[Keeper of Dol Guldur]

I guess I'll point out a few more circumstantials.

Legolas sat quiet the entire council until it was deemed his part to speak. Others involved themselves in the conversations prior to that point, so he may have felt guilty and not wanted to bear bad news ... not that it emplicitly pegs him as being at fault feeling bad, or maybe as a Mirkwood elf he simply didn't have much say in matters concerning the Ring, since he didn't know of it.

"Alas! alas!" cried Legolas, and in his fair elvish face there was great distress. "The tidings that I was sent to bring must now be told. They are not good, but only here have I learned how evil they may seem to this company. Smeagol, who is now called Gollum, has escaped."

He's on first name basis with Gollum. So either the guard who lost Gollum gave some pretty detailed information to Thranduil, who remembered it and gave pretty ridiculously detailed information to Legolas to go tell the Council ... or you know ... Legolas IS in charge of prisons and that makes it easier.

I'll argue here that being in charge of prisoners in the elf realm of Mirkwood doesn't imply a lowly or measly task. I don't imagine in a place as nasty as the black woods they actually TAKE a lot of prisoners so when they did, they tended to be important prisoners (prisoners of state, even). Any and all prisoners they took were a big deal. Being in charge of prisoners could have been just one of Legolas' many tasks at home. Obviously we've seen him act in other capacities too ... like ambassador to Rivendell and warrior, and he's clearly pretty educated for a rustic elf.

The prisons in a King's hall are a big deal. We're not talking lockholes at Mitchel Delving here. Those are Royal prisoners.

"We guarded this creature day and night, at Gandalf's bidding, much though we wearied of the task. But Gandalf bade us hope still for his cure, and we had not the heart ..."

WE. "We" (my people) vs. "we" (a few buddies and myself). It's arguable. Like pretty much everything else Tolkien wrote. Tolkien writing follows standards, and if Legolas wasn't involved personally with the prisoner, he'd have said "our guards didn't have the heart" like some snooty, hands-don't-get-dirty prince. We all know Legolas doesn't mind getting his hands dirty with grunt work.

"You were less tender to me," said Gloin with a flash of his eyes, as old memories were stirred of his imprisonment in the deep places of the Elven-king's halls.

YOU. "You" (your people) vs. "you" (you and your damn buddies). Similar argument. If Gloin meant guards and not Legolas personally he'd have probably said "your men were less tender to me." Old-time style language might play a trick on our concept of the specifics of the wording.

Plus when Legolas finally relates the story of the escape, he's implicitly involved, and his use of the word "we" is too often used to be vague.

"In the days of fair weather we led Gollum through the woods; and there was a high tree standing alone far from the others which he liked to climb. Often we let him mount up to the highest branches, until he felt the free wind; but we set a guard at the tree's foot. One day he refused to come down, and the guards had no mind to climb after him: he had learned the trick of clinging to boughs with his feet as well as with his hands; so they sat by the tree far into the night."

See, here he describes at first some serious specifics - he knows the tree, and he was there, otherwise he'd have just said "the guards led him to some tree, and they lost him." He does eventually blame the guards, implying that either he wasn't with them the night they lost Gollum, or that he was with them, but when he asked his guys to climb up, but they didn't want to. I doubt they'd defy their own prince, so my guess is he wasn't there. Either that or he suggested it, but agreed with them that it might be pointless, because Gollum is pretty quick.

But then ... he must have been nearby at the least, because in the next paragraph he's involved again.

"It was that very night of summer, yet moonless and starless, that Orcs came on us at unawares. We drove them off after some time; they were many and fierce, but they came from over the mountains, and were unused to the woods. When the battle was over, we found that Gollum was gone, and his guards were slain or taken. It then seemed plain to us that the attack had been made for his rescue, and that he knew of it beforehand. How that was contrived we cannot guess; but Gollum is cunning, and the spies of the Enemy are many."

Legolas clearly was involved in the fight, he seems to have run off to combat the Orcs and left those same guards at the bottom of the tree to wait for Gollum to come back down. When he got back, his men were vanished and Gollum escaped ... he probably felt pretty guilty. Heck, he then mentions leading several attempts to recapture Gollum. Either he volunteered (very likely), or Thranduil yelled "Find that damn prisoner, Gandalf entrusted me with him!" (not so likely ... since Legolas would be fully aware, and elves are seldom jerks to each other.

We have failed to recapture Gollum. We came on his trail among those of many Orcs, and it plunged deep into the Forest, going south. But ere long it escaped our skill, and we dared not continue the hunt; for we were drawing nigh to Dol Guldur ..."

Of course ... just after Gandalf's speech on Saruman's betrayal Boromir drops quotes like "I know the Men of Rohan, true and valiant, our allies, dwelling still in the lands that we gave them long ago."

"We", (my people). Because obviously Boromir wasn't around when Eorl the Young rode from the Wilderland.

But Legolas' describing every single aspect of Gollum's escape implies he was on hand. I guess I can't stress that part enough. You could argue that, okay ... so Legolas was on hand ... maybe Thranduil tasked his princely warrior son with the prisoner because it was Gandalf's special request and he didn't want it blown by his normal jailers since they're drunks. However ... how many prisoners could that place typically have? In 80 years the only prisoners we've heard of are the dwarves and Gollum. Any case involving prisoners was a special event worthy of Thranduil's or one of his prince's special interest.

(Perhaps that's why the jailer and his friend in the Hobbit were so insistent on wine-drinking ... the place NEVER has prisoners, and they just happen to get some prisoners on the night of the big party? Well ... no blasted dwarves are going to ruin their night ... break out the wine! I know, I know ... that's PURE speculation).

So not only could Legolas have been the drunken jailer, or likely enough, his wine-bearing friend ... he was personally responsible for Gollum's escape, and possibly joined the Fellowship because he felt he owed Gandalf BIG TIME for failing that task - enemy conspiracy or not.

He certainly didn't join the Fellowship because he wanted to hang out with four hobbits, a dwarf and two men ... (although Aragorn and Boromir he no doubt respected immediately and likely knew of somewhat, and Frodo Baggins he also no doubt respected greatly).

That was a long one.

Failure as a jailer? Might as well try his hand at saving the world to prove he's not completely worthless!