On April 3, 1781 Thomas Jefferson noted in his Memorandum Book, "Sent David Watson a British deserter, house joiner by trade, to work at Monticello." He came to work about the same time William Orr joined the work force. Orr started working in January 1782.
Watson was apparently a convivial bachelor in his first years at Monticello, and he and his compatriot, William Orr, were fond of their whiskey, losing numerous work days during their binges. In his Memoirs of a Monticello Slave, Isaac remembered the two workmen and mentions them together, "The blacksmith was Billy Ore; the carriage maker Davy Watson...". Isaac also remarked that, "Both workmen, both smoked pipes, and both drinkers. Drank whiskey; git drunk and sing; take a week at a time drinkin' and singin.'". Jefferson's accounts substantiate Isaac's memories. After hiring Orr in January 1782 there are many entries over the next several months of charges of whiskey to both Watson and Orr. In spite of their conviviality they were apparently skilled workmen, as Isaac relates in his Memoirs that "Mr. Jefferson came down to Williamsburg in a phaeton made by Davy Watson.
While at Monticello, Watson worked as a wheelwright, carriage maker, cabinetmaker, and undoubtedly also in his trade as a house joiner. In addition to the phaeton, there are references to Davy Watson making wheels, a writing desk, laying off a timber yard, and supervising other Monticello carpenters. He gave the slave John Hemmings his first training in skilled woodworking.
David Watson returned to work at Monticello in 1793, now married. A son is mentioned in 1797. It was December 2, 1797 when Jefferson recorded that he "Settled with D. Watson...He leaves my service this day." Watson went to work at Blenheim and Enniscorthy after leaving Monticello, but he must have left with a good reference for in February 1798 he was working for Jefferson's son-in-law, Thomas Mann Randolph.
1781 October 28. (David Watson to Jefferson). "Watson would be 'much obleadged' if TJ would consider his state, for he is 'full of want' and has not "any Spair Clothing to Change my Self.' 'sume Stockings...publicklly' which caused him 'very much Concern: as I have a Spirit above thos things although Never So poor: has Come of Good people and good principle is Sorey to be Accomodated by Neagros."
1782 January 12. "Watson has had 3 galls. whiskey. 3. galls. do. 1/2 galln. do."
1783 October 15. "Settled with Watson & gave him note for balance L25-8-5."
1784 February 1. (Jefferson to John Key). "TMR's phaeton...Watson to be kept..."
1784 February 2. (Jefferson to David Watson). "Watson. TMR"s phaeton-list of work-provisions-my return home-will get watch, drawing instruments, clothes when I go to Phila-write to me."
1784 March 2. (Jefferson to John Key). "Watson may be discharged when stairs done, or before, if necessary--settle lost time since I came away as he pleases-keep L8 or L10 in hand for watch unless Wats. chuses money, then give me notice-not tell him I have been consulted...Watson lay off timber yard..."
1790 March 7. (Jefferson to Nicholas Lewis). "Watson attacks me here with his account. To satisfy him I gave him a line for you. I inclose you his account and will be obliged to you to compare it with the one settled between Mr. Key and him, and if any injustice has been done him, be so good as to have it rectified."
1792 September 19. "Pd. Watson 21 days work 12.D."
1793 October 22. "I have agreed with Watson to come & work for me at 120.D. a year, 500 lb. pork & corn."
1793 October ca. 22-25. (Memorandums to Thomas Mann Randolph). "Memorandums with respect to Watson. The waggon is to be sent for him on Monday Nov. 4. to bring his things. He is to work in the shop near the sawpit, and he must lodge there till Claxton moves. Then his wife is to live in Claxton's house till I return and can fix them elsewhere. Johnny is to work with him for the purpose of learning to make wheels, and all sorts of work. He is do do the following work, and in the order here mentioned unless any good reason should arise for changing it. Make a pair of wheels for Tom's mule cart. Mend or make wheels for the two oxcarts. Make a pair of forewheels for the Phaeton. Make 2. pr. of wheels for wheelbarrows. 3 f. diameter. Make a set of waggon wheels. The Phaeton wheels should be of ash, but the rest may be of the oak I bought of Gaines. Watson is to be furnished with provisions till I come home which may be done from the Plantations at the same time with Mr. Biddle. In rainy weather the carpenters are to be employed in splitting, planting, jointing and rounding shingles, which may be under the eye of Watson."
1794 November 1. "On settlement with Samuel Biddle I owe him for ...an order of David Watson 5. Charge D. Watson the above order for 5.D."
1794 November 12. "Recd. from Shadrech Reynolds in discharge of his smith's acct. Mr. Dyer's note for 42/. This note is to be to my credit with Dyer in part of my assumpsit for Watson."
1794 November 13. "Charge Dav. Watson L8-1-11 for goods recd. from Flem. & Mclanahan to my debit."
1794 December. (Farm Book Entry. Bread list for top of mountain for 1795.). "Watson 1."
1794 December 9. "Credit John Lively Mr. Dyer's assumpsit for him 49/ in full of his acct. for smith's work, and debit this to Dyer in part of my assumpsit for David Watson to him."
1794 December 11. "Credit Philip Gooch his assumpsit to Mr. Garland to pay the judgement Watson v. Dvid Watson, wherein I stood special bail. Qu sum? Assumed to Bruce for David Watson to pay Dr. Barber's demand against him. Qu. sum? Note I am to have Watson's cow & calf, valued at L5. but say L5-10."
1794 December 20. "Pd. Watson 4.D. assumed for do. to Peter 5.D. to Tom 4.D. = 13.D. Settled with Watson except blanks to be filled for some articles. Agreed that making up lost time his year is up this day, & the new year is to begin on his return from Augusta."
1794 December 24. "Pd. Peter the 5.D. assumed for Watson."
1795 January 17. "Credit Wm. Reynolds Saml. Dyer's note assuming for him 30/. which debit to Dyer on my assumpsit for Watson."
1795 January 26. "Watson begins the year's work."
1795 February 15. "Pd. Tom Shackleford for Watson 4.D."
1796 January 22. "Paid D. Watson on acct. 3.D."
1796 February 26. "Gave D. Watson order on Flem. & Mclanahan for hat & overalls."
1796 March 3. "Settled with D. Watson. His year (makg. up lost time) ends on the 5th. inst. Balance due him L5-1-9 3/4 but there is an article in the acct. (Feb. 26 ante) not carried out, and so to be taken into our next year's acct."