Sauron and Gollum

[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.

[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.