Sauron and Gollum

Sauron does a number of stupid things in the course of the story, but his most striking mistake is probably his attitude towards Gollum. First, he allows him to leave Mordor after torturing him in Barad Dur. Second, he sends orcs to Mirkwood to release him from the Silvan Elves. Without these two events, many things would have changed: Frodo and Sam would probably have been captured or died before they reached the borders of Mordor. Even if they would have managed to reach Mount Doom without Gollum's assistance, they would not have been able to destroy the Ring there.

Being the creator of the Ring, Sauron must have known about its powers better than anybody else. He must have known that possessing the Ring inevitably creates the desire to defend (or retain) it by any means. The Nazgul must of course be excluded here, because they are just slaves, but Gollum still has own will and personality. How could Sauron come to the idea that any other person could search the Ring for him? Do you have any idea?

[narfforc]

The only person who knew what Bilbo looked like was Gollum. Sauron thought in some way they were of the same kind, and that Gollum would eventually find where other halflings lived. If Gollum had found Bilbo, and murdering him took the Ring, Sauron knew that Gollum was already under the power of the Ring and would not be able to resist putting it on. Once Gollum had the Ring, it would be far easier to detect and catch him

[Kuruharan]

Evidently, Sauron did not understand his own Ring as well as he might have. You cite one particular way in which Sauron's understanding was lacking. His failure to comprehend what he supposed was the destruction of the Ring at the end of the Second Age is another.

His persistence in attempting to unleash Gollum on the world does seem a bit strange at times.

[Macalaure]

You have to keep in mind that Gollum was of no value to Sauron as another slave in Mordor. So why not release him and see what happens? If he's not able to take the Ring again, he at least can be a bug in the fur of his foes and a hindrance to whatever they are planning. Which he was in the beginning and in the end.

Not only was it beyond Sauron's imagination that his enemies would try to destroy the Ring (did he overestimate his Ring, or underestimate his enemies?), but he also couldn't imagine that Gollum would actually end up helping them. This came by the pity of Frodo, which is well beyond the scope of Sauron's comprehension as well.

Given Sauron's knowledge and views at the time, Gollum's release makes perfect sense to me. In hindsight, things are always different.

By the way, do we know Sauron was behind the attack on Mirkwood? Did he even know Gollum was captured?

[Kuruharan]

By the way, do we know Sauron was behind the attack on Mirkwood?

I guess we don't know, but it seems likely. Given that it was a major incursion into enemy territory by a large group of orcs from his secondary center of power...it seems unlikely that he didn't know about it or order it.

[Raynor]

Did he even know Gollum was captured?

He apparently did:

Originally Posted by The hunt for the ring, UT

Now Sauron learning of the capture of Gollum by the chiefs of his enemies was in great haste and fear

And seeing that in the Council of Elrond it is stated that the attack on Mirkwood was previously planned and it had as a purpose the "release" of Gollum, of which he knew, I would say that Sauron was behind that attack too, directly or through the nazgul.

[The 1,000 Reader]

It's simple really. Sauron's dumb. Over the course of the books, he does many laughable things, such as sending an army one by one to their deaths and overestimating the ring.

[A_Brandybuck]

Sauron isn't dumb. He had no choice. He tortured Gollum and even so he didn't get the knowledge about the location of the One Ring. He only knew the words "Baggins" and "Shire". But he knew the power of the Ring. He knew, that the only thing, that Gollum will do in liberty is to search the One Ring.

In this moment Gollum is Sauron's only connection to the Ring. To let Gollum free and escape from Mordor is the only decision Sauron could make in the case of Gollum. And when Gollum was caught and hold in Mirkwood, Sauron had to fear, that Gollum will lead the Wise to his Ring. So the only logical decision was to free Gollum, that he won't lead the Wise to the Ring. Not because he feared that the Wise could destroy the Ring, but they could use it against him (as mentioned above).

But the only fault was, that Sauron didn't thought about destroying the Ring. When the Wise have decided to use the Ring, Gollum wouldn't have had the chance to get the Ring.

[Farael]

Originally Posted by narfforc

If Gollum had found Bilbo, and murdering him took the Ring, Sauron knew that Gollum was already under the power of the Ring and would not be able to resist putting it on. Once Gollum had the Ring, it would be far easier to detect and catch him

I think nafforc is on the ball here...first of all, I believe that Sauron knew nothing of hobbits and the Shire, so as far as he was concerned, they might have been in league with the Wizzards and the elves, and perhaps they were all waiting for the right time to start using the ring. Of course, the right time for them would have been a bad time for Sauron.

We know that no-one but Gandalf might have defeated Sauron while using the Ring but... did Sauron know this? perhaps he feared that, if given time, they'd manage to overthrow him. Same principle why he actually attacked the Captains of the West when they marched to Mordor with ALL his might rather than a sufficient amount. If he had left some orcs behind, he would have caught Frodo and we can guess what happens next.

So perhaps, knowing that Gollum would use the ring as soon as he got it, Sauron let him go free in hopes that he'd somehow manage to find The Shire, get the ring and use it... thus revealing where the ring is to his minions.

Keep in mind that in Sauron's mind it was a win-win situation, as mentioned before. Pitty was not something very likely in him, nor the desire for something other than power... thus Gollum, a wounded beast that was far beyond healing, had some upside and no downside... if Sauron couldn't think that they'd try to destroy the Ring, then how could he think that Gollum might be of assistance on that same quest he cannot imagine?

[Raynor]

I agree with most of the above; there is this statement in UT:

Originally Posted by The Hunt for the ring

But Sauron perceived the depth of Gollum's malice towards those that had "robbed" him, and guessing that he would go in search of them to avenge himself, Sauron hoped that his spies would thus be led to the Ring.

which is in agreement with LotR:

Originally Posted by Councilf of Elrond, FotR

He was loth to speak and his tale was unclear, but it is beyond all doubt that he went to Mordor, and there all that he knew was forced from him. Thus the Enemy knows now that the One is found, that it was long in the Shire; and since his servants have pursued it almost to our door, he soon will know, already he may know, even as I speak, that we have it here

[The 1,000 Reader]

Originally Posted by A_Brandybuck

Sauron isn't dumb. He had no choice. He tortured Gollum and even so he didn't get the knowledge about the location of the One Ring. He only knew the words "Baggins" and "Shire". But he knew the power of the Ring. He knew, that the only thing, that Gollum will do in liberty is to search the One Ring.

Dude(ette), he sent his army one by one to their deaths when he could have just looked out the window overlooking the island. Seriously, that's quite possibly the dumbest tactical maneuver in all of Middle-Earth. He could have at least sent the troops in pairs.

On the subject, Sauron wouldn't know where Gollum was unless news of Gollum spread, and apparently the only way it would spread was if he was captured, and Gollum was very good at hiding. Overall, Gollum wasn't any more effective than a mere beggar stumbling upon it.