Gabriel Lilly was overseer at Monticello from 1800 to 1805. Settling on the plantation with his family and slaves, Lilly likely lived near the border with Tufton farm; he received rations, an annual salary of £50, and an additional £10 per year to oversee the nailery. Lilly also supervised the “jobbers,” hired slaves tasked with building the Shadwell canal and mills, and other projects. Although Jefferson praised Lilly as “as good a one [overseer] as can be,” Lilly’s management was punctuated by violence. In 1801, Jefferson was concerned with his overseer’s “treatment of the nailers.” In 1804, joiner James Oldham charged Lilly with “Barbarity … moast cruel” after whipping an ill James Hemings. Lilly’s departure for Kentucky in 1805 threatened to separate Jefferson’s slave James Hern from his wife and children, who were owned by Lilly. But Jefferson bought Lilly’s “negro woman Lucretia Jame’s wife, her 2. sons John & Randall and the child of which she is pregnant” for £180.