Sauron and Gollum and Gollum’s escape?


Well-Known Member
We were asked to speculate from little evidence on what might be the most plausible answer to how and why was Gollum’s escape from the Elves of Mirkwood orchestrated. Here is an attempt.

  • What are Sauron’s intentions in letting Gollum go?
Sauron lets Gollum go as a second-string attempt to recover the Ring. His primary plan is to send the Nazgul. However, one plan is not enough. Sauron thinks that Gollum, as a long-term Ring-bearer, will be drawn to the Ring. If the Nazgul fail, Sauron will be happy for Gollum to get the Ring. First, it will keep the Ring from being claimed by someone powerful who Sauron might fear. Sauron does not fear Gollum as a Ring-bearer. He thinks this would create no threat to Sauron. He also thinks that Gollum is cunning, and might evade capture and surrender of the Ring to someone more powerful. He also thinks that he has enslaved and terrorized and cowed Gollum enough, that Gollum is likely to return to Sauron, should he recover the Ring. If Gollum does not, Sauron is confident of being able to find Gollum and get his Nazgul to deliver Gollum and the Ring. Of course, Sauron is probably wrong in some of these assessments. He, like many others, underestimates the essential toughness and bloody-mindedness of Hobbits. Nonetheless¸ that is why Sauron lets Gollum go. He is a fallback plan, should other better, and more likely plans somehow fail.

  • How does Sauron find out where Gollum is?
Sauron knows where Gollum is because his spies (probably birds) have tailed Gollum since he left Mordor. They witnessed Gollum’s capture by Aragorn, and delivery to and captivity amongst the Woodelves. They reported this back.

  • Did Gollum initiate the escape, or did Sauron’s agents?
Gollum did not initiate his own escape, nor initiate the communication with the orc attack. Gollum is not a team player. Gollum is a loner. Sauron’s spies have reported back and Mordor, or perhaps more probably Dol Guldur, has orchestrated the rescue.

I don’t think the Nazgul have departed on the quest for the Shire quite yet when Gollum escapes. He escapes on the 20th of June 3018, which is the same date as the Enemy’s assault on Osgiliath and the bridges over the Anduin. We know from Boromir’s testimony at the Council that it was in June, in this attack on Osgiliath, that a great black horseman caused ‘a madness in our foes, but fear fell on our boldest’. Then it was, that Boromir and Faramir had to hold the bridge while it was destroyed behind them, and then swim the river to escape. So, at least one of the Nazgul was at the battle, and not on the way to find the Shire on the 20th of June. Probably one or more of the other Nazgul were still in Dol Guldur. Perhaps it was they who received the report of the spies, and orchestrated the attack of the orcs? Legolas reports that the Orcs "came from over the mountains, and were unused to the woods" 'The Mountains', here, probably mean the Mountains of Mirkwood, not the Misty Mountains. So the Orcs came from Dol Guldur, and were unused to the north Mirkwood woods, not any woods. That is certainly the direction in which they retreated.

The Nazgul must have gathered and left on their search for the Shire some time after the attack on Osgiliath. (Though the timing is tight, as Gandalf meets Radagast on the 29th of June, and Radagast reports that ‘the Nine are abroad again. They have crossed the River secretly and are moving westward.’ Now Radagast may have spies of his own, likely birds and beasts, who possibly communicated rapidly and from afar on the movements of the Nine. Though Radagast said that he got his news from Saruman, not from birds nor beasts. Saruman, might have been able to detect the movements of the Nine instantaneously, through his Palantir, but unless Radagast had fast messengers from Saruman, he would still have needed time to get up to the Southern borders of the Shire to meet Gandalf.) I think the time-line might have been: Gollum is rescued and the battle of Osgiliath is fought on June 20. On June 21 the Nazgul cross the Anduin, searching for the Shire (they probably don’t link up on the West side of the Anduin for several days), and are detected by Saruman via Palantir. Saruman communicates to Radagast sometime shortly after June 21. Radagast arrives near the Shire to communicate with Gandalf on June 29.)

