16 Famous People Who Tried to Outsmart the Tax Man

Despite the glamorous facade of fame, celebrities are not exempt from the harsh consequences of taxes. In fact, there are instances where certain celebrities have been found guilty of evading taxes and cheating the system. In this article, we will explore the stories of 16 celebrities who faced convictions for tax evasion.

Lionel Messi

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Photo Credit: kivnl _ Shutterstock.com.

In 2017, prosecutors in Spain successfully established that soccer star Lionel Messi had utilized offshore bank accounts and companies as a means to evade tax payments.

Consequently, Messi received an initial prison sentence of 21 months. However, he later converted the prison term into a fine, thereby avoiding imprisonment.

Mike “The Situation” Sorrentino

Mike “The Situation” Sorrentino - Kathy Hutchins _ Shutterstock.com
Photo Credit: Kathy Hutchins _ Shutterstock.com.

Along with his brother, Mike Sorrentino served prison time for falsifying their tax documents so they won’t have to pay as much. Unfortunately for them, the IRS caught on to what they were doing, leading the “Jersey Shore” star and his brother to plead guilty in 2018.

Wesley Snipes

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Photo Credit: Andrea Raffin _ Shutterstock.com.

In 2008, Wesley Snipes was sentenced to three years in prison after failing to file his taxes from 1998 to 2001. He tried to appeal the decision in 2010 but lost, leading to Snipes serving nearly three years in prison.

Ja Rule

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Photo Credit: s_bukley _ Shutterstock.com.

To avoid a total tax bill of over a million dollars, rapper Ja Rule did not file any tax returns for his earnings from 2004 to 2008. But instead of keeping that money for himself, he got a 28-month prison sentence in 2011.

Cristiano Ronaldo

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Photo Credit: ph.FAB _ Shutterstock.com.

Ronaldo, another world-class soccer player, was also charged with tax evasion in 2019. According to the Spanish government, Ronaldo did not pay any taxes between 2010 to 2014.

Although the tax fraud charge earned him a 23-month prison sentence, he settled the case and paid a fine of €18.8 million ($20.1 million) instead.

Joe and Teresa Giudice

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Photo Credit: Sam Aronov _ Shutterstock.com.

The IRS went after the “Real Housewives of New Jersey” couple in 2015 when they failed to pay nine years’ worth of property taxes. The Giudices were hit with a tax lien of over $500,000.

Separately, Joe was charged with failing to file a tax return in 2013. He pleaded guilty and served prison time before being deported back to Italy.

Lauryn Hill

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Photo Credit: Ben Houdijk _ Shutterstock.com.

Hill may have withdrawn from the music industry to focus on her family, but it seems she didn’t focus on her taxes. According to the IRS, she failed to pay taxes between 2005 to 2007, with her bill totaling up to $1.8 million.

Her lawyer argued that she eventually paid back that money, but that wasn’t enough to spare her prison time.

Fat Joe

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Photo Credit: lev radin _ Shutterstock.com.

This rapper from New York City didn’t file any tax returns from 2007 to 2010, so he got a four-month prison term. He was supposed to have paid $718,038 in taxes; instead, he ended up in prison, along with a fine of $15,000.

Stephen Baldwin

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Photo Credit: lev radin _ Shutterstock.com.

To the prosecutors’ eyes, Stephen Baldwin didn’t file any income tax returns from 2008 to 2010. Baldwin racked up a tax bill of over $350,000 after interests and penalties.

Baldwin claimed that his accountant had misinformed him and was eager to repay the IRS. He avoided prison by paying back $300,000 of his tax debt.

Richard Hatch

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Photo Credit: CarlaVanWagoner _ Shutterstock.com.

Hatch may have been able to prove his wits in “Survivor,” but it wasn’t enough for the IRS. He failed to file income tax on his earnings and rental properties. However, he maintained his innocence even while serving his prison term.

Heidi Fleiss

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Photo Credit: Featureflash Photo Agency _ Shutterstock.com.

Heidi may have wished to keep the sordid details of her business a private matter, but she couldn’t keep her tax matters hidden. After all, Fleiss was convicted of tax evasion after trying to hide income from her “call-girl” business and property. She received a 37-month prison sentence.

Sophia Loren

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Photo Credit: Denis Makarenko _ Shutterstock.com.

In 1982, Sophia Loren was sentenced to 30 days in jail after the Italian government found her guilty of misfiling her tax return in 1974. Although she only served 17 of the 30-day sentence, she insisted that her accountant, who had since died, made a mistake.

Fast forward to 2013, and Italy’s Court of Cassation finally ruled that her 1974 tax return was correct.

Pete Rose

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Photo Credit: Kathy Hutchins _ Shutterstock.com.

Baseball legend Pete Rose was found guilty in 1990 of failing to report his income from 1984 to 1988.

For his tax bill of $162,000, Rose received a five-month prison sentence, a $50,000 fine, 1,000 hours of community service, and three months in a halfway house.

Abby Lee Miller

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Photo Credit: DFree _ Shutterstock.com.

“Dance Moms” star Abby Lee Miller must’ve thought she could dance her way out of her tax bills, but the IRS didn’t think so. Miller filed for bankruptcy in 2010, only for her to hide her earnings so she won’t have to pay taxes.

The government caught up with her in 2015; in 2017, Miller was sentenced to one year and a day in prison.

Michael Avenatti

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Photo Credit: SCOOTERCASTER _ Shutterstock.com.

Michael Avenatti’s offense isn’t as simple as avoiding his bills. Avenatti actively tried to hinder the IRS from collecting $3 million worth of payroll tax against his coffee business.

Along with other charges, Avenatti earned himself a 14-year prison sentence and orders to pay back $10 million to the IRS and his previous clients.

Joe Francis

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Photo Credit: s_bukley _ Shutterstock.com.

It seems Joe Francis’ legal troubles were also going wild, especially with his tax fraud charge. But instead of deliberately avoiding his bills, he falsely claimed $20 million worth of deductions.

He ultimately pleaded guilty to filing a false tax return and was ordered to pay $250,000 to the IRS.

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