8. Captain Obvious

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As stated previously, there are all kinds of insurance one can purchase, and a lawyer in North Carolina actually insured his expensive cigars in case of flood, storms and fire. Think about that for a second. Sure enough, the man later filed a claim after he said his precious cigars were lost in a fire. Although his claim was dubious at best, a court ruled that the man’s claim was valid since the policy did not specify what kind of fire the cigars were protected from. After the man won in court, the insurance company promptly filed criminal charges against him. As a result, he was sentenced to two years in jail and a $24,000 fine, after being found guilty of 24 counts of arson and insurance fraud.