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| Date | Type: Subtype | Occupation | Location | Enslaver | Role | Brief Description | Source |
| 1787 | Labor: Agricultural | Overseer | Monticello | On list of "Overseers & Stewards employed." | Thomas Jefferson’s Farm Book, page 29 | ||
| 1810 Feb. | Provisions: Food | Monticello | Bread supply list. | Thomas Jefferson’s Farm Book, page 134 | |||
| 1810 Dec. | Provisions: Food | Overseer | Albemarle County | List calculating hogs killed for rations for overseers, enslaved people, and other residents. | Thomas Jefferson’s Farm Book, page 135 | ||
| 1812 Mar. 09 | Commercial: Services | William Watson to Thomas Jefferson | |||||
| 1813 Dec. | Provisions: Clothing | Lewis was hired out to TJ and supplied clothing. | Thomas Jefferson’s Farm Book, page 145 | ||||
| 1814 Dec. | Provisions: Clothing | Lewis was hired out to TJ and supplied clothing. | Thomas Jefferson’s Farm Book, page 147 | ||||
| 1815 June 26 | Labor: Agricultural | Overseer | Monticello | Oversaw wheat harvest. | Thomas Jefferson’s Farm Book, page 149 | ||
| 1815 June 26 | Labor: Agricultural | Lewis labored during wheat harvest and received mutton and whiskey. | Thomas Jefferson’s Farm Book, page 149 | ||||
| 1821 Feb. | Provisions: Food | Overseer | Monticello | Overseer of 31 people on bread supply list. | Thomas Jefferson’s Farm Book, page 171 | ||
| 1822 Sept. 09 | Labor: Agricultural | Overseer | Monticello | Advices TJ on Jeremiah's mule team, Joseph Fossett's work, and carriole repair. | Edmund Bacon to Thomas Jefferson | ||
| 1822 Sept. 11 | Labor: Artisanal | Requests Joseph Fossett to iron a wagon and discusses financing with TJ. | Edmund Bacon to Thomas Jefferson |