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Originally Posted by alatar
Unlike Gandalf, didn't the Eye see that Gollum would have a part to play in the end game? Did Sauron see this, yet remain hopeful that things would still 'fall' in his favor?
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I doubt Sauron ever thought of such a possibility, as seen later in the decisions he makes. If he had considered this possibility, he would have made sure nothing would ever come into Mordor unwanted.
He probably thought that Gollum would never come close to repentance and would never lead anyone into Mordor, but would instead try to kill the Ringbearer and hide himself with the Ring somewhere, where he would eventually, sooner or later, be discovered by Sauron's minions.
Too much self-confidence...