Social media has ushered in seismic shifts to communication structures in society and these effects extend to the world of sport, where athletes and sports figures routinely divulge content on social media platforms. This chapter discusses athletes’ and other sports figures’ social media use to express their identity, which includes showcasing more of their personality, expressing dissent, and providing commentary on political and social issues. The chapter discusses legal implications for sport organization administrators as they seek to balance organizational reputation with First Amendment rights. The chapter also addresses related issues that can manifest in the online sphere, such as private commentary becoming public, threats made to athletes, and social media use by organization employees that can negatively impact athletes and harm the organization.