When: 1986

After successfully defending his belt in London against Frank Bruno, Tim Witherspoon was promised a $2M purse. In typical King fashion, Witherspoon received a check for $100K. Ouch. Disheartened and confused after years of feuding with King, Witherspoon lost his third defense of the title with a first-round knockout by James "Bonecrusher" Smith.

Following the loss Witherspoon took King and his son Carl to court, suing on the grounds of fraud and conflict of interest to the tune of $25M. During the suit, King froze Witherspoon out of a title bout and dragged the court case out to drain Witherspoon's prime years. Witherspoon eventually settled out of court for $1M, a fraction of his due and potential earnings.