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A tale about a cigar aficionado who insured his stogies against first and then tried to collect after he smoked them has been making the online rounds for over twenty years: This legend began its Internet life after it was posted to the newsgroup alt.smokers.cigars in early 1996, and it has continued to circulate as a true story in newsgroups, email, and social media ever since, despite its having been long ago identified as a tall tale. The version posted back in 1996 was, in fact, nearly identical to one that had been published in a collection of amusing anecdotes back in the mid-1960s: Another anecdote from that same volume suggested this legend stemmed from a joke whose basic premise had been used in a few different ways: Sometimes, as in this 2006 example, the basic legend is given a darker ending: In 2003 this legend was turned into a song recorded by Brad Paisley: https://youtu.be/uGUAeVxFpI0As to whether there could be any truth to the legend's premise, we note that insurance policies are generally written so that deliberate actions on the part of the policyholders cannot trigger payouts. Furthermore, destroying your own property isn't arson, as long as the act isn't intended to defraud anyone. If a court had already ruled that the insurance company was required to pay, then it had been determined no fraud was committed, and thus the burning could not be considered arson. The structure of this legend — a person's exploiting a regulation for personal gain, then being punished under an unforeseen aspect of that regulation — is similar to the collegiate legend about cakes and ale.
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