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On one of his first trips he went with a good friend only. Once deep in the “ Kaintuck “ region they set up a semi-permanent camp. They would split up most mornings and explore in different directions, meeting back at camp each evening to discuss what each had found.
One evening, his friend did not show up. In fact he never returned. Boone searched for him for days, worried that he may have had a bad encounter with a bear, hostile Indians, or had some accident. Not found.
Years later Boone was part of a military expedition, acting as a guide and scout or something. The army was traveling in a slow-moving column led by a contingent of axe men chopping a crude road path through the dense trees and brush.
One day, the front of the column stopped, and Boone, at the time riding some distance to the rear, was called forward. While everyone waited he made his way to the front to see what was going on.
When he got there, the axe men showed him a large trunked hollow dead tree with an opening at the bottom, that had been upright until they chopped it down. Inside was a human skeleton with a broken upper arm, with patches of clothing on. Attached to the skeleton was a personalized powder horn on a strap that Boone recognized instantly as the one carried by his friend that had disappeared all those years before. The victim had apparently been seriously injured somehow, and, hiding inside the tree had died some time later.
What were the odds of Boone’s old friend being found like that??!!
Sorry I do not remember the man’s name, but I have seen it in print several times years ago, and he had been the one to talk Boone into making the trip with him.

PS- I just now, 20 minutes after posting my comment above, remembered that the guy who disappeared had the last name of Findley.
Fairly sure that was the name.

That was Stewart, his brother in law, he went missing on Boone's first trip to Kentucky. Stewart and Boone had split from their main party, which included Finley, who originally told Boone about Kentucky. There were several that made that trip and they split up to trap beavers and kill deer for hides. This was in 1769, Boone stayed there 2 years before returning. The rest returned and Boones brother, Squire brought him more supplies before he went back. This was also when he came home and his wife had a baby by his brother Ned.
 
That was Stewart, his brother in law, he went missing on Boone's first trip to Kentucky. Stewart and Boone had split from their main party, which included Finley, who originally told Boone about Kentucky. There were several that made that trip and they split up to trap beavers and kill deer for hides. This was in 1769, Boone stayed there 2 years before returning. The rest returned and Boones brother, Squire brought him more supplies before he went back. This was also when he came home and his wife had a baby by his brother Ned.
Thanks for the correction. I like to be accurate when putting out information, and confess I was working from memory about something I read 35+ years ago.
 
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