In 1975 Mailer published The Fight, an account of the Muhammad Ali and George Foreman “Rumble in the Jungle” in Kinshasa. His portrait of Ali during the days leading up to the famous face-off punctuates Mailer’s ongoing fascination with the sport, which he covered in his journalism for decades. In all of these pieces, Mailer expounds on the existential and moral aspects of boxing, drawing connections between boxing, moral courage, masculinity, and existential leadership, which also appear in novels like The Deer Park, An American Dream, and Tough Guys Don’t Dance. This chapter engages with boxing as a journalistic focus of Mailer’s but centers on his ongoing fascination with Ali as the symbol of all that boxing symbolized.