In this paper I discuss the relationship between the Buddha and his archnemesis Devadatta, specifically as depicted in the Lotus Sutra. In traditional Buddhist lore, Devadatta is something of the “Judas of Buddhism,” in that he tries to usurp Buddha’s role as leader of the sangha, encourages a royal patron to murder his father, and even seeks to kill the Blessed One on several occasions. He is, thus, regarded as one of the greatest villains in Buddhist history, yet in the Lotus the Buddha proclaims to his rapt audience that Devadatta was his “good friend” (kalyna mitra) whose life and teachings were instrumental in his (the Buddha’s) own awakening. Devadatta’s example in the Lotus suggests that common understandings of “friendship” may be inadequate and even misleading from a Buddhist spiritual standpoint. Paradoxically, perhaps a “bad friend” can turn out to be the best friend we could ask for.