Did President James Madison ever free any of his slaves?
There are no reports that indicate that President James Madison ever freed any of his slaves. However, there are cases in which enslaved African Americans at Montpelier were able to gain their freedom. Paul Jennings was an enslaved man who served as Madison’s body servant in both Washington, D.C., and at Montpelier. The 47-year old Jennings was sold in 1846 by Dolley Madison to cover debts. Daniel Webster subsequently purchased Jennings in 1847, and he made an agreement with Jennings for him to work off his debt at $8 a month until he was fully free. Jennings was a member of the free black population of Washington from 1847 until his death in 1870. Billey, another enslaved man from Montpelier, also eventually gained his freedom. Billey accompanied President James Madison to the Contintental Congress in 1780. In 1783, Madison wrote to his father to tell him that he was reluctant to bring Billey back to Montpelier.