This paper tries to study the role of political leadership and how it influenced victories and failures during history. Therefore, in a journey through fluctuating Iranian history, four prominent and influential wars of past two centuries – initially Iran-Russia war and finally Iran-Iraq war- have been studied. While comparing Iran's political leadership in these wars and their consequences, this question has been duly answered: what were the reasons of Iran's failures in three wars during Qajar dynasty and desired results of Iran-Iraq war?