This study investigates the methods by which President John F. Kennedy arrived at decisions to deploy the military in the conduct of foreign policy. Specifically, the events covered are the Bay of Pigs, which represents the nadir of Kennedy's foreign policy experience, and the Cuban Missile Crisis, regarded as his high water mark as a world leader. Further, this study examines how effectively Kennedy employed the military once he arrived at the decision to deploy them in pursuit of his policies. President Kennedy served during a period of extraordinary turbulence. His preferred instrument of choice in foreign policy matters was the military. This study explores the maturation of Kennedy's decision-making process and how its evolution most affected the military. The study focuses on Kennedy's personality and the Cold War political realities to arrive at an understanding of the decision making mindset of the era. From this point of reference, the measure of effectiveness of Kennedy's "flexible response" strategy is validated and his employment of the military can be judged a qualified success.