Fly By Night begins with the  story of Andrew Carter Thornton III:  a Kentucky pilot and skydiver who was a privileged son of the Bluegrass state. Thornton's long strange trip went from growing up as a child of a hard working and successful family to becoming a soldier, and then a detective in the newly created narcotics squad in Lexington, Kentucky.

With stories of suspected corruption hanging over him, he left the police department for a short-lived stint as a lawyer, and then, using his skills as a pilot,  and with the help of other corrupt former cops and a DEA agent, Drew Thornton became one of the biggest drug smugglers in Kentucky history. This episode features interviews with retired FBI Special Agent Jim Huggins and retired DEA Agent Rick Sanders.