Fielding Lewis, Jr. (1751-1803), was the oldest son of Fielding Lewis (1725–1781) and GW’s sister Betty Washington Lewis (1733–1797) of Fredericksburg, Virginia. Fielding Lewis, Jr., inherited from his father 1,000 acres in Frederick County, Virginia.  Lewis was married before he was 19 years old, and in the latter 1760s, he was living in Fairfax County, Va., with his wife Ann (Nancy) Alexander. The couple and their children later lived on the land he inherited in Frederick County. Lewis spent much of his life in dire financial straits. His extravagant lifestyle and careless handling of money were already evident at the age of 18. By 1790 Fielding had sold not only most of the land he had inherited but also most of his worldly goods such as livestock, books, and furniture. Still he could not pay his creditors, and he was incarcerated in debtors’ prison in Winchester, Va., later that year. Fielding seems by 1799, however, to have improved his condition and was living in Fairfax County.

Robert Alexander, Lewis's brother-in-law, owed Fielding £200 on account of his wife's fortune, and asked GW to pay Lewis that amount or to use it to purchase slaves. Fielding wanted it used to purchase slaves (see Ledger A, 96; see also Fielding Lewis, Jr., to GW, 13  Sept. 1769).