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I am thinking that since Gandalf enjoyed being with Hobbits and liked to visit them, I am wondering if there is anything in LotR canon that mentions whether he had visited the Stoor Hobbits during his travels around Middle-earth, and if so, whether he had met Sméagol during one of these visits. This would have taken place at least 500 years in the past, sometime before Sméagol got the One Ring.

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    Had he done so, Gandalf would most likely have mentioned it in The Shadow of the Past. Commented Oct 7, 2022 at 20:46

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No. In Chapter 2 of The Fellowship of the Ring ("The Shadow of the Past"), Gandalf describes how he captured Gollum and interrogated him, learning of his history and how he obtained the Ring. Everything in that chapter is described as what Gandalf was able to learn from Gollum, with much uncertainty, since Gollum's memory is not perfect, and because Gollum lies. Nothing is described as being Gandalf's direct knowledge, not even the presence of hobbit-like beings by the Great River.

'Long after, but still very long ago, there lived by the banks of the Great River on the edge of Wilderland a clever-handed and quiet-footed little people. I guess they were of hobbit-kind; akin to the fathers of the fathers of the Stoors, for they loved the River, and often swam in it, or made little boats of reeds.

Gollum is a liar, and you have to sift his words.

I have no doubt that Sméagol's grandmother was a matriarch, a great person in her way, but to talk of her possessing many Elven-rings was absurd, and as for giving them away, it was a lie.

If Gandalf knew things about Sméagol/Gollum or his people from direct knowledge, he would have said so in this scene.

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    Sméagol's grandmother needs a movie trilogy or series! Commented Oct 7, 2022 at 23:11
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    Give Peter Jackson a minute...
    – Andrew
    Commented Oct 7, 2022 at 23:14
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There is no such mention in The Return of the King, Appendix B, "The Tale of Years."