Ricky Williams Trade (1999)

Mike Ditka's 1999 trade for Ricky Williams is a masterclass in franchise sabotage. The New Orleans Saints sent all their draft picks—eight total, including their first-rounder that year—plus first- and third-round picks in 2000 and 2001 to Washington for the running back. Williams rushed for 884 yards as a rookie but never justified the haul; the Saints missed on 10 potential future starters. The trade is slower in payoff than Bill Russell Draft-Night Trade (1956)'s Bill Russell deal, which at least netted 11 titles, while Ditka's gamble left the Saints with a 3-13 record within two years.