Classifying people as Great Captains is largely a subjective perception. What attributes, accomplishments, positions attained or battles won that make one person a Great Captain and the other not? Herein lays the dilemma, for ages academics have argued what criteria should be included or not, but it remains a highly subjective yet colloquial anti-analytical process. This paper examines the argument that Great Captains are a product of their family, highly educated from an early age, possess qualities of a genius, encounter grand life experiences compared to their contemporaries, espouse leadership from a young age, and capsulate their experiences by mastering their cultural ethos with domineering influence via political-military accomplishments. This examination will look into the education, life experiences, leadership, and ethos mastering of Gustavus Adolphus, Napoleon, and Grant. This examination will be analytical in nature and highlight those common attributes that carry across the ages of Great Captains. Armed with this information, it may be possible to prospect future leaders, appropriately guide and develop their maturation defining the cultural ethos of tomorrow’s political military society.