The social function of sport has traditionally been to develop an economically efficient workforce and to prevent young men from becoming effeminate, and by extension homosexual. However, since the 1980s both the social positioning of homosexuality has changed, as has the economic requirements of the Anglo-American workforce. As such, the social function of contemporary sport is negated. With modern athletes now opting for softer masculine presentations, we start the debate on the intersection of sport, health, and inclusive masculinities, an area lacking scholarly attention so far. Through exploring masculinity-challenging discourses, participation rates and athletes’ self-withdrawal from sport when injured, we begin to theorize how modern athletes may view potentially risky and injurious sporting activities, showing that boys today are less inclined to engage in injurious activities, and, when they do, opting for softer and safer strategies.