Checkmate is a comprehensive look into the current Middle Eastern political and strategic reality which views the region as a giant chessboard to better understand the relationship between the players. However, in viewing the complexities of the Middle East, it is important to understand that strategy is not everything. This is a region of the world where emotions, passions, and cultural heritage have played the protagonists' roles. Considering historical implications, memories both physical and emotional, and the unfortunate consequences of cultural displacements, this essay explores the effects on social identities, which may result in prolonged strife and conflict. This work does not attempt to be a sociology treatise nor a policy paper. Rather, it is a collection of personal observations and experiences placed in the context of historical events. It focuses on the Middle East, but the concept could be applied to any area of the world. With this book, the author suggests that conflict, in the greater Middle East, cannot be mitigated until Western expectations are modified to include an understanding of the effects that cultural heritage has on regional dynamics.