Hemings

Recently I watched "Finding Your Roots," a TV show created by Henry Lewis Gates Jr., in which a celebrity is introduced to ancestors he or she knew nothing about. In this recent episode a famous black actor discovered that one of his enslaved direct ancestors had been taken by his master on a trip into Canada. A band of abolitionists had captured the black man and attempted to persuade him to remain in Canada, where slavery was illegal. Instead the black ancestor followed his master back into the United States and voluntarily returned to slavery (until the Civil War freed him again).

My assumption is that this sort of thing happened from time to time. The man probably chose not to be separated from his wife and children. 

A similar incident can be found in the life of Sarah "Sally" Hemings and her older brother.  Thomas Jefferson had them sent to join him in France, where slavery was illegal. They apparently found out that they did not have to return to Virginia, but they did, after striking bargains with Jefferson.

The brother had been trained as a French chef.  Jefferson agreed to free him in Virginia after he had trained a replacement chef for himself. The brother had learned a really good trade and could support himself. (Imagine the two of them working out this arrangement in Paris.)

I don't know what the laws on freed slaves were in Virginia at the time. In some states, freed slaves had to go north etc. 

Sally Hemings, enslaved and greatly under-age, was Jefferson's dead wife's half-sister (they had the same father) and looked like her. Hemings was three-quarters white (her children with Jefferson looked white and three of the four passed into the white community). In France, at the age of about 15, she apparently bargained with Jefferson. She would return with him to Virginia provided their children were taught a trade and freed, an agreement Jefferson kept.

Sally was not freed, because as an attractive free black woman, her presence in the Jefferson household would have violated the pretenses of Virginian gentry. When Jefferson died, Sally moved into town as a retired person, more or less, and lived to see a grandchild. 

I've wondered about the relationship between Sally and Jefferson's white daughters, which was apparently good. Maybe it was partly because they were all related, and the daughters wanted no step-mother to deal with. The hypocrisy in this culture (where black women were regularly owned by white men and no one would comment about it out loud) was astonishing.