Randolph received a private education suitable to his class, and partly grew up at Monticello as well as his grandfather's Poplar Forest plantation.

Meanwhile, Thomas and Jane Randolph had thirteen children: Since the late 20th century, some criticized Randolph for falsely telling historian Henry Randall that his uncle Peter Carr (Thomas Jefferson's nephew) was the father of Sally Hemings' children (rather than his blood relatives, as was later found true).

A planter and leading citizen of his native Albemarle County, like his father and grandfathers, Randolph operated plantations (including Monticello) using enslaved labor.

[8] His mother withheld Sally Hemings from the auction and gave her "her time," which informally allowed her to live freely in Charlottesville, Virginia with her two younger sons.

[9] In the 1850 federal census, Randolph owned 46 enslaved people in Albemarle county, ranging from 79- and 70-year-old women and a 75-year-old man to a 9-year-old boy and girls aged 5, 3 and one year old.

During several of Thomas Randolph's legislative terms, he often served alongside Alexander Rives, younger brother of William C. Rives, who was this Randolph's friend since their school days and who had frequently visited Monticello and built his plantation home Castle Hill nearby after marrying a daughter of Thomas Walker who owned that plantation.

[13] After Nat Turner's slave rebellion of 1831, Randolph introduced a post nati emancipation plan in the Virginia House of Delegates.

[14] This would have provided for gradual emancipation of children born into slavery after July 3, 1840, requiring that they serve an apprenticeship, then leave the state upon coming of age.

Randolph also allowed his wife and unmarried sisters to teach school at what had been the original house on his Edgehill estate beginning in 1829.

His sister Cornelia Randolph (1799-1871) taught painting, drawing and sculpture there before the American Civil War, during which she moved to Alexandria, Virginia to live with female relatives.

[20] Albemarle County voters also elected Randolph along with Southall and James P. Holcombe as their delegates to the Virginia Secession Convention of 1861.

Randolph also drew praise during the one battle his artillery fought near Yorktown, and became the Confederate States Army Secretary of War for eight months in 1862.

[a] In the 1850s, Randolph told the biographer Henry Randall that Jefferson's nephew Peter Carr had been the father of Hemings' children.

He said in one instance, a gentleman dining with Mr. Jefferson, looked so startled as he raised his eyes from the latter to the servant behind him, that his discovery of the resemblance was perfectly obvious to all.