Oprah is no stranger to the Kennedy family. While working for a TV station in Baltimore, she befriended John's cousin Maria Shriver—her mother, Eunice, is a sister of John, Robert and Ted Kennedy.
Once while visiting the Kennedy family home at Cape Cod for a party in Maria's honor, Oprah even struck up a conversation with John's mother, Jackie. "Your mother was behind the counter serving clam chowder," Oprah says. "And we sat down and we had a really wonderful conversation about life."
Oprah says she always dreamed of interviewing Jackie—but the former first lady stayed out of the media spotlight until she died in 1994. John says there was no grand decision behind his mother's silence. "It was just her life was easier if she lived it privately. And once you start answering those questions, then where do you stop with it?" he says. "It was a practical consideration that made more sense for her."