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Sauron should have not been so single minded. He didn't believe anyone would want to destory the ring, he would never believe anyone would have the audacity and stupidity to creep into mordor, and, most importantly, he was too single mided when torturing Gollum. As stated in unfinished tales, the Hunt for the Ring section, Sauron assumed that te shire was an area near to where gollum lived. If he had put thought into it, and got more information out of Gollum, it would have been Game Over. As Tolkien states:
"This was a very small and natural error – but possibly the most important mistake that Sauron made in the whole affair. But for it, the Black Riders would have reached the Shire weeks sooner."
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