Miami Celebrities Who Got In Trouble With The Tax Man

April 15, 2022 by Michael Light

Categories: Buying & Selling Real Estate, Celebrity Real Estate

Marc Anthony Performing

It’s tax day! While we’re all stressing our finances and measuring our burden to Uncle Sam, let’s take a moment to remember some Miami celebrities that have gotten into trouble with the tax man.

Marc Anthony

Dios mio! Marc Anthony (also famous for being Jennifer Lopez’s previous husband) got into it with the bureau. In 2007, he got popped with $2.5 million in back taxes, interest and penalties because he neglected to file tax returns for 5 years according to the Associated Press. He settled it up and went back to his latino heartthrob ways, eventually buying and selling the historic Bacardi Mansion in Cocoplum.

Lauryn Hill

Instead of calling Tyrone, the Fugees crooner should have been calling her accountant in the aughts. According to the Department of Justice, she failed to file her tax returns from 2005 to 2007. She pled guilty to tax evasion charges for $1.8 million of income, but also underestimated additional income and tax losses for 2008 and 2009 that amounted to $2.3 million according to the prosecutor.

She explained herself by saying, “When I was working consistently, I filed and paid my taxes. This only stopped when it was necessary to withdraw from society, in order to guarantee the safety and well-being of myself and my family.” She had to withdraw from society a little further when she spent three months in a federal prison.

Ultimately she lost a modest house in South Miami to foreclosure and received an eviction on the house she was renting in New Jersey.

Leona Helmsley

Despite keeping her base in New York, the “Queen of Mean” does have ties to Miami. She was the original owner of the penthouse atop The Palace at 1541 Brickell Avenue that is affectionately known as the Brickell Taj because of its opulent finishes. She had intended to make it her Florida base before her trouble started.

After years of terrorizing employees and contractors, the billionaire was busted for claiming $2.5 million in fake expenses and landed in the big house. It certainly didn’t help that she uttered the most famous quote in tax history in front of one of her terrorized employees. She said, “We don’t pay taxes. Only the little people pay taxes.” That employee testified and to lockdown Leona went.

To double down on her nickname, she left the majority of her fortune to her Maltese dog named Trouble when she passed away in 2007. Queen of Mean indeed.

OJ Simpson

We’ve all heard about OJ Simpson’s legal drama, so maybe his tax problems got brushed under the media rug. Does anyone remember when he got liened up for not paying $180,000 of taxes from 2007-2012? This was during the same time as his prison stint for armed robbery and kidnapping, so we’re guessing the media already had more to talk about with regards to The Juice.

A few years later, his house in Kendall was sold after he lost it to foreclosure.

Lil Wayne

Weezy needed about $14 milli after getting slapped with liens for not paying up for as far back as 2002. It is said that Jay-Z assisted with the mission to help keep him on this side of the clink. After the dust cleared and a series of swatting issues, Lil Wayne sold his Miami Beach mansion on La Gorce Island. We’re not sure which is more annoying. The tax man or the swatting.

Helio Castroneves

Life in the fast lane sometimes catches up to you and the IRS doesn’t stop… but neither can 3-time Indianapolis 500 champ, Helio Castroneves. He has been in trouble with the bureau more than once. In 2009, he was acquitted of six counts of tax evasion for not declaring earnings between 1999 and 2004. Instead, he and his sister allegedly set up a Panamanian shell company to hide the earnings. He cut a $5 million check to the courthouse to clear it up and narrowly avoided jail time. Slick.

The disputed taxes were on income he received from Penske Racing Team between 2000 and 2004 for the use of his name, image and endorsement on licensed merchandising sold by the team. The income – around $15 million – was supposed to have be placed in a Panamanian tax shelter but instead was transferred to a Dutch annuity account and then allegedly not properly disclosed to the IRS for taxation purposes.

Now that it’s all cleared up, racing champ has also competed and won on “Dancing with the Stars.” He currently lives at Marina Palms in North Miami Beach (which is actually on the mainland).

We always like to say that celebrities are just normal people with abnormal jobs, but there’s also the famous song by Notorious BIG and Puff Daddy… “Mo Money, Mo Problems.” Now get that paperwork done and do it right!


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