Born on November 27, 1957, in New York City, Caroline Kennedy lived with her parents in Georgetown, Washington, D.C., before moving to the White House in 1961. Like the offspring of Teddy Roosevelt, the Kennedy children enjoyed having pets in the Executive Mansion—primarily Caroline–because she was the oldest. Reporters loved taking photographs of her on the back of her pony, Macaroni. Every moment, it seemed, was observed by somebody. When she attended a swimming pool party in July of 1961, and slipped underwater for a moment or two before being pulled out by a parent—she was surrounded by people; the incident became front-page news that was analyzed inside and out by reporters across the country. A syndicated “special report” on Caroline wondered, “Will success spoil Caroline Kennedy?” She wasn’t even four years old at the time.[1]

After Jack Kennedy was gunned down in Dallas, Caroline and John, Jr., entered the public spotlight again, photographed endlessly as they mourned a tragic event they could hardly understand. Seeking some degree of anonymity, Jacqueline Kennedy whisked them away, to live in a Fifth Avenue apartment in New York City, stocking it with the animals that Caroline so enjoyed. Jackie focused on the children’s education, sent them to private school, restricted television, and encouraged them to read (Caroline was fascinated by Dolley Madison).

Still, though, the media followed wherever the Kennedys went; on a visit to Ireland in the summer of 1967, reporters pressed the children so closely that police had to intervene, and toss several members of the media in jail. Incidents like these, and Uncle Robert F. Kennedy’s assassination in 1968, caused Jacqueline to seek even more desperately for places to protect her children from the limelight. After she married Greek businessman Aristotle Onassis that year, Jacqueline took Caroline and John to the Greek islands. Still, reporters looked for opportunities to waylay the Kennedy children wherever possible. Interviewed by a writer for the Associated Press in 1970 just as she was about to turn thirteen, Caroline said, “I don’t think of myself as famous . . . I’m not really bothered by too many reporters or photographers. . .. I just don’t think of what it’ll be like when I’m older.”[2]

Caroline Kennedy graduated from Concord Academy, Massachusetts, in 1975, and from Harvard’s Radcliffe College in 1980. Journalism interested her—ironically–given the media scrutiny that had dominated so much of her life, but pursuing the vocation seemed impossible since “she could never make her living observing other people because they were too busy watching her.”[3] Instead she entered law school, and earned a J.D. from Columbia in 1988. Two years earlier Caroline had married museum professional Edwin Schlossberg, with whom she had three children.

Since her graduation from Columbia, Caroline Kennedy has, in addition to her work as an attorney, supported a variety of charities and nonprofits, including educational and civil rights initiatives. She created the Profiles in Courage award sponsored by her family. And although she has been active in Democratic Party politics, she has also forged strong relationships with the families of Republican presidents such as presidents Gerald Ford, Ronald Reagan, and George H.W. Bush. In 2008 she gave some consideration to seeking the U.S. Senate seat vacated by Hillary Clinton, but subsequently decided against it. Instead, she served as U.S. Ambassador to Japan from 2013-2017.

Born on November 25, 1960, in Georgetown University Hospital, John Kennedy, Jr., spent the first few years of his life as–probably–the world’s most popular toddler. His presence in the White House, along with that of his older sister Caroline, lent youthful authenticity to the Kennedy mystique. Some members of the press took to calling him “John-John” as a term of endearment—bemusing his parents–who had never used the name. When President Kennedy was assassinated just days before John, Jr., and Caroline’s birthdays, a photograph of the boy saluting his father’s coffin captured the nation’s grief.

John, Jr., followed his mother and sister to New York City and Greece, but–like them–he was subjected to intense media scrutiny everywhere he went. Events that would have gone unnoticed in the life of any other child became national news; for example, when he got into a minor spat with another child at school, or had his bicycle stolen in New York City’s Central Park.[4]

Graduating from Phillips Academy in Andover, Massachusetts, and then from Brown University with a degree in American Studies in 1983, John Jr., became fascinated with travel, international charity, kayaking in the Baltic Sea, and journeying to India and South Africa to address poverty and civil rights issues. Though he received a J.D. from New York University’s School of Law in 1989, John, Jr., was neither as active in the law nor politics as his sister, with whom he remained close throughout his life. Instead, he concentrated on business, culminating in 1995 with his founding of the sometimes-controversial society magazine, George. Pursued to the end by the media, that now featured remorseless paparazzi, John Jr., secretly married Carolyn Bessette; He and wife, along with her sister, were killed in an aircraft accident on July 16, 1999.