One thing that seemed to me an inherent contradiction that I just couldn't shake after reading was in letter 246 when Tolkien states that "Gandalf as Ring-Lord would have been far worse than Sauron." Tolkien is making a pretty bold claim here. Sauron by any definition we have come up with in class is absolutely evil, he is a shadow upon Middle Earth in more ways than one. Tolkien in the margin of letter 246 writes, "thus while Sauron multiplied evil, he left 'good' clearly distinguishable from it. Gandalf would have made good detestable and seem evil." While this is fine to say, one reason this seems to me an inherent contradiction is that I am having a hard time imagining what Tolkien means by Gandalf as Ring-Lord being "far worse" than Sauron, since Sauron as Ring-Lord seems like the worst of all the possible futures for Middle Earth.
Sauron as Ring-Lord would have completely dominated Middle-Earth. All the humans, hobbits, and good things of the world would have been killed or enslaved. Sauron's thirst for power would have spread out indefinitely and none would have been able to oppose him. Gandalf on the other hand hand would have continued to rule and order things for 'good', and to the benefit of his subjects according to his wisdom which was and would remain great. Gandalf as a Maiar is a lesser angel, and therefore a certain amount of self-righteousness seems pretty reasonable out of him. Therefore why would it be such a bad thing that Gandalf, the only one who could take Sauron in a straight up 1v1, rule over Middle Earth in the name of 'good'. What does it mean for good to be detestable and seem evil?
If i had to make a guess I would tend to go back to the question posed a couple classes ago of, 'would you rather be good or evil'? While the general answer was somehow yes, the 'being evil sounds a lot more fun' argument holds quite a bit of sway. Gandalf as Ring-Lord and ruler would continually tried to "order things for 'good'". While his wisdom is great, is it possible that by trying to order the world for good, Gandalf would in turn be limiting the people of Middle Earth's free will. This was one potential definition that was brought up for evil, but does preventing people from being evil or going down an evil path by limiting their free will to do so count as an evil act? Illuvatar gifted humans with a certain amount of free will and power to shape their lives and histories, so does Gandalf limiting this count as evil? Could this be what Tolkien means by making good detestable and seem evil? Or could it be something even more vicious like Gandalf forcing humans to be like the angels and sing praises to Illuvatar all day every day? To me such a good doesn't seems so much as evil rather it seems like evil itself.
The question of how the ring would work on and dominate Gandalf also seemed to boggle my mind. Gandalf seems to think that upon bearing the Ring he would have "power too great and terrible" and that he could "become like the Dark Lord himself". One suggestion that was made of how the ring works is that it somehow uses one's shadow or gives more power to one's shadow to control how we act. As Le Guin writes, our shadows are " all the qualities and tendencies within us that have been repressed, denied, or not used." Gandalf is very righteous, therefore would he have quite a terrible shadow? or little to no shadow at all? As a lesser angel, does Gandalf have to continually repress all that is bad in order to remain righteous, or as a Maiar is he so righteous and good that he simply doesn't have to worry about evil thoughts? Melkor was able to corrupt Maiar, therefore we know that Maiar certainly have the ability to be turned thoroughly evil, and Saruman was certainly evil at time in some senses.
I would tend to lean towards the opinion that Gandalf's shadow is not too great. Gandalf is good, he is certainly the most good of any character we meet in the Lord of the Rings, therefore i would think that he is not repressing some huge inner evil inside himself, rather there is little to no evil to be repressed. The ring would certainly have a some sort of sway over Gandalf, however as he says, the way for the ring into Gandalf's heart "is by pity, pity for weakness and the desire of strength to do good." While it is impossible to know whether or not Gandalf would have somehow slowly become like the Dark Lord himself, it seems like his desire to do good would have a difficult time being dominated.
In summary i am unconvinced by Tolkien's assertion that Gandalf as Ring-Lord would have been far worse than Sauron as Ring-Lord. Gandalf may have created a world that was not overly enjoyable for humans to live in, but at least they would have had a world to live in. Perhaps i am not thinking into this deep enough, but my instincts have a hard time believing that someone who deep down desires good ruling the world would create a "far worse" world than someone who is pretty much evil incarnate.