The mass of impoverished commoners in Shakespeare’s period (as opposed to the prosperous middling sort) experienced daily conditions of extraordinary distress. Sketching their miseries, this essay affirms Shakespeare’s surprising degree of sympathy with plebeian suffering. In Kent, many plebeians were indicted for longing for a Spanish invasion, as liberation from “slavery.” Kent had for many centuries a reputation for rebelliousness, and in the later sixteenth century emerged a discourse of “Kentishmen” as oppositional and unsubdued. Shakespeare’s fiery rebel Jack Cade, in Henry VI Part Two, was the culmination of this discourse. Portrayed by Shakespeare as both comically inept and heroic, Cade embodied a radical class anger hidden from sight in medieval rebellions by the “principal parishioners” who strategically managed the face of insurrection, but now visible in risings, as the middling sort rejected risings. Shakespeare’s Cade is thus the inexperienced subaltern as de facto rebel leader: as in the Oxford Rising, and again in the Midlands Revolt. Embodying the insurgence of the leaderless, post-medieval bloc of impoverished commoners created by the secession of the middling sort, the charismatically oppositional “Kentishman,” a term circulating before “Digger” and “Leveller” were coined, was arguably the earliest English signifier for a “working-class” rebel-hero.