In the twentieth century Bakhtinian reading, Jack Cade in Shakespeare's Henry VI, Part 2 was regarded as a trickster because he disobeys the ruling class and brings an inversion of values to the world of the play. However, unlike other Shakespearean villains, Cade displays the anarchic nature inherent in heroes of the picaresque narrative which started to spread across Europe contemporaneously with Shakespeare’s writing career. Ever a picaro, Cade is consistently a carefree rascal who uses satire to expose society’s flaws. The plot revolves around the innocent but willful character of Cade, who claims to be a legitimate successor to the throne, and not a mere puppet of York. Rather than functioning as a subversive character slotted into a story about Henry VI’s weak kingship over his nobles, Cade provides an autonomous side story about how a rebel’s revolt was stirred up and contained. This paper examines Cade’s language and anamorphic discourse to show how Shakespeare created him as an emerging picaresque hero. It then goes on to propose that Shakespeare’s use of Cade not as a clownish anti-hero but as a prototype picaro anticipates his later creation of the rogue Autolycus in The Winter’s Tale.