In late 2018, Nike was sponsor to an NFL quarterback who had begun a movement of silent protest during the national anthem and had subsequently been unable to find a team willing to sign him. The polarizing controversy surrounding this athlete Colin Kaepernick might represent an opportunity for Nike to connect with its young target segment in a bold manner and differentiate itself from competitors. However, care was necessary in assessing the risks involved with courting widespread social media backlash when polls seemed to suggest the majority of the public was against his actions. The company must first explore the social and political context surrounding Kaepernick’s activism as well as his own words regarding his motivations. Through this Nike could project the lingering impressions and biases the general public still associated with Kaepernick, and how they might drive consumer response. Furthermore, Nike’s understanding of how its business and relation to the controversy differed from the NFL and how its customers compared to the dissenting majority might be crucial in bringing value to the brand through meaning and connection. However, should Nike prove successful by taking action that alienates an entire political segment, what might that mean for businesses and society moving forward? If a polarizing society drives businesses to choose sides in search of success, that might also serve to generate further division. Beyond the moral question of whether it was appropriate for Kaepernick to kneel or not, is another moral question of what separated “connecting with divided customers” from “capitalizing on social division”?