Caroline Kennedy Schlossberg, son Jack and her husband, Edwin Schlossberg, leave their New York apartment en route to a Mass to remember her brother, John F. Kennedy Jr., and his wife, who were killed July 16, 1999, in a plane crash. (Lynsey Addario / Associated Press)
Then-Democratic presidential candidate Barack Obama shares a moment with Caroline Kennedy before addressing supporters at a rally in Scranton, Pa. (Charles Rex Arbogast / Associated Press)