ONE HUNDRED YEARS ago, the 24-year-old Pablo Picasso painted the masterpiece Portrait of Gertrude Stein. The portrait was a landmark and a turning point for both artist and model. The painting, completed in 1906 in Paris, marked a radical stylistic change for Picasso and was a transitional work signaling the beginnings of Cubism. Gertrude Stein, along with her brothers, was a collector of modern art at the turn of the century. Her weekly “salons” in Paris became legendary and provided a place for intellectuals of the day—writers, painters, critics, and poets—to congregate and exchange ideas. Gertrude Stein’s collecting was paralleled by her writing of avant-garde prose. Her style was radical and influential, and the construction and syntax of her works was a literary analog of the Cubist artwork she was collecting in the early 1900s. Gertrude Stein became an enduring cultural icon and her portrait stayed with her in France from the time of its creation in 1906, through both World Wars, and until her death in 1946. The portrait remained with her companion, Alice B. Toklas, until its bequest to the Metropolitan Museum of Art in New York. Universally recognized as one of the classic and pivotal works of Picasso’s late Rose period, Portrait of Gertrude Stein brilliantly captures the psychological character of one of the great American writers and cultural figures of the last century.