[mark12_30]

"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 ..."

Hmmm.

I'm not agreeing that this proves your Hobbit-jailer-theory (which is cute and fun)-- but this does bring up some interesting points.

One, it seems that Legolas knew Gandalf, or at least knew of him. Perhaps that is another reason why Legolas is included on the quest.

Two-- they wearied of the task. All right. Weary elves would turn to partying, in order to cheer up-- singing, dancing under the stars, and maybe even drinking. Okay, definitely drinking. I can buy the idea that the walking-jailers-party were trying to keep themselves cheered up.

Three-- "Gandalf bade us still hope for a cure." Did they remind themselves of this daily? Perhaps. How do youy heal somebody who shrieks when you touch him or tie your rope to him? Elf-music has a healing quality to it. I don't doubt that they would sing to Gollum (poor, poor Smeagol) in the hopes that something would stir in his stringy little heart. And singing and wine do seem to go together.

Four-- It does seem that Legolas has a level of authority over the jail system such as it was. Tolkien's text supports this.

Now for the text from The Hobbit...

Then Bilbo heard the King's butler bidding the chief of the guards good-night.
"Now come with me, " he said, "and taste the new wine that has just come in. I shall be hard at work tonight clearing the cellars of the empty wood, so let us have a drink first to help the labour."
"Very good, " laughed the chief of the guards. "I'll taste with you, and see if it is fit for the King's table. There is a feast tonight and it would not do to send up poor stuff!"

Neither of these sound like Legolas to me. Certainly not the butler. And the chief of the guards is called by his title-- which isn't a high enough title to say "prince".

It must be potent wine to make a wood-elf drowsy; but this wine, it would seem, was the heady vintage of the great gardens of Dorwinion, not meant for his soldiers or his servants, but for the king's feasts only, and for smaller bowls, not for the butler's great flagons.
Very soon the chief guard nodded his head, then he laid it on the table and fell fast asleep.

There is the proof that Legolas is not the chief of the guards. Legolas would know the wine, know which bowls to use, and anyway, he would have been at the feast as the king's son, and not have to sneak the wine downstairs. Nor would Legolas have been dressed on the day of the feast with the jail-cell-keys rattling on his belt.

A page later, by the elves arriving from the feast, the butler is named: "old Galion". And the chief of the guards is referred to as "the turnkey". Since elves delight in jibes, surely if Legolas was snoring with his head on the table, they would have said "the princeling" or "the king's son", to emphasize the irony of the situation.

The remote possibility remains that Legolas was one of the party enlisted to roll the barrels down the hatch. I confess I have pondered this possibility before, and had some fun with it. However, there is a pargraph that makes this extremely unlikely, and that is Galion's reaction to the party when they complain of the heavy barrels.

"Get on with the work!" growled the butler. "There is nothing in the feeling of weight in an idle toss-pot's arms. These are the ones to go and no others. Do as I say!"

Not the way you'd address the group if one of the members was the king's son.

EDIT: I agree with Rune on of Bjarne that the "you" and "we" argument holds no water. It was an elves versus dwarves statement, not a Legolas versus Gloin statement.