This may be wildly inaccurate but I heard somewhere that his infamous wager might have been a parody of religious arguments, in a similar way that Schrödinger's cat was intended to show the 'absurdity' of quantum mechanics (at least as it pertains to the macro world).
At the age of five, Skagra decided emphatically that God did not exist. This revelation tends to make most people in the universe who have it react in one of two ways - with relief or with despair. Only Skagra responded to it by thinking, 'Wait a second. That means there's a situation vacant.'