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 (respectively), 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 the allegations, Agnew would resign as Vice President and would be sentenced to three years probation and fined $10,000. Less than 10 years later, he would be 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.
3. Willie Nelson
4. Darryl Strawberry
5. Richard Hatch
6. Leona Helmsley
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
9. Al Capone
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.
Stefanie Fontanez is an occasional contributor to mentalfloss.com. She also designed this t-shirt.