I did look at your website and I wish I could be more help. I am not really researching Caldwell Jefferson or Jefferson Caldwell. You could say I temporarily adopted him and am hoping someone else will run with it, now that he is on the Internet. If it wasn't clear, he was free. I guess I was struck by his story, enough to seek him out in later years, with no success. I note you have some Pence/Prince connections. Prince may also be found with Printz. I know they are somewhat common names, and not in my direct line, but I have seen them in Rockingham County VA and Loudon County, Virginia. Also in Ohio, with migrations west in the 1830s and earlier.