Ethiopia is a country of diverse historical, cultural, geographical, archeological, and ecological resources and is well known as the cradle of humanity. It is also the tenth-largest country in Africa and endowed with vast land and water resources. This country was unable to translate these potential resources into positive development outcomes. This paper examines the historical perspective of Ethiopia’s underdevelopment mystery under the last three regimes (i.e., Haile Selassie (Imperial), Derg, and the Ethiopian People’s Revolutionary Democratic Front (EPRDF)). Qualitative approaches mainly interview, discussion, document analysis, and personal experiences were employed in generating relevant data that were analyzed and presented thematically. The results show that Ethiopia ranked the least in many global human development indexes such as Human Development Index, Corruption Index, and Global Hunger Index in the last decade. The underlying historical development challenges include political instability, despotic leadership, corruption, dependence on foreign aid and assistance, controlled freedom of expression, lack of diversity within unity, and inconsistent development policies. Over the last three successive regimes, the state-society relationship has been characterized by conflict, disagreement, and supremacy of state which messed up available national development opportunities. If Ethiopia has to come out of poverty and underdevelopment, it needs to improve its political stability and governance. It must be governed by ‘popularly elected’ not by ‘self-elected leader’ and put in place a system of accountability for a better future and wellbeing of its population. Consistent and pro-poor policy, good working culture, and unity in diversity must be other areas of concern for future development.