This article explores the life and images of Huang Bamei (1906–1982)—a female bandit, guerrilla leader, and women's organization coordinator. During the Second Sino-Japanese War (1937–1945), Huang was involved in smuggling and trade with pro-Japanese forces. The Nationalist authorities recruited her troops and hid her past by portraying her as a wartime heroine and model housewife. Yet, in later times she participated in guerrilla warfare and was portrayed as a pirate queen and a Han traitor, and her roles and images changed dramatically with the wars. Drawing on government archives, newspapers, memoirs, and films, this article examines how Huang developed survival strategies during turbulent times and how competing regimes used her images discursively to promote various social and political agendas and stimulate Chinese patriotism and war commemoration in different historical periods. Through a close reading of the life history of a woman made legendary by the state and the media, the article shows how Huang's changing roles and competing representations were deeply embedded in the wartime politics of modern China and Taiwan. The author argues that Huang's guerrilla practices, as well as her involvement in banditry, formed an integral part of not only her survival strategies but also a range of options for achieving legitimization.