Infamous A-Listers and CEOs Who Dodged Their Taxes

Matthew Libassi

Tax Dodging Celebs and Business Icons

You can run, but you can’t hide! When Uncle Sam comes to collect, even A-list celebrities and powerful CEOs have to cough up the tax dollars. Here is a roundup of the most infamous tax dodgers to-date.



Michael “The Situation” Sorrentino

MTV’s “Jersey Shore” star Michael “The Situation” Sorrentino and his brother Marc have been charged with allegedly filing fake tax returns and listing luxury cars and expensive clothes as business expenses. The pair previously pled not guilty to similar charges in 2014. If convicted “The Situation” may face up to 20 years in prison.



Dolce and Gabbana

Famed designers Domenico Dolce and Stefano Gabbana were up to their neck in tax problems for years. In 2013 the designing duo was convicted of failing to file tax returns for their company in Italy. They owed approximately $50.7 million for 2004 and 2005. They were also facing up to 18-months of jail time for running a “sophisticated tax fraud” scheme involving the sale of an allegedly fake company, Gabo. Dolce and Gabbana were vindicated in October of 2014.



Willie Nelson

Up in smoke! Country icon Willie Nelson was slapped with a $32 million bill for back taxes in 1990. He settled for nearly $17 billion, however Nelson was unable to pay. The IRS seized most of his assets leaving the country crooner with a $15 million tax bill. To raise funds, the IRS tapped into Nelson’s musical prowess and allowed him to record the album “Who’ll Buy My Memories? (The I.R.S. Tapes)” to raise funds.  Finally in 1993, Nelson signed his last check.



Ty Warner

He created the collectible and adorable Beanie Babies and founded Ty Warner Hotels and Resorts. H. Ty Warner was also convicted of tax evasion in January 2014 when he failed to report $24.4 billion in gross income to the IRS from 1999 to 2007.  Warner’s net worth is approximately $1.7 billion and he was forced to pay a civil penalty of $53 million and $14 million in back taxes, however he didn’t serve any jail time.





Al Capone

His vault wasn’t the only thing empty, so were his tax forms. Famed Chicago gangster Al Capone served one of the longest prison sentences for tax evasion in 1931. Capone was found guilty on 5 counts of income tax evasion and sentenced to 11 years in prison. 



Christie Brinkley

Model and former wife of “Piano Man” Billy Joel, Brinkley had a tax lien filed against her in 2011. She failed to pay $500,000 in taxes on her $30 million Bridgehampton home. Brinkley was quoted as saying “I was surprised to learn of the tax lien filing and took immediate steps to rectify this matter, which for most people is a private matter.” She paid her bill.



Martha Stewart

Stewart has had her fair share of run-ins with the law, including a host of back taxes that caught up with the lifestyle guru. Martha Stewart owed $221,677 in back income taxes from 1991 to 1992. Stewart tried arguing that she only spent a half a year in New York and didn’t owe a dime. The judge said that wasn’t a “good thing.”



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