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The most infamous cases of tax evasion in U.S. history

Sure, no one likes to pay taxes. Tax evasion is a serious crime, but that doesn’t stop some people from trying to get away with it.

Some cases of tax evasion are so brazen that it seems inconceivable that the perpetrator thought they could get away with it. These particular cases of tax evasion have become notorious, and should serve as a warning for anyone who is tempted to evade paying their taxes.

Leona Helmsley

Leona Helmsley was a notoriously vicious real estate mogul who was convicted in 1989 of evading $1.2 million in taxes. She was fined an additional $7.1 million and served 18 months in federal prison.

Tom Daschle

In 2009, Tom Daschle, then a senator from South Dakota, paid over $120,000 in back taxes and withdrew his name from the running for Secretary of State after he failed to pay taxes for several years.

Abbott and Costello

After years of evading taxes, William “Bud” Abbott and Lou Costello, beloved entertainers from the 1940’s and 50’s, had to pay so much in back taxes that they were forced to declare bankruptcy and sell the rights to their films.

Walter Anderson

Walter Anderson, an entrepreneur and billionaire, was convicted of the largest tax evasion case in American history. At the time of his conviction, he owed the United States government nearly a quarter of a billion dollars in back taxes.

Al Capone

Perhaps the most notorious tax evasion scandal of all is that of Al Capone. The Chicago gangster dodged taxes until 1931, when he was convicted of five counts of tax evasion and served 11 years in prison.

Willie Nelson

Country star Willie Nelson was given a hefty fine of $16.7 million for failing to pay his taxes, though he managed to negotiate his payments down to $6 million.

Martha Stewart

The homemaking guru was convicted not only of insider trading, but of evading income taxes on her New York home. She was fined a quarter of a million dollars in back taxes for her crime.

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