Tax Loopholes Throughout History

By: Professor B. Slick, Esq.

In ancient Mesopotamia, the Sumerians developed the first known tax loophole:

The "Gift Tax Loophole": A wealthy merchant would give a small gift to the local king, and in return, the king would exempt their estate from taxation.
The Loophole Lawsuit of 3000 BCE: A Sumerian merchant was sued for exploiting the Gift Tax Loophole, but the court ruled in their favor.

In ancient Rome, the Roman Empire developed the "Villa Loophole": wealthy Romans would build their homes in areas that were technically outside the city limits, thereby avoiding city taxes.

See a list of notable Villa Loopholes in the Roman Empire

In modern times, the "Double Exemption Loophole" was used by a certain Enron executive to hide billions of dollars in tax evasion, resulting in the largest corporate bankruptcy in history.