Ten Celebs Who Did Hard Time after Cheating on Their Taxes

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It may be one of life’s few certainties, but that doesn’t mean anyone enjoys paying taxes. Still, we get it done. Every year, April 15 comes around, and Americans fill out their 1040 forms and send them in to Uncle Sam. Most of us do it and move on. But some people really have an aversion to giving up their proverbial pound of flesh. And for those tax cheats, things don’t always end well.

When celebrities and other famous people cheat on their taxes, transgression quickly turns to scandal. In fact, big tax bills and high-profile reputations sometimes make celebrities attractive candidates for prosecution. And when the IRS decides to prosecute, they don’t hold back. In these ten cases, celebs who declined to dole out dollars to the government found themselves facing real prison time.

Related: 10 Weird Things That Used To Be Taxed

10 Wesley Snipes

How Did Wesley Snipes Evade Taxes?

Wesley Snipes has had a storied career. The star broke through in the 1980s with several film roles, including speedy Willie Mays Hayes in Major League. Since then, he’s had star turns in action gigs like the Blade trilogy. In 1998, his body of work was recognized with a star on the Hollywood Walk of Fame. However, a decade later, it all fell apart.

In 2006, IRS officials accused the star of filing false tax returns over several years in the 1990s. They also claimed he failed to file any tax returns for several years. As a result, the government charged him and two others with conspiring to defraud the United States. Two years later, Snipes was convicted of three misdemeanor counts of “willful failure to file federal income tax returns” and sentenced to three years in prison.

The actor appealed the sentence in 2010, but later that year, he reported to a prison in Pennsylvania to serve the time. His appeal eventually made it to the U.S. Supreme Court in 2011, but they declined to take the case. Early in 2013, he was released to a halfway house and completed his sentence a few months later. The problems didn’t end there, though: Snipes still faced a $23 million lien from the IRS. He negotiated it down, and in 2018, a judge ordered him to pay a $9.5 million fine.[1]

9 Mike “The Situation” Sorrentino

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Mike Sorrentino rose to fame on the reality TV show Jersey Shore, which ran on MTV from 2009 to 2012. Known to castmates as “The Situation,” he was responsible for many scandalous moments on air. There was scandal behind the scenes, too, because he wasn’t paying his taxes. In 2014, the U.S. government charged Sorrentino with tax evasion for failing to report nearly $9 million in income.

In court, the government argued Sorrentino and his brother Marc established phony corporations to lighten their tax bill, claim fake personal expenses, and shield income from the IRS. In January 2018, Sorrentino accepted a plea deal on one count of tax evasion. That October, he was sentenced to serve eight months in prison. He began the sentence at a federal prison in New York in January 2019 and was released later that year. His brother caught a tougher case and eventually served nearly two years at a federal prison in New Jersey.[2]

8 Ja Rule

Ja Rule Details Prison Experience: They Respected Me

In 1999, Ja Rule released the hit single “Holla Holla.” More music and acting roles solidified the rapper’s stardom in the 2000s. Along the way, the New Yorker invested in various businesses. And yet taxes have proven difficult. In 2010, the rapper was in state prison serving a two-year sentence for weapons possession when the federal government brought tax evasion charges against him.

Prosecutors claimed Ja Rule failed to pay taxes on $3 million in earnings between 2004 and 2006. In March 2011, he pleaded guilty to the charges, and in July, he was sentenced to a 28-month federal prison term. The judge ruled he could serve the bid concurrently with his prior sentence. When he was released from the state lockup in February 2013, the feds took him into custody to finish the tax term. He was finally released in May of that year.

While he appears to have been paying his taxes ever since, Ja Rule can’t stay out of the news. The rapper was slammed with fraud lawsuits in the infamous Fyre Festival debacle in 2017 but was eventually cleared of wrongdoing two years later.[3]

7 Teresa and Joe Giudice

Teresa Giudice Talks Life Post Prison and How She’s Standing Strong

Teresa Giudice was an instant sensation when she took Bravo by storm in The Real Housewives of New Jersey in 2009. But long before that, she and her husband, Joe Giudice, were engaged in shady business behaviors. Years later, the consequences caught them. In 2013, the Justice Department accused the couple of mail and wire fraud. The government produced proof the pair falsely represented income on mortgage loan applications as early as 2001.

From 2004 to 2008, the government alleged, Joe made nearly $1 million in income but failed to file taxes. And in 2009, the couple concealed Teresa’s TV income in a bankruptcy filing. They were indicted on 39 counts of fraud and tax evasion. In 2014, they pled guilty. Teresa copped to four counts and spent 15 months in federal prison. Joe admitted to five counts and served a 41-month sentence.

Joe, who is an Italian citizen, was immediately deported from the United States following his prison sentence. The two then divorced. Today, Joe remains in Italy. Teresa remarried and continues to lead the reality TV show.[4]

6 Richard Hatch

Richard Hatch Headed to Prison

Richard Hatch made television history in 2000 by winning the first season of Survivor. Marooned on an island with a group of prize hopefuls, Hatch pranced around naked and manipulated his competitors. The openly gay man formed an unlikely alliance with a conservative military veteran that took him all the way to victory. Hatch’s shrewd work on air earned him a spot as one of the most villainous reality TV personalities of all time.

