Sports
Entertainment
Business Moguls
Pop Culture
100
Famous for Baseball
Tax Bill: $410 K
Penalty: base balls’ career hits leader served 5 months in prison in Illinois.
Pete Rose
100
Famous for acting in films like Blade and Demolition Man
Tax bill: $7million
Penalty: 3 years in prison
Wesley Snipes
100
Before the home and garden guru was sentenced to prison for insider trading in 2004, she was forced to pay $220,000 in back property taxes and penalties to the State of New York for her home there. She tried claiming that she didn't owe taxes on the property because she didn't spend much time there.
Martha Stewart
100
The former Representative (D–IL) pled guilty on Feb. 20, 2013 for fraudulently obtaining $750,000 of funds from his election campaign, and his wife, Sandra, pled guilty to one count of tax fraud for covering up the receipt of those funds from 2006 to 2011. He was sentenced to 30 months in prison, while his wife was sentenced to one year.
Jesse Jackson Jr.
200
On Feb. 9, 1995, the former New York Mets outfielder pleaded guilty to a single count of tax evasion and was sentenced to three months in prison and three months of house arrest. He acknowledged that he had not paid more than $100,000 in owed federal taxes after knowingly failing to report more than $350,000 in income from autograph shows and other promotional appearances from 1986 to 1990. He was originally indicted on three counts of evasion and conspiracy.
Darryl Strawberry
200
Famous for country music
Tax Bill: $16.7million
Penalty: avoided prison by blaming his accounting firm and paying off the IRS by releasing a double album titled “The IRS Tapes”
Willie Nelson
200
The Chicago gangster managed to avoid the feds until 1931, when he was indicted and found guilty of five counts of income tax evasion. After failing to bribe those involved in his hearing, he was sentenced to 11 years in prison and heavily fined. One of his prison terms was spent in the then-new Alcatraz prison.
Al Capone
200
The former Democratic senator from South Dakota "unintentionally" failed to pay taxes on the free use of a car and driver for several years, for which he paid $128,203 in back taxes and $11,964 in interest in January 2009. He said that he had become aware in 2008 of the fact that the service valued at more than $250,000 over three years.
Tom Daschle
300
The IRS filed a $1.7 million tax lien against the World Cup champion skier and her estranged husband, on April 2, 2012. She responded quickly and announced via Facebook that the lien was paid off before the end of that month. She claimed to be completely unaware of how her taxes were being managed. She said, "Not being in control of my finances and relying on someone else who you believed had your best interest at heart was a mistake and one I will not make twice."
Lindsey Vonn
300
The comic duo of "Who's On First?" fame split up and became bankrupt when the IRS charged the two for so much in back taxes in 1956 that they had to sell their homes and the rights to many of their films.
William "Bud" Abbott and Lou Costello
300
The billionaire creator of Beanie Babies toys was sentenced to two years' probation, 500 hours of community service and a $100,000 fine on top of paying a $53 million civil penalty and about $27 million in back taxes on Jan. 14, 2014, for evading taxes on a gross income of more than $24 million, which was hidden in Swiss bank accounts. The tax evasion charge he received carried a maximum penalty of five years in prison with a $250,000 fine, but the judge did not sentence Warner to prison, saying that it was best to allow him to "continue his good works."
Ty Warner
300
“The Situation” and his brother were indicted with a tax fraud charge in April of 2017. According to federal prosecutors, the brothers filed fake tax returns and claimed luxury cars and clothing purchases as business expenditures.
Charged with tax evasion, avoiding reporting requirements, and providing false records. However, it wasn’t the first time they’ve been in tax trouble. Previous allegations against the pair included a refusal to pay taxes on an approximate $8.9 million earned from 2010 – 2012. According to the U.S. attorney’s office for the district of New faced 10 years for structuring bank deposits, 5 years for tax evasion, and 20 years for obstruction.
Michael Sorrentino
400
Former football star - Was serving a 33 year prison sentence for armed robbery and kidnapping, but his troubles don’t stop there. Has been in tax trouble since 2000, and his latest tax lien finally put him over $500,000 in debt to our government.
O.J. Simpson
400
Kimberly Denise Jones (born July 11, 1974 or 1975), is an American rapper, songwriter, model, and actress. Born and raised in Brooklyn, New York. Ran into problems with the IRS in late 2009, owing money every year from 2002-2009. TMZ reported that her total owed was over $1,000,000.
Lil Kim
400
Big name design duo, were part of a large scale tax scandal dating back to 2007. In June 2013, the pair was convicted of failing to pay taxes for their company in Italy. Prosecutors estimated $50.7 million was the amount owed in 2004 and 2005 from their sale of the company’s main brands to Gado, a Luxembourg-based company. Though the high court in Italy found the duo not guilty, two lower courts had found them guilty of “sophisticated tax fraud”, using Gado as a means to deduct taxes. An 18 month term had been imposed upon them with prosecutors advocating for even more jail time. In March of 2014, an unexpected turn of events occurred where a prosecutor argued that Gado was indeed a real company.
Domenico Dolce and Stefano Gabbana
400
Tried to steal the Declaration of Independence in National Treasure, but he also tried to steal a large sum of money from the government when he didn’t pay his taxes. Facing tax troubles amounting to nearly $13 million dating back to 2002. Unfortunately for him, National Treasure was only a movie, because that treasure could have definitely helped pay off his tax bill.
Nicholas Cage
500
June of 2017 saw another tax scandal rise to center stage. Celebrities including Gary Lineker, this famous soccer star, and Ant and Dec failed in their attempts to create tax deductions in their investments with a company called Ingenious. The original thought was to invest heavily into big-budget movies such as such as Die Hard 4.0, The Life of Pi, and Avatar. Each of these stars invested at least £100,000 in the scheme, totaling £700 million. Ingenious then recorded losses adding up to more than £1 billion, which they believed could be offset against other earnings to reduce tax. The treasury caught wind of the situation and cracked down on these “aggressive and contrived” tax avoidance schemes by issuing demands to Ingenious clients. Though the charges were appealed by these celebrities, a tax tribunal stated that their investments were not “allowable deductions”.
David Beckham
500
In July of 2017 Earl Simmons was arrested and charged with tax fraud. New York federal prosecutors claim he had created a long-term scheme to hide millions of dollars in income from his earnings of more than $2.3 million. Simmons avoided taxes by creating bank accounts in others’ names, eschewing personal bank accounts, and covering expenses with cash. An approximate $1.7 million was said to be the remaining tax balance.
The rapper DMX
500
Famous for business
Tax Bill: $7.1 million
Penalty: the Queen of mean served 21 months of a 4 year sentence. She famously stated “We don’t pay taxes. Only the little people pay taxes.”
Leona Helmsley
500
This eccentric, flamboyant, and energetic fitness guru owes the IRS about $24,000 covering Tax Years 2007-2015.
Richard Simmons
