The famous writer and expatriate Gertrude Stein was among the first Americans to respond enthusiastically to European avant-garde art. She held weekly salons in her Paris apartment populated by European and American artists and writers. For Picasso, Stein’s early patronage and friendship was critical to his success. He painted this portrait of her between 1905 and 1906 at the end of his so-called "Rose Period." He reduces her body to simple masses—a foreshadowing of his adoption of Cubism—and portrays her face like a mask with heavy lidded eyes, reflecting his recent encounter with Iberian sculpture.