Tax season has finally wrapped up more or less for individual taxpayers – well, except for those of you (like me) with extensions. After sorting through my inbox filled with questions from panicked last-minute filers, I decided that what I really needed to post was a “What Not to Do” list. So, enjoy this list of how to get caught, taken from the real-life exploits of those convicted or indicted for cheating on taxes:

1. Fail to file taxes for your brother like you promised you would… when your brother is married to Jennifer Lopez. Marc Anthony’s brother has pleaded guilty to tax felonies for failing to file tax returns for the singer’s income for five years, and for the singer’s companies for four years. Marc Anthony escaped prosecution for failing to file but is responsible for the tax, interest, and penalties due.

2. Gloat about the amount of money that you make – and don’t pay taxes on. No, Richard Hatch laughing it up with Howard Stern about how he didn’t pay taxes on his Survivor winnings (um, Richard, don’t you know that people listen to the radio?) wasn’t the first case of a big mouth landing a taxpayer in trouble. Leona Helmsley might have felt important by claiming “We don’t pay taxes. Only the little people pay taxes.” But her big mouth landed her convictions for conspiracy to defraud the United States, tax evasion, filing false personal tax returns, assisting in the filing of false corporate and partnership tax returns, and mail fraud. Oh yeah, and the title “Queen of Mean.”

3. Grossly understate your earnings. Washington telecommunications mogul Walter C. Anderson plead guilty earlier this year to tax evasion charges for failing to pay more than $200 million in taxes. In 1998, Anderson received than $126 million and yet reported a paltry $67,939 on his 1040. Not to be outdone, Wesley Snipes filed amended 1997 return claiming that his adjusted gross income as originally reported of $19,238,192 was actually zero.

4. Market your tax evasion scheme as “approved by the IRS”. Someone apparently fell asleep during Marketing 101 in college… While I grant you that the IRS probably doesn’t have the resources to investigate every single time someone invokes their name, using a former IRS agent to promote your scheme as approved by the IRS is just begging for trouble. C’mon. Even the IRS knows how to use Google.

5. Make deals with politicians. Just ask Jack Abramoff. He was convicted in 2006 of numerous charges involving his role in accepting kickbacks and bribes in exchange for favors. Even kickbacks and bribes are taxable. And in Mr. Abramoff’s efforts to erase the trail leading back to him, he filed false documents and false entries to financial books and records, and filed a false income tax return in 2002, “all for the purpose of concealing additional unreported taxable income received by or on behalf of” himself.

Of course, all of this pales in comparison to the top way to cheat on your taxes and not get caught…

1. Win a government contract.

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Kelly Erb is a tax attorney, tax writer and podcaster.


  1. Why, oh why is the IRS so interested in going after the middle class when clearly they can collect more from the weathy and corporations. I just don’t get it…

  2. “Why, oh why is the IRS so interested in going after the middle class when clearly they can collect more from the weathy and corporations. I just don’t get it…”

    Lets use the correct terminology, the term the gov does not like to use. “working class” not “middle class” .

    The gov needs to control the working class because its the largest class in terms of population that can revolt.

    Taxation is not about “taxes”. Its about working class population control.

    You are required to keep working until you die. To become a government “dependent” on Social security. You can never revolt as long as you are a intimidated dependent.

    Also, keep in mind the gov owns the printing presses that print the paper. And they print all the paper they need to cover their own expenses. They dont need to collect taxes. In addition to population control they also collect “taxes” to conceal the fraud that there is no real money in circulation. Gold and silver was removed from circulation many years ago. (The real money) That they dont want you to have…

  3. My (female) partner and I,..have a son. She makes more than I. She claims “head of household”, and therefore gets that tax deduction.
    Can I file seperately, as head of well, and get the deduction too…and possibly not get noticed?
    You may respond to my email

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