Criminal Justice Degrees Guide

10 Most Surprising People Caught Cheating On Their Taxes

You’ve no doubt all heard the story of Al Capone, the notorious American mob personality that was finally caught because of tax evasion. He coined the audacious statement, "the government can’t collect taxes on illegal money." And whether you’re involved in organized crime or not, there’s nothing surprising about cheating on your taxes. If you’ve ever worked a job that’s mostly tip-based, for example, you’ve probably done it. But you’d better believe that some of the richest and most ethically turned people have been caught red-handed cheating on their taxes. And here they are. Check out these 10 most surprising tax cheats, and be sure to correctly file before April 17th!

  1. Walt Anderson

    Convicted of the largest tax evasion in the history of the United States, telecom executive Walt Anderson maintains his innocence on the web and beyond. Hiding more than half a billion dollars in offshore accounts in places like Panama and the Virgin Islands, the most surprising thing about this perpetrator is that he continually and publicly denies that he’s ever done anything wrong. While it’s a bum wrap to catch so much flak for not paying the government what it’s owed, it’s absolutely no surprise that he was caught and convicted, and that he’s been put in jail. As of March 2011, the executive’s tax bill came in at $248,962,929 with interest. Anderson’s continual hubris, even from behind bars, is a gentle reminder to even the most honest of working stiffs that once you’ve been caught in a lie, it’s much more advantageous to your reputation (and, of course, your sanity) to swallow your pride and admit to the wrong. Although he was offered a bit of absolution when the government had to retract $100 million of his fine due to a typographical error in his plea agreement, Anderson’s reputation is still in the toilet. The tax cheat is currently scheduled to be released from prison on Dec. 29, 2012 — just in time for a new fiscal year.

  2. Leona Helmsley

    We don’t pay taxes. Only the little people pay taxes.
    Prior to her death in 2007, Leona Helmsley had long been called the "Queen of Mean," and it’s no surprise that the sourpuss real estate mogul got caught shirking her tax duties to the government. What’s surprising about her case, however, is that she — as with Walt Anderson — never once showed an ounce of remorse for her deeds, or even a hint that she’d had a much-needed reality check. Although she is clearly American aristocracy, the billionaire tax cheat seemed to completely forget that her royal title was a social status, not a monarchical one. Originally sentenced to almost 20 years in prison, the mogul and meanie only did time for 18 months. Having very few friends, she lived the remainder of her days in a penthouse apartment overlooking Central Park — and left her $5 billion fortune and a trust to her dog. You can watch the entire 1990 Lifetime-style movie of her life, below. Bonus: Suzanne Pleshette!

  3. Billy Zane

    No wonder California’s broke — they can’t get their famous residents to pay any of their taxes. And while it’s not surprising that many celebrities are too busy, stupid, or unethical to pay their entire share of the tax pie, one of the most surprising tax cheats ever is Billy Zane. The Titanic and Tombstone actor has upped his acceptance of bit parts and non-headlining roles after the news was released that he owed more than $100,000 to the state of California. Now that’s acting your way out of a hole.

  4. Richard Pryor

    Sentenced to 10 days jail time for not paying his taxes in 1974, the comedic genius served the jail time in Los Angeles County. His reason for failure to remit? "You know, I forgot," Pryor said to the judge. Although his jokes and tropes changed American comedy forever, no one can avoid their debt to Uncle Sam.

  5. Rev. Dr. Martin Luther King Jr.

    And speaking of people who changed America, there’s no tax cheat more socially influential to the fabric of the country that Dr. Martin Luther King Jr. The veritable American saint put his thumbprint on the world, pioneering the civil rights movement and preaching non-violence throughout his public career, cut short by his assassination in 1968. But even a saint can’t be perfect — in 1960, the good reverend was brought in on two warrants from the state of Alabama for signing fraudulent tax returns in 1956 and 1958. With an all-white jury (in 1960 Alabama, no less), King was acquitted with the help of Brown v. Board of Education litigator William Robert Ming, but the press continued to draw attention to King’s tax woes.
    Fun Fact: Though it’s probable that the inspirational leader didn’t actually cheat on his taxes, his lawyer (Ming) was sentenced and jailed in 1970 for tax evasion, even though the litigator had paid all back taxes and fines. Maybe the good old days really weren’t that good, especially for the good guys.

  6. Janice Dickinson

    How surprising is it, really, that Janice Dickinson is in trouble with the IRS for the second time in as many years? Originally having liens over $200,000 filed against her for unpaid taxes, this supermodel O.G. now owes $43,000 more, according to reports from January 2012. Can the former alcoholic and catwalk strutter turned reality television trainwreck pay off all of her debts by November 2012? Forget the upcoming Presidential election — we’re sure that PerezHilton trolls and VH1 watchers alike will prefer to tune in to this news cycle. And that comes as no surprise, although it really, sadly should.

  7. Pedro Espada

    You wish it would come as a shock that a politician illegally re-routed money and ended up getting caught for cheating on his taxes, but you would be sorely mistaken. The former majority leader of the New York state senate was charged in late 2011 with rerouting charitable monies to his family, political cohorts, and friends. His trial is ongoing, and getting major press nationwide, and his son has also been indicted in the crimes. One of his accountants shared an April 15, 2010 e-mail from Espada, that included the line, "just wanted to make sure you filed my extension and I’m not going to jail." Time will tell, Senator. Time will tell.

  8. Lil Wayne

    How much more can you get out of your FREE WEEZY shirt, anyway? It’s a bit surprising that one of the world’s most outspoken gangsters wouldn’t just take care of his business so the government would be off of his back. And it will be infinitely more surprising if he’s arrested for tax evasion instead of illegal gun possession. (Maybe he took a lesson from famed mob boss Al Capone?) The IRS branch in Miami, Florida filed a $5.6 million lein against the hardcore rap superstar in early 2011. The star told Interview magazine (founded by Andy Warhol, by the way) in the same year that he intended to make $50 million last year. Not just "generated $50 million," the rapper added, "but actually banked $50 million." In 2010, the IRS filed a lien against Weezy for $1.1 million, allegedly for back taxes owed from 2008-2009.

  9. Wesley Snipes

    Owing almost $3 million in back taxes, the Blade actor (best known in cult communities for his drag role in To Wong Foo) was arrested in 2006 with two others for conspiracy to defraud the United States. First claiming that he was a "non-resident alien," the American born actor was acquitted of the original charges (his cohorts were convicted), but still managed to rack up a three year prison sentence for willful failure to file his federal tax returns. He began serving time in December of 2010, and the Supreme Court has refused to hear his appeal.

  10. Nicholas Cage

    Nicholas Cage just can’t pull it together these days, can he? The stalwart star of many classics (Raising Arizona, anyone?) and classic flops (Ghost Rider; Ghost Rider 2; Ghost Rider 2 3D) paid off a $14 million dollar debt in 2009. Immediately after paying off his taxes (and beginning his descent into the dregs of Cage-d weirdness) that year, he was served another tax lien from the state of California, this time for $3.8 million. So it’s not just the quality of his work that’s suffering, as you can see. The super strange movie star has his share of surprising problems, on screen and off.