I think it was Sauron (or more likely his agents in the form of Nazgul) who mustered the orcs, planned the rescue, and initiated Gollum’s escape. They managed to get a message to Gollum that rescue was coming on a given date, and that he should contrive to remain in his tree after dark, and wait.
  • How did they communicate
Assuming that spies have been tracking Gollum; are aware of his captivity amongst the Elves of Mirkwood; know that he likes to climb a certain tree. All they need do is climb the tree themselves after dark, once Gollum and the Elvish guards have departed, and leave a message in the tree, saying: “Rescue is on it’s way. Contrive to stay in the tree, and not come down at dusk x days from now, and the guards will be driven off, and you can escape.” We don’t know if Gollum is literate, but a written note, placed high in the tree, where Gollum would find it, but his Elvish guards would not, would be the simplest means of communication. If Gollum were not literate, other, and more complicated means of communication would need to be employed. Pictograms?

In any event, the plan worked. Gollum was free. He was indeed drawn towards the Ring. He probably would have picked up its trail sooner if his route to Eriador through Moria was not blocked at the West Gate. However, he found the Fellowship in Moria, and successfully trailed them thereafter.

I think we must assume that Mordor’s spies lost track of Gollum (possibly when he entered Moria, though Gollum is cunning and might have detected and evaded the spies earlier) and Mordor had no idea where he was before and after he picked up on the trail of the Ring.
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Kate Neville

Active Member
I think the first problem to consider is Why Sauron Let Gollum Go.

1. He had learned from Gollum two things: A. Gollum's ring was His One Ring, and B. He had lost it to a Baggins from the Shire, a not-Man, not-Elf, not-Dwarf who had been in the company of dwarves now residing in Erebor (those darned Durin-folk no less!).

2. What does Sauron know about the behavior of ring bearers? Not much about Elves, but then he'd not had any direct personal involvement in the making of their rings. The nine Men came to him fairly easily. The Dwarves less so, but they apparently had a tendency to become fixated on their treasure, or their kingdoms, making them susceptible to the predation of dragons. Sauron would, however, know well the fates of Isildur, Thrain, and Gollum. Isildur tried to use the Ring to save himself, but was 'betrayed by it' while traveling up the east bank of the Anduin (the Mirkwood side). Thrain was captured while camping beneath the eaves of Mirkwood, taken to Dol Guldur and tortured by Sauron. Gollum, instead of going west to find the Shire, chose to go south, to Mordor. It would seem that mortal ring bearers tend to either draw evil to themselves, or are drawn to strongholds of evil.

3. Most importantly, while Gollum could tell him that Baggins of the Shire had the Ring as of 2941, he could not be sure that Bilbo still had the Ring in 3017, nor even that he was still in that Shire place. So the Nazgul are sent to find the Shire, because they can move more quickly, and were more trustworthy, than Gollum. But I think Gollum was sent to go back to his old stomping grounds, on the theory that if Bilbo were to take to wandering, under the influence of the Ring he would eventually wander back to the Misty Mountains and the Vale of Anduin and, eventually, like Gollum, to Mordor.

Flammifer rightly points out that Gollum escaped on the same day that Osgiliath was attacked, providing cover for the crossing of the Nazgul. The Tale of Years tells us that three Nazgul had been occupying Dol Guldur for many years, and although Aragorn was smart enough to avoid Dol Guldur on his march north with Gollum, I expect that those Nazgul learned pretty soon that Gollum had been captured by a Man. While there might have been a way for the Nazgul rings to act as "cell phones" to Sauron, I prefer to assume that they used bird messengers (quicker and more efficient than orcs), and that they were ordered to arrange Gollum's escape before meeting up with the other six Nazgul at Isengard.

And so I posit that the active agents were birds -- first as reconniscence, and then as messengers to coordinate with Gollum. [There is, of course, a part of me that likes to imagine it was really evil moths.] Were the orcs supposed to bring Gollum back to Dol Guldur? Maybe, but maybe Sauron preferred to have him out there as an agent of chaos. Either way, Gollum would have had his own plans.


