In the first months of 1960, my grandfather managed to get out of Cuba thanks to some connections to Fidel Castro, an old prep school buddy of his, and left on a jet also carrying the senator from Massachusetts, John F. Kennedy. My grandfather’s kids—including my mother, who was 3—made such a scene that he sent the senator a letter apologizing. Kennedy responded, assured him the kids were fine, and soon after, my grandfather and his family settled in Greenwich, Conn.