Age-related decline may not be as pronounced in complex activities as it is in basic cognitive processes, but ability deterioration with age is difficult to deny. However, studies disagree on whether age is kinder to more able people than it is to their less able peers. In this article, we investigated the “age is kinder to the more able” hypothesis by using a chess database that contains activity records for both beginners and world-class players. The descriptive data suggested that the skill function across age captures the 3 phases as described in Simonton’s model of career trajectories: initial rise to the peak of performance, postpeak decline, and eventual stabilization of decline. We therefore modeled the data with a linear mixed-effect model using the cubic function that captures 3 phases. The results show that age may be kind to the more able in a subtler manner than has previously been assumed. After reaching the peak at around 38 years, the more able players deteriorated more quickly. Their decline, however, started to slow down at around 52 years, earlier than for less able players (57 years). Both the decline and its stabilization were significantly influenced by activity. The more players engaged in playing tournaments, the less they declined and the earlier they started to stabilize. The best experts may not be immune to aging, but their previously acquired expertise and current activity enable them to maintain high levels of skill even at an advanced age.