In 2016, Colin Kaepernick, then playing for the San Francisco 49ers, began a silent protest by kneeling during the national anthem. His actions in that moment, and his subsequent activism made Kaepernick one of the most divisive and galvanizing figures in sports. Kaepernick’s actions sought to bring attention to the growing Black Lives Matter movement, which has in the years following the death of Trayvon Martin expanded widely. Kaepernick has raised awareness, and money in the years following his ousting from the league. Through his activist work via his “Know Your Rights Campaign” and more, Kaepernick like (Black) athletes before him has shown the world that sports are far from apolitical. Sports are reflective of the society in which we live, and though divorcing sports from politics seems to be the current call, athletes are human beings, and it is difficult to separate the human from the political. In this chapter we examine the ways in which athletes like Kaepernick, Tommie Smith, and John Carlos have been critiqued and scrutinized. At the time of the 1968 Olympic Games, Smith and Carlos were pariahs, today they are celebrated. What will be the legacy of Kaepernick in decades to come?