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Mike Tyson
At his peak, ‘Iron’ Mike Tyson was worth a whopping $300 million. Mike had been raised in abject poverty and used that tough upbringing to inspire himself to a World Heavyweight Boxing Championship at just 20 years old. His early success brought excessive spending that included three Bengali rare white tigers that cost $70,000 each and $1,500 a day to feed and train. His legal woes, divorce settlements, tax evasion, rape accusations, and a prison sentence made Mike file for bankruptcy in 2003.