Well-Known Member
Hi Kate,

Good post.

Let's look at some of the curious history of Gollum. Gollum did not know that 'Baggins' came from the Shire when he emerged from under the Misty Mountains. He also did not know that Baggins had been travelling in 'company with dwarves now residing in Erebor'? Bilbo does mention dwarves, when he introduces himself to Gollum; "I have lost the dwarves and I have lost the wizard, and I don't know where I am." But how does Gollum connect this one brief mention of dwarves with 'dwarves now residing in Erebor'? ,

Gollum emerged from under the Mountains in 2944, three years after losing the Ring. So, in the ensuing 7 years, until he 'turns towards Mordor' in 2951, Gollum must have learned these things. Mostly in Lake Town and Dale, according to Gandalf. But, how did Gollum track Bilbo and Co. across the Anduin, across Mirkwood, through the lands of the Wood-elves, and down the River to Lake town? Gollum's tracking and detective abilities are pretty impressive.

Then, Gollum turned towards Mordor in 2951, but he is not captured by Sauron until sometime between 3009 and 3016. So, for 58 -65 years, Gollum lurks around the fringes of Mordor. Too drawn to continue searching for the Ring and Baggins, but too resistant to enter Mordor and give himself up to Sauron.

Finally, of course, he is captured. Sauron learns that the Ring still exists! What is the impact of this on Sauron's mind-set and strategy? And, of course, why then does he release Gollum?

Questions to ponder. But, as Sauron's mind-set and strategy goes well beyond the homework problem of Gollum's escape from the Wood-elves, I think I will address it in a separate post.


New Member
When Sauron had tormented Gollum and learned everything he could, he could have killed Gollum or kept him as a prisoner but instead he lets him go. Why? It may be that he, like Gandalf, has the notion that Gollum still has ‘some part to play yet’. But opposite to Gandalf he does not add ‘for good or ill’, but, being arrogant, thinks that this part would be for his, Saurons, good. As Gollum still lusts for the Ring and wants revenge, Sauron believes that he might be able to lead him to ‘Baggins’ and the Ring. Unfortunately (for Sauron) the Spell of Bottomless Dread doesn’t work on Gollum, so Sauron has to trick Gollum by letting him escape thinking that it was a deed of his, Gollums, own cunning, but of course Sauron sends his spies, probably orcs and birds, after him. Their order would be to keep a close eye on Gollum without him noticing, and send regular reports - by bird, probably.

When Gollum is unexpectedly captured by Aragorn, the orcs don‘t know what to do, as Sauron had not let them into his plans. So they send him their report. But before they get a new order, Aragorn has already changed to the other side of the Anduin and is, for the time being, out of their reach.

The winged spies however are able to keep an eye on Aragorn and Gollum and report their coming to Thranduils realm and - even more significant - Gandalf‘s arrival shortly after.

Sauron now has to assume that Gandalf has the same information about the Ring he has. What he does not know (and that would bother him) is, how Gandalf could have known about Gollum and the Ring, and if he has some connection to these halflings.

To learn this he would have to question Gollum again, so when he learns from his spider-spies, that Gollum is allowed to get out and climb a tree in fine weather, Sauron decides to attack Thranduils Realm and get Gollum back.

Gollum is naturally cooperative when the spiders tell him (we know they can speak) that he is going to be freed, and stays in the tree on the appointed day. He does not, however, let the orcs bring him back to Sauron again, but escapes them – and this time it is a deed of his own cunning.

Now Gollum is in the Vale of Anduin. He had told Sauron, that the Shire was somewhere here, though he knew well that it wasn‘t, having searched the Vale himself long ago. Sauron however believed him and sent the Nazgûl there to look for the Shire - and for the escaped Gollum who is able to avoid them by sneaking into Moria. He has to stay in there for several months, but in the end he meets indeed ‘Baggins’ and the Ring– just as Sauron had foreseen.