In 1809, the Stephenson family moved to the newly created Illinois Territory.
The Northwest Ordinance, which governed the development of the entire Northwest Territory including Illinois, clearly outlawed “involuntary servitude;” therefore, slavery, as it existed in the south, was clearly illegal in the Illinois Territory. Many of the settlers, and almost all of the political elite of the Illinois Territory, were southerners and slave holders. There was an immediate search for a legal loophole. The loophole was the term “involuntary.” As long as servitude was voluntary, then it was deemed to be legal; therefore, a legal fiction was embraced. Slaves brought into the territory had to be registered in the county where their owners lived. A contract, or “indenture,” was required. The slave and the owner agreed on a term of servitude. At the end of that time, the servant was to be freed.
As residents of Kentucky, the Stephensons owned a number of slaves. These slaves were registered in Kaskaskia when they moved to the Illinois Territory in 1809. Several of these slaves were apparently freed at the end of their indenture: The 1820 census shows two free blacks living with the Stephensons. After Benjamin Stephenson’s death in 1822, “one negro man and four children” were sold at the estate auction. All of these slaves, or servants, were repurchased by Lucy Stephenson at the estate auction.