This chapter reads the issue of complicity in William Shakespeare’s sixteenth-century English history play Richard III in conjunction with the recent Netflix hit House of Cards, which adapts Shakespeare’s early-modern monarchical politics to a twenty-first-century American democratic setting, in order to create a vocabulary for understanding the problem of complicity in Trump’s campaign and administration. Examples from these three different cases allow us to theorize three different kinds of complicity: conscienceless complicity (evil minions doing their master’s bidding in exchange for wealth and status), conscientious complicity (silence that serves as support for a villain due to fear of the consequences of speaking out), and unconscious complicity (when a villain’s charismatic personality exerts more of a pull upon the affections of an audience than his obvious immoralities and bad policies). At present, however, it is unclear if the tragic fate of the villain who cultivates complicity in Richard III and House of Cards also awaits the protagonist of our other story.