The Nazis could not ignore or suppress Shakespeare without alienating members of the educated middle classes. But to present him on stage involved directors and actors, many of whom were not friendly to the regime. Shakespeare posed a more fundamental conundrum because he encourages audiences to look beyond and above the divisions between protagonists and resist unalloyed support for either side. Through an exploration of the staging of The Merchant of Venice in Venice in 1943, this essay explores this conundrum and Nazi efforts to cope with it.