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I have always heard a couple of different answers to this question. The one that I think makes the most sense requires you to know that there used to be 4 outfielders and 3 basemen. In 1849, DL Adams invented the shortshop position by moving one of the outfielders in, basically having him "stop short" of his normal position (or possibly so that he could "stop the ball short" of the outfield). He realized that 3 outfielders would be able to handle almost any fly ball and that having another infielder "close the gap" between 2nd and 3rd would prevent a lot of ground-balls from getting past the infield.

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Q: Where did the baseball term 'shortstop' originate?
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