Kant has often been accused of being far too "optimistic" when it comes to the extremes of evil that humans can perpetrate upon one another. In particular, Kant's supposed claim that humans cannot choose evil qua evil has struck many people as simply false. Another problem for Kant, or perhaps the same problem in another guise, is his supposed claim that all evil is done for the sake of self-love. While self-love might be a plausible way to explain some instances of evil, it seems to be an implausible way to explain instances where people imprudently act in senselessly destructive and even self-destructive ways. Can Kant handle such extreme cases of moral evil? I shall argue that Kant can handle such cases by: (1) defending Kant's denial of the possibility of a devilish human being; (2) showing how Kant can conceptually account for agents who choose evil qua evil, and (3) putting Kant's account of passions to work in order to understand self-destructive evil.