I'm not entirely sure Saruman was "going after" the Shire, not before his fall. Certainly he found it profitable to prop up Lotho, rather like big nations today operate in the Third World, but I don't think "occupy and conquer" was much of a priority for an Ainu who was after the Great Ring and the whole ball of Middle-earth wax. And after his fall, Saruman's interest in the Shire was primarily ruination, an act of petty revenge.
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The entire plot of The Lord of the Rings could be said to turn on what Sauron didn’t know, and when he didn’t know it.
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