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Reply to "base stealing philosophy"

Simple answer: 0-2 or 0-2 with 2 outs with a guy up I wouldn't mind leading off the next inning.

Long answer: about 100 things go into it including; speed of my runner (and if he's that fast the count doesn't matter), their catcher, their pitcher's move to home, move to first, his effectiveness, who I have hitting, where we are in the order, the wind (we play on days that are so windy a hit ball is a tough out and you hate to give away one out of the precious 21)... the field; muddy? ...
basically any time you steal you are spinning the roulette wheel. You are taking your chances against leaving him on first and needing two hits or an extra base hit (or pitcher wildness) to get him home versus him being on 2nd and now you only need one knock to score him.

there's some mental rambling
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