Seems Like Someone's Rooting for the Wrong Side

[Raynor]

Originally Posted by the guy who be short

I suppose that more than anything, I'm pointing out the great flaw in Middle-Earth, which is that the evil are doomed to evil with no chance or choice of repentance.

The subject of irremediable allegiance to evil is not considered settled. Anyway, Tolkien stated in the letters that "there exists the possibility of being placed in a position beyond one's power", and he wasn't having only Middle Earth in mind - and I agree. While having a mythological-level power at one's disposal may ease almost complete corruption of others (Tolkien stated that no one can be absolute evil), even in our world there are, unfortunately, ways to condition persons into evil.

Originally Posted by the guy who be short

Melkor and the fallen Maiar and Valar may be evil by intent, but not the orcs and the trolls. They are victims as much as the Elves and Men.

However, there are characters (Gollum the most representative) that refuse repentance and persist in wickedness.