Great topic.
Every post is thoughtful and interesting. I'm no theologian but find this sort of conjecture interesting and enlightening. Here's my take:
Although I tend to fall on the Arminian end of Christianity, I think free will and sovreignty are not diametrically opposed. Both are forces at work in the fall and redemption of middle earth and (in Christian context) real earth.
In Christianity there is an understanding that God created mankind to have fellowship with Him. Several attributes of God that are generally accepted are that He is good, He is love, He does not abide with evil, He is sovreign, omnipotent and omnipresent. (In middle earth one gets the sense that some of this involvement is delegated to Manwe, et al.) Within these parameters it makes sense to me that free will would have to be inherent to any being that has a relationship with Him. It is not possible for will-less beings to love or be loved. Presupposing the necessity of a redemptive experience to restore relationship, then it would seem that beings would need to submit their wills to him in order to receive redemption.
Sam's journey from servant to mayor; from gardener to ring bearer and warrior represent a sort of redemptive process that occurs when free will is used to submit to a transforming process. Sam submitted to Gandalf and Frodo in the matter of Gollum. The moment when in despair Sam finds himself crying out in elvish (a language he does not speak) illustrates this sort of free will submission. He is willing to approach his source of help on whatever terms necessary rather than trying to define his own terms for the relationship. Sam's willingness to carry the ring, return it, carry Frodo, abide Gollum are all ways in which Sam submits himself to the quest and undergoes a redemptive transformation.
I find Tolkien often balances free will with destiny.
Although the ring was never supposed to be made, once it came into existence, provision was made to deal with it. It came into the hands of Isuldur, but he chose to act outside good. Gollum chose evil from the moment the ring entered his life in his murder of Feagol. Though he was utterly ruined he "still had some part of play in it's destruction." Gandalf says that Frodo and Bilbo were "meant" to bear the ring. Sam makes the comment "what a story we are in." From the time the ring came into existence through the free will of Malikor, there was an adaptation on the part of Ea and the Valinor to redeem the situation and restore Middle Earth to an existence that is reconciled to the intents of it's creator.
The Dwarves is another example of this sort the redemption. Dwarves were not an intended, but rather a result of Aule's impatience. Once they existed, in spite of their shortcomings, they were incorporated into Middle Earth and given a place in it's workings for good in that they were enemies of orcs and entered into alliances with men and elves culminating in Gimli's participation in the fellowship. His relationship with Galadriel and Legolas represent a transforming redemption.
Finally there is Frodo's moment at the Cracks of Doom. He has willed himself to do what he was "meant" to do and yet in the final moment he doesn't have the will within himself to throw in the ring. Gollum acting out of evil motives completes the good task and plays the role Gandalf hints at. Yet free will gestures like Bilbo's pity, Frodo's pity, Sam's submission are as as instrumental in getting Gollum in place as his own evil intents or any fate that may have brought him there.
It is further complicated in considering that at any moment Gollum might have repented. This would be the outcome desired by a good and loving diety. Yet an omniscient Supreme Being would know Gollum's choice and fully comprehend whether or not this is sane choice. There are moments when Gollum creeps into camp and almost submits to a transforming redepption, but the desire for the ring is too strong. This raises the question as to whether sin is irresistible to human will. Frodo's experience at the Cracks of Doom almost suggests that Tolkien thinks redemption might require a measure of divine intervention coupled with free will.
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Do justly, love mercy, walk humbly with your God. Micah 6:8
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