This chapter examines how Ted Shawn’s attempts to fulfill his vision of a “Greater Denishawn”—a physical and artistic expansion of the company and dance school into a full-fledged arts colony and dance guild—was thwarted by a number of personal, artistic, and financial factors, most especially the stock market crash of 1929 and the ensuing economic crisis. It also elucidates Shawn’s first serious relationship with a man as well as the unraveling of his marriage to Ruth St. Denis and the parallel dissolution of Denishawn, the company and school that they had founded together. It then follows Shawn to Germany where he attempted to rebuild his career as a solo artist with the financial and artistic support of Katherine S. Dreier, modern visual artist, philanthropist, and the founder of the Société Anonyme, as well as his return to the United States where he laid the groundwork for what became his all-male dance company.