Heroism, victory and leadership are, indeed, unique but not unrelated literary concepts. They have been long defined originally within the ancient Greek works. Ultimately, that which defines heroism in the literary context is a journey that takes the hero away from society, transforms him while on the journey, and a triumphant return to impart new knowledge upon the community. Victory is clearly defined as an achieved domination of one party by the other – but true victory is much harder to define and more commonly achieved by isolating a set of parameters necessary to be met before victory can be achieved – often that victory comes at a cost to all parties because it is never really clean. Leadership, particularly in literature, is necessary to drive the hero to his goals and to take credit for a victory. The main character of the story does not always take up a leadership role, but they must respond and react to that role. It is the purpose of this paper to examine these three concepts in the context of the “Aneid”, the “Iliad” and “Henry V”.