This chapter considers how strategies for representing the skyscraper indexed competing understandings of the nature of organization, a term with multiple valences in the early twentieth century. Whether one judged skyscrapers to be hideous blights or rapturous delights, few in the period failed to marvel at the powerful technic of organization marshaled by and for its mass. But to whom should its beholders credit that technic proved a harder matter to resolve. Descriptions of skyscraper construction by builder William Starrett and writers John Dos Passos and Willa Cather mark an oscillation between viewing this structure’s organization as an art, showcasing not just the skill but also the beauty of capital’s captivating choreography of bodies and materials used to materialize these structures, and organization as a politics, the active mobilization of laborers to resist modes of capitalistic organization by revealing the invisible and unaesthetic exploitation disguised by capitalism’s breathtaking arrangements.