"LIFE" magazine hired Rickerby in 1961 to cover the Kennedy administration. Rickerby photographed John F. Kennedy and Robert F. Kennedy in the Oval Office and covered Jacqueline Kennedy's public life, which included her historic trip to India and Pakistan. On the day John F. Kennedy was assassinated, Rickerby rode in the President's motorcade. His most famous photograph from the day of the assassination is of the vice president's limousine outside Parkland Hospital; inside the open limousine, Lady Bird Johnson’s abandoned bouquet of roses lay scattered. Rickerby was later assigned to photograph John F. Kennedy's funeral.