Michael Jordan supposedly justified his decision to stay out of politics by noting that Republicans buy sneakers too. In the social media era, the name of the game for celebrities is engagement with fans. So why then do celebrities risk talking about politics on social media, which is likely to antagonize a portion of their fan base? With this question in mind, we analyze approximately 220,000 tweets from 83 celebrities who chose to endorse a presidential candidate in the 2016 U.S. presidential election campaign to assess whether there is a cost—defined in terms of engagement on Twitter—for celebrities who discuss presidential candidates. We also examine whether celebrities behave similarly to other campaign surrogates in being more likely to take on the “attack dog” role by going negative more often than going positive. More specifically, we document how often celebrities of distinct political preferences tweet about Donald Trump, Bernie Sanders, and Hillary Clinton, and we show that followers of opinionated celebrities do not withhold engagement when entertainers become politically mobilized and do indeed often go negative. Interestingly, in some cases political content from celebrities actually turns out to be more popular than typical lifestyle tweets.