Banned for Life
You know things are bad when you're hiring someone to dig up dirt on one of your own ballplayers. In 1981, George Steinbrenner signed outfielder Dave Winfield to a 10-year, $23 million contract, an agreement that would have made Winfield the game's highest-paid player. The only problem: Steinbrenner thought the contract was for several million dollars less. The misunderstanding led to one of the most infamous public feuds in baseball history. In 1990, it escalated to the point where Steinbrenner paid Howie Spira — a known gambler with Mafia connections — $40,000 to find some embarrassing information on Winfield. The move led baseball commissioner Fay Vincent to ban him from the game for life. That "lifetime" ban was short-lived, as Steinbrenner was reinstated two years later.