When he published The Orphanage in 2017, prolific Ukrainian writer Serhiy Zhadan stated his aim in writing the work was to portray the real experiences of people in his home region in the Donbas as Russian troops aided anti-Maidan separatists. A function of realistic representation is the banishment of stereotypes, which begs the question: how does Zhadan deal with or even use common stereotypes about residents in so-called “post-Soviet states”in The Orphanage? Does he seek to actively banish those stereotypes, or does he let them remain, wanting the work to be seen as “authentically” Ukrainian? In this paper, I argue that Zhadan uses the “post-Soviet loser” concept, developed by theorist Tamara Hundorova, to construct the main character of Pasha. Like Hunderova’s concept of a “post-Soviet loser”, Pasha is apathetic and disillusioned with the state that he works on the behalf of. However, as the novel goes on, Zhadan seeks to subvert and replace the “post-Soviet loser” concept within Pasha, with a new concept of the post-Soviet citizen—one less pathetic and more fitting of, and more inspiring to, a war-weary people. He does this through connecting Pasha with his nephew, who as a member of a new and more strident generation is able to inspire Pasha towards greatness, compared to the apathy stirred in him by the older generations.