8. Joseph Kennedy: $500 million
While you wouldn’t have thought that someone related to the former President of the United States would necessarily involve themselves in criminal affairs, Joseph Kennedy couldn’t help himself when he allegedly helped a gathering of people smuggle alcohol over to the USA. This supposedly went on for years, and some even believe that Joseph might have had his fair share in other illegal businesses too, but fortunately for this Kennedy, he was never charged with the crimes he was alleged to have committed.
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