What are the best loopholes found in history?

Loopholes in laws, contracts, or systems have been exploited throughout history for various purposes, sometimes resulting in significant consequences. Here are some notable examples:

1. **The Bourbon-Orleans Loophole (18th Century):** During the French Revolution, the Bourbon-Orleans family exploited a legal loophole to secure their wealth. They transferred their assets to a corporation, making it difficult for the revolutionary government to confiscate their property.

2. **The Emancipation Proclamation (1863):** President Abraham Lincoln issued the Emancipation Proclamation during the American Civil War, declaring slaves in Confederate-held territories to be free. However, it had a significant loophole: it exempted the border-states and parts of the Confederacy already under Union control.

3. **The "Golden Share" Loophole (20th Century):** Governments and corporations have sometimes used "golden shares" to retain control over privatized entities. This loophole allows the holder of a single special share in a company to veto any decision, effectively maintaining influence despite private ownership.

4. **Tax Shelters and Offshore Accounts:** Over the years, individuals and corporations have exploited legal loopholes in tax laws by using offshore accounts and establishing shell companies in jurisdictions with favourable tax regulations to reduce their tax burden.

5. **The Volcker Rule Loophole (Dodd-Frank Act):** The Volcker Rule, part of the Dodd-Frank Act aimed at regulating banks after the 2008 financial crisis, prohibits banks from engaging in proprietary trading. However, banks found loopholes allowing them to continue similar activities under different names, such as market-making or hedging.

6. **Legalized Gambling in the U.S.:** some states have exploited legal loopholes to introduce forms of gambling, such as Native American casinos or state lotteries, despite broader prohibitions. These initiatives have allowed states to generate significant revenue while technically complying with existing laws.

7. **Insider Trading:** Insider trading involves trading stocks based on non-public, material information. While illegal, defining what constitutes "non-public" or "material" information can sometimes create loopholes that allow individuals to exploit their knowledge without facing legal consequences.

8. **Cryptocurrency Regulation:** The emergence of cryptocurrencies has presented regulatory challenges due to loopholes in existing financial laws. Some individuals and entities have exploited these gaps to engage in illicit activities such as money laundering or tax evasion.

These examples illustrate how loopholes in laws, regulations, and systems have been utilized throughout history for various purposes, often leading to significant societal, economic, and legal ramifications.