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Black entertainers operate within a unique set of boundaries when trying to advocate for racial justice. Scholarship has shown that while Black audiences may want Black entertainers to speak on racial justice issues and champion causes, their White audiences may also be willing to push back on them should they do so (Block & McClerking 2020). This research paper seeks to examine the complexity of contemporary Black entertainers as political leaders by utilizing the 2020 NBA Bubble Protest as a case study. This event saw a collection of many Black athletes maneuvering out of the political norms and boundaries set by precedent in their league in response to racial injustice, thus making their collective political behavior an outlier. Moreover, this analysis also seeks to examine both their political behavior and the outcome of their actions and collective decision-making to understand the dynamics at play when contemporary Black entertainers utilize their platforms to address racial injustices.