So how does one obtain headrights for an Indian?

Headrights in colonial America were rights to a certain amount of land, typically 50 acres, to be claimed by someone who imported an individual by ship from the mother country.  If people paid their own way, they claimed thier own headrights and those for their family members.  If someone else paid your way, they claimed your headrights. 

Some folks are found listed multiple times, which means they were transported more than once.  Yes, people did make multiple trips back to the mother country.  It may also be that some people were counted if they were transported from one location to another, like maybe from Maryland to Virginia – but this is beginning to fall into the category of speculation.  One thing you can be sure of – human nature being what it is – if there was a way to capitalize on a given situation – someone found a way to do it.

Regardless of how, indeed, Robert Caufield did claim headrights for Jacob, an Indian, as shown in the following record, leaving us to wonder how and why.

A Study of Virginia Indians and Jamestown: The First Century

http://www.nps.gov/history/history/online_books/jame1/moretti-langholtz/chap10a.htm (chapter 10 table link)

Abstracts: Acts of Assembly

Abstracts: Colonial Papers (Library of Virginia)

Abstracts: Correspondence

Abstracts: County Records

Surry County: