16 Infamous Tax Cheats

  • What Money?

    We’re sure many of you are knee-deep in tax forms right now, and probably feeling a bit frustrated by the whole process. So, if you feel like taking a few minutes away from staring at your W-2, take a look at our list of some of the most notorious tax cheats of all time. Some of the individuals and businesses on this list you already know, while others you’ve probably never heard of. But most tax cheats share at least one thing in common: They are rich. As past studies have shown, wealthier people are more likely to misreport their income and underpay their taxes. As a side note, if you know someone who isn’t on this list but is a big tax cheat, you might want to (strongly) consider ratting them out. The Internal Revenue Service offers a pretty substantial reward for doing so – up to 15% of the amount owed in back taxes. The award caps at a generous $10 million. Just be careful that you don’t then underpay your own taxes after you get all that money, or someone will come after you. It’s karma, man. Photo Credit: Getty Images
    Nicolas Cage
  • Nicolas Cage

    Nicolas Cage gets the award for current celebrity guilty of the most stupid money mistakes. Last year, Cage lost not one but two of his homes in New Orleans to foreclosure after he listened to some bad investment advice.  And, to make matters worse, he still owes $6.2 million in back taxes dating back to 2007 and other smaller federal debts dating back to 2002. What’s a celebrity to do except sell off more of his homes to make up for lost money? Photo Credit: Tostie14
    Wesley Snipes
  • Wesley Snipes

    Wesley Snipes had a very public fall from grace in 2006 when he was sentenced on charges that he had failed to pay as much as $15 million in taxes for almost a decade.  Initially, Snipes, a popular actor, responded by sending a letter to the IRS in which he claimed he was actually a “non-resident alien” of the U.S. and argued that the IRS aims to “terrorize, enslave, rape or pillage” taxpayers. That’s probably not the best way to say you’re sorry. Photo Credit: Wikimedia.org
    Dionne Warwick
  • Dionne Warwick

    Dionne Warwick may be a beloved American singer, but she is also one of the 10 worst tax cheats in California, owing $2.2 million. Warwick’s spokesperson has said she is currently working to make good on her debts, though it’s unclear how much, if any, has been repaid so far. Photo Credit: Wikimedia.org
    Winson T. Lee
  • Winson T. Lee

    He may not be a household name, but Winson T. Lee puts Warwick and all other Californians to shame. According to the state’s most recent list of delinquent taxpayers, Lee owes nearly $10 million ($9,940,513.49, to be exact.) This debt dates back to 2002. So, who exactly is this man? According to CNN, Lee is a “self-described investor and owner of apartments.” When reached on the phone last year, Lee told CNN that he has failed to file tax returns for more than a decade because of what he calls his “illness.” “I think my illness is the inability to deal with this, you know, the tax season, every year and to deal with the mound of paper that one needs to go through in order to prepare their tax returns.” Photo Credit: alancleaver 2000
    Duane Chapman
  • Duane Chapman

    Duane Chapman is better known as Dog the Bounty Hunter, and starred in a reality show of the same name. But Chapman also has a pretty big price on his head. As of last year, he reportedly owed more than $2 million to the IRS, though his accountant claimed much of this had actually been paid off. According to Wallet Pop, Chapman had also dealt with the IRS in the mid-‘90s for unpaid taxes. Photo Credit: dogthebountyhunter.com
    Leona Helmsley
  • Leona Helmsley

    Leona Helmsley was a billionaire real estate mogul who is considered by many to be one of the more arrogant people to have walked the Earth. In 1987, Helmsley was convicted of evading $1.2 million in federal income taxes (though she actually underpaid her taxes by $4 million.) At the time, Helmsley was in her 80s, but she was still sentenced to four years in prison.  At her trial, one of Helmsley’s housekeepers testified that the billionaire had once claimed she didn’t pay taxes because “only the little people pay taxes.” Too classy. Photo Credit: Wikimedia.org
    Martin Luther King Jr.
  • Martin Luther King Jr.

    Yes, even this man of peace was charged with falsifying his state tax returns in 1956 and 1958. But he was ultimately acquitted, and as Wallet Pop notes, the charge itself was probably just a sham to discredit King and the civil rights movement. Photo Credit: Wikimedia.org
    Bernie Madoff
  • Bernie Madoff

    According to the most recent list of tax delinquents in New York, Madoff currently owes $984,280.86 in back taxes. Let’s be honest, it probably would have been a much bigger surprise if he didn’t owe a ton of money. Photo Credit: philectric
    O.J. Simpson
  • O.J. Simpson

    Speaking of people with big problems, it turns out that O.J. Simpson is also an infamous tax cheat. Simpson made the list of California’s worst tax delinquents back in 2007, owing the state $1.44 million. However, Simpson has bigger problems to worry about besides paying his taxes. Since he is currently in prison for armed robbery he does not have to pay back that debt for the time being. Photo Credit: Wikimedia.org
    The Reilly Family
  • The Reilly Family

    Don’t know the Reilly family? Well, officials in Rhode Island certainly do. William and Marielle Reilly reportedly owe the state $1.1 million, according to the state’s list of tax delinquents. In an interview back in 2008, William Reilly claimed the state was trying to get tax money on income he’d earned since leaving Rhode Island for Florida several years earlier. Still, the Reillys remain at the top of the list in Rhode Island. Photo Credit: cookiepediachef
    Al Capone
  • Al Capone

    Back in 1931, Al Capone, the famous mobster, was sentenced to 11 years in prison for failing to pay $215,000 in back taxes (that would be more than $3 million today, adjusted for inflation). He was released seven years later after he’d somehow managed to pay that all back, in addition to other fines. Photo Credit: bradleygee
    Pamela Anderson
  • Pamela Anderson

    At the end of last year, the IRS announced the Baywatch babe owed $1.7 million to the federal government in addition to the $250,000 she owed the state of California. Anderson has chalked up her debt to “mistakes” made in calculating her taxes. Photo Credit: Wikimedia.org
    Abbott and Costello
  • Abbott and Costello

    Who’s on first? Apparently the tax man. The IRS came after the famous comedy duo back in the 1950s to collect their back taxes, reportedly bankrupting both men. Some have even argued that this was the ultimate reason they split up. Photo Credit: Amazon.com
    The U.S. Post Office
  • The U.S. Post Office

    As we reported recently, federal employees are also guilty of some dubious tax returns. Of all the federal employees, U.S. Post Office workers are the biggest tax cheats. They currently owe $257 million in unpaid taxes. Photo Credit: Wikimedia.org
    Maryland Tax Evaders
  • Maryland Tax Evaders

    Maryland, like several other states, publicizes a list of tax delinquents in an attempt to shame them into paying their debt, and apparently it’s working. State officials estimate they will make back about $3 million of the $8 million owed by the top 50 tax delinquents. But they may have to wait a while longer to get back money from Frank L. Tarbert. Tarbert owes $127,752 in taxes, earning him a spot on Maryland’s top 50. But in a recent interview with the Baltimore Sun, Tarbert said he was in debt “cause I ain’t been working.” He said he would pay his taxes “if I can get to it,” however he added that probably wouldn’t happen “too soon.” Photo Credit: Scaramouche
    Not Just An American Problem
  • Not Just An American Problem

    Obviously, it’s not just Americans who sometimes fail to pay their taxes. Mikhail Khodorkovsky, the Russian oil baron, was once worth an estimated $15 billion. Then the Russian government arrested him on tax fraud and evasion charges. He has since claimed that these charges were based more on politics than reality. Photo Credit: Wikimedia.org
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