Yes, but Gandalf was a Maia and so he understood Eru’s purposes more fully then others, and he knew that the hobbits would succeed. He refers to Sauron being a ‘wise fool’ because he doesn’t even contemplate the notions that two Hobbits would come into his impregnable fortress and actually throw away the ring. Sauron had become, in a sense a pacifist. He believed that although god did exist (he had probably seen him with his own eyes, before or during the music), he wouldn’t interfere with his affairs, and M-E was Saurons for the taking, hence Saurons stupid mistakes. (I.e., he thought that Sam and Frodo were spies.) Gandalf needed to the exact opposite of what Sauron would’ve done and that was the only way they could’ve beaten him. It was not mad, it was genius. Of course foresight played a large part in it too. Most elves and Maiar have large abundance of foresight. For example, who the hell would send 14 Dwarfs and a Hobbit to take some treasure off a mighty dragon. Gandalf even tells Thorin Oakenshield that the quest would fail unless Bilbo went with them, saying that a great foresight was on him.
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