These kinds of essay contests used to be all over the place. There was a woman some time back who managed to support her family entirely on winning contests such as this one, and writing jingles, and the like. There was a book about her, written by a daughter, but I've forgotten the title. (Probably one of you out there remembers it....) Anyway, if such a person could exist, who could win these contests with any kind of consistency, then it implies pretty strongly that there is a certain technique to winning them, maybe a specific type of phrase that resonated with contest judges.
Now, contests are a lot more likely to be about being the person who just happens to draw a winning game piece. A lot less vulnerable to gaming, but entirely uninteresting as "games."
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