This book presents the story of Ruby A. Black, a feminist who broke new ground for women in Washington journalism in the 1920s and 1930s as a correspondent for a Puerto Rican newspaper and the first biographer of Eleanor Roosevelt. It offers access to the secret correspondence that shows how Black used her friendship with Roosevelt to advance the political career of Luis Munoz Marin, Puerto Rico’s first elected governor. The book describes Black’s effort, ultimately unsuccessful, to become both a well-regarded journalist and a political operative in the nation’s capital, a feat particularly difficult for a woman. It contends Black’s closeness to Roosevelt proved both a help and a hindrance to Black’s stature as a journalist.