The agent's past isn't clear at first in the game, but in the novel it is explained through small bits of information. In the past, he had a partner named Flynn, and the two always worked together. They were known as "The Righteous Brothers", due to the fact that they never drank and never went against the rules. But one day, Flynn started talking about "darkness" and he would avoid shadows whenever he could. Nightingale told Flynn to get his act together, but one day, Flynn was "taken" by something. Nightingale became obsessed with finding out what Flynn meant, and he started to take to large bouts of drinking to wash away the guilt he felt for his friend's death. At one point, Nightingale began having terrifying nightmares, similar to the ones Clay Steward and Alan Wake were having. In his dreams, Nightingale saw a man who very closely resembled Alan Wake. Soon, Nightingale became completely obsessed and paranoid about finding the man in his dreams.