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The question has surfaced in many high school games about diving catch attempts by outfielders and how they should be scored. Example -- ball hit in front of right fielder, who attempts to make diving shoestring catch. He doesn't touch the ball and it rolls by him 20-30 feet. Runner advances all the way to third. Triple or 1B with error?
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As the dad of a senior outfielder, agree that a shoestring catch is not ordinary, but keeping the ball in front of him and holding the batter to a single is. IMO - missed diving catch to the side (touch or not), no error; missed diving catch in front, no error on the hit, but score any extra bases on error. I agree there is confusion on this and believe most scorekeepers score error if touched.
Regardless of the execution, the decision of how aggressively to play a ball in the outfield depends on a lot of factors - game situation, trajectory (i.e. "drive" or "fly"), location (in the gap - you have help, down the line - no help). There are many great major league outfielders who demonstrate this everyday and a few who would catch heck on my son's team for poor decisions - but of course these guys more than make up for it in the batters box.

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