Why was the result of the pie contest a joke on Grandma Dowdel?

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In the section of A Long Way from Chicago titled "The Day of Judgement," the joke is on Grandma Dowdel, because if she had not resorted to such a desperate measure as cheating at the county fair, she would have won the pie contest and, by extension, the biplane ride that she desperately wanted to gift to her grandson.

In the town pie-baking contest, the opponent that Grandma is up against is Rupert Pennypacker, who is widely regarded as the best home baker in the entire state. At the most opportune moment, Grandma switches the names on her's and Pennypacker's pie, which creates an ironic defeat for Grandma, as the pie she made was judged to be the best. Because of her interference, however, the award is given to Pennypacker.

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At the county fair "Fruit Pies and Cobblers" competition, Grandma Dowdel cheats by switching her pie card with Rupert Pennypacker's. This way, she's dead certain that she will win first prize: a free ride in Barnie Buchanan's plane. Rupert has the reputation of being the best home baker in the whole of Illinois, so it's not surprising that Grandma Dowdel feels she has to resort to such desperate measures to win the contest.

As it turns out, however, the joke's on her. Grandma's home-made gooseberry pie wins the contest after all. But, because she already switched pie cards before the judging began, first prize is awarded to Rupert Pennypacker, not to her. Grandma has to make do with the second-prize red ribbon instead. If she hadn't cheated, she would've won the contest—and against the best home baker in Illinois, too.

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