In 1765 James Cleveland of Loudoun County, Va., began working as the overseer of GW’s River farm on Clifton’s Neck. He served in that capacity until before the Revolution, when Alexander Cleveland replaced him. In January 1775 GW hired James Cleveland to lead an expedition down the Ohio to improve his Ohio and Kanawha lands. Cleveland reached GW’s tract near the mouth of the Kanawha in late April 1775, but his work went slowly, and he was forced to deal with runaway indentured servants.

In December 1764 GW bought a horse from Cleveland  (see Ledger A, 189).

Cleveland's wife may be the "Mrs Cleveland" whom GW paid in October 1767 "for her trouble of keepg" house at Mount Vernon in August of that year (see Ledger A, 255).