Seven Tax Dodgers Who Prove It Pays to Pay

The following is a guest post from All Over Tech.

Unless you enjoy running from the law, there’s not much point in evading payment of your fair share of taxes. While some people do try their hand at proving that they can avoid one half of the inescapable combo of ‘death and taxes,’ it’s usually not too long before the IRS comes knocking on your door to wring those dollars free of your grasp.

Many people have already helped the IRS to demonstrate its sleuthing powers. Here are seven whom history showed to have tried to cheat their way beyond payment.

1. Possibly more famous now, decades later, for his tax evasion than for his murderous deeds associated with the St. Valentine’s Day Massacre, Al Capone was a mobster brought down by his failure to file taxes. Of course, one could argue that if Al had filed taxes associated with his activities, such as bootlegging then-illegal whisky, he’d have been imprisoned even sooner!

2. Heidi Fleiss, who managed a prostitution ring that catered to the Hollywood crowd, was in roughly the same position as Mr. Capone – her business was illegal, so reporting income derived from it would have illuminated that fact. Regardless, not paying taxes helped to bring the law into her life.

3. Former Senator Tom Daschle mishandled his taxes to the tune of being $128,000 dollars short on payment as April 15th rolled around. This oversight cost him his nomination for an advanced political position.

4. Perhaps an honest man – it’s always hard to tell when taxes are involved – Willie Nelson famously owed nearly $17 million in back taxes in the early 1990’s. However, with a bit more valid of a reason than some other tax cheats, Willie claimed that his tax firm, then known as Price Waterhouse, had given him bad advice on tax shelters. He sued, the firm settled with him for an undisclosed amount, and Nelson went on to raise money with an album which made light of the entire tax situation. He even starred in some ads on TV which poked fun at the mess, although he stopped short of hawking H&R Block coupons as a method of reducing one’s total tax preparation bill.

5. The Artist Formerly Known as Prince, who is once again known as Prince, was accused of owing over $500 million in property taxes in Minneapolis, Minnesota. With a short history of previous tax non-payments, Prince may make good on the claims to avoid further troubles, but his repeated non-payments make a statement that he’d really rather not be bothered with paying taxes.

6. Wesley Snipes single handedly proved that trying to make a moral or legal objection to the law requiring that taxes be paid is no more effective than simply not declaring income in the first place. His mistake has landed him jail time.

7. Bernie Madoff. Well known for having defrauded investors out of their money, Bernie also didn’t pay taxes on the full sum of his exorbitant illegal profits, either.

There you have it; seven examples from various industries whose antics of tax evasion landed them in hot water. Some will never be free again due to their activities. None will be forgotten.

Comments

[MBTN]

Madoff isn't a good example, because he went to jail for fraud and not tax evasion. I think a better example for the list would be Al Capone, who was incarcerated not for murder or racketeering but for tax evasion! If only he had paid taxes on his ill gotten gains he may have not had to go to prison!

[RB Boren]

It is implausible that Prince - or anyone short of a billionaire - owes $500 MILLION in property taxes. A quick Google check suggests he had a delinquency of $506 THOUSAND as of last Feb 15.

Apparently, he paid up sometime last May.

Somebody, somewhere added three zeros and this error should never have gotten by an editor.

Or a blogger.