Valentine Crawford (d. 1777), who lived for a time near GW's Bullskin plantation in Frederick County (later Berkeley County, Va. [now W.Va.]), was the brother of Col. William Crawford (1732–1782) and half brother to John, Hugh, Richard, and Marcus Stephenson, sons of Richard and Onora (née Grimes) Crawford Stephenson. During the French and Indian War, Valentine served for a time as a wagon master, and as a veteran, he later received a warrant for 2,000 acres of bounty lands under the royal proclamation of 1763. Since he resided near Bullskin plantation, Crawford regularly carted GW's mountain tobacco from that plantation down to Alexandria. Crawford later lived on Jacobs Creek in western Pennsylvania, several miles north of Stewart’s Crossing on the Youghiogheny River (now the site of Connellsville, Pa.), where his brother William had settled. Both Valentine and William were involved in GW’s efforts to acquire large holdings of land west of the Allegheny Mountains. GW acquired tracts on the Kanawha and Ohio Rivers, and in an effort to preserve his titles to those lands, GW engaged Valentine in the spring of 1774 to take a party of workers down the Ohio and seat his tracts by building houses and cultivating fields as required by Virginia law. That expedition was canceled before it started. As a result, GW hired James Cleveland in 1775 to do what Valentine had been prevented from doing, namely to lead an expedition down the Ohio to improve his Ohio and Kanawha lands.

Valentine Crawford borrowed money from GW on several occasions (see, for example, Ledger A, 63, 90).