This chapter covers Pickens’s participation in the Cherokee War of 1760-1761, his marriage to Rebecca Calhoun, and his and his relatives’ and neighbors’ attempts to re-establish order in the South Carolina backcountry in the midst of the crime and anarchy following the Cherokee War. Initially receiving little help in this project from the lowcountry elites who controlled the colonial legislature, backcountry men formed vigilante groups such as “Regulators” and “Moderators” to protect themselves and their families. By the end of the colonial period, some order had been restored and Pickens had established himself as a church elder, justice of the peace, and “leading man” of the Long Cane community near Ninety Six, South Carolina.