Hi Dave-
The earliest individuals I found in your line (so far) were the parents of Loni Jefferson FREEMAN:
Sam J. FREEMAN, born in Monroe Co., Tennessee. He married Martha AMMONS. She was born in Swain Co., North Carolina.
The 1759 tax list for Rowan Co., North Carolina included the following individuals with the Freeman Surname, including two Samuels:
John FREEMAN
Samuel FREEMAN
Jona. FREEMAN
Saml. FREEMAN
Jona. FREEMAN
One thing I've seen with my Freeman line is the tendency to repeat the same given name within same generations and then to hand down the same names to successive ones. It drives me crazy, because it's hard to tell which record goes with which person.
I think there's still a good chance that we're connected up there, somewhere.
Happy hunting!
Jean