AbstractThe biological world is rapidly changing following decades of anthropogenic disturbances. Under these conditions, species with stable or increasing abundances have been described as winners with the potential for future success, but this assertion is unreliable without knowledge of the selective basis of winning. The incentive to find winners is acute for reef corals, for which large declines in abundance have motivated restoration efforts targeting winning corals. On Caribbean reefs, Porites astreoides has emerged as a potential winner, but the demographic basis of this categorization is poorly known. Here we test for demographic benchmarks of winning in this species by quantifying abundances and sizes of colonies over 28 yr on the south coast of St. John, US Virgin Islands. From 1992 to 2001, the density of colonies of P. astreoides showed little variation while colonies increased in size by 58%, but from 2002 to 2019, population density increased 2.7‐fold, and colony size declined by 41%; accompanying these trends, the mean absolute cover of Porites spp. declined by 46% from 2010 to 2019. Low recruitment and rising abundances of colonies ≤4 cm diameter suggest that partial mortality and fission depressed colony sizes. The reversal over three decades of a positive demographic trend for a ubiquitous coral underscores the challenges of identifying winners from short‐term population performance. Without a mechanistic understanding of fitness, the search for winners based on demographic trends may be futile.