This thesis will examine how Churchill's experience in the Boer War affected his career and leadership style. Initial research revealed that Churchill planned to make some major life decisions in 1899 the year he participated in The Boer War. Fate and other variables such as his financial independence and celebrity status enabled rapid realization of his goals to attain political office in the British government. Research indicated that Churchill's experience while a Boer prisoner of war (POW) and his subsequent escape proved to be an especially formative experience for him professionally. In addition, his POW experience taught him the Boer perspective of the conflict, which developed his leadership and personality. Secondary questions answered are: How did his experience as a POW affect him? What did his experiences in Cuba, India, and Sudan teach him? What were Churchill's motivations during his time in the British Army? Using a chronological approach throughout this paper will provide the reader with the most logical and easiest method of answering these questions.