Political scientists have found that early life experiences powerfully affect future leaders. Drawing on a variety of sources, this article investigates the formative role of Xi Jinping’s youth during a tumultuous time period in Chinese history. Xi’s life before and during the Cultural Revolution help explain his toughness, idealism, pragmatism, and caution. However, the evidence on how Xi’s childhood and young adulthood shaped his view on how to best handle political contradictions is ambiguous.