Ann Cary Randolph Bankhead (January 23, 1791–February 11, 1826), Thomas Jefferson's eldest grandchild and the daughter of Martha Jefferson Randolph and Thomas Mann Randolph, was born at Monticello in January 1791. On September 19, 1808, she married Charles Lewis Bankhead, the son of Mary Warner Lewis Bankhead and one of her grandfather's closest friends, John Bankhead. Three sons and a daughter from this union reached adulthood. In 1811 the Bankheads purchased Carlton, an 800-acre farm adjacent to Monticello. Charles Bankhead proved to be alcoholic, abusive, and improvident. Trustees managed his estate after 1815, when Jefferson sought to ease a financial crisis by adding 130 acres to the couple's holdings. Ann Bankhead died of complications following childbirth five months before her grandfather, on February 11, 1826, and was buried in the family graveyard at Monticello.
1791 February 2. (Thomas Mann Randolph to Jefferson). "Polly has allready informed you of the addition of a little Grand Daughter to your family and of its unexpected arrival; which was pleasing to us as it was not in the least premature. Mrs. Fleming had been kind enough to offer her assistance to Patsy during her confinement which we expected would have commenced about the end of February, and I had gone down to accompany her up. But Mrs. Lewises attention and tender concern supplied the place of Mrs. Fleming and made some amends for the want of my Sympathy. Patsy has had one slight fever only which lasted for a very short time: the little girl is perfectly well and grows fast."
1791 February 8. (Thomas Mann Randolph to Jefferson). "The little one is perfectly well and increases in size very fast. We are desirous that you should honor her and ourselves by confering a name on her and accordingly have deferred the christening till we can hear from you."
1797 June 12. (Mary Jefferson to Jefferson). "Mr. Randolph and the children arriv'd here last tuesday all in perfect health Ann and Jefferson grown so much as to amaze us, Ann seems to promise more every day of resembling her mother. Her disposition is the same allready she will no doubt be worthy of her."
1801 January 31. (Martha Jefferson Randolph and Thomas Mann Randolph to Jefferson). "my 2 eldest are uncommonly backward in every thing much more so than many others who have not had half the pains taken with them. Ellen is wonderfully apt. I shall have no trouble with her, but the two others excite serious anxiety with regard to their intellect. of Jefferson my hopes were so little sanguine that I discovered with some surprise & pleasure that he was quicker than I had ever thought it possible for him to be, but he has Lost so much time and will necesarily lose so much more before he can be placed at a good school that I am very unhappy about him. Anne does not want memory but she does not improve. she appears to me to Learn absolutely without profit."
1801 February 5. (Jefferson to Martha Jefferson Randolph). "I have formed a different judgment of both Anne & Jefferson from what you do; of Anne positively, of Jefferson possibly. I think her apt, intelligent, good humored & of soft & affectionate dispositions, & that she will make a pleasant, amiable and respectable woman."
1811 May 7. (Elizabeth House Trist to Catharine Bache). "Bankhead has given up the scheme of going to Bedford and has made a purchase of that Farm adjoining Monticello .... I fancy it is a great disappointment to Mr Jefferson who pleased him self with the Idea of Anns living in Bedford as he shou'd be a great part of his time there ... Ann notwithstanding she will be so near her family regrets the change as she thinks it will not be so much for their interest to be so near Charlottesville."
1814 August 22. (Elizabeth House Trist to Catharine Bache). "I heard too with great concern that Bankhead has turn'd out a great sot always frolicking and carousing at the Taverns in the Neighbourhood poor Ann I feel for her and Mr. R. is so much involved that tis thought he can never be extricated."
1826 February 11. (Cornelia Jefferson Randolph to Mary Jefferson Randolph). "you had better come down this morning for you will never see sister Ann again if you do not, there is no hope for her. Virginia ought to be told for she must know the worst soon, and grandpapa."
ca. 1852. (Robley Dunglison). "On the last day of the fatal illness of his granddaughter, who had married a most unworthy person of the name of Bankhead, a man of the most intemperate habits, and, so far as I know, possessed of no redeeming virtues, Mr. Jefferson was present in the adjoining apartment, and when the announcement was made by me, that but little hope remained,—that she was, indeed, moribund, it is impossible to imagine more poignant distress than was exhibited by him. He shed tears; and abandoned himself to every evidence of intense grief."
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