Scandal
When she was about nineteen years old, Ann went to live with her sister Judith and brother-in-law, Richard Randolph, at Bizarre Plantation, an Antebellum tobacco plantation at what would become the corner of East Second and North Main Streets in Farmville, Virginia. Richard and his brothers Theodorick Randolph and John Randolph of Roanoke lost their father in 1775, and three years later their mother married St. George Tucker, a prominent lawyer and future law professor at the College of William and Mary as well as Virginia appellate judge. The eldest and therefore heir to most of their late father's estate had studied at Princeton as well as with noted Virginia jurist George Wythe (St. George Tucker's mentor and friend) before taking control of his late father's plantation. However, the tobacco economy was collapsing at the time.
Ann became engaged to Theodoric Randolph, against her father's wishes. However, he died in the spring of 1792. Some later claimed that Ann and Richard were too fond of one another, and in the summer of 1792, Ann began gaining noticeable weight. On October 1, 1792, Judith, Richard, and Ann traveled to the Glentivar (or Glenlyvar) estate thirty miles northeast of Farmville to visit their cousin Randolph Harrison and his wife, Mary. The following night, Ann screamed, awakening the Harrisons. A servant told Mary Harrison that Ann was sick and needed laudanum. Richard was in Ann's dark room and would not allow a candle to be brought in, but Mary Harrison was able to sit with Ann for a few minutes. Judith remained in bed in the room she was staying in. The next day, blood was found on Ann's pillowcases and the stairs; her bedding had been removed; and she remained in her room. The Randolphs left the Harrisons’ estate at the end of the week. The Harrisons were later told that the plantation's enslaved people found the corpse of a baby in a pile of old shingles.
In April 1793, the local prosecutor accused Richard Randolph of murdering the baby born to Ann. Prominent lawyers John Marshall and Patrick Henry defended him at a trial before the judges of the Prince Edward County court. During the trial, Martha Jefferson Randolph stated that she had obtained gum guaicum, which she believed could be used to abort a baby, and had given it to Ann two weeks before the trip to Glentivar. Other people also testified during the trial that Ann had been pregnant.
Enslaved people were precluded from testifying by Virginia law, so no evidence could be presented about the body found in the stack of shingles. Judith Randolph either did not testify or she testified that Richard did not leave their room that night. Richard Randolph was acquitted. Despite the acquittal, one modern author noted Ann faced severe consequences: "before the year was out, the girl [Ann] had become the Jezebel of the Old Dominion and the young man who was the alleged father [Richard] had become its laughing stock. Idlers in taverns made ribald jokes at his expense."
Upon hearing of the scandal, Thomas Jefferson wrote a letter to his daughter, Martha Jefferson Randolph, saying he considered Ann "the pitiable victim" and encouraged his daughter to be a kind influence in her life. In fact, Ann had been engaged to Richard Randolph's brother, Theodoric, who had died eight months before the stillbirth. Jefferson stated that he only found one person guilty.
For her [Ann] it is the moment of trying the affection of her friends, when their commiseration and comfort become balm to her wounds. I hope you will deal them out to her in full measure, regardless of what the trifling or malignant may think or say. Never throw off the best affections of nature in the moment when they become most precious to their object; nor fear to extend your hand to save another, lest you should sink yourself. You are on firm ground: your kindnesses will help her and count in your own favor also.
Martha responded that the "vile seducer" had both destroyed Ann's reputation and corrupted her mind, and she was concerned that some people may be swayed from what a "person of sense" would deduce about the scandal.
Richard Randolph died mysteriously in 1796, leaving behind a will which scandalized many because it manumitted his slaves, a direction Judith Randolph fought for years to implement; afterwards, Ann continued to live at the Bizarre plantation. Richard's brother, the childless and unmarried John Randolph of Roanoke, thought that Ann had poisoned Richard, and came into power the guardian for Richard and Judith's underage sons. In 1805, John asked Ann to leave the Bizarre Plantation. She spent the first couple of nights in the abandoned Tuckahoe mansion before living with various friends. She then lived at Monticello with her brother, Thomas Mann Randolph Jr., who had since married their cousin, Martha Jefferson Randolph. She also lived in Richmond, Rhode Island, and Connecticut. Ann had very limited means, at times receiving small sums of money from her brothers, and she may have taught school in Rhode Island.
