This essay explores the contradictory, prejudicial attitudes towards circumcision and Jewish male sexuality circulating in eighteenth-century English print culture. I argue that while Jewish men had long been accused of lustfulness, effeminacy and sexual deviance, eighteenth-century culture added to these concerns a unique interest in sexual pathology, borne in part from the growing medical anxiety around venereal disease. Consequently, while Jewish men were still widely condemned for their lechery, they were also increasingly ridiculed for a range of penile and sexual disorders that were believed to make sex unsatisfying, difficult or even impossible—most notably impotence, a condition often associated with venereal disease. I link these paradoxical eighteenth-century characterisations of Jewish male sexuality with a similarly paradoxical understanding of circumcision as a procedure that could prevent, but also cause, various penile or sexual disorders. I conclude that these prejudices not only constitute an example of what Sander Gilman has identified as the ‘bipolar’ nature of anti-Semitism; they also indicate a darker trend towards the pathologising of the Jewish body.