But after his rise to fame, Hatch became a real-life villain to the IRS. In 2006, he was sentenced to 51 months in federal prison after not paying taxes on his seven-figure TV earnings. By 2009, he had served his time and transitioned to supervised release. His tax troubles weren’t over, though. A judge ordered Hatch back to jail in 2011 after he failed to re-file and pay his original tax bill from the Survivor win. After nine more months in jail, Hatch was again freed in December 2011.[5]

5 Pete Rose

Pete Rose finally admits to betting on baseball – Primetime Interview – 2004 – Cincinnati Reds

Baseball legend Pete Rose had quite the rise to fame, followed by a spectacular fall from grace. In his career as a player, the “Hit King” passed old-time star Ty Cobb for MLB’s all-time hits title. Known as “Charlie Hustle,” Rose was renowned for his hard-nosed, unforgiving style of play on the field. But off the field, he had problems.

After retiring as a player, Rose accepted a job managing the Cincinnati Reds. But in 1989, he was banned from baseball for life after he got caught betting on games. A year later, he was convicted of tax evasion. The government claimed he failed to report more than $350,000 in income from memorabilia sales, autograph events, and gambling wins. He was fined and ended up serving five months in prison. After his release, Rose served nine months of probation, spent three more months in a halfway house, and performed one thousand hours of community service. In 2003, after fifteen years of denial, he finally admitted he bet on baseball games while managing the Reds.[6]

4 Leona Helmsley

Fame Is No Protection From Prosecution For Ducking Taxes

Notoriously disagreeable hotel magnate Leona Helmsley was known as the “Queen of Mean.” She leaned into it, too, going so far as to name her beloved dog Trouble. Leona’s husband Harry owned nearly $10 billion in property around the world. The couple lived in an incredible New York City penthouse and maintained several other homes. When it all came crashing down, it didn’t end well.

In 1989, Helmsley was accused of tax fraud. In response, the billionaire enraged the public by saying, “Only the little people pay taxes.” Convicted in 1992, she was fined more than $7 million, ordered to serve four years in prison, and given 750 hours of community service. Federal Judge John Walker slammed Helmsley’s “naked greed” in court and criticized her “arrogant belief that you were above the law.”

She ended up serving 21 months in federal prison. Her post-prison life was controversial too. A judge added 150 more hours of community service to her sentence after it came out that Helmsley ordered her employees to do volunteer work in her place. When the Queen of Mean died in 2007, she left $12 million in her will to Trouble.[7]

3 Sophia Loren

Why Was Sophia Loren Arrested In The ’80s? – Sophia Loren Jailed

Academy Award winner Sophia Loren has had a legendary film career. The Italian actress rose to fame in Cary Grant’s 1958 film Houseboat. Three years later, Loren’s amazing performance in Two Women earned her an Oscar. But the Italian government wasn’t moved when it brought tax evasion charges against her in 1974. Prosecutors claimed she cheated the government out of 5 million lire—at the time US$7,000—in a tax filing.

Loren countered her accountant made an error on her tax return. Years of legal battle raged over the comparatively small sum. In 1982, Loren was ordered to serve 30 days in prison on the charge. She served 17 days and was released to throngs of fans. But the tax caper didn’t end there. Forty years later, in 2013, she was officially cleared of wrongdoing in the case. After four decades, Italian officials finally determined she hadn’t cheated the government. “I am happy,” she told the media. “A saga that has been going on for almost 40 years has finally ended.”[8]

2 Abby Lee Miller

Abby Lee Miller’s tax troubles started before her rise to Dance Moms fame. In 2010, she filed for bankruptcy after being ordered to pay the IRS more than $400,000 in unpaid taxes. The next year, she was hired on the reality TV show, and her financial situation improved. Instead of paying off the tax bill, though, the Department of Justice claimed she created a secret bank account to hide her new salary.

As her reality TV fame continued to grow, the IRS prepped their prosecution. In 2015, the government indicted her on bankruptcy fraud and tax evasion charges. More charges came in 2016 after she allegedly received undeclared cash income from a Dance Moms tour in Australia. By June 2016, Miller reached a deal with IRS investigators and pleaded guilty to lesser tax evasion charges. In May 2017, she was sentenced to serve one year and one day in federal prison, along with two years of supervised release. After ten months of incarceration and some time spent in a halfway house, she was released in May 2018.[9]

1 Lauryn Hill

Lauryn Hill Having Trouble With ‘That Thing’ Called Taxes Again? – Trending Topics

Lauryn Hill was an original member of the Fugees, with Wyclef Jean and Pras Michel. In 1998, her debut solo album The Miseducation of Lauryn Hill exploded onto the music scene. It was an instant hit, winning five Grammys and selling more than 15 million copies. In the years after, Hill turned down what could have been a lucrative future and retreated from the spotlight. She chose instead to raise a family, including five children with Bob Marley’s son Rohan. She wasn’t too secluded to hide from the IRS, though.

The government brought tax evasion charges against Hill in 2012, claiming she failed to pay up on nearly $2 million in earnings between 2005 and 2007. Later that year, she chose to plead guilty to three counts of failing to file tax returns. At her sentencing hearing in 2013, Hill told the court she was “a child of former slaves who had a system imposed on them… [and] I had an economic system imposed on me.” A judge was unmoved and sentenced the singer to three months in prison.[10]

fact checked by Darci Heikkinen

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