Gandalf Captured!?
 

In the Fellowship of the Ring, in the chapter A Journey in the Dark, Gandalf says the following:

"I alone of you have ever been in the dungeons of the Dark Lord, and only in his older and lesser dwelling in Dol Guldur."

How and when did this happen?

Yes, Gandalf did indeed venture into Dol Guldur once. I don't have the books with me at te moment, so I can't tell you te exact date, but it was in the time that Sauron was still in Mirkwood and known as the Necromancer (as they also call him in the Hobbit). I have often wondered wether that wasn't what Gandalf had been doing when he left Bilbo and the dwarves to do something important for the White Council.

Anyway, the White Council was ofcourse aware of something evil lurking in Dol Guldur, and they suspected it was Sauron. Gandalf ventured into the fortress to find out if it really was Sauron. It was! Gandalf got back out, fled to Lothlorien and consulted the council. The White Council then went to Dol Guldur to fight Sauron, but he knew of their plans and had already commanded his Nazgul to make Barad-dur ready for his coming. Thus, the White Council came to Dol Guldur and found no Sauron there, for he was already in Mordor.
However, Gandalf says in the Unfinished Tales (in his own version of the Hobbit as he tells it to Frodo) that he believes that if Sauron wasn't forced to move to Mordor, he would probably have attacked the North first, thus wiping out Lothlorien and maybe Rivendell. And... would the dwarves have succeeded in killing Smaug, probably them as well.

I don't know if you know the game MERP (Middle-Earth Role Play), but in their version of the book 'Dol Guldur', there's the story as they think it happened.

greetings,
lathspell

Gandalf didn't go sneaking into Dol Guldur when he left the Dwarves in Mirkwood.
On that occasion he went to help the White Council drive Sauron out.

He was in Dol Guldur's dungeons many years before. That's where he found Thorin's father and got from him the map and the key to the side door of the Lonely Mountain.
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Gandalf's little ride to Dol Guldur&dragon-fire as bonus...
 

Actually, as Selmo correctly said, this was the moment when the White Council attacked Dol Guldur and wiped Sauron out! (well... actually he retreated to Mordor, but that's not our problem for now) Gandalf says it to Frodo in the Shadow of the Past:
And it is even mentioned in the Hobbit:
This is one of the most wonderful moments in The Hobbit for me! Gandalf, right from the parting by Beorn's house, rides south to Dol Guldur to kick the Necromancer! I love when these pieces come up together, you know?

Ahem, to be more precise: not "would the dwarves have succeeded in killing Smaug, probably them as well" - or why, of course - but mainly: "would the dwarves NOT have succeeded in killing Smaug, he'd send his emissaries to the Dragon and then..."
And ninja, great topic. Ask these things, because this is one of my favourite subjects of study ;) :cool:

How do you suppose Gandalf managed to get into the dungeon and speak with Thráin? Were there no guards?

I suppose right down there there weren't any guards. Cf. Bilbo and Thorin in Thranduil's halls, something like that. Gandalf says that Sauron took the Ring and didn't care anymore (he even didn't take the map and key of Erebor - read the UT, he speaks very much of it there).

That is another point I found quite bizarre: here Sauron finds the Dwarf who has one of his rings, and he doesn't even search him fully. He could have had dozens of other rings for all he knew!

Well, no, I suppose Sauron saw he has one ring, three handkerchiefs, one map, seven shovels, a key, and four thousand thirty-five golden pieces in his pockets. He took the ring and then just threw him to the dungeon. He didn't care of the rest.

Even though the key would make an alliance with the dragon much easier, as in getting to see the dragon?

The key was not labeled "this is a key to Erebor" and Sauron probably didn't bother to look at the map, since it showed the Lonely Mountain, which he knew. Maybe in the lust for the Ring he didn't even look at it. And if Sauron wanted to ally with Smaug, he'd probably send some of his classic Horsemen In The Night through the front gate. It does look suspicious if you sneak through the back entrance to a person (or Dragon) you want to make a fair deal with.

Sauron is meant to be the big, scary Dark Lord. Yet he captures a Dwarf who has one of his rings of power, and doesn't even bother to strip him of everything he has, slay him, or keep a watch on him. That's dodgy management; that's poor decision-making if you ask me.

Related point: could Sauron not sense that Gandalf was in Dol Guldur? I'm presuming Sauron was there at all times. If Sauron was hiding behind the curtains in Rivendell I'm sure Gandalf or Elrond would have felt something. :D

Another question that has me a little confused- wasn't Sauron unable to take physical form? So, how would they "find him" in Dol Guldur as the Necromancer?

That's one of the main things Tolkien points out: the blindness of those who lust for power. This repeats in Professor's works again and again, I think it is quite obvious and one of the central parts of it. "Hurrah, I have the Seventh Dwarven Ring!" Finish. I think its very logical.

About Gandalf - I suppose Gandalf's presence was not so strong as Sauron's, and Dol Guldur wasn't Mordor. I think if Gandalf wanted to be hidden, he remained hidden there (if he avoided going too close to Sauron).

MatthewM - what do you mean by "find Sauron"? No one ventured to Dol Guldur except Gandalf. The Elves who lived there fled when the Shadow came, and there were dark beasts in the woods, they knew there is something evil in Dol Guldur, but no one went there to check it. After all, some "evil power" was for example also in Moria, and no one also went there except Thrain.

Fair enough, it fits Tolkien's point. It just makes me think that I'd be a better Dark Lord than Sauron.

Matt, Sauron did have a physical form. There's a bunch of stuff on the Downs about it. Just type 'Sauron', 'physical' or 'eyeball' into the search engine. :)

Yes, Sauron is really just an idiot with power and too many names. A session with Silmarillion and UT reveals this, though not directly. I know Tolkien wanted good to win, but I also get the feeling that he was trying to say that evil was dumb.

Ah, yes. What have I been thinking? I've read those books a million times and still can make quite stupid remarks. I guess it's a gift.

Yes, evil always destroys itself in greed and pride. Morgoth was finished because he didn't care about the people at the end of the Sirion (Earendil) and didn't count on the Valar coming to help. (pride) Sauron gets dead because he wants to kill Aragorn so badly he's blinded to the fact two hobbits are destroying his ring (greed).

This 'problem' is just down to The Hobbit being written way before Sauron was thought up. In TH, Thrain is just captured by 'the Necromancer' - an evil figure that's left in the dark. We aren't told what the Necromancer wants or even what he is - he's just a far off villain that Gandalf goes to confront. We don't know if he has any interest in Erebor or Smaug.

The problem comes when Sauron becomes the Necromancer - because we knopw his objectives, suddenly he seems stupid for letting such an opportunity slip through his fingers. Perhaps it just would have been better if Tolkien had Sauron in Mordor all along and the Necromancer as a separate villain.

I don't agree. I think Sauron and the Necromancer have the same behavior and the same problems of overlooking things: for example, Sauron, again blinded by his lust for the Ring and not caring of all things in detail, did not even bother to ask Gollum whether "Shire... Baggins..." come from the same area as in which Gollum lived (Anduin Vales). He, in his lust for the Ring and anger and arrogance and ignorance (thinking that of course there is nothing else to be obtained from this little stupid creature - much the same he probably thought about Thrain), assumed that the Shire is located somewhere around Gollum's motherland. This results in the Black Riders' sweeping the ancient Stoor villages in Anduin until realizing that there is no Shire and no Baggins, and riding to knock on Saruman's door (Unfinished Tales, Third Age, pt. IV). Tolkien himself says that