Prof. David Kalupahana’s desire to fashion early Buddhism into a site of exciting interchange and contestation of meaning can be seen in the way he initiated dialogues with celebrated Western philosophers such as William James and Wittgenstein. It was David’s firmly held conviction that a strong pragmatic impulse coursed through early Buddhism, and according to him, this is borne out by the fact that the Buddha rejected metaphysics, absolutism and essentialisms of any form or kind. Here, he saw certain parallels with William James’ thought. His point was not, that there was a perfect congruence between the thought of the Buddha and William James, but there are sufficient points of affinity to warrant instigating a dialogue, clearing a theoretical space for further inquiry. Similarly, he took the idea of suffering (dukkha) which is so central to Buddhism and compared with some notions of early Wittgenstein which revolved round notions of human will and ethical imagination.