The Cuban Missile Crisis goes back to 1959, when Fidel Castro became the dictator of Cuba, an island nation just south of Florida. Over the next two years, he began to move toward a Communist-style government, while seeking aid from the Soviet Union. After taking office, JFK went forward with a plan to topple the Cuban dictator by backing an invasion force composed of anti-Castro Cubans. When the invasion fell apart in the Bay of Pigs disaster, the Soviet Premier, Nikita Khrushchev, saw an opportunity to protect his Cuban ally and shift the global balance of power by installing nuclear weapons in Cuba. When this came to light in October 1962, many of JFK's advisors and generals urged an immediate invasion of Cuba. Instead, JFK decided to try for a peaceful solution. On October 22, 1962 he announced a naval quarantine to seal off Cuba, and demanded that the Soviets remove all of their nuclear weapons already in place. Khrushchev, fearing nuclear war as much as JFK, eventually backed down, and a settlement was reached in which the Soviet missiles were removed, while the U.S. promised not to molest the Castro regime, and pledged to dismantle their installations of Jupiter missiles in Turkey. Both sides could claim victory, but JFK's diplomacy had managed to protect U.S. interests while preventing a general war.

Thwarted in his own political ambitions, Joe Sr. had always intended for his sons to succeed in politics. Initially, he had hoped that Joseph Kennedy, Jr., his eldest son, would be the most successful–but when Joe Jr. died in World War II, Joe turned without hesitation to his second son, JFK. "It was like being drafted," JFK remembered it later. "My father wanted his oldest son in politics. Wanted isn't the right word. He demanded it." Joe Sr.'s money and connections made a tremendous difference, particularly in JFK's early races, in which he was elected first to the House of Representatives and then to the Senate from Massachusetts. In addition, his father's influence in the world of publishing and the media played a large role in JFK's rise to national prominence during the 1950s. The same Kennedy fortune that helped JFK in his first campaigns proved a key ingredient in the 1960 presidential race. JFK was an immensely skillful and appealing politician, but one cannot discount his father's willingness to pay any price to see his son in the White House as a factor in JFK's rise to the top.

In the public eye, JFK always seemed remarkably virile, the picture of good health. Meanwhile, his family life–with his beautiful, cultured wife, Jackie, and their lovely children–appeared to be idyllic. Both of these images, however, were built around deception. In fact, JFK suffered from a bad back and from Addison's Disease, a potentially fatal condition that made him reliant on cortisone injections throughout his political career. His doctors kept quiet, and the state of his health was never revealed to the general public, since it would have torpedoed his aspirations to higher office. Similarly, only a select few were aware of JFK's romantic affairs. He had been something of a playboy in his youth, and his womanizing continued throughout the 1950s and during his years in the White House. His many mistresses included, most famously, the film star and international sex symbol Marilyn Monroe. These indiscretions were kept secret by the loyalty of his family and advisors, by the power that his brother Robert wielded as attorney general, and by the unwillingness of the press to print frank sexual gossip.