What did the interaction of Apollinaire, Picasso and Stein, three seminal figures of the avant-garde, mean for Modernism? This paper analyzes the exchanges between the poet, prose writer, and painter and how their encounters, direct and indirect, contributed to the shaping of modernism via a re-thinking of verbal and visual forms in the early years of the 20thcentury. How they met, who they knew and what they created are as important as their criticism and complaints of each other as they shaped the art of the time. Stein wrote a poem entitled “Apollinaire,” Picasso painted Stein’s portrait and Apollinaire wrote a study of Cubism. These are only a few of the surprising intersections examined in this study. One remarkable element is the way artistic distinctions dissolved among the three. Apollinaire’s views of Cubism, Picasso’s view of Apollinaire’s art criticism and Stein’s view of both men intersected and overlapped so that the ideas of one were absorbed by the other. In this way, the modernist enterprise, at least between 1900-1920 possessed a kind of unity of approach and understanding. The death of Apollinaire in 1918 and the visual advances undertaken by Picasso, as well as new work by Stein, separated the three-but for a certain period they interacted on multiple levels: artistically, socially and historically forming a remarkable triumvirate that remade art, poetry and prose setting the path for others to follow.