This chapter first provides a historical perspective through a factual overview of Caesar’s life, career and achievements during the years 100 to 70 BC before enquiring into his leadership competencies and career development from a modern perspective. Because upbringing, early life experiences and significant encounters serve as obstacles to as well as springboards for leadership success, Caesar’s life, career and origins are examined. Key questions that are addressed are: What was the influence of his family, upbringing, education and the context in which he grew up on the development of his personality and career? What were the key events and individuals that shaped his character and forged his ambition, values and view of the world? How did his formative years set him up for a career in leadership? What was the social and psychological platform that launched his career? What obstacles could have potentially prevented his later career success?