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Colonialism as a topic of discussion has retained a level of sensitivity both within and outside academia. Questions revolving around its merits and legacy, amongst other related issues within post-colonial societies, have remained an issue of debate; with different sides arming themselves with historical evidences to back their positions. Contemporary revival of the topic within academia warrants a relook at colonialism and an analysis of its utility or the reverse, from the perspective of the third world. This essay uses a historical lens to assess colonialism and how its legacy has influenced and affected the development of former colonies. The author draws on secondary data to make arguments and highlight inherent inconsistencies within debates that glorified the colonization of the global south. The essay draws on a historical approach and attempts to demonstrate the linkage between contemporary developmental challenges of former colonies and colonial policies pursued by imperial Europe. In highlighting the links between development challenge and colonialism, the author draws on historical records, and related works to demonstrate the influences of colonialism on development.