26. Mike Ditka
Ditka was heavily responsible for one of the worst trades in NFL history in 1999 as head coach of New Orleans. The Saints traded all six of their 1999 draft choices as well as their first and third-round picks in 2000 for Washington’s Ricky Williams. Ditka pleaded with GM Charley Casserly to make the deal happen as he loved Williams after an unbelievable showing for the University of Texas.

Needless to say, this turned out to be one of the worst decisions ever. The Saints fired Ditka after a 3-13 season with minimal contribution from Williams. Furthermore, the whole scenario was more like a circus than a professional sports environment. At one point Williams wore a wedding dress and posed with a suited Ditka for a picture. This was just bizarre and the trade haunted Ditka for perpetuity.