Barnaby Gillette was one of the 12 children of Edward and Jane Gillette, an enslaved family who lived at the Monticello quarter farm. While Jefferson was president, the Gillettes were leased to John H. Craven, tenant of the southern half of the Monticello plantation. The Gillette family possessed a wide array of skills. Barnaby made nails in the nailery from age 11 to 15, and learned shoemaking from Phill. Coopering was his main trade; he worked adjacent to the Shadwell mill making barrels for flour. He earned a bonus of one barrel for every 30 barrels he made, thus earning as much as 40 dollars per year. Gillette trained others in the trade, including his brother Moses. Gillette had three children with his first wife, Lily Hern, before their separation. He lost Milly, his second wife, to a “malignant” fever that swept the plantation in 1819.