Billy Joel
Billy Joel, $30 million
Billy Joel hasn't had the best luck with his managers: He was tied to his first by contract for 15 years, even when the two weren't working together. Then he married his second manager, but in their divorce, she took half his assets. Joel hired his ex-brother-in-law, Frank Weber, whom he later sued for $90 million — $30 million for fraud and misappropriation of funds, and another $60 million for punitive damages. While reports are that he has had to file for bankruptcy three times, it was Weber who pleaded poverty — although Joel did have to go on tour to make up for the millions lost. He ultimately settled for $8 million.
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