In 1725, Jane Webb, a free woman of color, sued Thomas Savage, a slave owner and middling planter, in Northampton County Court, on the Eastern Shore of Virginia. Webb v. Savage was an unusual lawsuit, the culmination of over twenty years of legal wrangling between two parties who had an uncommon and intimate connection. The case originated in a 1703 contract between the pair, and at the time it was written, its terms, assumedly, were clear and mutually agreed upon. Two decades later, however, a tangled skein of circumstances obscured the stipulations of that original agreement. Over the course of those same years, the legal meaning of freedom for individuals like Jane Webb had fundamentally changed. Both fraught interpersonal relations and the evolution of race-based law mattered to the 1725 chancery case for one simple reason: Thomas Savage owned Jane Webb's husband. Despite the fact that Webb's spouse, named only in the records as Left, was enslaved, their marriage was legally recognized, and the seven children born to the couple, following the legal doctrine partus sequitur ventrum, took their free status as well as their surname from their mother.