Lem Billings, John F. Kennedy’s roommate from boarding school, takes center stage in this imagining of JFK’s courtship of Jackie. Billings knows Kennedy to be a true friend who opened up both the doors of power and to his own family, the rambunctious Kennedy tribe, to him after Lem lost his own father. He also knows that JFK has never been, and will never be, faithful to any woman. But the time for John to ally himself with someone suitable is coming. JFK’s political star is rising and, to be elected to the US Senate in the 1950s, he needs to be married. Jacqueline Bouvier, raised to marry into wealth, seems to fit the bill. Lem is deputized to ensure that Jackie understands her role in her future marriage, but at the fateful moment, Lem fails both Jackie and JFK.
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