8. Wayne Newton
Wayne Newton, also known as Mr. Las Vegas, found himself in some legal and financial hot water due to his part ownership of the Aladdin Hotel on the Vegas strip. In 1992, Newton filed for Chapter 11 bankruptcy in an attempt to reorganize his finances and take care of an estimated $20 million in debt.
Newton was also dealing with a lawsuit against NBC for libel because he claimed they reported he had partnered with the Mafia in order to purchase the Aladdin. In 2005, the IRS filed a lawsuit against Newton claiming he owed them over $1.8 million in taxes. Despite his long, successful career, Newton has never been very good with his money.
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