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4 Most Famous Tax Evaders of All Time

As the old saying goes, death and taxes are the only certainties in life. Unless you’re a celebrity, that is.

Before we get into this, let’s note the difference between tax avoidance and tax evasion. The former is a way of using legal means to lower the amount owed. The latter refers to the practice of evading taxes in an illegal manner.

In the history of the IRS, there have been plenty of cases that fall into the latter category. Here are the 4 most famous tax evaders of all time.

  1. Wesley Snipes

Say what you want about the Blade star, but he’s a fighter. When accused of tax fraud charges in 2008, he tried every defense. He blamed his advisers, claimed the IRS was illegitimate, argued that he was a nonresident alien, and so on.

In a lengthy trial, though, Snipes was unable to shake off the IRS. He was eventually sentenced to three years in prison for willful failure to file his tax returns. His total debt was in the range of $23.5 million.

  1. Leona Helmsley

Known as the “Queen of Mean,” Helmsley was a famous hotel tycoon. Despite being worth more than $1 billion, she was loath to pay taxes. In an attempt to escape them, she billed millions in personal expenses to her business.

During the trial, Helmsley’s reputation caught up with her. At one point, her former housekeeper testified to Helmsley saying that “only little people pay taxes.” She received a sentence of 16 years but served only 19 months.

  1. Al Capone

In his heyday, Capone was the most powerful mobster in America. He orchestrated a wide variety of illegal acts, from bootlegging to murder. Still, the only thing that the police could pin on him was a tax evasion charge.

See, the 16th amendment in 1916 stated that even illegal income was subject to tax. In other words, Capone could file proper taxes (and admit breaking the law) or risk getting jailed for evasion. The court sentenced him to 11 years in prison.

  1. Willie Nelson

During the ’80s, the legendary musician made a few bad financial decisions. The worst one involved investing money in a tax shelter questioned by the IRS. By the time this shelter crumbled, Nelson had a $16.7 million tax bill on his hands.

In a flash of inspiration, Nelson decided to release an album that poked fun at his plight. He titled it The IRS Tapes: Who Will Buy My Memories? All the profits went to the IRS, which helped Nelson deal with his tax evasion penalties.

More on Famous Tax Evaders

As you can see, very few people can escape the long arm of the IRS.

Keep in mind that this is just a shortlist of the biggest offenders. We haven’t even mentioned other famous tax evaders, such as Pete Rose, Martha Stewart, and Ja Rule. The main takeaway is that crime doesn’t pay — even if you’re famous.

Want to know more about how the rich and wealthy spend their time? Interested in the latest news in the entertainment industry? Check out our Entertainment section!

About RJ Frometa

Head Honcho, Editor in Chief and writer here on VENTS. I don't like walking on the beach, but I love playing the guitar and geeking out about music. I am also a movie maniac and 6 hours sleeper.

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