James Wilkinson
Wilkinson's grandfather had been good enough rich to buy a large property known as Stoakley Manor in Calvert County. Even though James Wilkinson's family lived on a smaller estate than those of Maryland's elite, they still saw themselves as members of the higher social class. According to historian Andro Linklater, Wilkinson grew up with the idea that "the image of respectability excused the reality of betrayal". His father received Stoakley Manor but by then the family was in debt. Joseph Wilkinson died in 1763, and in 1764 Stoakley Manor was broken up and sold. Wilkinson's older brother Joseph received what was left of the manor property after his father died. As the second son, James Wilkinson received no land.