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We have at least one clue:the Nazgul were first sighted around SA 2250, or roughly 550 years after the First War. Now, I have no idea how long it took a Great King of Men to become a wraith, but it couldn't have been less than a couple of centuries, could it? On ther other hand, I doubt he would resist as long as Gollum (some 500 years). In other words, passing out rings was something Sauron decided to do after his attempt at conquest by brute force had been thwarted.
Obviously, Sauron would only have given Rings of Power out so long as he held the One and could control them, so deff. in the Second Age.
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The entire plot of The Lord of the Rings could be said to turn on what Sauron didn’t know, and when he didn’t know it.
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