Defining good leadership is difficult. To help clarify what traits make good leaders, it appears useful to conduct a historical analysis of previous leaders. In the era of World War II, Dwight Eisenhower, Douglas MacArthur, and Chester Nimitz stood out as formidable battlefield strategists and apt politicians. One way to understand how each leader ascended to his position and how he led in it is to study how their own motivations and talents, the influence of others on them, and plain luck marked their lives and careers. A comparative analysis of these attributes can help demonstrate how different styles of leadership can be successful and which attributes were most useful in unique circumstances. Taken together, these examinations can inspire the next generation of leaders as they form their own leadership styles while building on the legacy of those before them.