Shakespeare's final play, The Two Noble Kinsmen, contains profound psychological insights. Like all of Shakespeare's reworkings of old material, the result is not merely a variation on a theme but a psychological statement in and of itself, which respects and revisits the past even as it presents a new and original statement. In this paper I argue that the transformation of the Chaucerian into the Shakespearean has a premonition of the Freudian in it also: Shakespeare not only delivers insights on development and sexuality, he anticipates an important Freudian concept in his introduction of the theme of the jailer's daughter whose “love-sickness” requires an understanding of transference before sense can be made of it!