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  • If You Think Tax Day Was Bad For You

    No one I know enjoys Income Tax Day. For some it is expensive. For some it is a paperwork nightmare. Even those that are going to get a refund already seem to have it spent two times over.

    All in all April 15th is not the best day on the calendar.

    But, before we get all wound up about it here are five people who REALLY had tax trouble.

    Al Capone was sent to Alcatraz.



    He was the most notorious gangster of the roaring 20s, but even famous G-man Eliot Ness could not bring him to justice. He was the original “Teflon Don” and beat criminal raps many times.

    Finally, in 1931, IRS agent Frank Wilson figured out how to bring Capone up on charges of income tax evasion on his illegal income.



    Heidi Fleiss found taxpaying challenging.

    The “Hollywood Madam” as she was called, did not pay taxes on her illegal prostitution ring earnings.

    Her 1997 sentence of 7 years was served partly in Federal Prison and partly in a halfway house.

    Actor Wesley Snipes spent three years behind bars.



    The IRS convicted him of willful failure to file income tax returns. He tried to pay off the $17 million in back taxes with penalties and interest.

    When that failed he went to prison in December 2010 and after serving his time was released in April 2013.

    Willie Nelson has some amazing friends and fans.

    The IRS seized most of his assets in 1990. His friends and fans came to the rescue. They bought back his property, including his home and gave it to him.



    The IRS still wanted him to pay the remainder of the over $16 million in taxes and fines because of his involvement in a crooked tax shelter.

    In one of the governments strangest agreements ever,. The IRS shared in the proceeds of an album that Willie wrote and produced. It was called: The IRS Tapes: Who’ll Buy My Memories?

    The IRS ended up collecting about $3.6 million on that deal.

    When Willie won a settlement with his former accounting firm, the IRS was finally out of his life, at least on this deal.

    Photographer Annie Leibovitz gave up all of her pictures.



    Leibovitz is considered one of the most famous photographers of our time with an extensive list of famous pictures.

    Apparently Annie was not a very good money manager.

     When the IRS caught up with her they wanted over 2 million bucks in unpaid taxes.

    In her settlement, she pledged the copyright to every picture she had ever taken or ever will until her tax debt was paid off.

    Martha Stewart was NOT imprisoned as a tax evader.



    She had already paid $220,000 in back taxes to the state of New York. Her five-month prison sentence was because of her conviction for insider trading.

    So, in this land with some of the most economic personal and religious freedom we have a lot to be thankful for. But we still have to pay our taxes. Consider it a price of admission for being in the United States of America.

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