Wayne Newton smiling

American entertainer Wayne Newton has been entertaining people since a young age — Biography reports that he started performing professionally by age 6. In the 1960s, the musician began a singing career and also played the banjo, piano, and guitar. His top hits included "Danke Schoen," "Red Roses for a Blue Lady," and "Daddy Don’t You Walk So Fast." But although Newton is revered as a talented musician and one of Las Vegas’ longest-performing musical acts, he has had a long history of money trouble. From lawsuits to property disputes to allegations of animal neglect, Newton has lost millions of dollars over the years.

As Biography reports, part of Newton’s money problems began in 1980, when NBC News reported that the singer was actually a member of organized crime. They reported that he was affiliated with criminal activities linked to the Gambino family and was potentially funding criminal operations through a casino and hotel that he co-owned. The New York Times reports that Newton sued NBC for libel, and in 1986, he won over $19 million dollars in the case. Despite his big win, the sum was reduced to about $5 million and was overturned entirely in 1990 after an appeals court found insufficient evidence to establish that NBC had purposely lied. And his problems didn’t stop there.

Tony Orlando