Skip to main content
/living

Tax-troubled celebrities, politicians, outlaws

  • Story Highlights
  • Leona Helmsley spent 18 months in prison for tax evasion
  • Famous crime boss Al Capone was brought down by tax charges
  • Former IRS Commissioner Joseph Nunan accused of tax evasion
  • The IRS sold most of Willie Nelson's belongings to pay his tax bill
  • Next Article in Living »
By Stefanie Fontanez
Decrease font Decrease font
Enlarge font Enlarge font
Mental Floss

(Mental Floss) -- We hope your initial reaction to this story wasn't "Wait, when is tax day again?" If you haven't filed yet, you'd better hurry. You don't want to find yourself on this list next year.

art.nelson.gi.jpg

When singer Willie Nelson got behind on his taxes, the IRS sold nearly everything he owned.

1. Spiro Agnew

It should come as no surprise that the right-hand man of "Tricky Dick" Nixon may not have been quite on the straight and narrow. In 1973, just after Nixon and Agnew were elected to their second term as president and vice president, Agnew became the subject of an investigation that alleged the vice president was not only a tax evader, but a money launderer to boot.

As a result of these allegations, Agnew resigned, was sentenced to three years' probation, and fined $10,000. Less than 10 years later, he was in court again. In 1981 he was ordered by a Maryland court to repay the nearly $300,000 he accepted in bribes while in office.

2. Boris Becker

German tennis star Boris Becker was convicted of tax evasion in 2002. Officials say in the early '90s, Becker was trying to avoid paying notoriously high German taxes by living in Monaco, a tax haven. What he forgot to mention was that he also owned an apartment in Munich, which officials claim was his real place of residence.

After a ten-year investigation, Becker admitted to the court that he knew little about German tax laws and may have done something wrong, but that the apartment was only a place to sleep between tournaments. The court was skeptical and forced him to repay the over 3 million euros he owed the government; he was also given a suspended jail sentence. Becker has since sold the Munich apartment and officially moved to Switzerland, another tax haven.

Don't Miss

3. Willie Nelson

Willie Nelson is the poster boy for tax evasion. In 1990, the IRS sent him a bill for $16.7 million dollars in back taxes. Faced with this rather large debt, Willie decided to try and pay the IRS back by releasing a double album entitled The IRS Tapes: Who'll Buy My Memories? The IRS, ever helpful, sped up the process by selling nearly everything he owned.

Lucky for Willie, his friends purchased most of the items and returned them to Willie either free of charge or for a nominal fee. He managed to pay back the IRS in only three years.

4. Darryl Strawberry

He was the baseball's number one draft pick in 1980 and the Rookie of the Year in 1983, but talent, fame and fortune couldn't keep Darryl Strawberry out of trouble with the law.

In addition to allegedly breaking the nose of his first wife, Strawberry was accused of hitting his pregnant girlfriend, violating his probation, soliciting sex from an undercover police officer, possession of cocaine, and a hit-and-run while on painkillers. If that wasn't enough to keep him busy, in the late 80s, he failed to pay taxes on income he made from autograph and memorabilia shows (The exact same thing Pete Rose would go to prison for in 1990).

Strawberry was convicted of the tax charges in 1995 and ordered to pay back more than $450,000 in back taxes. Allegedly, he didn't. The government sued again, and in February of this year, Strawberry was ordered to pay the more than $430,000 he still owes for not having given the government the money they were due.

5. Richard Hatch

The first winner of the American version of Survivor was well known for his lack of clothing on the show, as well as for his lack of paying his taxes. Hatch was convicted in 2006 of failing to report his over $1 million in winnings as a result of the show. In court, Hatch's lawyer said his client was "the world's worst bookkeeper" and that Hatch just forgot to report it. The judge didn't buy it and now Hatch is serving time in prison for his forgetfulness. He is expected to be released in October of 2009. Hopefully Hatch has learned this very valuable lesson. It's hard to hide a million dollars from the government, especially when an estimated 51 million people watched you win it.

6. Leona Helmsley

In 1989, the late "Queen of Mean" was convicted of tax evasion relating to renovations she and her husband were making on their $11 million estate. During testimony, Helmsley's maid quoted her as saying "We don't pay taxes. Only the little people pay taxes," an allegation she would later deny.

She would spend 18 months in prison for cheating the government out of more than a million dollars. Helmsley passed away in August of 2007. At the time of her death, her estate was worth over $4 billion -- $12 million of which she left to her white Maltese, Trouble.

7. Joseph Nunan

He's not exactly the most high profile tax evader in the world, but Joseph Nunan may hold the record for being the most ironic of our alleged cheaters. That's because Nunan was a former commissioner of the IRS (1944-1947) and in 1952 was busted for tax evasion. What sort of horrible fraud did he commit? Apparently Nunan won an $1,800 bet that Harry Truman would win the election, but forgot to claim his winnings on his taxes.

8. Wesley Snipes

In 2006, the famous actor was indicted on conspiracy charges that alleged he falsified past tax returns. (He claimed he was due a refund of nearly $12 million.) The government alleges that Snipes claimed the refunds using the "861 argument," which states not all income is taxable. They also accused him of failing to file tax returns from 1999 to 2004.

He went to court earlier this year and was acquitted of the major conspiracy charge, but the court found him guilty of the three lesser misdemeanor charges for failing to file his tax returns. He faces up to three years in prison and will be sentenced on April 24 of this year.

9. Al Capone

As head of the Chicago underworld during the 1920s, Al Capone was involved in some less than legal activities. Dubbed Public Enemy No.1, he became the focus of an intense investigation by the FBI. It was tough going for law enforcement; Capone owned nothing in his own name and used front men, making it almost impossible to get the charges the government threw at him to stick. That is, until a stack of paper would rat him out.

During a routine raid of one of Capone's warehouses, Eliot Ness and his "Untouchables" stumbled across a desk drawer containing account information for the mobster. It would be just enough to seal his fate.

The man responsible for Chicago's then-illegal alcohol trade, the corrupting of local government and the St. Valentine's Day massacre wouldn't be taken down by some lousy capital murder charge. The king of Chicago would be done in by paperwork. Capone once allegedly said "The income tax law is a lot of bunk. The government can't collect legal taxes from illegal money." But this time, the government did collect.

After his trial in 1931, Capone was ordered to pay $80,000 dollars in fines and was sentenced to 11 years in prison. He would serve only six and a half of those years, but they took their toll. While locked up, numerous attempts on his life were made and the syphilis he contracted during his youth would rapidly progress, leaving him a shadow of his former self. Suffering from syphilitic dementia, he was released 1939 and after another stint in jail, would live out the remainder of his days with his family in Florida. E-mail to a friend E-mail to a friend

For more mental_floss articles, visit mentalfloss.com

Entire contents of this article copyright, Mental Floss LLC. All rights reserved.

All About Income Taxes

  • E-mail
  • Save
  • Print
Home  |  World  |  U.S.  |  Politics  |  Crime  |  Entertainment  |  Health  |  Tech  |  Travel  |  Living  |  Money  |  Sports  |  Time.com
© 2014 Cable News Network. Turner Broadcasting System, Inc. All Rights Reserved.