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He started betting at a roulette table were he won $9,990.
An engineer named Joseph Jaggers took his skills to the Casino Beaux-Arts in Monte Carlo and won the most famous series of bets in gambling history. Jaggers came to the realization that the Roulette wheels at the casino couldn't produce truly random numbers as each wheel would have a different balance. He hired some people to record every number that came up on each wheel and quickly realized that one of the six wheels produced the same nine numbers more frequently than possible. Jaggers chose this wheel to sit down at and started placing bets - within four days he had made himself $300,000. The casino realizing something was wrong moved the table elsewhere. The next day when Jaggers went to play at the table he started losing money and soon realized it wasn't the same table. He went looking for it and when he found it won another $450,000. The wheel was later modified and when he came back to play on the roulette table he lost $125,000. Although he hadn't broken the bank he still walked away with $325,000.
Soviet Leader Nikita Khrushchev in 1962 made a bet that President Kennedy would not take action against the installation of nuclear missiles in Cuba. He was wrong: Kennedy did not do this in fact he enforced a naval blockade of the island, doing this was a gamble that Khrushchev would back off. Kennedy made the right bet, but came very close to a nuclear war with Russia.
Brian Molony was 24 when he placed $5,000 each on 40 college football games of which he lost all his money. He then put $500,000 on the Superbowl and won. But in an incredible betting spree that lasted 18 months he lost $10 million, which was the sum of money he had stolen from the Canadian bank where he worked.
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