As another long-term project to draw analogies between past and present, this paper will aim to explore the irony of the transition from virtuous mercantilism to darker sides of modern Capitalism by examining Shakespeare’s representation of antagonism between Judaism and Christianity in The Merchant of Venice. This paper will probe the compatibility between Christianity and Capitalism as well. Antonio and Shylock are early capitalists, and Shylock’s interpretation of Jacob’s reward to his own advantage is no better than Antonio’s understanding of mercantile venture to his own profit. Together with the nobles’ hypocrisy and materialism, their stances are contradictory to their faith. Mammonism seems unavoidable in a capitalist’s worldview, but it is not the core value of Judeo-Christianity. Therefore, Shakespearean rendering of problematic aspects of Christians from the antagonism between the Jews and the Christians is overlapped with criticism against financial Capitalism. The amalgam of eclecticism all the characters adopt in the play is the prophetic mimesis of widening income polarization where interest and speculative capital play a vital role.