Mike Ditka
In 1999, Ditka became one of the biggest losers in NFL Draft history when he bet the house on Ricky Williams. Williams had a good career with one All-Pro appearance but he wasn’t the player Ditka thought he was. This didn’t stop the former Bears coach from trading all of New Orleans’ draft picks to secure Williams’ arrival.

It was ludicrous because nobody does this for a running back. This was also the first time that a team only selected a single player in the Draft but Williams wasn’t worth it. Ditka lost his job after a bizarre season. Fans remember a bizarre ESPN photoshoot that saw Ditka and Williams dress up as a groom and bride (via Sportskeeda).