Who can forget the famous gangster Al Capone, also known as Scarface. He spent seven years avoiding the feds as a crime boss, and even more time as a bootlegger. The federal government could not find any substantial evidence to bring him in. However, in 1931, he was finally brought in for tax evasion. He spent 8 years in prison for his $270,000 owed in taxes (over 4 million dollars today).
Martha Stewart is infamous for her insider trading scandal, but also for her back taxes on her New York home. She tried claiming that she didn’t owe taxes on the property because she didn’t live there, but that didn’t fly. She had to pay the money, but she was able to avoid doing jail time on her $220,000 tax bill.
The country singer, Willie Nelson was slapped with a $16.7 million dollar tax bill. His lawyer took that down to $6 million, partially by blaming his accountant. However, he did not have the $6 million on hand, so for the next three years, he created an album entitled “The IRS Tapes: Who’ll Buy My Memories” and used that money, and the money collected from suing his accountant to pay off the debt.
Walter Anderson has been convicted of the largest tax evasion case in US history. He was a businessman in the telecommunications business, as well as his work with various space groups. He hid his income in bank accounts located in Panama and the British Virgin Islands, but eventually, it all caught up with him. He owes over $200 million in taxes, and is still fighting the case from his prison cell.
Jesee Jackson Jr.
This democratic Illinois congressman fraudulently obtained $750,000 from his election campaign, and he and his wife covered up the receipts from their personal use of that money. He was sentenced to 30 months in prison, and his wife spent one year.
H. Ty Warner
22H. Ty Warner, the creator of Beanie Babies hid a lot of over $100 million in Swiss bank accounts in an attempt to avoid paying taxes. He avoided a jail sentence, however, he was forced to pay $16 million in back taxes, and a $53.5 million penalty.