Can you give a little clue to this one,
Saucy? I have no idea where to start looking; it sounds like something that could have belonged to the time of his youth and the clubs that were begun then, but must have been after the writing of LotR.
As to the reason it would be appropriate, I assume because of his "love of the Halflings' leaf"...
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'Mercy!' cried Gandalf. 'If the giving of information is to be the cure of your inquisitiveness, I shall spend all the rest of my days in answering you. What more do you want to know?' 'The whole history of Middle-earth..
.'