This article examines the contradictions of the contemporary literary field that appears both increasingly capacious and more exclusionary than in the past. Discussing the expansion of publishing enabled by digital and online technologies, we note that these changes did not reshape the demographics of most published works in the US, which remain overwhelmingly white authored. We then turn to literary prizes as an indicator of who writes prestige literature, narrating the twentieth-century formation of a racially segregated field and its slow changes against the backdrop of publishing overproduction. Combining a history of prestige literary culture with a demographic analysis of prizewinning writers (1918–2019), we discuss how a mostly white, New Critic-dominated field became the much more diverse and wide-ranging scene of the present. While this area has importantly opened up to writers of different backgrounds, our data show that the inequities of earlier prizegiving now take shape as drastic educational barriers to entry. Observing that a great deal of contemporary literature dramatizes the peculiarity of performing racial difference—often under the auspices of white audiences—we argue that the path to “excellence” has never been more narrow for writers who are not white, and Black writers in particular.