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For one thing, two different people. I will give you Wikipedia links first and then Geni profile links, but the most important question is back to you - who is your later possibly Cherokee person?
https://en.wikipedia.org/wiki/Oconostota (1703 - 1783) AKA Stalking Turkey
https://en.wikipedia.org/wiki/Ostenaco (1703 - 1780) AKA Judd’s Friend
I got your tree merged up as requested. So tell us: why is it thought that Lucy Tomerlin was the daughter of a Cherokee woman, who was the daughter of (from location, I’d say “Judd’s Friend”). ?
His only known daughter married Lt. Henry Timberlake, Adventurer & Author and there are Timberlake Descendants.