This chapter outlines the key events of and Julius Caesar’s achievements during the civil war to permit a thorough analysis of Caesar’s leadership behaviours and detail his career progression as a military leader. The chapter focuses on two key challenges: preventing and winning the civil war. Starting from the premise that Caesar would have preferred to avoid the civil war, the description concentrates on what Caesar did to prevent it. While explaining the other challenge—winning the civil war—the chapter focuses on his leadership style. Some of this chapter’s driving questions include What were the keys to Caesar’s success? How did he overcome setbacks? How did his brand and reputation develop now that his enemies were Roman citizens—the effective result of having crossed the Rubicon?