Is pragmatism, as focused on a future considered producible by our finite actions, ill equipped to analyze religion (or “Erlösungswissen”, as Max Scheler said); is it unable, as Stanley Cavell writes, to sufficiently explore “skepticism” and negativity? This paper argues that William James succeeds in pragmatically re-thematizing “Erlösungswissen”, and that Josiah Royce—who develops a post-pragmatic, pragmaticist concept of; religion—carefully re-investigates “negativity”, in a Peirce-inspired mode, by focusing on the “mission of sorrow”.