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Welcome to the forums, and thanks for asking a great question. Checkers and Cracker Jack were competitors at one time, but Cracker Jack eventually bought them. I'm not a historian, or a collector of Checkers' prizes, but there are a few members here who are & do. Hopefully they can flesh out some of the details for you.
Thanks for the info. Besides collecting Cracker Jack prizes, I have a drug store museum and I concentrate on Kansas drug stores. I just got a picture post card with a store front picture of a Munden, KS, drug store. In the front window is a neat stack of Checkers boxes and a pennant hanging above them that reads Wholesome // Pure // Candied // Popcorn // And // Peanuts. The card is post marked 1916. Neat way to tie my two collections together!
That seemed to work. That contraption on the curb is, I think, an early gasoline pump. Notice the Crown Gasoline advertising sign nailed to the tree beside the drug store. When cars first became popular, there were few filling stations, especially in small towns, so you bought gas where you bought other chemicals: the drug store.