"... I knew that Sauron had arisen again and would soon declare himself, and I knew that he was preparing for a great war. How would he begin? Would he first try to reoccupy Mordor, or would he first attack the chief strongholds of his enemies? I thought then, and I am sure now, that to attack Lorien and Rivendell, as soon as he was strong enough, was his original plan. It would have been a much better plan for him, and much worse for us." ( Gandalf in 'The Quest for Erebor, Unfinished Tales of Numenor and Middle-earth )
Well, if he had, no Quest, therefore no 'The Lord of the Rings', therefore no -shockhorror!- fandom.
But seriously. Why didn't he, this Maia who had so cunningly manipulated Ar-Pharazon of Numenor? Everything that Sauron did after the downfall of Numenor seems to have been *hasty*... and, of course, a hasty stroke often goes astray and all that. Thoughts, Mordorks?