Gandalf as Ring-lord

[Evisse the Blue]

Originally posted by Maedhros in another topic, quoted from the Letters of JRRT

Gandalf as Ring-Lord would have been far worse than Sauron. He would have remained 'righteous', but self-righteous. He would have continued to rule and order things for 'good', and the benefit of his subjects according to his wisdom (which was and would have remained great). 'Thus while Sauron multiplied [illegible word] evil, he left "good" clearly distinguishable from it. Gandalf would have made good detestable and seem evil.'

This paragraph represents a perpetual mystery to me, and having seen it mentioned I'd like to bring it into discussion. (I used the search function, but I found only discussions that briefly touched this topic but didn't delve into its depths). How could Gandalf as Ring-lord remain righteous and wise, and yet worse that Sauron? And how can one make good appear detestable?

Maybe he means that during Gandalf's reign the world will become many shades of grey (no pun intended!) instead of the white vs black clear-cut distinction that had existed when Sauron was the Lord of the Ring. Even in those times, Gandalf was particularly sensitive to 'grey characters', such as Gollum, whom he showed mercy and understanding towards. If all the responsbility of the world's rule were to rest on his shoulders, he would probably take his wisdom, his pondering of choices and his great ability for compassion to its limits, therefore living in a perpetual 'twilight of doubt as to sides'. He would thus become less of a mythical hero and more of a 'modern' hero, resembling, if you will, a character of Dostoievski's or Kafka's. That's the way I see this ambiguous quote.