Webb School at Bell Buckle
I found out a little more about the Webb School, where the Tucker boys went to high school. It is a boarding school near Bell Buckle, TN and was found in 1870. A wikipedia article says that many of the graduates went to Vanderbuilt. Several of my relatives did indeed go on to Vanderbilt. So my great grandfather went to boarding school during his late teen years. A good way to research is to find old yearbooks to see what my great grandfather was like in High School, etc. From all of the stories I have heard, my great grandfather loved to have a little too much fun!
My grandmother also went to a boarding school, but I can’t remember the name or if it was a private girl’s college.
Notable alumni- 
TRAPPER JOHN!! He later went to Princeton University and is from Alabama. Didn’t know that!
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