Year: 1990
What happened: Steinbrenner's nine-year feud with outfielder Dave Winfield began over a contract which Steinbenner mistakenly thought was worth $16 million, but was actually worth $23 million. The feud boiled over when Steinbrenner paid gambler Howie Spira $40,000 to find embarrassing information on Winfield. As a result, Steinbrenner was banned from running the Yankees for two years and Winfield was traded to the Angels later that season.
Complex says: R.I.P., George.