Eston Hemings Jefferson was born into slavery at Monticello, the youngest son of Sally Hemings, a mixed-race enslaved woman. Most historians who have considered the question believe that his father was Thomas Jefferson, the third President of the United States. Evidence from a 1998 DNA test showed that a descendant of Eston matched the Jefferson male line, and historical evidence also supports the conclusion that Thomas Jefferson was probably Eston's father. Many historians believe that Jefferson and Sally Hemings had six children together, four of whom survived to adulthood. Other historians disagree.

Thomas Jefferson Randolph of Albemarle County was a Virginia planter, soldier and politician who served multiple terms in the Virginia House of Delegates, as rector of the University of Virginia, and as a colonel in the Confederate Army during the American Civil War. The favorite grandson of President Thomas Jefferson, he helped manage Monticello near the end of his grandfather's life and was executor of his estate, and later also served in the Virginia Constitutional Convention of 1850 and at the Virginia Secession Convention of 1861.