George Steinbrenner

Before Steinbrenner made a name for himself when he acquired ownership of the New York Yankees, he owned a small basketball team called the Cleveland Pipers back in 1960. By 1962, as a result of Steinbrenner’s direction, the entire franchise went bankrupt.

That stretch of failure seemed to follow Steinbrenner when he took over the Yankees in the 1970s, as the team struggled with a number of setbacks and losses throughout the 1980s and 1990s. However, despite public fear and criticism of Steinbrenner’s controversial decisions, eventually he led the team to an amazing comeback, with six World Series entries between 1996 and 2003, and a record as one of the most profitable teams in Major League Baseball.

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