Voltaire, a famous philosopher and writer of the 18th century, was massively wealthy. He gained his wealth through some not-technically-illegal shenanigans with the early French lottery system.
The lottery system was majorly flawed and offered more prize money than the total cost of tickets. Voltaire rounded up a group of friends to buy most of the tickets and win the lottery. They repeated this numerous times until the French government caught on and discontinued the system.
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Photo Credits / Sources:
After Maurice Quentin de La Tour [Public domain], via Wikimedia Commons