Two Monticello Workmen: David Watson 
and
William Orr
On
April 3, 1781, Jefferson noted in his Memorandum Book, "Sent David
Watson a British deserter, house joiner by trade, to work at Monticello."
In August of that year, there is a payment to "Wm. Orr the smith,"
and then the following January 8, "Wm. Orr the smith begins to work
at L3 the month." Over the following months, the names of these
two men are often linked in Jefferson's accounts.
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 reference to Orr, Jefferson noted in February 1782 that "He has lost 5. days work" and again in March, "Orr has been absent 4. days." 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. Billy Ore did the ironwork." 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. Both men continued to work at Monticello through 1783.
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 must have left with a good reference, for in February 1798 he was working for Jefferson's son-in-law, Thomas Mann Randolph.
--G. Wilson, Monticello Research Department, August 1997
Sources: Jefferson's Memorandum Books, Volumes I & II; Memoirs of a Monticello Slave as dictated to Charles Campbell by Isaac; "David Watson -- Documentary Sources," compiled by Lucia C. Stanton; Langhorne, Lay, and Rieley, A Virginia Family and Its Plantation Houses, pp. 32-33.