The Council of Elrond is full of news, most of it bad. And not the least is the news that Gollum—previously captured by Aragorn and turned over to the Wood Elves for safekeeping—has escaped. How did he escape the watchful eyes of the Elves?
“Not through lack of watchfulness,” said Legolas; “but perhaps through over-kindliness.”
It turns out that the Elves were letting Gollum climb trees. They kept him part-time in a dungeon, of course, since after all he was a prisoner. But they “had not the heart” to keep him there all the time. Rather, they would often take him out into the forest and let him climb a high tree, “until he felt the free wind.”
It’s a picturesque and poignant way of treating a prisoner, isn’t it?
The rationale for the Elves’ treatment of Gollum is interesting. The Elves seem to be motivated largely by what we might call a remedial view of incarceration. “Gandalf bade us hope still for his cure,” says Legolas. Cure from what? Partially, the black thoughts of his own heart. And that meant removing Gollum from darkness in general, including the darkness of his underground prison.
Unfortunately, as well-intentioned as the Elves’ remediation program is, it does not work. (Interestingly, I can’t think of a single case of remediation in the Lord of the Rings that does work. Saruman is kept under lock and key by Treebeard, who hopes to cure him eventually; but Saruman just ends up deceiving Treebeard and escaping. Something similar happens with Sauron in his prior imprisonment by the Valar. This is an interesting trend, but it’s also probably a digression for a different post.)
In any event, Gollum takes advantage of the Elves’ good will, escapes, and returns to attempt worse things in the end.
I don’t think Tolkien is offering any ideological reflections here on the treatment of prisoners. Instead, I think he’s observing something about the difference between good will and ill will. Good will does what is best for others, even in the case of enemies and prisoners. Prisons are not places for gratuitously inflicting pain on the wicked. They are (or should be) places for lost souls to be restrained in the hope that they can be made good again.
But an ill will is one that takes advantage. It harms even the people who attempt to do it the most good. And in the last analysis, even the best wills may not succeed in reforming the worst wills. This, I think, is the burden of Tolkien’s thoughts on remedial imprisonment. And it is a burden worth keeping in mind when we get to more imprisonments in The Return of the King.