Tobacco was one of Colonial Virginia's most successful crops, dating back to the 1600s, eventually forming the basis of the economy. While small planters often sold their crops locally through agents in exchange for manufactured goods, larger planters typically shipped their tobacco back to England. Once in England, a consignment agent sold the tobacco in exchange for a cut of the profits. John Caygill and Josias Clapham likely had such a consignment arrangement, with Clapham shipping his tobacco to England and Caygill, serving the consignment role, selling the goods on his behalf. While the 1750s saw a stabilization in the price of tobacco in England, much of the surrounding decades saw significant instability and fluctuations in the price due primarily to overproduction and a series of British wars causing a disruption in shipping.

John Caygill was born circa 1708 to John Caygill, the wealthiest merchant in Halifax, a small town in West Yorkshire, and his second wife Martha Stead. One of at least eight children, and one of the only to survive past infancy, the junior John Caygill also became one of the town's most prominent and influential citizens. During the Georgian era he contributed substantially to the building and creation of several prominent buildings and landmarks including The Shay mansion, two terraces of red brick houses later known as The Square, and The Piece Hall, which still stands today. Caygill married Jane Selwin and had one surviving child, a daughter also named Jane, but known as Jenny. He died on May 22, 1787 at the age of 79. His memorial can be seen in the northeast corner of Halifax Minister, the town's parish church.

Josias Clapham was descended from an ancient family of Yorkshire, England. His uncle, also named Josias Clapham, owned significant land in the Northern Neck area of Virginia at the time of his death circa 1740s. In his will, Clapham left a portion of this land, two hundred and forty-three acres, to his nephew, Josias. At the time, the younger Josias was living in Wakefield, Yorkshire and very much in debt, so in the hopes of changing his financial situation he emigrated to Virginia to assume residence and ownership of the land willed to him by his uncle. Over the course of his life, Josias became a notable figure in colonial Northern Virginia, including positions in local government, an operational interest in a profitable Potomac River ferry business, and several other ventures including a water mill, warehouse, and mercantile. Josias lived a long life, eventually deeding his estate located in present day Lucketts, Loudoun County, later known as Chestnut Hill, to his son Samuel, sometime before his death circa 1800.