Where'd He Get That 'Cool'

My Kennedy Listicle

On this, the 50th anniversary of JFK's assassination, I jot down a list to answer the question: "Where'd he get that 'cool":

1. As a wealthy man from a prominent family he had those 'high hopes' upon which ambition feeds.
2. His wife, Jacqueline.  She had a serious, classically trained mind that must have challenged him to greatness.
3. He read and studied history.
4. The experience of war would be enough to remove any uncertainty of character resulting from his privileged background.
5. He was, for the most part, successful, politically.
6. His extramarital affairs, though they point to his downfall, meant that he thoroughly experienced life.
7. All the cool kids were Democrats when his time came.  Franklin and Eleanor Roosevelt and then Adlai Stevenson led the way.  His elite Harvard education meant he was a player.
8. In his final years he took many drugs, some of which would have had psychoactive effects.  Which leads us to:
9. His health was terrible (very bad back, serious adrenal disease), but he was able to rise above the pain.  How could this not have been a source of strength?
10. Compared to what?  To the white bread banality of Nixon and Eisenhower.
11. His secret that he probably kept to himself: he didn't fear death.