Between 1956 and 1957, four Broadway producers–Cheryl Crawford, Roger L. Stevens, Robert E. Griffith, and Harold S. Prince–working in different configurations, each crucially impacted West Side Story’s development. Recognized then and retrospectively as a huge gamble for anyone involved, these four producers arrived at the project from different career stages and positions of financial security, which ultimately decided who could reasonably take a gamble on bringing a musical drama to Broadway. Here I survey different ways these producers helped birth West Side Story, such as providing dramaturgical advice, securing backers, coordinating a difficult casting process, and identifying productive tryout venues. These producers’ struggles with West Side Story’s innovations also signaled necessary evolution in established practices such as the backers’ audition. Placing these producers’ work on West Side Story in the context of their career trajectories will reinforce the role of timing and good fortune to any musical’s potential success.