Sporting events for older adults are proliferating in both popularity and participation numbers, mirroring the growth that is occurring globally with an aging population. Preliminary evidence indicates that older athletes have a tendency to compare themselves (in terms of their performance, participation, and aging) to inactive older adults deemed “worse-off.” Our aim was to examine the stories and experiences of older, male Masters athletes, not only in terms of their own lives and in relation to others but also in the broader context of current (neoliberal) policies that promote sport across the lifespan. We use social comparison theory to interpret our findings and highlight the strengths and limitations of social comparison as a psychological strategy. For this study, 17 male competitive athletes (age range from 70 to 90 years) who participated in either the 2013 or 2017 World Masters Games were interviewed as part of a larger project on the meaning of sport in their lives. Seven different sports were represented, and participants hailed from multiple countries. Within the interpretive paradigm, we used qualitative methods to interview each participant, analyze individual transcripts, and develop common themes across the data set to address the aforementioned aims. Our two major themes were, Sport as social comparison:“It’s the competitive nature” and Downward comparisons. A number of participants commented on the nature of sport, and competitive sport in particular, as being important to their motivation to train and prepare. Within the theme of Downward comparisons, we established two categories: Resisting loss and Assigning blame. While downward comparisons were used by our participants to separate themselves from other seniors of the same age, thereby bolstering their sense of self, participants also tied those comparisons to neoliberal notions of individual and moral responsibility for health. Participants believed that compromised health was due to individual negligence and bad decisions, with little reference to uncontrollable factors, such as non-modifiable risk factors for disease, disability, and/or socioeconomic status, which could be affecting people’s lives or decisions. Ultimately, our findings show that the useful psychological strategy of social comparison for maintaining a positive sense of self and performance may also have some negative individual and societal consequences.