Throughout the narrative literature of early Indian Buddhism, we find the Buddha using tricks to help people along the path to awakening. These tricks, which involve both deceptions and illusions, enable those who experience them to put an end to defilements through unmistakable and often funny encounters with their own impermanent limitations. This article asks how such tricks relate to the Buddha’s other activities as a compassionate teacher of the Dharma. By placing the Buddha’s trickster-like qualities at the forefront of our investigation, we come to see the Buddha as an embodiment of the unconditioned, whose paradoxical status directly accounts for the transformations he works in others’ lives. The category of the trick, though not indigenous to Buddhism, highlights structural similarities underlying all the Buddha’s actions, thus easing the tension that seems to exist between his role as a teacher of sober sermons and a performer of awesome miracles.