999 7th Round Pick
  • 2000 1st Round Pick
  • 2000 3rd Round Pick

This trade generated so much buzz that ESPN The Magazine had Ditka and Williams dressed as a bride and groom for their August cover in 1999.

Did this trade work out? Not exactly.

Unfortunately for Ditka, this trade never really lived up to the hype for New Orleans. Even though Williams had 3,129 rushing yards and 18 total touchdowns with the Saints, he was ultimately traded to the Miami Dolphins in March of 2002.

After going 3-13 during the 1999 season, Ditka was fired by the Saints. He ultimately got one season with Williams before being shown the door.

While this blockbuster trade didn’t work out for Ditka, it was a reminder of how bold he was on and off the field.

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This story was originally published October 9, 2026 at 10:42 AM.

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