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Why Do Mob Bosses Get Busted for Tax Evasion?

It can sometimes feel a bit strange that the bosses of organized crime syndicates get glorified in the media and popular culture. And while the movies might have you believe that the mafiosos are an evil, murderous bunch, interestingly, they seem to go down for tax evasion more often than whacking their rivals.

One might expect that after Al Capone got busted for tax evasion, others involved in organized crime would've wised up and hired the best accountants money could buy. But recently, Salvatore "Sallie" Demeo was arrested and charged with tax evasion related to some alleged real estate and other business dealings he tried to keep in the family.

A Fool Thinks Himself to Be Wise

When it comes to organized crime, or any business that deals in large sums of money, one of the big legal problems that will be encountered is accounting. There are quite a few ways to reduce tax liability, and hiding large sums of money is really not a good one, especially if those sums come from legitimate sources like a real estate transaction.

The usual problem organized criminals face is using the money gained from illicit activities on legitimate things. The case against Mr. Demeo is a little different though. It stems from a series of legitimate real estate transactions where he sold shares in various properties he inherited from his father. Allegedly, he attempted to hide some of the proceeds. In the process, the IRS claims that he ducked a little over $350,000 in taxes.

But a Wise Man Knows Himself to Be a Fool

Demeo, over the past few decades has found himself in quite a bit of criminal legal trouble. In 1996, he was involved in an armored car heist and bank robbery, and after evading authorities for a year, he was caught, convicted and served nearly five years. 

He remained trouble free for nearly a decade, until recently. In addition to the tax evasion charges he is currently facing, Demeo was put on probation earlier this year in connection with an illegal offshore gambling ring. If convicted on these newest charges, Demeo could find himself back in custody, particularly as another conviction is not likely to play nicely with his current probation.

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