Bombadil in the Last Alliance?
 

On my fifth reading of LotR, a passage about Tom Bombadil struck me as odd... Tom picks up a brooch from the Barrow Wight's tomb to bring home to Goldberry.

He looked long at it, as if stirred by some memory, shaking his head, and saying at last: "...Fair was she who long ago wore this on her shoulder."

...he goes on to mention the Dunadain who still wander.

The tone of the piece seems to indicate that Bombadil is closer to the events he is describing (or refusing to describe) than he will let on. Perhaps remember some personal tragedy. Could he have played a greater part in this history? Perhaps before "going native?"

I never caught that. So, who is she? Princess Peach of Cardolan? Hmm.....
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Marijuana bubbler

No, not Last Alliance. He refers to the collapse of the kingdom of Arnor and the petty kingdoms that followed and destroyed each other or/and the assault from Angmar.

It is possible. One does get the impression that perhaps Bombadil wandered over a wider area in the past.

However, I doubt he played a great role in history. It would seem to go against the theme of observation, which is one of the reasons why Tolkien put him in there in the first place.

Here's a previous discussion which I think was quite interesting...
http://forum.barrowdowns.com/showthread.php?t=891